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Holiday Apartments and Homes Siesta Key, FL

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From
$527
Per Night
1 / 25
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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From
$200
Per Night
1 / 16
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (2) Make Enquiry
From
$200
Per Night
1 / 12
2 Bedrooms, 2 Bathrooms, Sleeps 6
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$1,777
Per Night
1 / 14
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Gym
  • Internet Access
  • Private Fishing...
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This second floor 2 bedroom, 2 bath, laundry and 1 car garage has been completely remodeled for that serene home away from home feel. It is a Gulfside, large garden condo with a screened in lanai with a peaceful pond view. Siesta Key Beachfront Vacation Rentals Peppertree is the perfect home... View all property information
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5 of 5 stars Reviewed 19 May 2014
My husband, 2 kids (7&6), and myself have stayed at this condo several times and we highly recommend it to anyone considering a beach vacation in Florida. Bottom line... This...
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From
$210
Per Night
1 / 21
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Upscale town home with private heated pool in superb location. Find yourself just around the corner from Siesta Key village and a short walk or bike ride to Siesta Key beach. Situated on a quite street with lush landscaping, this town home can sleep up to 6 guests. On the first floor you will... View all property information
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5 of 5 stars Reviewed 17 December 2014
We rented this town home for 1 week to get away from the brutal winter we have been having back home. We were looking to come down as a last minute trip and found this property...
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From
$164
Per Night
1 / 16
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Balcony
  • Dishwasher
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Lovely Gulf Front Condo on Siesta Key with your very own path to the beach! This is a one-month-minimum rental but we can rent for a week during spring break for the rental rate of $1800, plus fees and taxes. This spacious, charming condo is located on third floor of the gulf-side building of... View all property information
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From
$259
Per Night
1 / 16
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2 Bedrooms, 2 Bathrooms, Sleeps 5
Booking
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
This vacation rental offers a full view of Siesta Key Beach/ The Gulf upon entry; relax and enjoy from your lanai or master bedroom. The property has been newly transformed to accommodate our guests best welcome to Siesta. From the comfort of the home décor to your fully stocked kitchen: cookware,... View all property information
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5 of 5 stars Reviewed 4 December 2014
Sandy was great, made us feel welcome. The condo was perfect. Not only was it clean but it was in the perfect location. Had a wonderful time and will definitely be brining my...
5 of 5 stars Reviewed 2 December 2014
Incredible view with a clean and up to date condo, What more can you ask for ?? We loved our stay and DEFINITELY will return very soon !!
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From
$210
Per Night
1 / 25
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Studio, 1 Bathroom, Sleeps 2
Bookings
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Amenities & Details
  • Air Conditioning
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Relax, get away and enjoy Siesta Key's laid back lifestyle! Nestled in a quiet residential neighborhood, you’ll love this large and comfortable 500 square foot studio apartment. It has a queen bed and comfortably sleeps 2. The studio is attached to the owners' home, and features a queen bed,... View all property information
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From
$228
Per Night
1 / 8
1 Bedroom, 1 Bathroom, Sleeps 3
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Newly Upgraded 1BR/1 BA condo with full sleeper sofa and twin sleeper chair in LR. New Top of the Line King Size Bed will give you a great night sleep after a wonderful day at the beach and a great night in the village(2 miles from condo with free taxis,run on tips, available to take you to and... View all property information
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From
$210
Per Night
1 / 12
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (12) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Sauna
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
1-800-624-9276 www.seashellcondos.com Beautifully maintained complex is located directly on Siesta Key overlooking the Gulf of Mexico. Named Best Beach and No.1 Beach in Florida. Our unit is a 2bdrm/2bth, fully furnished, livingroom, diningroom and fully equipped kitcken, Private Balcony with a... View all property information
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5 of 5 stars Reviewed 15 July 2014
Outstanding week of vacation with family. Cottage was very clean and in excellent condition. We especially enjoyed the beach cart and chairs that were provided. Siesta Key and...
5 of 5 stars Reviewed 1 July 2014
We just returned from a wonderful week in Siesta Key. It was our first visit there. Needless to say, we WILL be back! We stayed at Sea Shell Condos (#407) and just loved it...
