We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Villas Anna Maria Island, FL

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
All 706 Rentals in Anna Maria Island
loading...
Sort by
From
$634
Per Night
1 / 16
4 Bedrooms, 4 Bathrooms, Sleeps 10
Details Reviews (11) Make Enquiry
From
$151
Per Night
1 / 23
Anna Maria
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) Make Enquiry
From
$1,798
Per Week
1 / 19
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 7
Details Reviews (4) Make Enquiry
From
$2,330
Per Week
1 / 22
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (25) Make Enquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Internet Access
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Escape to the Breakers, one of the finest luxury gulf front vacation homes on Anna Maria Island, located at 102 31st Street in Holmes Beach. Enjoy the tropical breezes and aqua-blue surf from the deck overlooking the white sand beach and sparkling Gulf of Mexico. Watch the dolphins cavort in the... View all property information
Make Enquiry
3 of 5 stars Reviewed 25 August 2014
Beach house is in a good location, right on beach and set off main Gulf Drive which can be noisy. Was somewhat dirty with moldy showers but I guess this is expected from a highly...
5 of 5 stars Reviewed 7 July 2014
This is a great little house. Well kept and well stocked. Only drawback is that it sets flush to the public access - parking in the side drive may result in your car getting...
See all reviews
From
$204
Per Night
1 / 21
Payment Protection
Bradenton Beach
3 Bedrooms, 3 Bathrooms, Sleeps 7
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Anna Maria Island boasts one of the longest stretches of sugar white beaches in Florida, and clear, aqua-marine water. Enjoy the natural setting from this spectacular townhouse on Bradenton Beach. This three bedroom, two-and-a-half bath home offers direct Gulf views, a king size master suite,... View all property information
Make Enquiry
5 of 5 stars Reviewed 7 June 2014
We stayed here to go to my sister's wedding at The Beach House. We loved this townhouse. It had spacious rooms, beautiful decor, and a great view of the ocean from the balcony...
4 of 5 stars Reviewed 13 May 2014
We really enjoyed our stay here. The condo was beautifully decorated. We loved sitting on the deck. The beach is beautiful, and the pool is nice too. The condo is spacious and...
See all reviews
From
$234
Per Night
1 / 12
Anna Maria
1 Bedroom, 1 Bathroom, Sleeps 3
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This is a beautiful beach home located on Anna Maria, Florida. This home has 1 bed room, 1 bath room, a garage with accessible laundry equipment, and an outdoor patio. The beach is just across the street. $800.00 a week. Exceptions can be made. Beds: 1 King Bed, 1 Sofa Bed View all property information
Make Enquiry
From
$333
Per Night
1 / 12
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (24) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Internet Access
  • Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
Chillifish is a gorgeous, idyllic and luxurious vacation home from Pineapplefish. Its decor is Bali-inspired and its fabulous location means it is minutes from the beach. Chillifish has a delightful and secluded garden, full of palm trees and other native plantings and a gorgeous swimming pool... View all property information
Make Enquiry
4 of 5 stars Reviewed 8 July 2013
My family of 6 stayed for a week in June, we had a great time and the house is fabulous but as the people in August 2012 stated the carpets in the house were a bit grubby also the...
5 of 5 stars Reviewed 4 March 2012
Great space for a family to chill out after a week at the parks. Brilliant family size pool for fun and games. This is a truly luxurious experience. Island is so laid back, beach...
