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Osprey Rentals for Seniors

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    The following rentals are within 10 miles of Osprey, Florida.

    1 / 10
    5 of 5 bubbles (4) Excellent
    Venice
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 38
    5 of 5 bubbles (1) Excellent
    Siesta Key
    2 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    1 / 24
    5 of 5 bubbles (8) Excellent
    Venice
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 28
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    This gorgeous townhouse is located 2 short blocks from Siesta Key Village and a block from the white sands of Siesta Key Beach. VIew the gorgeous sunset and Gulf and beach views from the Master Bedroom on the top level. This unit is immaculately appointed and will make your Siesta Key Vacation... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 15
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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    • x
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    • x
    About this property
    You will feel like you have arrived in Paradise when you enter the lobby. The facility is more like a resort than a condominium. Unit has 2 bedroom, 2 baths, split plan. Both bedrooms and living room open to screened lanai facing the Gulf of Mexico. Perfect setting for 4 adults or for a family with... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 7
    5 of 5 bubbles (3) Excellent
    Venice
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    This smartly decorated Venice Fl vacation rental home features a master and guest bedroom w/ queen bed, daybed/pop-up trundle and living room (sofa bed) also available, home theater w/ stadium seating and surround sound, and 3-seasons room. Master bath has whirlpool tub/shower, and 2nd bath... View all property information
    Location Information
    Venice, Southwest Gulf Coast 34293
    1 / 23
    5 of 5 bubbles (1) Excellent
    Venice
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    NOW AVAILABLE !!! Located on the Myakka River in beautiful Venice Fla. This 800 Sq.Ft Studio apartment is newly renovated. Clean, Clean, Safe, Safe, Safe!!! Asking $500.00 weekly or $1600.00 a month in season. Your Front door opens on to the Myakka River where fishing is available right off our... View all property information
    Location Information
    Venice, Southwest Gulf Coast 34293
    1 / 26
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Steps from the islands best restaurants, shops (in the Village area) and a short walk to the #1 beach in the USA! Great home with 2 car and 1 car private garages. Recently renovated including a screened in patio, hot tub and pool. Brand new appliances making this home a great place for monthly... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 24
    Gulf Gate Branch
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    • x
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    About this property
    Enjoy the pond view and bird life from the patio area. With 3 bedrooms, 3 bathrooms, 2 car garage, the house can accommodate up to 7 persons The house is located in a wonderful and quiet area of Sarasota. Within a ten minutes you are on one of our many beaches long on one of our 3 islands Siesta... View all property information
    Location Information
    Gulf Gate Branch, Florida 34231
    1 / 12
    Venice
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    About this property
    Plan your vacation today in beautiful Venice Florida at our quite, sunny Gulf of Mexico tropical beach town with everything you could desire. Venice Island is a truly a southern vacation town with lots of charm and an easy going life style. Enjoy our miles of safe clean sandy Gulf beaches. Lock in... View all property information
    Location Information
    Venice, Southwest Gulf Coast 34293
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    1 / 12
    Siesta Key
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    Siesta Sun Villas Sand dollar villa is a 2 Bedroom 1 bathroom. A short walk to the number 1 beach in the USA. Our villa is fully furnished and ready to start your vaction Full Kitchen. Free wifi. Free parking. Located within walking distance to almost everything. The beach is just down the street.... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 18
    Venice
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Highly sought after condo in Farmington Vistas. Newly furnished property perfect for extended vacation and/or leisure. Everything you need is furnished from the kitchen to ironing etc., just bring your suitcase. Master bedroom with King bed and patio off master. Guest room with twin beds. The... View all property information
    Location Information
    Venice, Southwest Gulf Coast 34293
    1 / 36
    3.5 of 5 bubbles (4) Average
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    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
    Location Information
    Siesta Key, Florida 34242
    1 / 15
    5 of 5 bubbles (1) Excellent
    Venice
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
    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
    Location Information
    Venice, Southwest Gulf Coast 34292
    1 / 8
    5 of 5 bubbles (3) Excellent
    Nokomis
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    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
    Location Information
    Nokomis, Florida 34275
    1 / 15
    5 of 5 bubbles (10) Excellent
    Venice
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Time to plan ahead, beautiful Venice has been discovered. We have openings in June thru to Mid January 2018. This updated 2 bedroom/2 bath home is only a short bicycle ride from a quiet semi private beach. Think "old florida" where the crowds are few and the people friendly. This... View all property information
    Location Information
    Venice, Southwest Gulf Coast 34293
    1 / 17
    Siesta Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Located steps away from the whitest sand and the # 1 beach in America, known as Crescent Beach, Siesta Key. Our location 200 yards away has an easement for private beach access. We are located on the intercostal waterway of Little Sarasota Bay on the island of Siesta Key. The condominium has two... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 18
    5 of 5 bubbles (1) Excellent
    Siesta Key
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Upper floor. Walk to Siesta Key beach, only 0.2 mi from beach access 13. Clean, updated, with all the amenities you have at home. Fully equipped kitchen. Quiet and peaceful getaway yet close to shopping, dining, grocery, pharmacy, bars, pubs, bike, boat, & kayak rentals. Park your car and use free... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 32
    4 of 5 bubbles (1) Very good
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
    • ?
