Vacation rentals with a pool in Sarasota Springs

Sunshine House, close to Downtown

Great location! This is a family friendly home, close to downtown and beaches, with a pool, fenced yard, and a large, screened porch for lounging and having meals outside. Close to all the great things Sarasota has to offer- museums, gardens, theaters, shopping, Sarasota Bay, and beaches. The house is 1.5 miles from downtown, 10 min to St. Armands, 15 min to Lido Beach, and about 20 min Siesta Key Beach. One dog considered with a fee. Children must be supervised at all times in the pool area.

ROYS PLACE private, tropical, romantic paradise.

NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR 2022, 2023, 2024. An exceptional vacation is a frame for an exceptional life. Offered for you, a romantic boutique home. Sarasota Chic decor, quality furnishings, lush tropical landscaping. Only property in urban Sarasota with your own private (EXCLUSIVE to you, NOT shared) CLOTHING OPTIONAL heated pool for tropical fun. One block walk to beautiful sunsets over Sarasota Bay. All tropical serenity yet close to everything.

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

Relax at this modern heated pool house located just 15 min from the famous Siesta Key Beach. Nested in a quiet neighborhood with a lot of privacy, the house has plenty of space for an entire family or a group of friends. An additional family room with a TV for kids. Relax by the pool in the spacious outdoor area or explore the beautiful downtown filled with restaurants. Recently renovated, this home offers handmade authentic Mexican tile flooring to compliment a cozy and contemporary design.

1 House 1400sq. ft. 12 min from Siesta Key!

12 min. from Siesta Key Beach!! Perfect cozy vacation home in quiet, friendly neighborhood. Central to lots of shopping/restaurants. 1-king, 1-queen, bunk beds w/ 1-full & 1-twin. Dog & cat friendly w/ large private fenced yard, & 1-men's & 1-women's bike. Air hockey table w/ board games & pool toys. Fully loaded kitchen & W/D. Spacious living w/ large sectional, swing chair, & all bedrooms come w/ TVs & free Netflix & Hulu. Looking forward to hosting you! Message me anytime w/ questions.

La Hacienda / heated pool, hot tub, 6 mi to beach

Experience the allure of La Hacienda, a charming rental with a warm Southwestern-inspired interior with unique touches. This 4-bedroom, 2-bath home features a spacious living room with comfortable seating and multiple smart TVs. The private backyard awaits with a heated pool and hot tub for ultimate relaxation and entertainment. Located near downtown, you'll have easy access to beaches and dining. Indulge in the perfect blend of chillin', grillin' and sippin' at La Hacienda!

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.

Downtown Apartment w/ Pool, Gym, & Coworking 329

This 2/2 apartment features an oversized kitchen with island, slider with views of Downtown. Primary has a king bed and en-suite bathroom. 2nd bedroom has a twin bed with twin trundle. Shared amenities include: gym; sunset deck; massive roof deck with heated pool; gazebo with big-screen TV, fireplace, wet bar, dog run and access to the adjacent Cowork office space building. Also on-site is a full service cafe.

NEW 4/NTS AUG 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!

Tropical Luxury: Pool, Game Room, Near Beaches

Welcome to your luxury, pet-friendly retreat! Just 15 min to Siesta & Lido beaches and the airport, this 4-bed oasis packs resort vibes into one easy stay. Heated pool & covered game room Sun-filled lounge, fire-pit & fenced yard Plush luxury beds for dreamy sleep Chef-ready kitchen, washer & dryer Unwind, explore, repeat—your tropical getaway starts here.