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From
$149
Per Night
1 / 22
2 Bedrooms, 1 Bathroom, Sleeps 5
Details Reviews (7) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Gym
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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About this property
The Perfect Place to Stay When You Need to Get Away! Free Wi-Fi access, Fully Furnished, Gulf Beach Views, Screened Balconies, Cable TV, A/C/H, Free Local Calls, Elevators, Large Heated Swimming Pool, Shuffle Boards, Covered Parking, Laundry Facilities, all units Non-Smoking Rec-Room: pool table,... View all property information
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5 of 5 stars Reviewed 29 July 2013
We stayed in 402. It was great! Very nice and comfortable unit. AWESOME view from the screened in patio. Plenty of beach chairs and an umbrella to use on the best beach ever...
5 of 5 stars Reviewed 10 July 2013
What a terrific place! We stayed in Unit 403, and will most certainly rebook it. For all our travels, La Siesta is hands-down the cleanest place we've ever stayed, down to the...
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From
$156
Per Night
1 / 9
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2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
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About this property
Fabulous 2 bedroom/2 bath located in one of Siesta Key's finest Gulf to Bay complexes. This beautifully appointed unit epitomizes Island elegance with its hand-scraped dark hickory wood floors, plantation shutters and French doors enclosing the brick-paved lanai. The newly renovated kitchen... View all property information
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From
$123
Per Night
1 / 17
2 Bedrooms, 1 Bathroom, Sleeps 7
Details Reviews (7) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Study the water in the pool or wander to the beach and village. This relaxing oasis is framed by 70 year old banyan trees and rests on a quiet tropical street just one block from the best beach and two blocks from the best shopping dining and entertainment on the island. Your apartment has a view... View all property information
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5 of 5 stars Reviewed 12 August 2014
They provide most of the stuff you will need, I'm so glad they had chairs and umbrellas since we forgot ours, I would definitely come back, and recommend this property to anybody...
5 of 5 stars Reviewed 12 June 2014
Our family had an amazing time at Gertrude's Twin Banyan. Right from the time we booked Daniel the owner was really accommodating and helpful, his quick response to our rental...
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From
$437
Per Night
1 / 22
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Ocean Views
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
The condo benefits from its own private pool. The living room, master bedroom, and lanai (balcony) all have stunning ocean views. The lanai, with over $10,000 of new doors and windows, is furnished with a table and chairs to enable you to dine al fresco. There is also a comfortable couch to... View all property information
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5 of 5 stars Reviewed 27 July 2014
Beautiful ocean views just a few steps away from the beach. The condo is well furnished. You will have all the comforts from home. Vey well located if you are looking for peace...
5 of 5 stars Reviewed 8 May 2014
We had an excellent week here! It is perfectly located for the beach without bring in the middle of the main tourist area of Siesta Key or the impressive, but at times busy public...
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From
$1,137
Per Night
1 / 23
7 Bedrooms, 5 Bathrooms, Sleeps 16
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
This stunning home features 10 foot ceilings, top of the line VIKING appliances including a wall mounted double oven, stove, and side by side refrigerator. The kitchen has a massive center island with lots of room for multiple chefs or families and friends to sit and chat after a day a the beach.... View all property information
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From
$184
Per Night
1 / 18
5 Bedrooms, 1 Bathroom, Sleeps 20
Details Reviews (7) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Tropical Garden beach cottages located at Siesta Key Beach. The Beach Place is Old Florida charm that's becoming hard to find. Private, quiet and relaxing. Tropical gardens surround our heated pool with tiki cabana bar for guests, poolside and beachfront BBQ. Five fully stocked one bedroom... View all property information
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4 of 5 stars Reviewed 9 October 2014
I wanted to have a vacation that felt like I lived at the beach and that is what I got. The rental was plenty big enough for the two of us and we had a kitchen to cook, pool, bar...
5 of 5 stars Reviewed 4 September 2014
The Beach Place is a quaint, quiet group of cottages on Siesta Key. We stayed in "The Dolphin" which has a king size bed, dinning area and kitchen all of which was very clean and...