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    About this property
    Harbor Towers Yacht and Racquet Club Unit 503 provides one of the best views in the building (fifth floor facing south/east). The glass enclosed Lanai with floor-to-ceiling sliding glass doors provides bright sunlight during the morning and afternoon with excellent views of the intercostal water... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 9
    Lido Key
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Central Heating
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    • Pet-friendly
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    • x
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    • x
    About this property
    This beautiful spacious just-completed apartment, offers all the conveniences you will need to spend a fabulous and comfortable getaway! Just a block away from Lido Beach, ranked in the top 5 most beautiful beaches in the US. Turquoise water with dolphins, white sands like powdered sugar, with its... View all property information
    Location Information
    Lido Key, Sarasota 34236
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    1 / 41
    5 of 5 bubbles (61) Excellent
    Siesta Key
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • 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
    Location Information
    Siesta Key, Florida 34242
    1 / 39
    5 of 5 bubbles (4) Excellent
    Siesta Key
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    Our House on Siesta Key is located on one of the most beautiful streets on Siesta Key -- Avenida Messina "Sunset Point". You are literally a few feet from the cool, white sandy beach and a few feet from "The Village". No need to use your car to get to a grocery store, bank, restaurants,... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 18
    Venice
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Beautiful 4 bedroom, 2 bath home with screened in lanai in a highly desired gated community inside Stoneybrook. It has the following amenities: Jr. Olympic swimming pool Hot tub Tennis courts Basketball courts Inline skate rink Sand volleyball courts Baseball/softball field Exercise/workout room... View all property information
    Location Information
    Venice, Southwest Gulf Coast 34292
    1 / 22
    5 of 5 bubbles (1) Excellent
    Siesta Key
    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • x
    About this property
    Perfectly located, New, 6 bedrooms 4 1/2 bathrooms private home,in a gated community, combines luxury with convenience of location. We offer you a large 6000sf+ home within a short distance to the pristine beaches of Siesta Key and walking to the Village, Restaurants, shops and nightlife. Privacy... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 6
    Venice
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Beautiful ,bright and cheery one room studio, recently updated. King size bed, partially equipped kitchen including refrigerator, microwave, toaster oven, coffee maker, etc. Just a short walk to Venice beach, beach chairs, umbrella and beach cart provided. Largest outdoor pool in Venice. View all property information
    Location Information
    Venice, Southwest Gulf Coast 34285
    1 / 11
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Siesta key condo in sarasota Florida West coast of Florida beautiful sunsets and powdered sugar sandy beaches Condo completely tiled thru-out, Elevator, walk to number 1 rated beach, watch boats go by while enjoying your morning coffee Ringing museum, Florida studio theater St armounds Circle Fine... View all property information
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    Siesta Key, Florida 34242
    1 / 21
    Nokomis
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Newly Renovated Beach Rental in Historic Downtown Nokomis, Florida Available for Seasonal Rental 2 miles (5 minute drive) to Nokomis Beach/Casey Key! This is the beach rental you have been looking for in sunny Nokomis (Sarasota County), Florida! Front Unit: 2 Bedrooms, 1 Bath (sleeps up to... View all property information
    Location Information
    Nokomis, Florida 34275
    1 / 36
    5 of 5 bubbles (1) Excellent
    Venice
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Enjoy the Florida lifestyle at this sparkling and spacious modern luxurious villa in Venice’s finest resort community. Two month minimum for all rentals. Next availability is May 2017 thru Oct. 2017. See calendar for details. Jan thru April 2017 & 2018 are not available. Relax with the gorgeous... View all property information
    Location Information
    Venice, Southwest Gulf Coast 34293
    1 / 30
    4.5 of 5 bubbles (3) Very good
    Venice
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    The Lemon Bay Cottage is located within walking distance of the South Venice Beach ferry. A ferry pass is included in the rental of this facility. This property is one mile from Shamrock Park and Nature Center which includes hiking trails, basketball and tennis courts, and access to the Venetian... View all property information
    Location Information
    Venice, Southwest Gulf Coast 34293
    1 / 11
    Siesta Key