See all reviews
From
$361
Per Night
1 / 38
Holmes Beach
5 Bedrooms, 4 Bathrooms, Sleeps 10
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Beautiful, Brand New, 5 bedroom/3.5 bath Waterfront home with Heated Pool, Hot Tub, Dock, and just over a block to the beach! Covered Patio by pool area and peeks of the Gulf and Bay from the top patios. Great location in a quiet neighborhood, a few steps to the Trolley Stop, and a short walk to... View all property information
Make Enquiry
From
$214
Per Night
1 / 29
Payment Protection
Anna Maria
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This property can only accept 7 nights stays with a check-in on Saturday Brand New Heated Pool! This lovely ground level Anna Maria Island beach bungalow awaits you for the vacation you deserve! This rental home is stylishly decorated with touches of both new and old Florida. Rare and highly... View all property information
Make Enquiry
From
$751
Per Night
1 / 24
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (28) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Internet Access
  • Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Limefish, from Pineapplefish is one of the most stunning beachfront holiday rentals on Anna Maria Island, with direct access to a beautiful, almost private beach. With spectacular views across the Gulf, Limefish has a wonderful and spacious decked area across the whole of the property, where you... View all property information
Make Enquiry
5 of 5 stars Reviewed 9 November 2014
We were staying here with friends who were getting married on the beach. It is paradise. The villa was perfect for seven of us, though one couple had to have bunk beds, and we...
5 of 5 stars Reviewed 7 October 2014
Limefish has become a yearly destination tradition for my family. It is the ultimate in a beachfront location. Bike paths galore from this house, enabling touring the island...
See all reviews
Get the List
From
$417
Per Night
1 / 23
Payment Protection
Anna Maria
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Garden
  • Grill
  • Hot Tub
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
Beachie, Bright and Beautiful. Say no more. You’re there! Ready to satisfy that oh-my-gosh-we-need-a-vacation? Beach Nest will make you absolutely swoon. Kick off your shoes and throw them in the back of the closet. Promise yourselves to live in bathing suits from breakfast to bedtime!... View all property information
Make Enquiry
5 of 5 stars Reviewed 8 July 2014
Five of us ranging in age from 7 to 80 had the pleasure of staying in this home for a week. Everyone had a fantastic time! Many hours were spent in the pool and at the beach. We...
5 of 5 stars Reviewed 31 March 2014
We had a fabulous week staying at Beach Nest. We've been vacationing in the area for almost 20 years and this was our most favorite rental home. It's location is ideal, on a...
See all reviews
From
$316
Per Night
1 / 20
Payment Protection
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (76) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
PRIVATE ISLAND PARADISE - This unique custom home is hidden on a huge garden lot surrounded by palms, birds of paradise, tropical plants and a 6 ft fence. Few island homes offer this degree of privacy. SPACIOUS ELEGANCE - The home has 2,600 sq ft (240 sq m.) of ground level indoor living space with... View all property information
Make Enquiry
4 of 5 stars Reviewed 3 July 2014
The house is very nicely decorated and has many extras like beach toys, chairs, etc. The pool is very nice and makes the vacation so much better than just going to the...
5 of 5 stars Reviewed 4 June 2013
We stayed in the Clark House in March for a week, while visiting our aunt that winters in Bradenton, nearby. We had an excellent vacation. Yes, the weather was poor that week...
See all reviews
From
$467
Per Night
1 / 26
Anna Maria
4 Bedrooms, 4 Bathrooms, Sleeps 12
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dryer
  • Grill
  • High Speed Internet
  • Private Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Cayman Bay 505 Magnolia Ave. Anna Maria, Fl. 34216 Cayman Bay may well be one of the most exquisite private homes available for rent on all of Anna Maria Island. This 4 bedroom/4 bathroom 5300 sq. ft. custom home has all the fine touches and professional craftsmanship one would expect in a... View all property information
Make Enquiry
5 of 5 stars Reviewed 20 August 2014
We stayed here for two weeks this past August. This was our second trip to AMI - such a lovely place. This house was perfect for us. It is very spacious. All the bedrooms are...
See all reviews
From
$663
Per Night
1 / 24
Anna Maria
5 Bedrooms, 6 Bathrooms, Sleeps 10
Details Reviews (7) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Pool
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Located on the north end of Anna Maria Island in the city of Anna Maria, this family-friendly vacation rental was built for rest and relaxation. Beginning with the lush landscaping that meets you at the front door, all the way through to the putting green, kayak launch and boat dock, this house has... View all property information
Make Enquiry
5 of 5 stars Reviewed 15 August 2014
I searched for the perfect house for a family of 10 to celebrate our niece's vacation. All I can say is there was nothing on everyone's list that this house didn't have! We...
