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Vacation rentals in Osprey, FL and nearby

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All 483 Rentals in the Osprey Area
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The following rentals are within 15 kilometres of Osprey, Florida.

From
$128
Per Night
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1 / 16
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Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
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From
$4,178
Per Week
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1 / 22
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Siesta Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
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From
$203
Per Night
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1 / 20
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Siesta Key
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
Details Reviews (3) Make Enquiry
From
$78
Per Night
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1 / 12
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Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Refrigerator
  • Dishwasher
  • Washer
  • Safe
  • Microwave
  • Terrace
  • Dryer
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
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
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From
$248
Per Night
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1 / 19
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Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Hairdryer
  • Safe
  • Porch
  • Central Heating
  • Balcony
  • TV
  • Water Views
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Luxury condo right on the beach. Crystal Sands on Midnight Pass Rd is one of the most popular condos on Siesta Key's Crescent Beach, ranked as one of the whitest and most powdery sands in the world, as judged by the 'Great International White Sand Beach Challenge.' View all property information
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From
$122
Per Night
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1 / 22
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Siesta Key
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (3) Make Enquiry
Amenities & Details
  • Patio
  • Deck
  • Terrace
  • Refrigerator
  • Ceiling Fans
  • Waterfront
  • TV
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Sea Club II is Located steps away from the whitest sand and the # 1 beach in America, Siesta Key. Our location 200 yards away has an easement for private beach access. We are located on the intercoastal waterway of Little Sarasota Bay on the island of Siesta Key . Whether you are keen to enjoy... View all property information
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From
$116
Per Night
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1 / 33
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Venice
3 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Microwave
  • Dishwasher
  • Parking
  • Ceiling Fans
  • Patio
  • Washer
  • Playground
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Fully renovated Vacation Home is located in the heart of South Venice City, The property situated in a safe and quite neighbourhood, which is fenced around for privacy. It has a spacious interior with an open concept living room, kitchen and dining area, including three large bedrooms and two... View all property information
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From
$95
Per Night
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1 / 14
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Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (11) Make Enquiry
Amenities & Details
  • Sauna
  • Ceiling Fans
  • Washer
  • Dryer
  • Dishwasher
  • Refrigerator
  • Microwave
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Newly furnished, newly renovated 2BR (one king size & 2 single beds) + convertible sofa bed, 2 Bathrooms 2nd floor condo (sleeps 4-6), and with all the amenities of a comfortable home. Located in White Sands Village with 7 acres of lush tropical surroundings, our air-conditioned condo offers two... View all property information
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From
$140
Per Night
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1 / 34
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Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Microwave
  • Ceiling Fans
  • Grill
  • DVD Player
  • Dishwasher
  • VCR
  • Parking
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
We've got everything you need to make this your best vacation ever! The Vista Hermosa complex is very well maintained, quiet and a friendly atmosphere. Beautifully updated well equipped kitchen with granite counter tops and all the comforts of home. 2 queens beds in guest room with new bedding,... View all property information
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From
$87
Per Night
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1 / 8
Venice
2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Refrigerator
  • Stereo System
  • DVD Player
  • Microwave
  • Ceiling Fans
  • Dryer
  • Air Conditioning
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Fully furnished home with A/C, Free Wireless Internet, DVD, 40' flat screen HDTV, cable, washer/dryer, fridge, stove, microwave, 2 adult bikes, tennis racquets, basketballs and all beach accesories, charcoal barbeque with large back yard. Fully renovated bathroom. Beds: 1 King Bed, 1 Queen Bed, 1... View all property information
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From
$145
Per Night
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1 / 8
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Nokomis
3 Bedrooms, 1 Bathroom, Sleeps 5
Booking
Details Reviews (3) Make Enquiry
Amenities & Details
  • # Of Bathrooms
  • Dining Seats (6)
  • Living Room Seats...
  • Number Of Bedrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
We have a beautiful, Single Family Home on 1 acre in the heart of tropical nature with public access to the canal closeby. Florida la Palma, located in Nokomis, is a charming seaside resort, offering a warm space, fully renovated and completely equipped for up to five (5) people. Just 1 mile to... View all property information
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From
$1,235
Per Week
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1 / 12
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Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Microwave
  • Dishwasher
  • Refrigerator
  • DVD Player
  • TV
  • Parking
  • Patio
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Jamaica Royale condo #92 on the #1 beach in the USA, This 2 bedroom 2 bath garden view unit was recently updated, and is located in the garden area of our beautifully landscaped property. It has new furniture and is freshly painted, with tile floors in living areas and new carpet in bedrooms.... View all property information
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From
$108
Per Night
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1 / 10
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Siesta Key
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dryer
  • Grill
  • Washer
  • Safe
  • Parking
  • Satellite TV
  • Microwave
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Delightful beach bungalow at Ebb Tide , only 2 minute walk to pool and powder white sand of Crescent beach, right across the street from restaurants,shops, bike and boat rentals, marina, 7 Eleven, and more. This darling tropical villa had everything you need for a great vacation. No one above you... View all property information
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From
$81
Per Night
View Details
1 / 7
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Venice
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
Details Reviews (2) Make Enquiry
Amenities & Details
  • Parking
  • Fireplace
  • DVD Player
  • Washer
  • Microwave
  • TV
  • Grill
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
NOT AVAILABLE through 2014 and early 2015 Beautifully decorated for the Christmas Holidays Snowbirds-You will never want to leave this 1925 renovated house which has it all! WIRELESS INTERNET and HD TVs. Listed in the National Register of Historic places. This cozy cottage is located blocks... View all property information
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From
$145
Per Night
View Details
1 / 14
Venice
