Vacation rentals with a hot tub in Osprey

4/2.5 Oak Bahay, Heated Pool! 5min to Beach,4Acres

Welcome to Oak Bahay Ranch, our beautiful 4+ acre ranch home with pool! Enjoy the tranquility of this 4 bedroom/2.5 bathrooms with a pool (heated during winter). Bike or drive the quick 2.5 miles to Nokomis and Casey Key Beaches! Oak Bahay Ranch is a nature lover's paradise, close to Legacy Trail, Sarasota County's premier 20+ mile biking/walking trail. Oak Bahay Ranch is an easy drive to world famous Siesta Key Beach (15 mins), downtown Sarasota (20 mins), and downtown Venice (10 mins).

Quaint Cottage,150 steps away from Crescent Beach!

Nestled on the serene Crescent Street, this classic 1969 cottage, is just a short walk to the ground quartz sands of Siesta Key. The 500 sq foot private brick paver and stone backyard off the screened in lanai is fully fenced with custom built stainless outdoor kitchen, featuring a large grill, refrigerator, custom built stone bar with seating for 8 . Nearby is a blue glass gas fire pit with a seating area, over sized (9 ft. diameter) in ground "spool", loungers and a large circular daybed.

The Blessing House- Htd Pool/Spa, Close to Beaches

Welcome to The Blessing House, a beautifully curated Sarasota retreat designed for relaxation, comfort, inspiration, and quality time together. Enjoy a heated pool & spa, lush lanai, bright designer interiors, and a peaceful residential setting just 15 minutes from Siesta Key, Lido Key, and downtown Sarasota. Thoughtfully maintained and enjoyed by our family throughout the year, this home is ideal for couples, families, and discerning travelers seeking a restful and memorable getaway.

Private house with loft

Have fun with the whole family at this brand new, modern private free standing guest house. Full bedroom with king size bed, with a finished loft including a queen bed. There’s also a queen pull out sofa in the living area. Enjoy your privately fenced backyard with a hot tub and putting green. Centrally located between Siesta Key beach and Nokomis beach. Hot tub is available upon request in off season months, April-October. There will be an additional $30 fee in off season months.

Tiki Oasis 3bed on .6 acre paradise 5 min to Beach

Relax with the whole family at this peaceful place to stay. Enjoy 2 master suites with 3 bedrooms and 3 bathrooms. A 5 min drive to Nokomis beach or downtown Venice, and walking distance to legacy trail, tennis courts, and playground in Nokomis park. Fast 500GB up/down internet speed around the property, Tiki bar nestled next to a heated pool and spa ( adtnl charge for spa). Fully stocked kitchen, beach-ready with cooler chairs umbrella wagon, and toys. 4 smart tvs

Minutes to Siesta! 4BR 2BT Heated Pool Fenced Yard

Spacious 4-bedroom, 2-bath home with a heated private pool, just minutes from the #1 Siesta Key Beach! Located in the Gulf Gate area, you’re only a short drive to the beach, grocery stores, and dining. Enjoy a fully fenced backyard, plenty of parking, and outdoor grill. Inside, you’ll find beach supplies, a fully equipped kitchen, Keurig & drip coffee makers, and TVs in every bedroom—everything you need for a comfortable and convenient stay 🌴☀️

Osprey,Buttonwood Cottage.Hot tub -patio.Sublime !

Floridian Tiny Cottage! Buttonwood Cottage is wonderfully located central to the downtowns and beaches of Sarasota and Venice with a private patio space and hot tub. 15 minutes away for the number 1 beach in USA "Siesta Key" . You'll feel that you stepped back in time upon arrival to our charming homestead. I follow Airbnb’s enhanced cleaning protocol, which was developed with expert guidance. Here are a few highlights:

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

Experience luxury at this newly remodeled home with a brand-new pool, spa, and putting green. Centrally-located near downtown Sarasota, Siesta Key, Lido Key beaches, and St. Armand’s Circle, it features a full kitchen, 3 king bedrooms, 3 full bathrooms, outdoor dining, high speed internet, a 75” outdoor TV, fire pit, and EV charger. Pet-friendly with a fenced yard, pet crate, bowls & treats. License # VR24-00208

Sunny Paradise w/Pool&HotTub 5 min to Siesta Key!

Family-Friendly 3BR Home w/ Private Heated Pool, Hot Tub & Backyard– Near Siesta Key! Located just minutes from world-famous beaches, and a wide variety of dining, shopping, and entertainment options, this home is the perfect base for your Sarasota vacation. Whether you’re planning a family trip, a couples’ retreat, or a friends’ getaway, you’ll love the blend of comfort, convenience, and fun!

JULY AVAIL! Sarasota #1 Luxury Villa w/PRIV BEACH!

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Quiet Retreat-5mi to Beach-Hot Tub, Outdoor Shower

Our Quiet Retreat is in the heart of Sarasota - 5 miles to Siesta Key Beach. The home is 2B/2BA with a blow up mattress and can sleep 6. All the basics are supplied to make your stay more comfortable and your trips to the beach more fun! The backyard is private, secluded, and includes a hot tub, lounge area, a heated and private outdoor shower, fire-pit table, and grill.

Near Lido Beach w Hot tub + Fire Pit

Come find a space away in this 2 bedroom 2 bathroom Guest House with a backyard pergola located less than 15 Minutes from Lido Beach in Sarasota. Enjoy all that the area has to offer, and come home to the peaceful ambience of a hot tub and outdoor fire pit. The home is in a safe and friendly neighborhood, with the Legacy Bike Trail right around the corner