5 of 5 stars Reviewed 3 August 2014
This house was exactly as pictured and described. The attention to detail in how it was build was amazing. This place had everything you could imagine or want. Pool was...
See all reviews
From
$125
Per Night
1 / 10
Payment Protection
Holmes Beach
1 Bedroom, 2 Bathrooms, Sleeps 2
Details Make Enquiry
Amenities & Details
  • Dishwasher
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This property can only accept 7 nights stays with a check-in on Saturday Anna Maria Island's newest and finest condominium complex offers several fabulous holiday villas all designer decorated and with floor plans maximizing water views. A heated pool is a great place to relax after a day at the... View all property information
Make Enquiry
From
$234
Per Night
1 / 21
Payment Protection
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (7) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Spend your vacation enjoying the Island life in a quiet and well-kept family neighborhood snuggled between the Gulf of Mexico and Anna Maria Sound. Our house is less than a mile north of the Cortez bridge (SR 684) affording easy access to the mainland. Each unit has 2 bedrooms, 2 baths, A/C,... View all property information
Make Enquiry
5 of 5 stars Reviewed 6 July 2014
recently spent a relaxing time at the beach. great weather, beautiful beaches, walking distance to a variety of restaurants, enjoyed the 4th of july celebrations on the beach. a...
5 of 5 stars Reviewed 22 June 2014
When owner John Donato said "just a block away", he meant it! In fact one or two blocks either way got one to lovely beaches on Anna Maria Island in Florida. The rental had a...
See all reviews
From
$175
Per Night
1 / 19
Payment Protection
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Private Beach
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
One bedroom one bath condo located in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are... View all property information
Make Enquiry
4 of 5 stars Reviewed 3 September 2014
Yes, the room was very dated, as the pictures showed. It would seem for $200 a night, an upgrade in furnishings is due. But, it was clean, and the short walk to the beach made...
See all reviews
From
$234
Per Night
1 / 17
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Internet Access
  • Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Island Paradise #3 3708 Gulf Drive Unit 3 Holmes Beach, Fl. 34217 Island Paradise is just that- the best view on Anna Maria Island. Panoramic views of the beautiful blue waters of the Gulf of Mexico and the white sand beaches. And don't forget the legendary sunsets. It simply does not get any... View all property information
Make Enquiry
5 of 5 stars Reviewed 18 August 2014
The unit was very clean & well kept as well as the entire building. Our view of the Gulf of Mexico from the living room was breath taking. The pool was nice size and clean. We...
See all reviews
From
$525
Per Night
1 / 20
Payment Protection
Anna Maria
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Housekeeping...
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Our home is a Direct Beach Front 3 bedroom- 1 & 1/2 bath residence furnished with all the comforts of home. Panoramic view of the Gulf of Mexico from your soothing beach cottage style home and decor. The living level has a full size kitchen, half bath, great room and dining room in an open floor... View all property information
Make Enquiry
From
$516
Per Night
1 / 25
Payment Protection
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Island Paradise is just that- the best view on Anna Maria Island. Panoramic views of the beautiful blue waters of the Gulf of Mexico and the white sand beaches. And don't forget the legendary sunsets. It simply does not get any better than this. It is like you are sitting on the deck of a cruise... View all property information
Make Enquiry
From
$313
Per Night
1 / 37
Payment Protection
Anna Maria
5 Bedrooms, 3 Bathrooms, Sleeps 12
Bookings
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden
  • Grill
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
WELCOME TO ALL DECKED OUT! Whether getting away for a family vacation, with a group of friends, for a wedding or any other occasion, our gorgeous 5 Bedroom home offers everything you could want for a relaxing holiday on Anna Maria Island.... with incredible views of the Bay! Sit by the tropical... View all property information
Make Enquiry
5 of 5 stars Reviewed 9 June 2014
We loved this house which has 5 that accommodated our extended family age 18 months to grandparents. It has a porta crib, umbrella stroller and removable baby gates to block the...