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From
$159
Per Night
1 / 16
1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Private Beach
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
This one bedroom and one bathroom beach bungalow is located 150 yards away from the beach. You can walk to restaurants, shops and a great pool area. Queen bed and a sleeper sofa make it possible to sleep four. Enjoy your morning coffee on your private screened porch or while you walk on the beach.... View all property information
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From
$257
Per Night
1 / 17
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Gumbo Limbo Vacation Rentals: Honeymoon Suite 60 steps to the BEACH. Spacious 1 bedroom / 2 full baths townhouse (850sq/ft) over 2 floors, with 1 King size bed, and 1 Queen sleeper sofa in the living room. This townhouse also offers 2 balconies (Gulf, pool and garden views.) Fully furnished,... View all property information
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3 of 5 stars Reviewed 3 March 2014
You would expect a property in this price range to be above average. It does have an above average location, 1/2 block to Siesta beach and an inviting pool area with tropical...
5 of 5 stars Reviewed 12 September 2014
Wir waren begeistert. Der Appartment-Komplex mit den vier? Wohnungen ist sehr schön gestaltet, der "Innenhof" ist gut geschützt und gepflegt, der Pool schlichtweg traumhaft! Es...
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From
$200
Per Night
1 / 14
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (6) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Island House Beach Resort- Siesta Key Florida, Crescent Beach- This large 2 bedrooms, 2 bath villa is appox. 1000 sq. ft. It has a large living area, dining area, fully equipped kitchen, all appliances, 60' high def tv in living room, 50' high def in master, dvd, free wi-fi in unit, central... View all property information
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From
$668
Per Night
1 / 16
Payment Protection
6 Bedrooms, 2 Bathrooms, Sleeps 14
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Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Fishing...
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Brand New , Gated Residence steps from Siesta Key Beach . Perfect location between the village and crystal sands of Siesta Beach!! Bar's, Restaurants, Shopping, Sport Rentals……..EVERYTHING is within walking distance…..NO CAR NEEDED!!! This brand new 2700 sq ft private residence is simply... View all property information
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From
$214
Per Night
1 / 30
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (8) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Located directly on world famous Crescent Beach this Siesta Key beachfront condo is right across the street from South Village. This vacation condo is located in the Sea Shell Condominium Complex. Sea Shell is a smaller more intimate 5-story complex with only 49 units total. The condo complex is... View all property information
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5 of 5 stars Reviewed 1 May 2013
This well kept condo is a real treat. The owners and on site staff are easy to work with, the property is well maintained, and the local store, Crescent Beach Grocery and Curtis...
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From
$60
Per Night
1 / 15
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Visit our website www.RentSiestaKey.com under the property name 'Beach Road - Capri' for current rates This freshly renovated unit is located just across the street from Siesta Key public beach. Simple and elegant furnishings include a Queen-size bed, queen sleeper sofa, 32' LED TV, small but very... View all property information
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5 of 5 stars Reviewed 4 August 2014
We had an excellent time. The room was perfect for an anniversary getaway. Beach access was right across the street. The kitchen made it easy to buy some easy lunch groceries for...
5 of 5 stars Reviewed 23 June 2014
I absolutely loved this place!!! The location was perfect. The kitchen had everything we needed. The bathroom was nice and beautifully updated! It has off street parking in a safe...
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From
$203
Per Night
1 / 15
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (32) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Unique and rare large one-bedroom condo 4th floor penthouse with 200 sq. ft. open balcony featuring unobstructed and panoramic view of Siesta Key Public Beach and the Gulf of Mexico. This same view is also presented from the kitchen, dining room, living room and foyer. Balcony is a great location... View all property information
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5 of 5 stars Reviewed 14 October 2014
Yes you have to walk across the street but you have a beautiful view and still hear the gulf waves. Fantastic facility with great tv and in house surround sound. Lots of extras in...
5 of 5 stars Reviewed 24 July 2014
Everything about this condo lived up to our expectations: unobstructed view of the beach (across from public access), well equipped kitchen, large outdoor patio with table/chairs...
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From
$123
Per Night
1 / 14
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Internet Access
  • Sauna
  • Shared Outdoor Pool...
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
We invite you to settle in to a beautiful and very large 2 bed/2 bath 1280 sq foot beauty, approximately 200 yds. from the beautiful crystal sand of Crescent Beach. Serenity abounds in calm, aqua waters and miles of the most exquisite coastal sands in the world. Our spacious condo boasts all of the... View all property information
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5 of 5 stars Reviewed 5 October 2014
We stayed here for a week (family of 4, kids aged 13 & 11), following on from a fortnight in Orlando. We wanted somewhere to stay where we could walk to a beach. This condo is...
