Vacation rentals with a pool in Osprey

Windsor Lodge Unit #18, studio

Windsor Lodge is a luxurious and beautifully maintained vacation rental located on the golf course within the gated community of The Oaks Golf and Country Club. This elegant unit offers an open and inviting layout with a spacious living area and a comfortable bedroom, complemented by a separate bathroom for added privacy. Guests can enjoy the peaceful surroundings and manicured landscapes that make The Oaks such a desirable community. Access to the community pool provides a refreshing way to rel

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool

Whisk your favorite person away to BayDreaming! Escape to this quiet 1BR/1.5BA condo - just an 8-minute walk to Turtle Beach! Perfect for couples, it features a private deck with canal and Gulf views , a heated pool for sunset swims, 2 supyaks and a plush king bed for cozy nights in. Enjoy garage parking, beach gear, and a peaceful, welcoming community. Whether you're here to relax or reconnect, this coastal retreat offers the perfect mix of romance or just plain serenity on sunny Siesta Key!

3 bedroom Heated salt water pool close to Siesta

Your family will be close to everything when you stay at this centrally-located place. 15 minutes to Siesta Beach, 10 minutes to UTC mall, 15minutes to downtown, 20 minutes to SRQ airport. This home is fully remodeled, fully furnished, sleeps 8. We have 1 king size bed in the master, second bedroom is queen bed, 3rd bedroom is 1 full and 1 twin beds. This is open plan home with a big family room, 60" TV above electric fireplace, formal dining room seats 6 with the bar seats 4. Master has 55"TV

Quiet Peaceful Community! Minutes to Beaches!

Private, quiet tropical location. This Villa is our home away from home and furnished for comfort. Master has a King Bed and attached bath plus a huge walk in closet. Privacy with a Split bedroom plan. The guest bedroom has a full size bed & a twin. Spacious living room. 3 Flat Screen TVs. Plus internet. Private lanai with chairs & table. Single car garage. Beautiful Community with heated pool & hot tub. 20 min to Siesta Key Beach. Easy access to I 75. Lots of shopping & restaurants nearby!

Casey Key, Gulf Coast Gem, 4 Bedroom Private Pool

Bright and Sunny Gulf Coast Getaway, Welcome to Gulf Dream, property offers 4 bedrooms, 2 full bath rooms a washer and dryer as well as plenty of room to enjoy the screened in Lanai and in ground pool, located in a quiet serene Casey Key neighborhood, Ocean breezes, and lots of sunshine, and various fruit trees this property is located just minutes from Venice Beach ( Shark Tooth Beach) 9 minutes, Nokomis Beach, (Just 8 minutes) and Siesta Key Beach (12 minutes away) #1 Beach in the USA

Your Modern Beachside Getaway!

Search no more… we have it all! Enjoy this spectacular, newly remodeled beachside home in Siesta Key, equipped with a modern kitchen, hotel luxury pillow-top bed, and high-end finishes throughout! Amenities include private beach access (beachside 3 minute walk), pool access, patio, courtyard, BBQ, parking, and more. And the cherry on top, you’re right across the street for a plethora of restaurants, shops, and conveniences giving you everything you need to enjoy the best of Siesta Key!

Near Downtown/Beach | Tropical Villas Venice Beach

Tropical Villas of Venice Beach offers 10 Villas on the Island of Venice FL. The Villas give the Old time Florida vibe with a convenient location to the beach, stores and restaurants. - 3 blocks from the beach - 2 blocks from the downtown - Near the Legacy Bike trail - In front of the beautiful John N. Park (Picnic) - Tropical gardens & swimming pool - Smart TV : NFLX, DIS +, Hulu, Espn+ - BBQ and Bikes and beach gears provided - Shark teeth equipment - Farmer Market every Saturday

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach

The Siesta Key Bungalows offer a heated pool, courtyard, sun loungers, gas-grills, laundry facilities, kayaks & a private dock on Heron Lagoon. The Dolphin Bungalow's one bedroom space; connects a welcoming living room, full-kitchen, and a private backyard patio. A king bed, two HDTVs and a full bathroom will further enhance your overall experience. Fully stocked with linens, care essentials, eating & cooking utensils. A queen sofa bed in the living room, allows for a capacity of three.

Sunny Oasis/Beautiful House/Near Beach/Heated Pool

Beautiful House with 3 bedrooms, heated pool, mini golf and two-car garage. Great location. five-minute drive to the beach. near shopping plazas, restaurants, and the famous Legacy Trail perfect for biking, running, and more. Situated at a dead-end in a peaceful community. Lots of outdoor space around the house with beautiful palm trees and a large patio. bicycles, board games, cornhole, a gas grill, and more at your disposal. Lots of places to visit in the Sarasota and Venice area.

Beach Retreat•Renovated Pool Patio•Near Siesta Key

Stay at one of Sarasota’s top-rated Airbnbs, perfectly centered between the ever famous Siesta Key and several other stunning beaches. Lounge by the newly renovated heated pool with upscale chaise lounge chairs, lush garden views, and a stylish patio with ample seating. Inside, enjoy a modern, beach vacation themed design with an open layout, fully stocked kitchen, fast WiFi, and Smart TVs in every bedroom. Your on-site Superhost is nearby but works full time and gives total privacy.

Creekside Paradise I

The 1970 sqft living space hosts 3 bedrooms, 2 bathrooms, an open living room with attached ‘library’, a dining area, as well as a fully equipped kitchen. From the caged pool area you have a view of the North Creek and our Boat Dock. The pool can be electrically heated and measures 32.80ft in length/13.12ft in width. You enter Creekside Paradise I thru the attached 2 car garage, where you can find the beach equipment (chairs, umbrella, cooler).

Manasota Key

Direct Ocean Front Unit. Imagine having a glass of wine at sunset overlooking world class views of the Gulf of Mexico. Steps to the beach and unsurpassed views. Excellent restaurants and Tiki Bars within walking distance. This unit is a 1 bedroom 1 bath spacious unit that can comfortably sleep 4. It includes a King bed & Full size sleeper sofa. It also has a beautiful kitchen with granite countertops and tile floors throughout. No Pets.