3 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (1) Make Enquiry
Amenities & Details
  • # Of Bathrooms
  • Number Of Bedrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Fabulous home, completely updated and beautifully furnished for rental. Minutes to Manasota Beach or enjoy the couple of bikes to get there. On entry through the glass doors you come into beautiful entry, to the left there is spacious living room, and ahead is the casual family room. Brand new... View all property information
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From
$116
Per Night
View Details
1 / 9
Payment Protection
Venice
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (3) Make Enquiry
Amenities & Details
  • Dishwasher
  • Garage
  • Washer
  • Refrigerator
  • Dryer
  • DVD Player
  • Hot Tub
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This South Venice Vacation Pool Home welcomes you with 3 BR, 2 BA. The covered screened lanai is attached to the private pool and hot tub area. The Venice Florida vacation home is fully furnished and updated including on premise laundry facilities for your convenience. Enjoy free local and long... View all property information
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From
$1,813
Per Week
View Details
1 / 23
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Venice
4 Bedrooms, 4 Bathrooms, Sleeps 8
Details Reviews (3) Make Enquiry
Amenities & Details
  • Terrace
  • TV
  • DVD Player
  • Refrigerator
  • Washer
  • Microwave
  • Grill
  • Gym
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
This privately own Villa is rented directly from its U.K. owners with no agents or commissions. To watch a slide show of the home, please copy and paste the link below into your browser. http://www.tripwow.tripadvisor.com/tripwow/ta-06f7-679e-a4ac?lm The home is furnished and maintained to a... View all property information
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From
$174
Per Night
View Details
1 / 17
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Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (2) Make Enquiry
Amenities & Details
  • Refrigerator
  • Dishwasher
  • Safe
  • Ceiling Fans
  • Microwave
  • Fireplace
  • Parking
  • Garage
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
A short stroll down a private road to the #1 Beach in the US. You will love the location - you are located in the Resorts of SaraSea community and can walk to everything you might need or want... Grocery, restaurants, ice cream, pizza, sports rentals, drugstore or boat rental. You have your own... View all property information
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From
$635
Per Week
View Details
1 / 14
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Venice
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • TV
  • DVD Player
  • Satellite TV
  • Washer
  • Refrigerator
  • Dryer
  • Dishwasher
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Lakeside is located just 10 minutes drive from some of the most beautiful beaches on the Gulf Coast of Florida. Quiet and peaceful, yet with good shopping, restaurants and bars nearby. The spacious apartment is on the first floor of a small complex of only 9 units. The balcony overlooks the... View all property information
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From
$1,077
Per Night
View Details
1 / 23
Siesta Key
7 Bedrooms, 5 Bathrooms, Sleeps 16
Details Make Enquiry
Amenities & Details
  • Dryer
  • Parking
  • Grill
  • Hot Tub
  • Patio
  • Microwave
  • Refrigerator
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This stunning home features 10 foot ceilings, top of the line VIKING appliances including a wall mounted double oven, stove, and side by side refrigerator. The kitchen has a massive center island with lots of room for multiple chefs or families and friends to sit and chat after a day a the beach.... View all property information
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From
$140
Per Night
View Details
1 / 22
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Siesta Key
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (32) Make Enquiry
Amenities & Details
  • Dryer
  • Ceiling Fans
  • Microwave
  • Patio
  • Grill
  • Wi-Fi
  • DVD Player
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Very clean, bright & airy 1 bedroom, single- story cottage. Ebb Tide Villa #1 is waiting for you... - Beautiful, large, heated pool with plenty of loungers for relaxing. - Private, gated access to world renowned Crescent Beach, famous for its powdery, white, quartz sand and gorgeous sunsets! Both... View all property information
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From
$140
Per Night
View Details
1 / 25
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Siesta Key
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (21) Make Enquiry
Amenities & Details
  • Dryer
  • DVD Player
  • Grill
  • Refrigerator
  • Satellite TV
  • Parking
  • Patio
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Villa #3 at Ebb Tide is waiting for you: All quality furnishings & linens, fully equipped with everything you need for a fun and relaxing beach vacation! Rated the #1 Beach in the USA: Crescent Beach on Siesta Key is literally a 2 minute walk from your villa door! Beautiful, soft, white quartz... View all property information
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From
$252
Per Night
View Details
1 / 42
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Siesta Key
3 Bedrooms, 2 Bathrooms, Sleeps 10
Booking
Details Reviews (28) Make Enquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Patio
  • Ceiling Fans
  • Washer
  • Microwave
  • TV
  • Safe
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
3 Bedroom, 2.5 Bath Beach Villa (Sleeps 8-10) What makes us different than other homes you may be considering: · The Beach - The home is located on the ocean side of Beach Rd., so you just walk out your door and through our private access path. It’s literally 230 feet to Siesta Key Beach.... View all property information
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From
$1,677
Per Month
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1 / 21
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Nokomis
2 Bedrooms, 1 Bathroom, Sleeps 8
Details Reviews (2) Make Enquiry
Amenities & Details
  • Internet Access
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Get up in the morning and throw on your swimsuit, some shorts and flip-flops - it's just 2 blocks to the beach and it's too beautiful to miss a minute of the view. A long stretch sugary white sand beach is at your fingertips at Casey Key's Nokomis state beach park. A real favorite beach amongst... View all property information
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From
$232
Per Night
View Details
1 / 22
Venice
3 Bedrooms, 3 Bathrooms, Sleeps 6
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Ceiling Fans
  • TV
  • Washer
  • Parking
  • Dryer
  • Dishwasher
  • Patio
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Beautiful 1926 Italian Villa in Downtown Venice Fl. Four blocks from Venice Ave full of shopping and eateries and 1/2 miles from the scenic 17 miles of Venice Beach. The home is beautifully restored with new kitchen and appliances and bathroom fixtures. Three bedrooms and 2.5 baths. Two Queens... View all property information
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From
$116
Per Night
View Details
1 / 26
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Nokomis
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dryer
  • Patio
  • Microwave
  • Grill
  • TV
  • Ceiling Fans
  • Fireplace
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
On the Sarasota County register of historic homes, and built in 1925, this charming 550 square foot one bedroom, one bath Mediterranean-revival cottage is the guest house behind the property owner's home, and is one of a block of three vintage vacation resort properties the owner calls... View all property information
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From
$145
Per Night
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1 / 22
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Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Internet Access
  • Pool
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Just steps from the bay, our newly remodeled condo in a gated Key West-style community is the perfect destination for your Siesta Key vacation. With resort amenities and the ideal location for beach and bay access, Gulf & Bay Bayside is irresistible!