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This Beautiful 1 Bedroom, 1 Bathroom Condominium is located close to Beautiful Crescent Beach on Siesta Key. This unit has been newly renovated, has all Brand New Stainless Steel Appliances, Granite Counter Top, 55' Flat Screen TV, Wood Style Ceramic Tile Throughout. Heated Pool and a Storage area.... View all property information
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    Siesta Key, Florida 34242
    1 / 18
    Siesta Key
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    You will have a visit to remember in this elegant three bedroom, two and one half bath vacation condo with a path to the famous Siesta Key white sand beaches just out your door! Two levels with tiles lanais and Gulf views from each level. Enjoy the amazing Gulf Coast sunsets right from your own... View all property information
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    Siesta Key, Florida 34242
    1 / 11
    5 of 5 bubbles (1) Excellent
    Siesta Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Located on the Northern end of Siesta Key, the interior neighborhood of Sara Sands is a popular area for vacationers. This home is a 3 bedroom 2 bathroom fully furnished home on the canal with a heated pool. Granite counter tops in the kitchen and stainless steel kitchen appliances. Private boat... View all property information
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    Siesta Key, Florida 34242
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    Siesta Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Walk to beach!!~ 5 minutes, Siesta Village- 15 minutes. Walk miles of white sandy beach. 4 Kayaks & Canoe (provided), enjoy a ride down the Grand Canal- Private Dock (rent a boat or jet-skies). Swim in the heated private pool. Relax in the hot Jacuzzi. Beautifully decorated, spacious house with... View all property information
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    Siesta Key, Florida 34242
    1 / 15
    5 of 5 bubbles (4) Excellent
    Venice
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Relax and enjoy your vacation on Venice Island in this spacious, single-family home, located in Venice Island. Only 2 blocks to the beach, one mile to downtown shops, restaurants and the 27-hole public golf course with views of the gulf. Visit the many beaches, parks or take the kids to Disney... View all property information
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    Venice, Southwest Gulf Coast 34285
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    Lido Key
    6 Bedrooms, Sleeps 14 | Quick View
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    Get away to sunny florida. Watch dolphins from the sofa. People come from all over the world to stay here. We have top pro ball teams and famous names that enjoy this mansion. Everyone is welcome to experience this gold nugget of Florida. Private boat dock, Elevator, hot tub with Infiniti pool,... View all property information
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    Lido Key, Sarasota 34236
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    Siesta Key
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Quiet and serene, but close to local attractions, you will love this large 4 bedroom, family friendly home with 2 kitchens, new appliances, modern furnishings, and beach buggy with all the gear! Separate living areas can accommodate one large family or two smaller ones. Each living area has its... View all property information
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    Siesta Key, Florida 34242
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    Nokomis
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Newly Renovated Beach Rental in Historic Downtown Nokomis, Florida Available for Seasonal Rental 2 miles (5 minute drive) to Nokomis Beach/Casey Key! This is the beach rental you have been looking for in sunny Nokomis (Sarasota County), Florida! Front Unit: 2 Bedrooms, 1 Bath (sleeps up to... View all property information
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    Nokomis, Florida 34275
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    Nokomis
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Newly Renovated Beach Rental in Historic Downtown Nokomis, Florida Available for Seasonal Rental 2 miles (5 minute drive) to Nokomis Beach/Casey Key! This is the beach rental you have been looking for in sunny Nokomis (Sarasota County), Florida! Front Unit: 2 Bedrooms, 1 Bath (sleeps up to... View all property information
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    Nokomis, Florida 34275
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    5 of 5 bubbles (1) Excellent
    Venice
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Located in St. Andrews Park at the Plantation Golf & Country Club Overlooks Premier Golf Club Facility Country Club Membership A touch of Bermuda is evident in this environmentally friendly 1,300-acre community built around two championship golf courses, lakes and lush tropical preserves. Sand... View all property information
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    Venice, Southwest Gulf Coast 34293
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    5 of 5 bubbles (2) Excellent
    Siesta Key
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