See all reviews
From
$234
Per Night
1 / 30
Payment Protection
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (7) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • 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
Castnetter Beach Resort is located in the center of beautiful Anna Maria Island and directly across the street from the 7-Acre "Manatee Public Beach." Castnetter's has been a family favorite for Beach-Goers, Sun-Seekers, Boaters, Fishermen and Fun-Lovers alike since 1967. Extensive renovations... View all property information
Make Enquiry
5 of 5 stars Reviewed 8 April 2013
We just got back from a GREATweek on Anna Maria island and stayed in Castnetter #6 which is adjacent to and essentially identical to Castnetter 5. The 2 bedroom condo was...
See all reviews
From
$175
Per Night
1 / 21
Payment Protection
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Beach
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
One bedroom one bath condo located in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are... View all property information
Make Enquiry
5 of 5 stars Reviewed 11 August 2014
What can one say about the Coconuts Resort on Holmes Beach, FL. Well we have spent two months of every year for ten years there and expect to do so in 2015. They are a friendly...
See all reviews
From
$193
Per Night
1 / 20
Payment Protection
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Private Beach
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
One bedroom one bath condo located on the poolside. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are two... View all property information
Make Enquiry
5 of 5 stars Reviewed 17 August 2014
First I should let y'all know we were moved to 103 but it was right next door and actually a little closer to the pool so this is a review of 103. This place was great! The...
See all reviews
From
$1,168
Per Week
1 / 17
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This extremely bright condo offers everything you could hope for in a seasonal rental property. Brilliant morning sun fills the living areas of this spacious unit. The kitchen is fully equipped and the family room features a raised seating area ideal for entertaining or watching the dolphins swam... View all property information
Make Enquiry
From
$146
Per Night
1 / 15
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Hawaiian Tide 206 81st Street Unit B Holmes Beach, Fl 34217 Hawaiian Tide is a brand new ground level private duplex with a private heated pool! With tropical landscaping throughout the backyard and pool area you will feel as if you are transported to your own personal island. Centrally... View all property information
Make Enquiry
4 of 5 stars Reviewed 17 September 2014
Anna Maria is a dream location for any vacation for anyone who wants to relax. People are nice, kind and respectfull. You don´t have to worry about anything, not even...
See all reviews
From
$199
Per Night
1 / 52
Payment Protection
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
Details Reviews (9) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
A brand NEW 2300 sq/ft, 3 bedroom modern beach house with heated and very private pool. A perfect location just steps from the beach, marina and the main plaza with great shops, a grocery store and restaurants. No need to drive anywhere. Located in a quiet neighborhood with tropical greenery, large... View all property information
Make Enquiry
5 of 5 stars Reviewed 30 October 2014
We had a great time and the house was perfect. Our group was two families with 5 young children and 4 adults. Plenty of room in the house and everyone loved the pool. Alex was...
5 of 5 stars Reviewed 11 September 2014
We stayed in the house for a 4th of July holiday. The house is very well kept and had ample room for 4 adults and 3 children. The house is located a short walk from the beach...
See all reviews
From
$350
Per Night
1 / 38
Holmes Beach
4 Bedrooms, 4 Bathrooms, Sleeps 8
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • 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
Luxury is yours with this gorgeous ocean view four bedroom, four full bath luxury townhome vacation rental in Holmes Beach. Enjoy your own personal day spa experience from the privacy of the master suite fit for royalty with king size sleigh bed, separate shower and Jacuzzi tub. There is a... View all property information
Make Enquiry
5 of 5 stars Reviewed 23 July 2014
Spent a week at Tropical Sands with six friends and we all had an amazing time. I wondered why there are no reviews because this is an incredible house in a great location!! About...
5 of 5 stars Reviewed 15 July 2014
For my extended family (6 adults and 2 kids), this spacious well-equipped home was perfect. And while it is on the high side in terms of cost, we felt we got what we paid for...
