
Holiday rentals with a hot tub in Osprey
Find and book unique rentals with a hot tub on Airbnb
Top-rated rentals with a hot tub in Osprey
Guests agree: these rentals with a hot tub are highly rated for location, cleanliness and more.

APRIL OPEN 1 min to beach, New, PETS OK!, 2Br/2BTH
EXCLUSVE CASEY KEY beach just .5 mi. away!! Sarasota 10 mins away! Miles of uncrowded beach! Two KING bedrooms, two bath villa! The Villa is a short 1 minute drive from Casey Key Beach! Two new 55" 4K T.V's. New appliances and furnishings throughout! Kayaking, biking, boating... all right here! Lush tropical backyard and fire pit. There are many wonderful restaurants and shops within a five minute drive. Restoring this Villa has been a labor of love for us, read our reviews!! Come stay...:)

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).

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.

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.

South Water View - Residence 502
Residence 502 - Partial Water View SPACIOUS FIFTH FLOOR LUXURY RENTAL WITH OVERSIZED TERRACE. This beautifully appointed residence is one of the very few in the building offering four bedrooms to meet all your needs for the perfect island vacation. Thoughtfully laid out and professionally decorated, this residence truly has it all. The open floor plan features a fully equipped gourmet kitchen, dining area, and light-filled living area featuring floor to ceiling windows that open onto an

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.

Coastal Home in Sarasota-8min from Siesta Key
This pet friendly coastal home has everything you need to enjoy your visit in Sarasota! The home is nestled in a quiet neighborhood in the highly sought-after Gulf Gate community. Spend your day relaxing by the pool and spa or explore the area. The house is only 8 minutes away from worlds #1 Siesta Key beach and minutes away from shopping and restaurants. It’s also a short 15 min drive to downtown Sarasota and 20 minutes away from famous St Armand’s Circle.

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.

Private, beautiful house with a heated pool
Relax with the whole family or a group of friends at this peaceful place in paradise. A beautiful, clean home that can accommodate up to 6 guests. The home is fully remodeled with new furniture. Start your morning with a nice cup of Nespresso by the heated pool and end the night at the jacuzzi in the spacious master bedroom. Located 5 min away from water park(aquatic center) 10 min from the famous Warm Mineral Springs and 25 min from multiple beaches.

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:

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!

The Oz Parlor 2.9 mi beach
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, Amazon and YouTube TV 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.
Popular amenities for rentals with a hot tub in Osprey
House rentals with a hot tub

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

Mermaid's Treasure by Duncan Real Estate

Relax+ Jacuzzi | 9 Min to Siesta Key Beach

Gulfstream Haven

Resort-Style Vacation Villa

Luxury Canal Home | Pool, Spa & Dock Near Beach

Backyard Oasis, Htd Pool/Hot Tub, Beaches, No Fees

Saltwater Villa/Pool/Jacuzzi/MovieTheater/FishDock
Villa rentals with a hot tub

Florida Serene Luxury Retreat | Pool & Spa Oasis

Relaxation awaits in this bohemian inspired villa

Siesta Villa

Luxurious Mangoe 4 bed 2 bath, heated pool & spa

"Everglade Kiss" 3b 2b BBQ, hot tub

Oasis Getaway -Beautiful House-Infinity Pool-Beach

Sunrise Deluxe Villa-Heated Pool&Spa-7min to beach

3685 White Pine Court, Sarasota, Florida
Cabin rentals with a hot tub

Pet Friendly Cabin in Resort

5 star rated guest house on the water heated pool

Dream holiday and fishing house

Cabin with Resort Amenities

1 bedroom cabin in Sun resort

1 Bedroom Cabin with Resort Amenities
Quick stats about holiday rentals with a hot tub in Osprey

Total holiday rentals
Explore 10 holiday rentals in Osprey

Nightly prices starting at
Osprey holiday rentals start at £45 per night before taxes and fees

Verified guest reviews
Over 540 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Holiday rentals with a pool
10 properties feature pools

Wifi availability
10 of Osprey holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Osprey rentals

4.9 Average rating
Osprey stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with a hot tub Sarasota County
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- Rentals with a hot tub United States
- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Captiva Island
- John's Pass
- Turtle Beach
- Coquina Beach
- Vinoy Park
- Caspersen Beach
- Lido Key Beach
- Cortez Beach
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- Anna Maria Public Beach
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- Myakka River State Park
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