Vacation rentals with a pool in The Meadows

[The Bay St. Hideaway]Private Swimming Pool& Patio

Welcome to Bay Street Hideaway VR24-00156 A beautiful home to make your next family vacation the best one yet! The whole group will enjoy easy access to everything from this centrally located place. The patio fenced in backyard with a private HEATED pool provides a quiet and peaceful area if you want to avoid the crowds.The house is a 2 story completely furnished with 4 bedrooms and 3.5 bathrooms. TV's are provided in the living room, a few bedrooms, and lounge area upstairs. 3 E-bikes included

Location · Family · Pool

Serenity Lake

Keep it simple at this peaceful and centrally-located place. 15 minutes from beaches this lovely apartment sits on a pond full of fish with a dock. Large pool ready for swimming and sunning. Charcoal and gas grill available. Beautiful upper deck to sit and enjoy the large mango tree and view over the lake. Golf cart available for evening rides. There is a large driveway for a boat. Swim and fishing accessories available. Minutes from I-75 - also near the famous Lakewood Ranch downtown.

Location · Value · Comfort

Heated 3BR Pool Home Glen Oaks | Close to Downtown

Family-friendly pool home near Bobby Jones Golf Club, perfectly located in the heart of Sarasota. You’re less than 10 minutes from top attractions, dining, and shopping, Downton Sarasota and just a short drive to the world-famous Siesta Beach or Lido Beach. This private home features its own entrance, a heated pool, and a fully fenced backyard—ideal for families and added privacy. We’re pet-friendly too! Comfortable, central, and close to everything—perfect for your Sarasota getaway VR24-00164

Value · Family · Indoor spaces

Sunshine House, near Downtown, Legacy Trail, Beach

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.

Location · Value · Parks

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.

Value · Location · Pool

Tiki Bar Paradise! Heated Pool & Gaming Oasis!

Welcome to one of our beautiful properties, only 9 minutes to Siesta Key Beach! 24/7 Host Support - no AI messaging or hidden fees. Gorgeous HEATED POOL & Tiki Bar. Corn hole, ring game, or water pong on dry land or play volleyball, basketball, or beer pong in the pool. Bring the competition inside to the Game Room to play billiards or any number of family card/board games. Relax in the cozy living room w/ fireplace & fully equipped kitchen. Minutes to Siesta Key, the Village & Downtown SRQ.

Value · Family · Amenities

Luxury Pool Family Oasis-Siesta Key/DT 3BR/2BA

Welcome to your home away from home! This renovated, spacious, and bright pool home will immerse you in a luxurious experience the minute you arrive. Located on a lush, quiet street, yet close to all of Sarasota's best attractions! Close to Siesta Key Beach (#1 beach in the USA), 10 minutes to downtown (with fantastic restaurants and shopping), and within walking distance of the famous Fresh Fish Waltz Market. Easy I-75 access, Nathan Benderson Recreational Lake Park, and the new UTC mall!

Value · Location · Cleanliness

Dog Friendly -4 Bed 2 Bath w/ HTD Pool (Sleeps 13)

✨ Fully Renovated & Stylish! ✨ Family & Dog-Friendly | Single-Story | Private Saltwater Pool | Secluded Backyard. Enjoy the charm of Sarasota in our completely updated home off University Parkway. Bright, open spaces with new furniture, perfect for relaxation. Features a heated saltwater pool in a private, fenced yard. Close to beautiful beaches—10 miles to N. Lido Beach and 13 miles to Siesta Key Beach. Conveniently located 4 miles from SRQ Airport, ideal for your next memorable get

Value · Family · Quiet

Gorgeous renovation with pool, minutes from beach

Light, bright and newly renovated. Beautifully decorated 3 bedroom home minutes from Siesta Key and downtown. The spacious modern kitchen has a slider that leads to covered porch and large pool with private fenced yard. A second slider from the porch leads to the master bedroom with master bath and walk in closet. Open living room and 2 additional big bedrooms make the house perfectly comfortable for 6. Everything you need is right here! Siesta Key Beach Distance - 16 Min; 6.1 Mi

Location · Value · Grill

Pink Flamingo: 4 Beds/3 Baths Screened Pool Oasis

This wonderful pool home is located in the heart of Sarasota and just minutes away from the world-famous Siesta Key Beach! This fantastic vacation home offers 4 relaxing bedrooms and 3 full baths - there is also a Queen-size pull out sofa in the living room. A real bonus is having two master suites! The first offers a King-size bed with an adjoining bathroom featuring a walk-in shower plus his & her sinks. The second master is appointed with a Queen-sized bed and adjoining bathroom.

Location · Family · Quiet

Casa Cruz-3RM/2BA w/Heated Salt Water Pool

You'll have a great time at this modern 3RM/2 BA house with a heated salt water pool. This beautiful home is located 6 minutes to SRQ Airport, 20 minutes to the #1 rated beach in the country, Siesta Key, 5 minutes to Publix and local restaurants, and 10 minutes to high-end shopping at UTC mall. You’ll have access to major FL highways. The home is equipped with all the essentials needed for short term/long term stays. Book your stay today! Casa Cruz es su Casa!

Value · Family · Heating

Beaches, Shopping, Sculling-Sarasota is calling!

Escape to this 3BR, 2BA Sarasota retreat in a quiet neighborhood, just minutes from UTC Mall, Nathan Benderson Park, and a short drive to award-winning beaches. Sleeps 6 comfortably with a bright open layout, fully equipped kitchen, and cozy living spaces. The highlight is the private heated saltwater pool, perfect for relaxing after a day of shopping, dining, or beach adventures. Your Sarasota getaway starts here!

Value · Family · Kitchen