Vacation rentals with a hot tub in Osprey

4.97 out of 5 average rating, 33 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.

4.97 out of 5 average rating, 75 reviews

Sandy Feet Retreat- Cozy Bungalow & Outdoor living

Welcome to Sandy Feet Retreat! Our single family home is located in Sarasota Florida, only 8 miles from Siesta Key, 5 miles from downtown Sarasota, and only one block away from the Legacy Trail. The perfect Sarasota Home for your trip, featuring a cozy coastal theme with amenities, including a hot tub, grilling station, fire pit, and outdoor entertaining area. Just 2 miles off I 75, this charming vacation home is a short drive from many local restaurant options. Enjoy all Sarasota has to offer.

Apartment in Indian Beach-Sapphire Shores

4.96 out of 5 average rating, 173 reviews

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.

4.92 out of 5 average rating, 102 reviews

Spectacular Sunsets! 15 min Siesta Key!

This villa is spacious and bright with lots of windows. The interior has just been updated. Tropical decor makes you feel like your’e at the beach. Huge flat screen TV. Tile flooring in the living areas and laminate in the bedrooms. Screened lanai overlooks palm tree and mature landscaping. Wireless fast speed internet included. It has everything you need for a short visit or extended stay. Fully equipped kitchen. Washer and Dryer. Beach chairs and towels. One car garage and driveway space.

5 out of 5 average rating, 8 reviews

Heated pool/Jacuzzi/Pickleball/3637YPC

Just steps to the heated community pool, hot tub, clubhouse and tennis/pickleball courts. Spacious villa (sleeps 5 ) with 2 bdrm, 2 bath, 1 car garage and screened in lanai. Open and bright. Two outside sitting areas, one in front and one in the back lanai. Two community tennis courts (one with pickleball), putting green, shuffleboard, library and billiards. Close to Legacy Trail, Downtown Sarasota and Venice. Multiple Beaches within a 15 min drive including Award Winning Siesta Key Beach.

4.93 out of 5 average rating, 80 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, 325 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!

5 out of 5 average rating, 102 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!

Superhost

Bungalow in Osprey

4.77 out of 5 average rating, 358 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:

5 out of 5 average rating, 227 reviews

Apartment in Englewood

The Oz Parlor 2.9 mi beach hot tub pool

The Oz Parlor apartment was originally the main house of this whimsical property. It has loads of charm It is a great place to relax and Just Bee... Please note I don’t have cable TV my TVs are wireless I have Netflix and Amazon prime. Located in the Historic District of Englewood a lovely walk to fine restaurants, Indian Mound Park on Lemon Bay and 2.9 miles to Englewood Beach.

4.97 out of 5 average rating, 329 reviews

Island in Sarasota

NEW 3/NTS JULY OPEN! Sarasota #1 Lux BEACH Villa

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!