See all reviews
From
$1,512
Per Week
1 / 21
Anna Maria
2 Bedrooms, 2 Bathrooms, Sleeps 10
Details Reviews (17) Make Enquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Internet Access
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The Anna Maria Escape located at 725 North Shore Drive in Anna Maria city is just that - a peaceful, relaxed place to get away from it all. You can stroll on the beach for miles in either direction! It’s a perfect Anna Maria Island vacation home!This spacious and charming two bedroom, two bath Gulf... View all property information
Make Enquiry
From
$175
Per Night
1 / 27
Payment Protection
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
Warm turquoise waters and white sand beaches await your holiday on Anna Maria Island. Come join us at Our Place in the Sun. Our Place in the Sun is a 1925 Bungalow that has been fully renovated. Just 150 feet away to the white sands of the Gulf of Mexico. It is a 3 bedroom 2 bath home featuring... View all property information
Make Enquiry
From
$263
Per Night
1 / 14
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (18) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Housekeeping...
  • Internet Access
  • Private Beach
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
700 ft. of pristine beach frontage, only 16 Units! This beachfront condo is located right on Holmes Beach. Two bed room, 2 bath. Largest pool on the Island. Beach sand ranks in the top 5 worldwide. New elevator and all granite kitchen. Anna Maria has been voted the worlds "best kept secret" -... View all property information
Make Enquiry
5 of 5 stars Reviewed 4 August 2014
Frank thank you for a wonderful vacation in your exceptional holiday home from home. The condo is well equipped to a high spec and the layout is perfect, added to that the fact it...
5 of 5 stars Reviewed 31 July 2014
I selected Frank's condo on Holmes beach after his place came out as one of the few places that met all my key criteria via the TA filter and the very positive reviews. Our...
See all reviews
From
$1,390
Per Week
1 / 19
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (8) Make Enquiry
Amenities & Details
  • Dishwasher
  • Internet Access
  • Pool
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Coquina Moorings, located at 1407 Gulf Drive South in Bradenton Beach offers the best of all worlds. This bay front complex features a beautiful heated pool directly on the bay and a boat dock for fishing enthusiasts. Immediately across the street is the white, sandy beach and the Gulf of Mexico.... View all property information
Make Enquiry
5 of 5 stars Reviewed 6 December 2013
Coquina Moorings has 14 condos located on the bay and the gulf, with only Gulf Drive separating the condo from the ocean. The bay side has a boat dock. The pool is heated and...
See all reviews
From
$182
Per Night
1 / 13
Anna Maria
2 Bedrooms, 7 Bathrooms, Sleeps 4
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Birds Eye View 802 Gladiolus Street Anna Maria, FL 34216 This spacious and charming 2 bedroom, 2.5 bath elevated home is just three houses from the Gulf of Mexico! It is located near popular Bean Point at the prestigious northern tip of Anna Maria Island. It has fabulous island style... View all property information
Make Enquiry
4 of 5 stars Reviewed 7 September 2013
Lovely property...close to both gulf and bay beaches for sunrise/sunset. Loads of space with a huge master bedroom/bathroom. Clean and well kept but could use a few updates...
See all reviews
From
$292
Per Night
1 / 30
Anna Maria
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Fireplace
  • Garden
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
The Shady Mango was originally built in 1925. According to local history the heart pine used in constructing the original house came by steam boat to the City Pier and was hauled by horse-drawn lorry up Pine Avenue to the home's present site. In 2004 the home was given a major renovation... View all property information
Make Enquiry
5 of 5 stars Reviewed 22 September 2013
My husband, 2 kids & I stayed at the Shady Mango & LOVED it! It's the perfect place for a vacation for a small family. It's in a great location with walking access to the beach...
