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 Rentals and Apartments in Osprey, FL and nearby

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    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
    Payment
    Select
    Go to map view
    More filters
    All 429 Rentals in the Osprey Area
    loading...

    The following rentals are within 15 kilometres of Osprey, Florida.

    From
    $1,580
    / Week
    View Details
    1 / 23
    4.5 of 5 stars (29) Very good
    Siesta Key
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (29) Make Enquiry
    From
    $1,535
    / Week
    View Details
    1 / 23
    5 of 5 stars (7) Excellent
    Siesta Key
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (7) Make Enquiry
    From
    $1,119
    / Week
    Payment Protection
    View Details
    1 / 42
    4.5 of 5 stars (8) Very good
    Siesta Key
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (8) Make Enquiry
    From
    $573
    / Week
    Payment Protection
    View Details
    1 / 34
    4.5 of 5 stars (6) Very good
    Venice
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Gym
    • Private Outdoor...
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Look no further for an absolutely stunning private heated pool overlooking a peaceful lake. Perched above a serene lake, the blues of the turquoise pool blend to a happy mix with the deeper color of the waterway and the perfect clear sky above. The screened lanai turns the pool area an idyllic... View all property information
    Make Enquiry
    Location Information
    Venice, Southwest Gulf Coast 34285
    From
    $967
    / Week
    Payment Protection
    View Details
    1 / 35
    Venice
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • 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
    LOCATION, LOCATION, LOCATION!!. From this home, all amenities are 3-10 minutes away. Each evening can be spent watching an amazing sunset over the beautiful Gulf of Mexico in 3 minutes . If you are looking to just relax at the beaches or prefer an active lifestyle, Venice has it all! FULLY... View all property information
    Make Enquiry
    Location Information
    Venice, Southwest Gulf Coast 34293
    From
    $256
    / Night
    Payment Protection
    View Details
    1 / 28
    4.5 of 5 stars (31) Very good
    Siesta Key
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (31) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Gym
    • Hot Tub
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Siesta Key Florida House of Sun 307 rentals condos is very family-friendly, was recently renovated and has sensational sunset and Gulf views. Any questions? How about the added weight of the Travel Channel’s endorsement, recently voting Siesta Beach as the “Best Sand Beach” in the country? The... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $86
    / Night
    Payment Protection
    View Details
    1 / 12
    3.5 of 5 stars (4) Average
    Siesta Key
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • 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
    What a great location! walk to Siesta Key village or relax on your private Gulf Beach or fishing on the pier at Sandy Cove. This 2 bedroom 2 bath unit is a 2nd level condo with pool views from the balcony. Enjoy breakfast after a short walk at one of the villages' quite restaurants before... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $219
    / Night
    View Details
    1 / 14
    4 of 5 stars (5) Very good
    Siesta Key
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Internet Access
    • Satellite TV
    • Sauna
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Do you want to avoid crossing the street to get to the beach, or carrying your beach chairs with you? Then this is the place you've been looking for! Just open the gate and a beautiful stretch of sugar white sand awaits you. Loungers are already set up for you and there are also tiki shade... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $160
    / Night
    View Details
    1 / 23
    3.5 of 5 stars (10) Average
    Siesta Key
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (10) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Ping Pong Table
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Banana Bay Club Resorts offers vacation rentals on Siesta Key off the coast of sunny and beautiful Sarasota, Florida! 13 Villas only a 2 minute walk from the beach! Studios up to 4BR's! We rent daily, weekly or monthly and there is no minimum stay, except for weekends, holidays and springtime... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $1,105
    / Week
    Payment Protection
    View Details
    1 / 20
    Siesta Key
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Gym
    • Private Outdoor...
