Family-friendly vacation rentals in Sarasota County

4.98 out of 5 average rating, 162 reviews

An outdoor dining area features a wooden table set for four, overlooking a pristine pool. Lounge chairs are positioned nearby, providing a relaxing space for sunbathing. The screened patio ensures comfort while enjoying meals or relaxation outdoors.

Home in Sarasota Springs

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.

4.95 out of 5 average rating, 198 reviews

Modern 4BR Home *Heated Pool & Spa*

Discover elegance in this centrally located Sarasota gem, featuring four bedrooms and two bathrooms to accommodate up to eight guests. Enjoy a laid-back vibe while lounging at Sarasota's beaches or immersing yourself in local attractions. Siesta Beach and Lido Beach are within easy reach at 7.6 and 6.4 miles respectively. Rest easy knowing commitment to cleanliness aligns with your travel priorities. Your serene vacation awaits in this beautifully adorned home. *Brand new pool* VR24-00265

Superhost

A swing chair hangs from the ceiling in a cozy living space, complemented by a dark sectional sofa and a round coffee table. A decorative rug adds warmth to the wooden floor, while a wall-mounted television and a piece of artwork provide visual interest.

4.8 out of 5 average rating, 185 reviews

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.

A private backyard oasis is highlighted by a heated pool and a hot tub, surrounded by lush tropical landscaping. A shaded area with an umbrella and seating for outdoor dining is visible beside the pool, creating a serene environment for relaxation.

4.97 out of 5 average rating, 135 reviews

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

Welcome to Siesta Fiesta, where dreams of relaxation become reality. With the backyard heated pool and hot tub, you have your own oasis to channel inner peace. If you’re feeling froggy, hop over to the beaches, take a kayak tour through the mangroves, a beautiful chartered sunset cruise, or try some of the local eateries that guests rave about! Whether you want to stay in, or go out, this home offers you everything you could need or want and will satisfy for pure relaxation or adventure!

The exterior of a newly renovated home is shown, featuring a light-colored brick facade and a modern garage door. A well-maintained driveway leads to the entrance, which is accentuated by a bright orange door. Landscaping includes gravel beds and low-maintenance plants amidst partial cloud cover.

4.88 out of 5 average rating, 101 reviews

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

4.84 out of 5 average rating, 187 reviews

A spacious, screened-in lanai surrounds a shimmering pool, complemented by comfortable seating and a dining area. Light filters through the enclosure, highlighting the pink exterior walls of the home. Toys and colorful items are visible at the poolside, adding a playful touch.

Bungalow in Sarasota

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.

Home in Gulf Gate Estates

A nautilus shell rests on the sandy beach, displaying striking orange and white stripes. The calm ocean waves gently lap at the shore, while a clear blue sky with scattered clouds provides a serene backdrop to this coastal scene.

4.95 out of 5 average rating, 130 reviews

Beachside Bliss: Family Paradise/Siesta Key3BR/2BA

Private Family Home just 3 miles from Siesta Key Beach! This fully renovated 3BR/2BA retreat is located in the peaceful and prestigious Gulf Gate Estates. Everything inside is brand new, offering comfort and style for your perfect getaway. Relax with family, enjoy the famous white sand beaches of Siesta Key, explore nearby restaurants and shops, and unwind in your spacious private backyard—ideal for morning coffee or evening BBQs. Your vacation paradise awaits!

A modern house is presented with a neatly manicured lawn and a driveway leading to a garage. Lush palm trees and potted plants frame the entrance, while large windows allow natural light to fill the interior. The structure has a welcoming white facade under a gray roof.

4.95 out of 5 average rating, 116 reviews

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!

4.92 out of 5 average rating, 169 reviews

Condo in Sarasota

Cottage on Siesta Key Beachside & Stunning sunsets

Come experience Siesta Key and relax in our beachside cottage. It is sure to refresh you , whether you prefer an incredible one of a kind sunset or a long leisurely walk on the beach with the cool sugar white sand beneath your toes! This is an escape you deserve. The pool is beautiful and conveniently located on your stroll to the beach. If you enjoy music , we are close to several places you can sit & enjoy under the Tiki Huts with refreshments!

Home in Gulf Gate Estates

A spacious backyard features a heated private pool surrounded by a paved area. Lounge chairs are positioned around the pool, with umbrellas providing shade. Lush greenery and a fence frame the yard, creating a serene outdoor setting, ideal for relaxation.

4.8 out of 5 average rating, 136 reviews

Minutes to Siesta! 4BR 2BT Heated Pool Fenced Yard

Spacious 4-bedroom, 2-bath home with a heated private pool, just minutes from the #1 Siesta Key Beach! Located in the Gulf Gate area, you’re only a short drive to the beach, grocery stores, and dining. Enjoy a fully fenced backyard, plenty of parking, and outdoor grill. Inside, you’ll find beach supplies, a fully equipped kitchen, Keurig & drip coffee makers, and TVs in every bedroom—everything you need for a comfortable and convenient stay 🌴☀️

A caged outdoor space features a heated saltwater pool, surrounded by a spacious deck. Sun loungers are positioned nearby, and a covered area for dining is visible in the background. Lush greenery adds a touch of nature to the setting.

4.86 out of 5 average rating, 192 reviews

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!