See all reviews
From
$292
Per Night
1 / 23
Payment Protection
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 5
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Situated 3 blocks from the beach and 2 blocks from the bay with a secluded yard surrounded by mangroves, this two-story home includes 3 bedrooms on the first floor and a regal master suite on the second floor. Comes equipped with Wifi, cable TV in all 4 bedrooms, washer/dryer, dishwasher,... View all property information
Make Enquiry
From
$220
Per Night
1 / 27
Bradenton Beach
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) 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
Our Avenue B Hotel Homes, Margarita Shores and Pina Colada Shores, are two homes in a newly renovated duplex property located on a quiet residential street, just a 3-minute walk to beautiful Bradenton beach. These homes feature open concept living, dining and kitchen areas that make them a perfect... View all property information
Make Enquiry
4 of 5 stars Reviewed 17 July 2014
Beautiful home very close to the beach. The beach was about a 3-5 minute walk (easy even in the summer) and the 2 wagons provided were perfect to haul our 2 grandsons and the...
See all reviews
From
$110
Per Night
1 / 15
Anna Maria
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
A cozy One Bedroom, One Bath just a couple of Blocks to the beach. Everything you need for a quiet getaway with Queen bed, Cable TV, High Speed Internet, Washer and Dryer, Beach Chairs and Umbrellas, 4 Bicycles and Heated Pool AND Hot Tub! Sleeps 4. 650 Sq.ft. 733B Holly Rd. 1 Bedroom/ 1 Bath... View all property information
Make Enquiry
5 of 5 stars Reviewed 19 August 2014
We've stayed at 4 other rentals and Gentle Bens was by far the best! Beautiful rooms,pool and location to all that we were there to see and do!!
See all reviews
From
$245
Per Night
1 / 25
Payment Protection
Bradenton Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Overlooking the Gulf of Mexico Beach, these 1250 square feet each two bedroom beach townhouses (complex of 4 apartments) arranged on two elevated levels offer beautiful views of Anna Maria island sound. A nice yard with a access to a barbecue area and a six persons tub make our apartments an ideal... View all property information
Make Enquiry
5 of 5 stars Reviewed 3 September 2014
My husband booked a last minute trip to Bradenton Beach for Labor Day weekend. Sight unseen we booked @ the Birds Nest and were Happily surprised with our townhouse apt. Great...
5 of 5 stars Reviewed 7 July 2014
My family and I spent two nights in the apartment. It was very clean and maintained. Nice furnishings. Very roomy and comfortable. Great location for easy access to the beach...
See all reviews
From
$152
Per Night
1 / 20
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
High-end, high quality smaller units are almost non-existent as short term vacation rentals. So if you’re looking for a “comfortable, updated, style and convenience driven home” for a smaller number of guests, that usually means getting more space than you really need. With the Palm Shores... View all property information
Make Enquiry
5 of 5 stars Reviewed 28 August 2014
Condo was clean nice with full kitchen. Nice pool and patio. Walking distance to beach. Great restaurants nearby, ....try lobstahs
5 of 5 stars Reviewed 14 March 2014
Lovely unit, fully furnished kitchen, 1/2 block to beach, great location, easy to get around, clean pool, easy parking, comfortable beds.
See all reviews
From
$2,219
Per Week
1 / 25
Payment Protection
Anna Maria
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
PLEASE ASK ABOUT OUR THANKSGIVING SPECIAL 2014 UP TO 25% OFF Gaze out of your living room to the calming serenity of the canal as you sip on your favorite beverage at this comfortable and spacious home located in the prestigious north end of the island. This beautiful 3 bedroom 2 bath... View all property information
Make Enquiry
From
$350
Per Night
1 / 8
Bradenton Beach
5 Bedrooms, 9 Bathrooms, Sleeps 12
Details Reviews (1) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Coastal Winds 303 Church St. Bradenton Beach, Fl 34217 Coastal Winds is a brand new 5 bedroom + bonus room, 4.5 bathroom private rental home that is currently under construction with completion in early May 2014. Reservations excepted beginning June 1st, 2014. This luxury home offers sweeping... View all property information
Make Enquiry
5 of 5 stars Reviewed 1 November 2014
My family, consisting of four couples and one single, stayed in this home during October 2014. We all were very pleased with the accommodations. Every room was immaculately...