    • Satellite TV
    • Waterfront
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Nestled on the southern tip of Siesta Key is our ground-floor condo, Bay Tree Club 106. Located in an oceanfront complex, it will pamper you with brand-new HDTVs, spacious and well-appointed rooms, and a sunny lanai overlooking grassy grounds. The Gulf of Mexico is just steps away from Bay Tree... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    From
    $185
    / Night
    View Details
    1 / 8
    3 of 5 stars (1) Average
    Siesta Key
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • 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
    Location! Location! Location! Walk out the door, across the street and onto the # 1 ranked beaches in America! This beautiful condo is on the ground floor, no steps, with a tropical enclosed lanai. It features 2 televisions, Tommy Bahama furnishings, a barbecue grill and high speed internet for... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $320
    / Night
    View Details
    1 / 25
    3.5 of 5 stars (2) Average
    Siesta Key
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (2) 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
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This beautiful 3 bedroom 3 full bath home features unique siesta architecture only 50 steps to the world famous Siesta Key Beach sand and 2 blocks to the Village. Impecabbly furnished this home has balconies on every floor to view the gulf of mexico and white sandy beaches of famous siesta key!... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $123
    / Night
    Payment Protection
    View Details
    1 / 19
    4 of 5 stars (9) Very good
    Siesta Key
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Reviews (9) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    This Siesta Key Studio was renovated and refurbished in November 2013 it has all new furnishings throughout and is accompanied by a secluded outside area with table and chairs, BBQ and reclining sun loungers surrounded by tropical plants and foliage. Easy access - no stairs. Fully equipped... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $224
    / Night
    Payment Protection
    View Details
    1 / 39
    4 of 5 stars (13) Very good
    Venice
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Reviews (13) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Gym
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Ready to try out island life? We think you’ll like Riviera House is a fantastic family home on the Gulf Coast’s Venice Island, just 4 blocks to the private beach access where you can watch the sun rise. It’s an ideal vacation home, particularly if you love music. Unlike any other vacation rental... View all property information
    Make Enquiry
    Location Information
    Venice, Southwest Gulf Coast 34285
    From
    $256
    / Night
    Payment Protection
    View Details
    1 / 19
    Siesta Key
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Fishing...
    • Private Outdoor...
    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
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $377
    / Night
    View Details
    1 / 6
    2.5 of 5 stars (2) Poor
    Siesta Key
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (2) 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
    About this property
    Newly remodeled with a tiled kitchen and bath and new furnishings. Includes: King bed Pullout queen sleeper fully equipped kitchen Laundry facilities VCR/DVD Wifi Dishwasher/Micro Patio/gas Grills NOTE: PLEASE CONTACT US FOR AVAILABILITY. We do NOT always keep this calendar current. Thanks.... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $3,838
    / Week
    Payment Protection
    View Details
    1 / 15
    2 of 5 stars (3) Poor
    Siesta Key
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • 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
    Seasonal Luxury rental on the world famous Siesta Key! Relax in your tropical vacation home or step out to all Siesta Key has to offer! Is an absolutely beautiful and uniquely configured private pool home featuring four bedrooms, three bathrooms [sleeps 8], two living areas. This home is... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $139
    / Night
    View Details
    1 / 19
    Siesta Key
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Enjoy this 2 bedroom 1 bath property located just 1 block from the beach. This unit offers an adequate kitchen with stainless steel appliances and ample living space for 4. The master bedroom is furnished with a queen-size bed and guest bedroom is furnished with two twin-size beds. The unit is... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $320
    / Night
    Payment Protection
    View Details
    1 / 16
    Venice
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    A beautiful Florida home close to Manasota beach and within easy reach of a wide range of shops, restaurants and golf courses. This is a tastefully decorated home in the typical Florida style with all the facilities that you need to have the perfect holiday. As you step into the house through the... View all property information
    Make Enquiry
    Location Information
    Venice, Southwest Gulf Coast 34293
    From
    $5,628
    / Month
    Payment Protection
    View Details
    1 / 35
    Venice
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Gym
    • Internet Access
    • Safe
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Our building requires a 3 month minimum stay, and our Homeowners Association must approve the tenant. Flipkey has no way to indicate a longer minimum than 30 days, but please understand, we CANNOT RENT FOR A SHORTER PERIOD THAN 90 DAYS!!! The rental cost is $4,400.00 per month and $1,100. per week... View all property information
    Make Enquiry
    Location Information
    Venice, Southwest Gulf Coast 34285
    Get the List
    From
    $110
    / Night
    Payment Protection
    View Details
    1 / 17
    Siesta Key
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Sauna
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    White Sands Village is located on Siesta Key, just few steps from Siesta Beach and directly on the canal across from Philippee Creek. Highlights of White Sands Unit 303: Free high-speed WiFi Ground floor unit More than 200 channel cable TV DVR to watch your favorite show when you want to 50 inch... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $4,477
    / Month
    Payment Protection
    View Details
    1 / 33
    Venice
    3 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Gym
    • Hot Tub
    • Internet Access
    • Pool Table
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Get out of the cold and come enjoy a neighborhood full of amenities and social activities! This home was designed for relaxing and enjoying your surroundings. The lanai looks out onto a lake where Florida foliage provides the ambiance for quiet early mornings and a peaceful place to enjoy the end... View all property information
    Make Enquiry
    Location Information
    Venice, Southwest Gulf Coast 34293
    From
    $243
    / Night
    View Details
    1 / 30
    Siesta Key
    2 Bedrooms / 3 Bathrooms / Sleeps 5
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Fireplace
    • Internet Access
    • Private Outdoor...