2 of 5 stars Reviewed 1 September 2014
Location, location, location! The condo is a few feet from the busiest road on Siesta Key therefore you hear loud road noise in every room. Hard to believe no one mentioned this...
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From
$507
Per Night
1 / 23
4 Bedrooms, 3 Bathrooms, Sleeps 12
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
THE GRAND CANAL COTTAGE: (Two Week Minimum Rental) The Grand Canal Cottage, perhaps one of Siesta Key’s favorite luxury vacation homes, is a highly landscaped canal-front private luxury home featuring a heated pool with sun shelf and a separate 8-person spa. It is situated on Siesta Key within... View all property information
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From
$153
Per Night
1 / 36
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Hot Tub
  • Internet Access
  • Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
The accolades keep pouring in. Guests and media alike rate the Palm Bay Club as a perfect destination for romantic getaways and family vacations. Treat yourself to an idyllic holiday on Florida's Gulf Coast, at this luxury 4-person condo that is Gulf Side and next to the beach.

Just a... View all property information
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3 of 5 stars Reviewed 12 October 2014
Palm Bay Club is a lovely venue but this particular unit has no ocean view and the furnishings are very "tired". With some major updating the view could be overlooked.
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From
$200
Per Night
1 / 15
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Island House Beach Resort, Siesta key, Crescent Beach!New improvements in 2014! 60' tv and entertainment center ( netflix reaady), new ac unit, new dishwasher and ceiling fans in bedrooms. Professionally decorated in October 2011. This large 2 bedrooms, 2 bath unit is approx 1000 sq. ft. It has a... View all property information
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5 of 5 stars Reviewed 12 October 2014
A wonderful place to stay! Clean and updated. King bed was very comfortable. Problems with the wifi is my only complaint. Wifi is available, but not dependable. Couldn't...
5 of 5 stars Reviewed 25 June 2014
Our stay was fantastic, very clean, quiet ... the spectacular beaches, pool spotlessly clean condo. We were in town .. 39 is very comfortable and cozy, had everything we needed...
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From
$205
Per Night
1 / 25
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Private Fishing...
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Fisherman's Cove condo description Lovely 2 bedroom, beach front condo on the Gulf of Mexico with sunset views overlooking the gulf and sunrise views of the lagoon, expansive water views from every window. . Watch the sunset, the birds and ocean wild life swim by. Swim, snorkel, fish, surf or... View all property information
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5 of 5 stars Reviewed 7 August 2014
My Husband and I have stayed in this Condo several times. We come back year after year because it is a beautiful condo, clean, comfortable, and the location is perfect. It's...
5 of 5 stars Reviewed 2 August 2014
Working with the owner to arrange our week long stay was very easy! Check in a breeze! The unit was just as pictured and clean! The proximity to the Gulf unsurpassed......steps...
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From
$172
Per Night
1 / 15
2 Bedrooms, 1 Bathroom, Sleeps 8
Booking
Details Reviews (19) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
2BR (sleeps 8)- Perfect for travelers in search of uncomplicated seclusion. Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests and is a four unit Key West style home located just one marlin’s length (5 steps) from... View all property information
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5 of 5 stars Reviewed 11 December 2014
I made last minute plans to leave the northeast for some sunshine on my birthday and landed at the Old Man & The Sea. There I found the ideal combination of peace and quiet with...
5 of 5 stars Reviewed 13 November 2014
Great place for the money,can't go wrong with this one.very close to the water,very nice neighborhood, close to restaurants
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From
$194
Per Night
1 / 17
3 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Dishwasher
  • Dryer
  • Internet Access
  • Washer
  • Waterfront
  • Water Views
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Beautiful 3 bedroom canal front home with sparkling pool located just a short 3 block walk to the beach! Bright and spacious with almost 2000 sq.ft. Tastefully decorated and fully equipped, the home offers an open, split floorplan with bedrooms and bathrooms on opposite sides of the home for added... View all property information
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From
$168
Per Night
1 / 15
2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Island House Beach Resort - Siesta Key Florida - Crescent Beach. This 2 bedroom, 1 bath villa duplex is 1000 sq. ft. living room, dining area, full kitchen ( all appliances), lanai. Central heat/ac. The unit has a king, 2 twins, sleeper.3 tvs. It is located across from our large heated swimming... View all property information
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5 of 5 stars Reviewed 23 May 2012
El lugar es hermoso, la propiedad es muy confortable, tiene todo lo que puedas necesitar, la atencion desde el primer contacto hasta el ultimo fue Excelente, el único...