See all reviews
From
$234
Per Night
1 / 24
Holmes Beach
3 Bedrooms, 3 Bathrooms, Sleeps 10
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Bring your tanning oil when vacationing in this gorgeous and luxurious Mediterranean style home. Boasting three bedrooms and three baths, there is room to bring the whole family for a dream vacation on Anna Maria Island. Just a mere block and a half to the white sand beach or steps to the private... View all property information
Make Enquiry
From
$200
Per Night
1 / 23
Bradenton Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This beautiful three-bedroom vacation rental sits on the south end of Anna Maria Island in the city of Bradenton Beach. Located in Coquina Moorings, a small condominium complex, this end unit is just across the street from the beautiful Gulf of Mexico beach. With windows in every room, you will... View all property information
Make Enquiry
4 of 5 stars Reviewed 30 July 2014
Location really nice right across the street from Coquina Beach. We have a boat and the docks were easy to get in and out. The condo was was nice and had all we needed to make...
5 of 5 stars Reviewed 14 June 2014
This is the place to stay on Anna Maria Island if you like the beach, sunsets, the bay, fishing, walking, biking, boating and beautiful views from sunrise to sunset. Perfectly...
See all reviews
From
$467
Per Night
1 / 30
Holmes Beach
3 Bedrooms, 2 Bathrooms, Sleeps 10
Details Reviews (12) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Celebrate the day with the brilliant sunshine, glorious sunsets and star-studded skies! This luxury three-bedroom two-bath Gulf-front beach home is located in a quiet, secluded area of Anna Maria Island at 103-45th Street in Holmes Beach. The white sandy beach stretches for miles along the length... View all property information
Make Enquiry
3 of 5 stars Reviewed 12 August 2014
the view of the house was amazing, easy accesses to the beach, the worst of all was the condition of rooms and bathrooms they were super dirty, we had to take showers with sandals...
See all reviews
From
$565
Per Night
1 / 49
Payment Protection
6 Bedrooms, 4 Bathrooms, Sleeps 16
Bookings
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Garden
  • Grill
  • Housekeeping...
  • Internet Access
  • Private Beach
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
INFORMATION 207 Palm Avenue Anna Maria Florida 34216 Enjoy our Luxurious Villa di Palma, a new six bedroom, four bathroom luxury island home close to the beach. The Italian influence in the design is reminiscent of properties found in Venice and Tuscany. The two master suites each have... View all property information
Make Enquiry
From
$200
Per Night
1 / 12
Payment Protection
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 2
Details Reviews (1) Make Enquiry
Amenities & Details
  • Grill
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The "Flip Flop" duplex is a fantastic recently remodeled duplex located one block from the white sandy beaches boasting professional landscaping, beautiful retro interiors, and its own private pool for each side of the duplex. Flip (the orange side of the duplex) is a one bedroom, one bath duplex... View all property information
Make Enquiry
5 of 5 stars Reviewed 31 May 2014
Everyone I showed pictures of this home loved the retro look of it! The location is one block from the ocean in a very quiet neighborhood and everything you need is there. Ben...
See all reviews
From
$151
Per Night
1 / 23
Holmes Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (9) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Pool
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
** SPECIAL ** Book and stay 7 days anytime between November 1 and December 31, 2014, and receive 20% off your base rental fee! That’s a total savings up to $280! When booking, mention or use the promo code HIDEAWAY. Island Hideaway East has been newly renovated for your vacation pleasure! Over... View all property information
Make Enquiry
5 of 5 stars Reviewed 21 September 2014
Yet another great stay at Hideaway East, the house/pool are immaculately presented and perfect for a family of 4 maximum, it's only 5 minutes to a Superb beach and 20 yards from...
4 of 5 stars Reviewed 30 July 2014
This summer our family stayed at Island Hideout East for a week in early July. This was our first visit to Anna Maria, but we now plan on coming back every summer! The house was...