Relax in the large 11 x 16-foot lanai... View all property information
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From
$145
Per Night
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1 / 28
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Siesta Key
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Pool
  • Internet Access
  • Hot Tub
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Take to the water or stick to the shore - the world is your proverbial oyster while staying at Siesta Key's Palm and Bay Club G88. Enjoy great comfort and value in this gulf-view suite, with all the resort amenities you can imagine. Two pools and a fantastic hot tub, a large fitness center and lit... View all property information
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From
$174
Per Night
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1 / 34
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Venice
4 Bedrooms, 2 Bathrooms, Sleeps 12
Details Reviews (32) Make Enquiry
Amenities & Details
  • Internet Access
  • Air Conditioning
  • Pool
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Walk to downtown Venice in less than five minutes - it's only two blocks away. For any other requirements you might have of a perfect beach house, find them easily met at 328 Bayshore Drive. An elegant 4 bedroom house that sleeps up to 12, packed with Mediterranean flair. The private heated pool is... View all property information
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From
$414
Per Night
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1 / 24
Nokomis
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Dryer
  • Garage
  • Washer
  • Grill
  • Refrigerator
  • Ceiling Fans
  • Patio
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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
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From
$2,315
Per Month
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1 / 28
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Siesta Key
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
  • Pool
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Every sunset is a memorable experience at our condo at Crystal Sands 406 in Siesta Key. Overlooking the placid Gulf of Mexico, our 4th-floor condo on the shores of Crescent Beach is a great venue for your next sun, sea, and sightseeing vacation!