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From
$259
Per Night
1 / 18
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Island House Beach Resort! Crescent Beach, Siesta Key Florida. This beautifully maintained complex is located on the widest part of one of the best beaches in Florida. This condos offers a view of the palm trees, white sand and turquoise waters of the Gulf of Mexico. The view is picturesque and the... View all property information
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5 of 5 stars Reviewed 2 October 2013
Stayed in 9N and loved it. Could not say enough good things. But beware: the mattress beds are in need of replacing.
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$259
Per Night
1 / 14
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Island House Beach Resort - Siesta Key - Crescent Beach. This beautifully maintained complex is located on the widest part of one of the best beaches in Florida. This is a private beach. The condo offers beautiful views of palm trees, white sand and the turquoise water of the Gulf of Mexico from... View all property information
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From
$200
Per Night
1 / 16
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Island House Beach Resort, Siesta Key Florida. Newly remodeled 2 bedrooms, 2 baths villa located on the finest beach in Florida. This unit is 2 bedrooms, 2 bath and 1000 sq. ft. It has a large living area, dining area, fully equipped kitchen, all appliances, screened lanai, 3 flat screen tvs, 3 dvd... View all property information
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From
$245
Per Night
1 / 19
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Fishing...
  • Private Outdoor...
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Location: Fisherman's Haven, 9150 Blind Pass Rd #203, Siesta Key, Florida South West, Florida, USA (Tampa Int'l Airport, Busch Gardens - 1 hr; Disney - 2 hrs). Accommodations: Condo, 2 Bedrooms + Convertible bed(s), 2 Baths (Sleeps 6) Approximatly 1700 total square feet. Island living in this... View all property information
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From
$270
Per Night
1 / 24
3 Bedrooms, 2 Bathrooms, Sleeps 10
Details Reviews (13) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Casa Van Lopik (c), our canal facing suite, is a large 3BR home perfectly located 1.5 blocks away from the best beaches, shopping, dining and entertainment on the island. It was named for our father who was a ships captain and sailed the world for 30 years but always insisted Siesta Keys beaches... View all property information
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5 of 5 stars Reviewed 7 October 2014
This beautiful beach rental was perfect for ten friends for a wedding weekend! You can walk to all the restaurants which was a plus! Daniel with Gertrude rentals was incredibly...
4 of 5 stars Reviewed 25 June 2014
If you want family-size space, easy and walkable proximity to the beach, and restaurants right around the corner, this is a great choice!
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From
$259
Per Night
1 / 17
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Island House Beach Resort - Siesta Key, Crescent Beach, Ground Floor unit! This unit is located at Island House Beach Resort on sunny Siesta Key. It is 2 bedrooms, 2 baths, 1300 squart feet.King, full, futon. It has a large living room, fully equipped kitchen, all appliances, dining area, lanai... View all property information
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From
$221
Per Night
1 / 14
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Fishing...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
PLEASE BOOK THRU ME, CARRIE CAUDILL, FLORIDA, DO NOT SEND MONEY TO ANOTHER PERSON OR STATE. PLEASE CONTACT THE OWNER FOR PRICES AND DATE'S, DON'T GO BY FLIPKEY'S, CARRIE 941-587-4794 siestakeycarrie@gmail.com My ground floor rental is directly on the beach on the Gulf of Mexico, with... View all property information
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5 of 5 stars Reviewed 15 August 2014
My family and I stayed at Fishermans Cove unit 102 from August 1-13. We found the pictures and description of the condo online to be accurate. The condo included many amenities...
5 of 5 stars Reviewed 25 June 2014
My wife, grown son and I spent a week in this lovely condo directly on the beach on Siesta Key. The condo is a really nice 2 bedroom, 2 bath unit on the first floor so that you...
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From
$257
Per Night
1 / 21
9 Bedrooms, 9 Bathrooms, Sleeps 24
Details Reviews (43) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Siesta Key's newest beach house located across Beach Rd from access #7 to Siesta Key's Crescent Beach and one-block from the tropical Village of Siesta Key. Property has recently been completely remodeled and amenities include pool and spa, barbecue deck with lanai close to pool, free full property... View all property information
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5 of 5 stars Reviewed 4 December 2014
A group of friends rented the whole complex from Paul for our annual get together. We live in California but wanted a Florida experience. We were not disappointed! The complex...