See all reviews
From
$193
Per Night
1 / 11
Payment Protection
Holmes Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (10) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Private Beach
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Very spacious two bedroom Condo with a patio area off the living room. Recently remodeled and very nicely furnished. Flat screen TV, fully equipped kitchen with all the appliances. Across the street from the beach, and short distance to area shopping. Unit has heated pool, and a relaxing Pool deck... View all property information
Make Enquiry
From
$152
Per Night
1 / 15
1 Bedroom, 1 Bathroom, Sleeps 3
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Shell Cottage is situated just 200ft away from the beautiful white sandy beach of Anna Maria which is 7 miles long. Set in a quiet leafy lane Shell shares our heated pool with our other 2 cottages and can be rented together or separately. The property has a small sofa-bed therefore enabling it to... View all property information
Make Enquiry
4 of 5 stars Reviewed 2 December 2012
I've written this review after coming across the cottage again whilst browsing this website. I realised that I hadn't written a review after our stay. This little cottage is...
See all reviews
From
$175
Per Night
1 / 14
Payment Protection
Holmes Beach
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Private Beach
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
One bedroom one bath condo located in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are... View all property information
Make Enquiry
Go to map view
Popular cities
Book Online(166)
Use filters to find the best results!

Suitability

  • Wheelchair access (43)
  • Elder access (241)
  • Suitable for children (299)
  • Pet friendly (141)
  • Smoking allowed (1)

Amenities

  • Internet (611)
  • Grill (463)
  • All pools (458)
  • Other outdoor space (427)
  • Parking (396)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Waterfront vacation rentals on Anna Maria Island

Whether an experienced or a first-time vacation home renter, you’ll enjoy the many choices for beachside getaways on Anna Maria Island. Luxury gulf side villas, quaint beach cottages and canal front condos offer breathing-room space and countless amenities that traditional hotel stays can’t match. Beyond the advantage of preparing some meals at home, your beach rental allows you to slide right into islander life and feel very much at home.

“Old Florida” charm and easy island living

Three small communities share Anna Maria Island – Bradenton Beach, Holmes Beach and Anna Maria. Each gathers along 7 miles of silky white beach overlooking the Gulf of Mexico. The island offers the village feel of Old Florida, with simple beach cottages and sandy lanes dipping under lazy Florida oaks and beachfront villas overlooking turquoise bays. There’s plenty to do on the family-friendly island, but nothing quite as important as simple relaxation. Rent a bike to roam the island or a kayak to explore the waterways. Fish, sail, comb the beaches for shells, and pack a little picnic for a sunset meal.

One-of-a-kind dining and shopping

Shop names reveal that island boutiques are anything but ordinary. The Painted Gate, Egret’s Landing, Paper Panache and other local establishments offer everything from resort wear to arts and crafts. The free island trolley runs North and South, as a convenient way to explore. Ginny's and Jane E's at the old IGA is a popular spot, where vintage furniture mixes with home-baked quiches and brioches in an internet café setting. One restaurant you can’t miss is Rod & Reel located at the end of a wooden pier jutting out into the bay. Kick back, fish, eat and let that tropical seascape deliver complete relaxation.

Take a side trip south to “Shangri-la”

Don your best resort wear and head south along Highway 789 that links Anna Maria Island to Longboat and St. Armand Keys. The gulf front drive leads you to famous St. Armand’s Circle, where elite shopping and pampered dining venues merge in an elegant European atmosphere. After a gourmet lunch, venture over to Sarasota for a visit to the cherished Ringling enclave, home to the Museum of Art and Ca d’Zan Mansion. Set in a lush 20-acre garden overlooking the water, the Venetian mansion is considered “the last of the Gilded Age mansions” built in America.

Vacation rental homes, a superb value for families and friends

Spacious living areas, plenty of baths and bedrooms and every imaginable amenity explain why vacation homes are today’s most popular travel choices. From the comfort of your own island getaway, you’ll enjoy every pleasure Anna Maria Island offers.