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

Crystal House on Siesta Key Beach

This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!

ROYS PLACE Romantic, Private, Paradise!

NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR THREE YEARS. "I LOVE ROYS PLACE!" Words most commonly used by guests in reviews are "quality" "clean" "cute" "sexy" "cool" "safe" . This is a restored 600 sq. ft. one bedroom apartment in an old historic home located in the heart of coveted safe Northwest Sarasota. Offered for you, a romantic boutique apartment with your own private (exclusive to you, not shared) CLOTHING OPTIONAL lanai, outdoor shower and heated pool.

Private View Villa/Heated Pool/Pickleball/7883

Beautifully furnished, clean, and well equipped end villa with attached garage and private lanai. Newer furniture; master bdrm with king size and guest bdrm with one queen and one twin size bed. Large screen UHD 4K smart led tv´s in Living room and Master bdrm and flatscreen also in guest bdrm. Expanded cable, free wifi, and unlimited US-Canada calling. Washer and dryer inside. Heated pool, hot tub, grill area, mini putting green, shuffleboard, 2 tennis courts (one is made for pickleball).

Cozy & Beautiful Pool Villa in Sarasota County, FL

Welcome to our home! It’s our pleasure to host you! Your family & friends will be close to everything when you stay at this centrally-located place: shopping, dining, beaches, entertainment, Warm Mineral Springs, Aquatic Center, etc. This charming house located in a beautiful & quiet neighborhood, tastefully furnished & decorated, fenced for your privacy & perfect for making memories with family & friends. Plenty of amenities to make your stay as comfortable as possible. Great location.

Gorgeous renovation with pool, minutes from beach

Light, bright and newly renovated. Beautifully decorated 3 bedroom home minutes from Siesta Key and downtown. The spacious modern kitchen has a slider that leads to covered porch and large pool with private fenced yard. A second slider from the porch leads to the master bedroom with master bath and walk in closet. Open living room and 2 additional big bedrooms make the house perfectly comfortable for 6. Everything you need is right here! Siesta Key Beach Distance - 16 Min; 6.1 Mi

Your private retreat near Siesta Key Beach.

Completely Remodeled Private Retreat. COME RELAX, UNWIND, AND MAKE LASTING MEMORIES! From the moment you arrive, you’ll feel the calm, welcoming atmosphere that makes this property stand out. This spacious 3brm 2-bath features an amazing heated pool, a private backyard, and stylish finishes throughout. Whether you’re lounging by the heated pool, enjoying meals in the bright open-concept living space, or exploring the nearby beaches this home is perfect for an unforgettable vacation

Sarasota Surf & Racquet Club Siesta Key Condo

Our newly renovated condo is located on Siesta Key's award winning Crescent Beach. Our unit is has all of the amenities of home for your convenience. The primary bedroom has a king sized bed and its own ensuite with walk-in shower. The second bedroom has 2 double beds and a large closet for all of your belongings. The complex has two heated pools, multiple charcoal grills and just steps away from the unit are 3 tennis courts and 2 pickle ball courts. Restaurants and shopping close by

The Pineapple Escape

The Pineapple Escape is the perfect gateway vacation house that has everything you're looking for. With a heated pool for access year round and beautiful kitchen for all your desires. Just a short drive from some of Florida's finest beaches, such as Nokomis Beach on Casey Key,Venice Beach and about 15 minutes drive to #1 beach in US, Siesta Beach in Sarasota,. You'll find this neighborhood to be quite serene and peaceful. Book today to start making memories at The Pineapple Escape.

Peaceful waterfront home

Take it easy at this unique and tranquil getaway. Nestled alongside a serene canal, our home is a sanctuary of tranquility and natural beauty. From the moment you step onto the property, you are met with charm and allure that only canal front residence can offer. For those who enjoy outdoor activities, the canal provides a perfect venue for kayaking, fishing and lounging in our cocktail pool and hot tub. Surrounding sliding glass doors opens up to 3 separate patios.

Siesta Beach | Heated Pool | Pet Friendly |

☞ Sauna, Fire-pit, BBQ (gas) ☞ Giant Outdoor Chess♟️ ☞ King & 2 Queen Beds ☞ Ample Parking (RV, Boat, etc) ☞ Fast WiFi 🛜 ☞ 4 Smart TVs (largest 85 inches) ☞ Gourmet Kitchen Main side ☞ Kitchenette on Guest side ☞ 2 Onsite washer + dryers ☞ 2 Outdoor Showers 》30 mins to airport 》2 mins to Siesta Key Beach Bike to America’s #1 beach, morning coffee runs, sunset rides, live music, ice cream, shops or any of the amazing restaurants in Siesta Key village.

Spacious Cozy Tropical Retreat!

You will be impressed with the new Kitchen. The spacious master bedroom has been designed with you in mind. King size bed, large walk in closet and private bath. Both bedrooms have brand new laminate flooring! Relax and unwind in the brand new leather reclining sofas and chair with a 65” smart TV in the main livingspace. The villa comes with high speed WIFI internet and premium tv channels to make you feel right at home. Private lanai with a great view.