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    If you are looking for a place to unwind and decompress, this is the ideal place for you. Experience Siesta paradise with incredible sunsets and balmy breezes directly on the Gulf of Mexico with its beautiful white sand beaches stretching for miles. And not to brag, but the number one beach in the... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $122
    / Night
    Payment Protection
    View Details
    1 / 12
    Venice
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Furnished 3 bedroom, den, 2 bath, two-car garage. Large pool and spa – great entertainment home! Perfectly located in the gated, prestigious Sawgrass community of Venice with views of lakes. Near the championship Waterford, Capri Isles and Calusa Lakes golf courses. Adjacent to a woodland... View all property information
    Make Enquiry
    Location Information
    Venice, Southwest Gulf Coast 34292
    From
    $115
    / Night
    Payment Protection
    View Details
    1 / 16
    Venice
    1 Bedroom / 1 Bathroom / Sleeps 1
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Great house - newly tiled, freshly painted, very clean. It has everything you need, just show up and relax. The street is very quiet so there's no traffic noise. There is an empty lot across the street which increases the privacy. The back yard is completely fenced with privacy fencing. There's a... View all property information
    Make Enquiry
    Location Information
    Venice, Southwest Gulf Coast 34295
    From
    $1,919
    / Month
    Payment Protection
    View Details
    1 / 8
    Venice
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Sauna
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    About this property
    2 bedroom, 2 full bathroom, furnished condo apartment in Las Palmas of Venice Florida. A secure, three story builoding with elevator, large swimming pool, club house, and, lots of extra parking (a rare thing in SW Florida). Centrally located in the City of Venice, literally 5 minutes from... View all property information
    Make Enquiry
    Location Information
    Venice, Southwest Gulf Coast 34285
    From
    $238
    / Night
    View Details
    1 / 14
    Siesta Key
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview 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
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    THIS UNIT IS ALREADY BOOKED THROUGH April 20, 2015. Taking reservations for 2016 already. 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... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $139
    / Night
    Payment Protection
    View Details
    1 / 46
    4 of 5 stars (1) Very good
    Siesta Key
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Private Fishing...
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • ?
    About this property
    YOUR PRIVATE GETAWAY ON THE KEY ASK ABOUT OUR SUMMER SPECIALS!!!!!!!!! Rent 2 nights get third FREE!!!! Does not include Weekends or Holidays!!! Looking to relax, Flip Flop Cottages is the place to be for a quaint and private vacation in Siesta Key, Florida. Come and stay at our serene... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $281
    / Night
    Payment Protection
    View Details
    1 / 17
    Siesta Key
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Housekeeping...