4 of 5 stars Reviewed 12 November 2014
Good apartments in great location for the village about 5 minute walk Paul was superb host and rooms were well furnished and large with nice soft beds. Pool area could have been...
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From
$159
Per Night
1 / 20
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Washer
  • Waterfront
  • Water Views
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Lovely 2 bedroom Siesta Key home with a beautiful heated pool and caged patio/lanai area overlooking a picturesque canal. A boat slip is provided just steps from the home on the canal. Located in a quiet neighborhood approximately 1 mile from Siesta Key Village. Approximately 2 miles from Siesta... View all property information
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From
$221
Per Night
1 / 17
1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Located directly on Crescent Beach with private pool..... Sea Crest on Siesta Key sits right on the beach and has our own private gated access to the sand. Roomy one bedroom unit is fully furnished and has a seperate bedroom and in the living room we have an additional sleeping sofa if needed..The... View all property information
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3 of 5 stars Reviewed 5 August 2014
The location was excellent. We could walk out our door and in 50 steps be ON the sand. The beach was much shallower than the public beach... which we tried one day. Water pressure...
4 of 5 stars Reviewed 8 May 2014
This condo had everything we needed. There was a lot of storage space, more than my house! Large fridge, even a clothesline out back. Internet service spotty and slow. We were in...
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From
$200
Per Night
1 / 11
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Island House Beach Resort, Siesta Key Florida, Crescent Beach - This lovely unit is approx. 1000 sq. ft. It has 2 bedrooms, 2 baths, large living area, dining area, fully equipped kitchen, all appliances, central ac/heat, 3 tvs, dvd, dedicated, non-shared wi-fi in unit, covered parking, screened... View all property information
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From
$392
Per Night
1 / 27
3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Weekly Rental on Siesta Key, 600 Feet from the #1 rated Beach in the USA and the Village shops and Restaurants. Just park your car because everything is an easy walk from this property. Live entertainment abounds daily in the Village. The two units can be rented together or separate. This is... View all property information
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4 of 5 stars Reviewed 14 July 2014
We were 5 minutes walk from the Siesta Key beach which has to be one of the best beaches we have ever been on, 2 minutes walk from Ocean Drive where all the restaurants and shops...
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From
$200
Per Night
1 / 12
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Island House Beach Resort- Siesta Key Florida, Crescent Beach - The lovely villa is located on the widest part of Crescent Beach. It is approx. 1000 sq. ft. and is 2 bedrooms, 2 baths. The villa has a large living area, dining area, fully equipped kitchen, all appliances, central ac/heat, screened... View all property information
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From
$263
Per Night
1 / 10
1 Bedroom, 1 Bathroom, Sleeps 5
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
The Royal Palm is a comfortable Florida keys cottage on Siesta Key between Siesta Village and the #1 beach in the world. Shopping and dining are a few steps from your front door. The beach is a few steps in the other direction. Coffee first or beach first? These are your problems at Siesta Pearl.... View all property information
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From
$72
Per Night
1 / 6
1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Visit our website www.RentSiestaKey.com under the property name 'Beach Road - Bari' for current rates Terrific beach side studio. The unit has a queen bed, queen sleeper sofa, 32' LED TV w/ HD programming, and kitchen equipped with fridge/freezer, 2 burner cooktop, and countertop oven among other... View all property information
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5 of 5 stars Reviewed 12 November 2014
This place was fantastic! So close to the beach and village! We didn't want to leave! The kitchenette and convection oven were great for cooking and I loved having the full...
4 of 5 stars Reviewed 5 November 2014
Good place to stay. Clean. Close to the beach. The only problem was the bathroom sink drain stopper wouldn't open so we couldn't use that sink.