Rated one of the Top 10 Beaches of the... View all property information
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From
$312
Per Week
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1 / 22
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Venice
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (12) Make Enquiry
Amenities & Details
  • Internet Access
  • Pool
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Step into the good life, in this Nantucket home in Venice, FL. A great choice if you're looking for a 'greener' vacation, the private, heated pool is kept warm thanks for rooftop solar panels. A fenced in yard is great for privacy and your pet.

Six guests will sleep comfortably amongst two... View all property information
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From
$190
Per Night
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1 / 30
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Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (18) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Pool
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
There's plenty of room for everyone here at Our House. We have a split-level living/dining area, with a large living room made for a crowd! The huge sectional sofa faces our new HDTV with DVD player, so anytime you need a little downtime from all the outdoor fun, settle in with your favorite movie,... View all property information
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From
$716
Per Week
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1 / 33
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Venice
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (14) Make Enquiry
Amenities & Details
  • Internet Access
  • Pool
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • 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
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From
$104
Per Night
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1 / 18
Venice
4 Bedrooms, 4 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Patio
  • Ceiling Fans
  • Dryer
  • Washer
  • Dishwasher
  • Refrigerator
  • Garage
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Why would you rent a two bedrooms condo if you can get a big beautiful house for just as much.Brand new 4 bedrooms, 3.5 baths house has everything you need. Just under 4000 sq.ft. Sleeps 8. Located in one of the best gated community in town. Jacuzi, heated pool with waterfall, spa, unbelievable... View all property information
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Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Hot Tub
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  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
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  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
With the Bay in back and the Gulf in front, our condo at Excelsior 107 sits on a little strip of paradise! Located in a luxurious resort with everything from heated pools and outdoor grills to private beach access, it's a tropical getaway on one of the world's finest beaches.

Just yards... View all property information
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Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Pool
  • Hot Tub
  • Internet Access
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  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Do you have children who'll delight in the geckos and insects they can discover in the garden? Or do you love nature and the sight and scents of tropical flowers? An idyllic ocean side condo perfect for energetic kids or families seeking added privacy, Siesta Dunes Beach 38A is your perfect... View all property information
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Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Hot Tub
  • Pool
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
How long does it take you to walk 100 yards? Not very long at all. While on vacation at Crescent Beach, consider that your morning commute - from bed to pool. Enjoy the great convenience of a ground floor unit at Siesta Key's Jamaica Royale unit 91.