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    About this property
    I have tried to make this apartment as comfortable as your own home only at the beach. This unit has two bedrooms and two baths. It can accommodate six people with a king bed and two double beds. There are plenty of closet and dresser space, a fully-equipped kitchen, color TV's, VCR and/or DVD and... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $128
    / Night
    View Details
    1 / 7
    Nokomis
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    SINGLE HOME 3 BEDROON 2 BATH 2 BLOCK WALK TO BEACHES 2 RESTAURANTS across ST. BOATING, FISHING, SHRIMPING, BEACHES HAVE CLEAN REST ROOMS, SNACK BARS, PICNIC TABLES, GRILLS, SHADED AREAS, SHOWERS, LIFE GUARDS, AND BEST OF ALL (FREE PARKING). SHOPPING CENTER AND POST OFFICE ONE MILE... View all property information
    Make Enquiry
    Location Information
    Nokomis, Florida 34275
    From
    $150
    / Night
    View Details
    1 / 5
    Venice
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Just listed for sale. You will have a truly one-of-a-kind experience if you spend it in this newly renovated lovely gem. It is located in the Westchester Gardens community in the prestigious Plantation Golf and Country Club overlooking the ninth hole of the Bobcat course. The second floor... View all property information
    Make Enquiry
    Location Information
    Venice, Southwest Gulf Coast 34293
    From
    $219
    / Night
    View Details
    1 / 13
    Venice
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • 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
    Very spacious and beautifully furnished pool home. Three bedrooms and two bathrooms. Fully furnished, shuffleboard and horseshoe pit in back yard, outside speakers by the pool,24 hour recorded outdoor surveillance, too much to list. More pictures available upon request. Meticulously maintained,... View all property information
    Make Enquiry
    Location Information
    Venice, Southwest Gulf Coast 34285
    From
    $90
    / Night
    View Details
    1 / 7
    Venice
    2 Bedrooms / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    First floor condo with screened-in lanai overlooking heated swimming pool. Condo is located directly on Venice Avenue on the island of Venice, walking distance between the Gulf of Mexico and downtown shopping, churches, restaurants, tennis courts, and so many other amenities! Beds: 1 Queen Bed View all property information
    Make Enquiry
    Location Information
    Venice, Southwest Gulf Coast 34285
    From
    $1,327
    / Week
    Payment Protection
    View Details
    1 / 26
    Siesta Key
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Fishing...
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    About this property
    Very spacious, air-conditioned 4 bed detached ranch-type Villa on Siesta Key Bayside. Sleeps 8, 1 King, 1 Queen, 2 Full and 2 twin beds. 1 month minimum Jan-March, 2 week minimum April -Dec. Maximum 3 cars . Large Heated Communal pool, Own Outdoor patio area with BBQ , Table, seating and sun... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida FL34242
    From
    $139
    / Night
    View Details
    1 / 15
    Siesta Key
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Enjoy this 2 bedroom 1 bath property located just 1 block from the beach. This unit offers an adequate kitchen with stainless steel appliances and ample living space for 4. The master bedroom is furnished with a queen-size bed and guest bedroom is furnished with two twin-size beds. The unit is... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $216
    / Night
    View Details
    1 / 8
    Venice
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • 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
    Steps to the Gulf of Mexico to swim, relax, walk on the beach or evening sunsets. live in paridice at our two bedroom, two bath home and over 1,500 square feet of living space 4 minutes walk to a private beach directly on the Gulf of Mexico.. A single story floor plan that is ideal for senior or... View all property information
    Make Enquiry
    Location Information
    Venice, Southwest Gulf Coast 34293
    From
    $146
    / Night
    View Details
    1 / 13
    Siesta Key
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Gym
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    *** NEW *** Never miss a beach-scape sunset when you are just a couple hundred meters from Americans #1 beach, Siesta Key Beach. Enjoy this two bedroom two bathroom condo style unit in a great location: a short walk to the beach on a quite street but just minutes from shops, bars, and restaurants.... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $512
    / Night
    View Details
    1 / 24
    Nokomis
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • 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
    Just South of Siesta Key lies Casey Key. You won't find any chain hotels here- this is 'old Florida' at its very best. Covered in a canopy of tropical trees, the winding Gulf-front street will make for an unforgettable stay among some of Sarasota's most luxurious homes as well as sights. The twisty... View all property information
    Make Enquiry
    Location Information
    Nokomis, Florida 34275
    From
    $87
    / Night
    View Details
    1 / 12
    Venice
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    A lovely and spacious house for four, this Venice home boasts all manner of comfort and serenity. Enjoy a relaxing vacation. Sit out with morning coffee on your screened outdoor patio overlooking garden and trees for your privacy. Your inviting vacation rental is airy, spacious and bright, bathed... View all property information
    Make Enquiry
    Location Information
    Venice, Southwest Gulf Coast 34293
    From
    $1,426
    / Week
    View Details
    1 / 37
    Siesta Key
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Sauna