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From
$259
Per Night
1 / 20
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Gym
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Island House Beach Resort! Siesta Key Florida - Crescent Beach. This beautifully maintained complex is located on one of the finest beaches in central Florida. The condo is 2 bedrooms, 2 baths, 1300 sq. ft. and is on the 4th floor. It has a large living area, dining area, fully equipped kitchen (... View all property information
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From
$200
Per Night
1 / 16
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (10) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Island House Beach Resort - Siesta Key Florida - Crescent Beach. This large 2 bedroom, 2 bath villa is 1000 sq. ft. It has a large living area, dining area, full kitchen, all appliances, screened lanai. Central heat/ac, 3 tvs. Free Wi-Fi in unit! It has a king, 2 twins, sleeper sofa. this villa is... View all property information
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From
$184
Per Night
1 / 40
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (13) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Our condo is on the second floor and is only 3 doors from the lovely pool, jacuzzi and fishing pier. The private Cresant Beach which is deeded just for the Palm Bay Guests and is just across the street from the Bay side. It is raked every a.m. and loung chairs set out and also has a charcole... View all property information
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5 of 5 stars Reviewed 12 November 2012
The owner of the unit, Nancy, was very helpful from booking to departure. We found the unit to be spotless on arrival and just beautiful and comfortable.The unit has everything...
5 of 5 stars Reviewed 28 May 2012
My adult son and I stayed for several days while visiting an elderly aunt. We were delighted. I had some qualms about staying in a time share, but they have been vanquished...
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From
$294
Per Night
1 / 23
Payment Protection
4 Bedrooms, 5 Bathrooms, Sleeps 10
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
SIESTA KEY DREAM HOUSE!!!!!!!!!!!!!!!! Custom designed home. Open flow. Great for entertaining. Custom Kitchen with island. Eat-in area, granite & 2-tone wood cabinetry. Separate living, dining, family/ great rooms plus 4 bedrooms and 4 1/2 baths. 2 master suites. Heated pool with waterfall -... View all property information
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Siesta Key Vacation Rentals

Looking for world class powdery white quartz sand beaches, a relaxed low-rise life style, and about 100 nearby golf courses on Florida’s South Gulf Coast? This plus bay- and ocean-side views can be yours with a money-saving Siesta Key vacation rental. From Siesta Key cross Roberts or Little Sarasota Bay to Sarasota for museums, art, wildlife, circuses, opera, ballet, symphonies, theater, film festivals, botanical gardens, baseball spring training, and polo, cricket, and lawn bowling clubs.

Lions, Tigers & Circuses

When you need a break from basking in the sun or seashell collecting around Siesta Key, it’s Ringling Brothers and Barnum & Bailey Circus time at Circus Sarasota (Feb., March) and the Museum of the Circus (year-round) at the old Ringling wintering grounds. Visit the Ringling’s bayside winter mansion, Ca d'Zan, and savor their extensive art collection at the recently expanded John and Mable Ringling Museum of Art. The nearby Big Cat Habitat is a sanctuary for lions, tigers, bears and other animals. Hike or take a swamp buggy eco-tour with the kids at Babcock Wilderness in Punta Gorda, and see Florida’s native plants and animals in their natural habitats.

Gardens & Aquariums

Let the whole family enjoy the mazes, pirates ships, colorful flowers, and tropical birds at the Sarasota Children's Garden. Marvel at the orchids, bromeliads, and Sarasota Bay views at Selby Gardens. Enjoy the Parker Manatee Aquarium, plus the Bishop Planetarium’s digital projections of the heavens with Dolby surround sound at the South Florida Museum, near the Manatee River in downtown Bradenton. Schedule a Monday, Wednesday, or Friday morning for Mote Aquarium’s Narrated Shark Training Sessions; and visit Molly the Mollusk, a 27-foot pickled New Zealand giant squid.

Locomotives & Science

Learn some science and technology with the family at downtown Sarasota’s bay-front G.WIZ (Gulfcoast Wonder & Imagination Zone). In the evening, treat the family to Broadway theater, dance, or a jazz, pop, or rock concert at the Van Wezel Performing Arts Hall, next door to G.WIZ. Make a weekend visit to the Florida Railroad Museum, 45 minutes north of Siesta Key in Parrish, where you can get hands-on-training, take over the controls, and even rent a locomotive.

History & Baseball

From your money-saving Siesta Bay vacation rental home, apartment or condo, take Stickney Point Road across Little Sarasota Bay to the Tamiami Trail (U.S. 41) and Historic Spanish Point. This unusual museum and archaeological site has an intact prehistoric village with middens, as well as a pioneer home, citrus packing house, and old boatyard. In 1924, the New York Giants began a spring training tradition in Sarasota that is being continued by the Baltimore Orioles and the Grapefruit League in Ed Smith Stadium.