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    Siesta Key, Florida FL34242
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    PLEASE NOTE ! This newly renovated pool home is located close to everything, . This is our private second home and not a rental only income . Located just off the island and near shopping, the YMCA, easy access to Downtown Venice ,Sarasota, and interstate 75. If you want the beach, only minutes... View all property information
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    Venice, Southwest Gulf Coast 34285
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    Surrounded by lush, tropical garden, our private villa is situated on a quiet cul-de-sac bordered on two sides by Lake Nancy. A birdwatchers and nature lovers delight! Sip your coffee in your PJs on the private, sunny terrace. Enjoy a dip in the large heated pool, or explore the lake in "Red... View all property information
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    Siesta Key, Florida 34242
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    Venice
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    This house has it all! All the amenities of home and more. This is a quite neighborhood on a corner lot with a park across the street.Toddler friendly amenities including a pool safety gate, pack-n-play, booster seat, and stroller. Beach chairs, umbrellas, and beach buggy included for no... View all property information
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    Venice, Southwest Gulf Coast 34293
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    Our Top Location, Gertrude's Village House! Brought to you by Gertrude Rentals and named for our grandmother who traveled the world until age of 91 but always insisted this street on Siesta Key was the place she loved best. Leave the car behind. Gertrude's is richly furnished, perfectly nestled... View all property information
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    Siesta Key, Florida 34242
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    4.5 of 5 bubbles (10) Very good
    Siesta Key
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Newly upgraded ( September 2015 ) with new kitchen, new vanities, newly painted and with the tiles steam cleaned this Siesta Key villa is a gem. It comes with a with a lovely heated community salt water pool and private access to the beautiful white sanded Crescent Beach! Crescent Beach on Siesta... View all property information
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    Siesta Key, Florida 34242
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    Siesta Key
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    You'll feel at home in this clean, cozy condo by the beach. Quiet and peaceful yet close to shopping, dining, the village on Siesta Key. Ceramic tile floors. Tropical decoration. Fully equipped kitchen. Washer & Dryer on site. Ceiling fans. Central air & heat. Gas grill. Towels, umbrella &... View all property information
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    Siesta Key, Florida 34242
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    5 of 5 bubbles (1) Excellent
    Siesta Key
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    #1 Happy Hour on the dock #2 Walk to sunset on Shell Beach #3 Enjoy dinner in the Village!! New listing! Offering low rates to get good reviews to get me started on TripAdvisor, HolidayLettings, FlipKey, etc! Wonderful Siesta Key Duplex - Two separate units, upper and lower. Rent one or both.... View all property information
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    Siesta Key, Florida 34242
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    5 of 5 bubbles (12) Excellent
    Siesta Key
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Newly upgraded ( September 2015 ) with new kitchen, new vanities, newly painted and with the tiles steam cleaned this Siesta Key villa is a gem. It comes with a with a lovely heated community salt water pool and private access to the beautiful white sanded Crescent Beach! Crescent Beach on Siesta... View all property information
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    Siesta Key, Florida 34242
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    5 of 5 bubbles (1) Excellent
    Siesta Key
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Relax, get away and enjoy Siesta Key's laid back lifestyle! Nestled in a quiet residential neighborhood, you'll love this large and comfortable 500 square foot studio apartment. It has a king bed and comfortably sleeps 2. The studio is attached to the owners' home, and features a king bed,... View all property information
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    Siesta Key, Florida 34242
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    Nokomis
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Spacious, clean house in the safe and quite community within few miles from Nokomis or Venice beach. There is large screened private pool and covered outdoor lanai. Most of local attractions within 15 minutes drive. There is Oscar Scherer state park around the corner with lake, river and walking... View all property information
    Location Information
    Nokomis, Florida 34275
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