Compare Vacation Rentals with Pools in Sarasota, FL

Directly accessible from the Legacy Trail, this Sarasota apartment is a short bike ride from Pompano pickleball courts and a quick drive to Siesta Beach and Lido Beach, offering a fantastic location with a pool.
This family-friendly 3-bedroom apartment accommodates up to 8 guests and features a heated swimming pool, a private fenced backyard with a playset, complimentary bikes, and an outdoor fire pit for evening relaxation.

Just one block east of Ed Smith Stadium, this 2-bedroom apartment in Sarasota offers a private, fenced backyard with a heated swimming pool, perfect for a pool getaway.
This family home is centrally located, providing a 10-minute drive to downtown Sarasota and a 15-20 minute drive to Siesta Key and Lido Key Beaches, with high-speed internet and a fully equipped kitchen.

Centrally located in Sarasota, this apartment is just 8 minutes from dog-friendly Gillespie Park and 6 minutes from Payne Park, with Lido Beach 5 miles away and Siesta Key Beach 7 miles away.
This 1510 square foot apartment with a private swimming pool sleeps 8 guests and features a detached guest house, a fully stocked modern kitchen, and a screened lanai for enjoying the Florida weather.

This secluded, walled-in estate in Sarasota offers a luxurious escape with two custom swimming pools and a spa, ideal for larger parties with its 9 bedrooms and 5.5 bathrooms.
Enjoy elite fitness facilities, a basketball/pickleball court, and indoor entertainment like a pool table and shuffleboard, all within convenient proximity to Sarasota's cultural attractions, dining, and beautiful beaches.

Located in the Whitfield Estates neighborhood of Sarasota, Florida, this apartment is just 1 mile from Sara Bay Country Club and 4 miles from Sarasota Bradenton International Airport.
This 1780 square foot apartment offers a private heated swimming pool, a furnished lanai with a gas grill, and ample parking, accommodating up to 9 guests with 3 bedrooms and 2 bathrooms.

Enjoy panoramic Gulf of Mexico views from this 8th-floor, 2-bedroom apartment located within the gated Longboat Key Club, offering direct access to a private beach just 500 feet away and proximity to St. Armand's Circle.
This expansive apartment, perfect for up to 4 guests, features a gourmet kitchen, a luxurious master suite, and direct access to a swimming pool and hot tub for your ultimate beach getaway.

Just a few minutes' walk from Shell Beach and an 8-minute drive from Siesta Beach, this family-friendly apartment on Siesta Key offers a prime location for beach lovers.
This spacious 4-bedroom, 2-bathroom apartment accommodates up to 10 guests and features a private swimming pool, a large backyard, and modern comforts, making it an ideal getaway with a pool.

Enjoy a prime location in Sarasota's Southside Village, offering a walk-to-everything lifestyle with over 20 restaurants and Morton gourmet grocery nearby, and just a ten-minute drive to Siesta Key and Lido Key beaches.
This one-bedroom apartment provides a relaxing escape with a gorgeous new swimming pool and sun deck, complimentary bicycles and kayaks, and beach essentials for your convenience.

Prime beachfront access puts you steps from Lido Beach, with St. Armand's Circle a 15-minute walk away and Sarasota's attractions like the Ringling Museum just 6 miles distant.
This 780 sq ft apartment offers a family-friendly stay with a well-equipped kitchen, air conditioning, and a swimming pool, making it an excellent choice for your pool getaway in Sarasota.

Located just a short walk from downtown Sarasota and Southside Village, this apartment offers prime "West of the Trail" access to shopping, dining, and entertainment.
This spacious 2200+ sq ft apartment features a split floorplan with 4 bedrooms and 4 bathrooms, accommodating up to 10 guests, and boasts a private, fenced backyard with a swimming pool perfect for relaxation and recreation.

Enjoy a prime waterfront condo in downtown Sarasota, located 2.8 miles from the John and Mable Ringling Museum of Art and just 1.1 miles from Indian Beach.
This pet-friendly accommodation offers a resort-style swimming pool and spa, on-site fitness center, and complimentary parking and WiFi for up to 8 guests.

Just 2 minutes from St. Armands Circle and a 5-minute walk to Lido Beach, this newly renovated apartment in Sarasota's Saint Armands Key offers prime beachfront access and proximity to upscale shopping and dining.
This comfortable apartment with a pool sleeps up to 4 guests and features a recently renovated kitchen and bathroom, king-size bed, queen-size pull-out couch, and convenient first-floor access with covered parking.

This newly renovated apartment in Sarasota offers a private heated swimming pool and spa, perfect for a relaxing getaway.
Conveniently located a 15-minute drive from Lido Key Beach and Siesta Key Beach, this family-friendly apartment also features a spacious lanai, a fire pit area, and is within walking distance to Arlington Park.

Centrally located in South Sarasota, this apartment is just a short drive from white sandy beaches like Siesta Key and Lido Key, as well as attractions such as the Ringling Museum and Mote Marine Aquarium.
This family-friendly apartment sleeps up to 10 guests and features a private screened-in lanai with a swimming pool, a spacious backyard, and a BBQ grill, perfect for outdoor relaxation.