Delight in the great value of this... View all property information
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Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Hot Tub
  • Air Conditioning
  • Internet Access
  • Pool
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  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Decked in pure tropical style, Siesta Dunes Beach 104 in Siesta Key, Florida is an ideal choice for families planning to spend all their daytime hours at the pool or the gorgeous on-site beach. As a gulf-side property, it's easy on the wallet while its lovely atmosphere makes it a great home to... View all property information
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Venice
2 Bedrooms, 1 Bathroom, Sleeps 4
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  • Pet-friendly
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  • ?
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  • Elder access
  • x
About this property
This property is beautifully landscaped and offers a spacious and private backyard. Enjoy your breakfast on the screened lanai and relax in a comfortable lounge chair. Features include bicycles, new furniture, a washer & dryer, gas stove, fully equipped kitchen, new linens, beach towels, a flat... View all property information
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Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Hot Tub
  • Pool
  • Air Conditioning
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • 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?... View all property information
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Venice
3 Bedrooms, 2 Bathrooms, Sleeps 8
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  • Pet-friendly
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  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
This beautiful Italian styled house with tile floors and a gorgeous electric heated pool is only 2 blocks to a private beach access. It is a beautiful Florida vacation rental house and has 3 bedrooms and sleeps up to 8 people.

Reward yourself with something sweet in this fully stocked... View all property information
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Venice
3 Bedrooms, 2 Bathrooms, Sleeps 8
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  • Internet Access
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  • Pet-friendly
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  • Elder access
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About this property
Give yourself plenty of vacation choice. Book your vacation at 308 Circle Drive and you're only a short 1 1/2 block walk from Venice's private Gulf Shore Beach. Located on Venice Island and equally close and within walking distance is the Venice Pier and Sharkey's and the charming town center. It's... View all property information
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$716
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Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Internet Access
  • Hot Tub
  • Air Conditioning
  • Pool
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Come vacation on the white sands of Siesta Beach! When you stay at our condo at Gulf & Bay Club 204C, you'll enjoy luxury and comfort in more than 1,500 sq ft of beachfront property, including a lovely lanai. And use of resort amenities is included! 28 day minimum stay.

Gulf & Bay Club... View all property information
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Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Internet Access
  • TV
  • Cooker
  • Dishwasher
  • Linens Provided
  • Fax
  • Refrigerator
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Island House Beach Resort - Siesta Key Florida, Crescent Beach - This large villa is approx. 1000 sq. ft. It has a large living area, dining area, fully equipped kitchen, all appliances, screened lanai, central ac/heat, covered parking, 3 tvs, dvd, free wi-fi in unit!. It has a king size bed, 2... View all property information
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Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Internet Access
  • Pool
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Siesta Key's largest heated pool is begging for all the games and excitement you can give it. Ample pool beds and an adjacent covered area mean you can happily spend all day, every day, lazing around.

From your 2 story split level condo, it's just steps to a perfect white sand beach. This... View all property information
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Venice
2 Bedrooms, 1 Bathroom, Sleeps 6
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  • Washer
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  • Grill
  • TV
  • Microwave
  • Dryer
  • Ceiling Fans
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Our Venice Beach Duplex resort home is perfect for your Venice Florida holidays and Venice Florida family vacations. Rent either the 2 Bedroom on the first floor or the 1 Bedroom unit on the second floor or both units for your family reunion vacation in our quaint beach town. Call for rates for... View all property information
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$216
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Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Internet Access
  • Pool
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
So what if you don't have a beach house of your own? When you stay at Our House at the Beach, you'll feel right at home.

Our House at the Beach 504W is located on the barrier island of Siesta Key, home to parrots, pelicans, and a beach that residents and visitors alike say has the finest... View all property information
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Siesta Key
4 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Garage
  • Patio
  • DVD Player
  • Dishwasher
  • Washer
  • Satellite TV
  • Microwave
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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
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Siesta Key
4 Bedrooms, 3 Bathrooms, Sleeps 12
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  • Parking
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  • Ceiling Fans
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  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
THE GRAND CANAL COTTAGE: (Two Week Minimum Rental) The Grand Canal Cottage, perhaps one of Siesta Key’s favorite luxury vacation homes, is a highly landscaped canal-front private luxury home featuring a heated pool with sun shelf and a separate 8-person spa. It is situated on Siesta Key within... View all property information
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