Vacation rentals with a pool in Sarasota Springs

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Sarasota Springs

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in Lido Key

4.96 out of 5 average rating, 132 reviews

Lido-Key- Tiny Studio Holiday Cottage-A

**No Kids allowed** Lido Key- 7-10 min walk to the beach & St Armands. Quaint main floor tiny (smaller than a hotel room) studio is in a Great location and an affordable way to enjoy this popular area. This cozy cottage features a Queen size bed, refrigerator, stove, microwave, coffee maker, washer & dryer, and fully stocked cooking items & dishes, There is a pull-out large kitchen table. Beach chairs, umbrella & towels are provided. Located at 170 Roosevelt Dr Drive, Sarasota, Fl 34236.

Guest favorite

Guest suite in Sarasota

4.93 out of 5 average rating, 307 reviews

Beach & Town Posh Location! Jungle Paradise Studio

PRIME Town/Beach 3.2 miles location! *Private Studio* Access Non shared Pool. Studio w/private entrance & private patio @Designers private Home,Tropical Jungle, like Posh Resort! Quiet, residential area. Sought-after amenities. 10 min/Siesta Beach, shops, dining, & 5mins/Downtown Sarasota. Walk/local markets/ dining/movies & shopping New King bed. New 50" TV. Off street parking. No Smoking/Vaping! Wet Bar, No kitchen, lite meals only! No hotels in my exclusive area! Live like a local!

Guest favorite

Home in Sarasota

4.98 out of 5 average rating, 133 reviews

Heated Pool Oasis 3BR/2BA near Siesta Key Beach

This Modern House with a heated pool near Siesta Key will be your home away from home! Renovated house has plenty of privacy, space and a lot of sunlight. Luxurious sleeping arrangements will guarantee a relaxing sleep. A quiet neighborhood with a lot of privacy and convenient proximity to all main attractions. A very spacious outdoor space at the pool will be your favorite spot for family dinners and entertainment. This house is located just 15 mins from the famous Siesta Key Beach.

Guest favorite

Home in Sarasota

4.95 out of 5 average rating, 195 reviews

The Oasis-Heated Private Pool Hot Tub-5mi to beach

"The Oasis" is a newly renovated beach cottage with a heated private pool & hot tub in the heart of Sarasota. It's 5 miles to the #1 beach in the USA, Siesta Key Beach. The cottage offers 2 bedroom & 2 bath, with a bonus room which can be used to sleep 6 comfortably. The one-of-a-kind fully private, fully enclosed backyard includes heated pool, hot tub, BBQ grill, outdoor dining table & fire pit for snowbirds & families to enjoy Florida living in style!

Guest favorite

Home in Sarasota

4.93 out of 5 average rating, 157 reviews

Sarasota Sandpiper: 4 Bed/3 bath + Pool

Your Ideal Getaway: All-Inclusive Comfort and Convenience Discover the perfect retreat that's close to everything you desire in a vacation. Whether you're seeking the beach, family-friendly activities, nightlife, mini golf or championship golf courses, you'll find it all at your doorstep. It's a place where you can unwind and savor life's simple pleasures. Embrace the great outdoors with an outdoor space that's perfect for relaxation and enjoyment.

Guest favorite

Rental unit in Sarasota

4.88 out of 5 average rating, 121 reviews

Little gem just 6 min from Siesta+heated pool

★ "Second floor 1 bedroom 1 bathroom apartment" ★ "An incredible apartment and 6 star hospitality!" • 6 min drive from Siesta • Shared heated pool just 200 feets • Screened lanai • pet friendly, no pet fee, no deposit • Fully stocked kitchen • 555 sqft home • walking distance Publix, restaurants, bars • 30 min. drive from SRQ Airport • 60 min. drive from Tampa Airport • 8 min. drive from I-75 • 20 min. drive from the downtown and St. Armand Circle

Guest favorite

Guesthouse in Sarasota

5 out of 5 average rating, 43 reviews

Low Cleaning Fee - Classy Guesthouse mins to all

Surround yourself with style in this standout space with lots of trees and the sound of birds. Everything you need for a peaceful well needed rest and more. Close to SRQ Airport, downtown, UTC and mins away from Siesta Key and Lido Beach. At walking distance from restaurants such as Outback, Metro Diner, McDonald's and Burger King. At a short distance of Detwiler's Farm Market and Walmart Supercenter. Gas stations, laundromats and gyms close by.

Guest favorite

Guesthouse in Sarasota

4.99 out of 5 average rating, 132 reviews

Maggie's Hideaway

This adorable little bungalow is hidden away in one of Downtown Sarasota's oldest historical neighborhoods and only a couple miles from Sarasota Bay and surrounding beaches. Beautiful Lido Beach is only five miles west, Siesta Key is seven miles southwest, with Benderson Park being only seven miles east. Fabulous shopping and world class dining is plentiful in this downtown community. There is plenty to see and do in Sarasota - Come see us!

Guest favorite

Rental unit in Sarasota

5 out of 5 average rating, 5 reviews

Glam 1/1 condo+6 min from Siesta + heated pool

★ "Second floor 1 bedroom 1 bathroom apartment" ★ "An incredible apartment and 6 star hospitality!" • 6 min drive from Siesta • Shared heated pool just 200 feets • pet friendly, no pet fee, no deposit • Fully stocked kitchen • 766 sqft home • walking distance Publix, restaurants, bars • 30 min. drive from SRQ Airport • 60 min. drive from Tampa Airport • 8 min. drive from I-75 • 20 min. drive from the downtown and St. Armand Circle

Guest favorite

Place to stay in Sarasota

4.95 out of 5 average rating, 185 reviews

Sunshine Inn Paradise

Sunshine Inn Paradise Come as guests, stay as friends, leave as family! Step into your private oasis with a sparkling pool, outdoor shower, and deck surrounded by lush gardens. Whether you’re here to relax or explore, everything you need is here We don’t just offer a place to stay—we offer a place to belong. We can’t wait to welcome you as a guest and see you off as family.

Guest favorite

Island in Sarasota

4.97 out of 5 average rating, 317 reviews

New NOV Openings! Sarasota #1 Lux BEACH Villa

BOOK 2024 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!

Guest favorite

Rental unit in Sarasota

4.97 out of 5 average rating, 167 reviews

Gillespie On The Park, Walk to Downtown

Contemporary Studio apartment with balcony above garage. Studio is half block from Gillespie Park with its public walking/jogging/biking paths, tennis courts, basketball court, and retention pond. Within walking distance to downtown and Rosemary District: restaurants, shops, movie theaters, cultural events, Whole Food Market, Starbucks etc.