Holiday rentals with a hot tub in Osprey

4.97 out of 5 average rating, 35 reviews

Villa in Nokomis

Family Oasis-Beautiful House-Infinity Pool-Beaches

Do you love the beach? Do you love lounging in a beautiful pool surrounded by palm trees and South Florida's world-renowned weather? Look no further because Sunny Oasis is waiting for you! We are located just 2 miles from the beach and 3 miles from Venice Downtown, you are choosing the right place! There is large heated Infinity pool with hot tub, spacious 1-acre courtyard with monkey bars, zip line and much more for the whole family! Make some memories at this unique and family-friendly place.

4.89 out of 5 average rating, 9 reviews

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).

4.93 out of 5 average rating, 81 reviews

Home in Osprey

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.

4.97 out of 5 average rating, 326 reviews

Condo in Siesta Key

On the Beach; Siesta Key SunBum Studio

Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking!

4.95 out of 5 average rating, 22 reviews

Home in Osprey

3 Bed Penthouse w/ Waterview!

Sparkling pool view, tennis courts, and ample open space on Blackburn Bay. 2 Oversized Master EnSuite with King sized bed, walk in closet, and private access to enlarged screened patio. Dedicated garage parking space in building with direct access to elevators. Enjoy exquisite finishes in this tastefully renovated condominium. Large Enjoy sunsets every night on the screened in Balcony. There is no better peaceful quiet location to spend the season in style.

4.85 out of 5 average rating, 34 reviews

Luxury 6BR Retreat with Beach Access

Experience the ultimate Siesta Key lifestyle in this luxurious 6-bedroom coastal retreat. - Private pool and spa with tropical landscaping - Gourmet kitchen with granite countertops and stainless steel appliances - Spacious game/workout room and state-of-the-art movie theater - Smart home features including intercom and security systems - 3-car garage with electric car charger and boat storage - Relaxing balcony overlooking the pool area

5 out of 5 average rating, 103 reviews

Home in Bradenton

AMI Beaches + IMG Sports + Hot Tub & Pool!

🌴Welcome to Beachway Haven! This 5-Star ⭐️ hideaway is just mins from Anna Maria Island's Pristine Beaches & the Gulf of Mexico. Dive into relaxation with your own Heated Saltwater Pool & Spa Hot Tub, nestled in a tropical oasis. Only a skip away from Golf Courses, Nature Parks, IMG Academy, & Palma Sola Causeway's Beach Access – your gateway to Horseback Riding, Kayaking, & endless sandy adventures. Shopping & dining are only a few mins away too!

5 out of 5 average rating, 15 reviews

Home in Nokomis

Spacious 3 Br Home w/ Heated pool -1 Mile to Beach

Forget your worries in this spacious and serene space. As you enter, you will immediately feel at ease with the open floor plan where the living room and kitchen look out to the pool area and a very private backyard.(Private outdoor space to enjoy grilling, dining, and games.) Split-floor plan allows for extra privacy. Intercostal kayak launch in neighborhood (2 included w/ rental). 1 mile walk to the beach and beautiful Casey Key.

5 out of 5 average rating, 5 reviews

Luxury Pool Home by Siesta/Lido

Stylish 3BR/3BA+office centrally located Sarasota home with private heated pool, spa, and fenced yard—just minutes to Siesta Key & downtown. A short bike ride to Arlington Park and Southside Village. Features upgraded kitchen, smart features and putting green. Bedroom not pictured has a bunk with a queen on bottom, twin XL on top. Perfect for families or couples looking to relax, work remotely, or explore Sarasota’s best spots

Superhost

Bungalow in Osprey

4.77 out of 5 average rating, 359 reviews

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:

4.8 out of 5 average rating, 10 reviews

Bayfront Beauty: Heated Pool, King size Bed

Conveniently located near plenty of Sarasota's shopping and dining areas, your new home away from home is nice and isolated, surrounded by gorgeous views and just a quick walk from the waters of Sarasota Bay. You will have whole house except two rooms which will be locked and no one will be there. One bedroom with a king size bed. Full size kitchen, family room, pool and gorgeous view on the salty bay for nature lovers.