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    This gorgeous Siesta Key luxury beach view condo is directly on world famous Crescent Beach located mid-Key, just south of the south bridge and right across the street from South Village with fast access on/off the island. This Siesta Key vacation rental condo is located in the Siesta Breakers... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $1,266
    / Week
    Payment Protection
    View Details
    1 / 21
    Siesta Key
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
    Overview Make Enquiry
    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
    • x
    • x
    About this property
    Luxurious Villa at Crystal Sands on Siesta Key Beach Florida - sleeps 6 and includes everything your family needs for your stay at the #1 beach in the USA. This Villa has easy access to the beach without leaving the property or crossing streets. Our kitchen is COMPLETELY equipped (appliances &... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $137
    / Night
    View Details
    1 / 11
    Siesta Key
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • 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
    Location, Location, Location! Siesta Key #1 Beach in USA Our condo is only a 3 minute walk to Crescent Beach on beautiful Siesta Key FL. Siesta Key Beach rated #1 beach in the USA. We rent by the month or for the season. Our two bedroom, two bath has a screened in lanai, large great room with all... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $128
    / Night
    View Details
    1 / 10
    Siesta Key
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Gym
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    **NEW** Walk the soft sandy shores of Siesta Key beach from this 1 bedroom1 bath vacation rental on Siesta Key. The unit offers an open floor plan with full kitchen, dining area, and living room with flat screen TV. Through the large sliding doors you can sit out and enjoy the pool area on the... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $128
    / Night
    View Details
    1 / 8
    Siesta Key
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Gym
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    *** NEW *** Take a look at this well appointed 1 bedroom 1 bath unit just a couple hundred meters from the #1 beach in America, Siesta Key Beach. This vacation rental unit has an open living area with full kitchen, dining area, and living room with flat screen TV. Walk through the large sliding... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $173
    / Night
    Payment Protection
    View Details
    1 / 7
    Lido Key
    Studio / 1 Bathroom / Sleeps 2
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Sauna
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Studio apartment with Queen size bed; fully equipped kitchen with all cooking and serving items. Located across the street from LIDO BEACH and 3-4 min walk to St. Armand's Circle. Private Backyard with BBQ grill, table, chairs. Large flat TV (cable, WIFI). All linen, towels, beach chairs... View all property information
    Make Enquiry
    Location Information
    Lido Key, Sarasota 34236
    From
    $192
    / Night
    View Details
    1 / 20
    Siesta Key
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview 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 2 bedroom 2 bathroom private condominium, Unit 204 at the El Presidente in Siesta Key is directly on the world's most beautiful Crescent Beach. This newly renovated, fully furnished air conditioned unit sleeps 6. The heated pool and jacuzzi are right on the beach. Unit 204 has a garden... View all property information
    Make Enquiry
    Location Information
    Siesta Key, Florida 34242
    From
    $77
    / Night
    View Details
    1 / 17
    Venice
    Studio / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Sweet spot just steps to Golden Beach at the Gulf of Mexico in Venice, FL. We call it the Turtles Nest for the abundance of sea turtle nests found on Golden Beach in the summer months. This quiet beach is always a welcoming place where you can relax and unwind to the sound of gentle waves. There... View all property information
    Make Enquiry
    Location Information
    Venice, Southwest Gulf Coast 34285
    From
    $119
    / Night
    View Details
    1 / 22
    Venice
    1 Bedroom / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • 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
    BEACHFRONT, ONE AND TWO-BEDROOM, FAMILY FRIENDLY VENICE FL CONDOMINIUM UNITS, LOCATED ON THE GULF COAST ISLAND OF VENICE, FLORIDA - FAMILIES with CHILDREN, COUPLES, and SENIOR CITIZENS ARE ALWAYS WELCOME! Venice Vacation Rentals provides spacious, full-furnished ranch-style Venice FL... View all property information
    Make Enquiry
    Location Information
    Venice, Southwest Gulf Coast 34285
    From
    $146
    / Night
    View Details
    1 / 21
    Venice
    3 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • 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
    On a quiet street walkable to spectacular Venice beaches and the picturesque palm tree-lined town center, our centrally located Venice Island pool home offers the perfect week vacation! Many of our guests are repeats we are very happy to say! We are strictly no pets & we can only offer Saturday... View all property information
    Make Enquiry
    Location Information
    Venice, Southwest Gulf Coast 34285
    From
    $217
    / Night
    Payment Protection
    View Details
    1 / 10
    Nokomis
    1 Bedroom / 1 Bathroom / Sleeps 2
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Located on the ground floor, this efficiency unit opens in to our beautiful Tropical Courtyard and includes queen size bed, TV & DVD player, dinette table with two chairs, full mini-kitchen with 4 burner stove, oven, refrigerator, microwave, toaster, coffee maker, all utensils and a private bath... View all property information
    Make Enquiry
    Location Information
    Nokomis, Florida 34275