Just minutes from Downtown Sarasota's dining and entertainment, this fourth-floor condo in The Strand offers an exceptional Sarasota getaway with a pool.
This 810 sq ft apartment sleeps two and features a modern kitchen, air conditioning, and access to The Strand's luxury amenities, including a resort-style swimming pool and fitness center.

This South Gate Ridge apartment offers proximity to Siesta Key beach, just a few minutes' drive away, and is conveniently located for exploring downtown Sarasota, St. Armands Circle, and the Mall at University Town Center.
Enjoy 2200 square feet of living space in this family-friendly apartment with a swimming pool, accommodating up to 10 guests with four bedrooms, three bathrooms, and modern amenities including a private terrace and a one-car garage.

Directly on the Legacy Trail, this 4-bedroom apartment is a 5-minute drive to Downtown Sarasota and a 15-minute drive to Siesta Key Beach.
This family-friendly apartment offers private swimming pool access, a fitness center, and a rooftop deck with sunset views, accommodating up to 10 guests.

This Sarasota apartment is located in the Cultural Arts District, a short walk to The Bay Park and Van Wezel Performing Arts Hall, and approximately 6 miles to Lido Key Beach and St. Armands Circle.
Enjoy a resort-style experience with this dog-friendly apartment featuring a community saltwater swimming pool, a spacious wrap-around balcony with canal and bay views, and a modern kitchen, perfect for your getaway.

Located in Sarasota, this vacation home is just 3.6 miles from the Sarasota International Convention Center and 3.9 miles from the Ringling Museum, offering excellent access to local attractions and close proximity to IMG Academy and Siesta Key Beach.
This spacious 4-bedroom vacation home features a private heated swimming pool and a garden, ideal for families and sports enthusiasts seeking a getaway with a pool.

This waterfront apartment in Central Sarasota offers direct Gulf access and is located just 2 miles from St. Armands Circle and Lido Beach.
Enjoy resort-style amenities including a swimming pool, spa, and private boat docks, with kayak and paddleboard launches available from the boardwalk.

Just 500 feet from Lido Beach and a short stroll from St. Armands Circle, this apartment in Sarasota's Lido Key district offers an exceptional location for beach lovers and shoppers.
This expansive 4830 square foot apartment, perfect for 16 guests, boasts 8 bedrooms and 8.5 bathrooms, featuring a private swimming pool with a waterslide, a hot tub, and a rooftop deck, ensuring a luxurious getaway with a pool.

Prime waterfront canal location in Bailey Hall, Siesta Key, this apartment is just blocks from Out of Doors Academy and approximately 1 mile from the village center and closest beach access.
This spacious 2590 sq ft apartment offers a private heated swimming pool with jacuzzi, accommodating up to 16 guests with 5 bedrooms and numerous entertainment options including a putting green and arcade games.

Just steps from Lido Beach and St. Armands Circle's upscale boutiques and dining, this one-bedroom apartment in Sarasota offers a prime location with excellent ratings for both its setting and cleanliness.
This newly remodeled condominium provides a relaxing retreat with a private screened balcony, shared access to a swimming pool, Jacuzzi, and outdoor patio with a charcoal grill, perfect for guests seeking a getaway with a pool.

Centrally located in Sarasota, this apartment is less than 1 mile from Marina Jack's bayfront attractions and just 1 mile from Main Street's dining and entertainment.
This apartment offers a spacious 1 bedroom + den layout with a pull-out couch, accommodating up to 4 guests and featuring a swimming pool, hot tub, and fitness center for your enjoyment.

Located in Downtown Sarasota, this apartment is just minutes from Siesta and Lido beaches, a stone's throw from Arlington Park, and 2 miles from the Legacy Trail.
This modern designer apartment with a new saltwater swimming pool and spa accommodates up to 8 guests, featuring 3 bedrooms, 2 workspaces, and a luxurious outdoor living space with a fire pit and grill.

Just 3 minutes from Siesta Key Beach, this apartment offers exceptional walkability to Siesta Key Village's dining and entertainment.
This pet-friendly apartment sleeps 8 and features 2 bedrooms, 3 bathrooms, a shared swimming pool, and a BBQ area, making it ideal for a relaxing getaway with a pool.

Centrally located in the Arlington Park neighborhood, this apartment is just 2 miles from downtown Sarasota.
This spacious 5-bedroom, 5-bathroom apartment accommodates up to 16 guests and features a private swimming pool, an outdoor kitchen, and a unique 4-hole mini golf course.

Steps from Lido Key's world-renowned white sand beaches, this luxury apartment offers easy access to St. Armand's Circle, just a 4-minute bike ride or 10-minute walk away, perfect for exploring premier dining and shopping.
This expansive 3,300 square foot apartment with a heated swimming pool and waterslide accommodates up to 16 guests across 6 en-suite bedrooms, featuring a resort-style saltwater pool, a rooftop deck with panoramic Gulf views, and a fully fenced backyard with entertainment options.