Family-friendly vacation rentals in Downtown, Sarasota

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Popular amenities for Downtown, Sarasota family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favorite
A screened-in pool area features a sparkling pool surrounded by a spacious patio. Lounge chairs provide seating options, while colorful floaties rest on the water's surface. The backyard is lined with lush greenery, offering a sense of privacy and relaxation.
Home in Sarasota
4.98 out of 5 average rating, 141 reviews

Gorgeous Home / Heated Pool and Spa

svitlanaRating, 5 stars2 weeks ago
Another great stay at this house! Love the location, very clean throughout, has everything you would need and more. We spent most of our time in covered outdoor area which has lots of seating options, the pool/hot tub is perfect! The only small issue we had was the door to the pool does not lock securely, therefore adding a safety risk if you have young children. It needs to have an added safety lock on top or something to that nature.
Guest favorite
A landscaped pathway is flanked by vibrant flowering plants and palm trees. Neatly trimmed grass lines the walkway, leading to a serene courtyard. Soft lighting from a garden lantern adds to the peaceful ambiance of this tropical setting.
Condo in Siesta Key
4.93 out of 5 average rating, 148 reviews

Siesta Key Serenity At The Palm Bay Club

LauraRating, 5 stars1 month ago
Super clean, quiet, comfy bed. We enjoyed the bayside pool. Nice views. Palm Bay club nice benefit as after a short walk over to the beach we enjoyed the chaises delivered and set up close to the water and hole drilled for our beach umbrella. Amazing sand is not over rated. Warm gulf waters and easy entry and exit. Breeze Trolley with their app made getting around without driving convenient . Lots of fun food and shops minutes away. This bayside spot a was a delight.
Guest favorite
A stunning pool area is surrounded by lush greenery and tropical plants. A prominent rock feature with multiple waterfalls is visible, providing a serene focal point in the outdoor space. The vibrant blue water complements the natural elements, creating a tranquil retreat.
Island in Sarasota
4.97 out of 5 average rating, 327 reviews

NEW 3/NTS JULY OPEN! Sarasota #1 Lux BEACH Villa

KaraRating, 5 stars1 week ago
We had a fantastic stay! The beach was just a short walk away and so easy to access, which made our days relaxing and stress-free. The private pool was a huge hit—our kids were entertained for hours, and it gave us plenty of time to unwind. Christopher was incredibly friendly and went above and beyond to make sure we had everything we needed. You can tell he truly cares about his guests’ experience. We would absolutely stay here again!
Top guest favorite
A sandy pathway leads through lush greenery, providing access to a charming two-story building. The structure features a spacious balcony, surrounded by palm trees and local vegetation, under a bright blue sky with scattered clouds.
Apartment in Longboat Key
4.95 out of 5 average rating, 103 reviews

Longboat Key-OCEAN FRONT- on the beach

JimRating, 5 stars1 month ago
Absolutely loved our stay! The place was spotless, beautifully decorated, and had everything we needed for a relaxing getaway. The location was perfect—just steps from the beach with stunning views and peaceful surroundings. Cindy was incredibly responsive and welcoming. We’ll definitely be back—highly recommend
Superhost
A private pool area is surrounded by tropical greenery, featuring a wooden deck with smooth steps leading down to the water. Bright lounge chairs sit nearby, and pool floats are casually draped over the railing, inviting relaxation and enjoyment.
Home in Sarasota
4.76 out of 5 average rating, 114 reviews

5min to Siesta, Heated Pool & Jacuzzi, Grill, WiFi

JulianRating, 5 stars4 weeks ago
Our stay was amazing, Ven was a great host, unfortunately there are always minor issue that come about when staying in properties but their communication was so great it over shadowed all of our concerns! Thank you for the stay!
Guest favorite
A spacious backyard is showcased, featuring a six-hole putting green with vibrant green turf. String lights are draped overhead, creating a warm ambiance against a pastel sunset sky. Outdoor seating areas and a solid fence provide privacy, enhancing the inviting outdoor environment.
Home in Sarasota
5 out of 5 average rating, 9 reviews

Putt 'n Plunge Paradise: 3/2 15 mins to Beach!

PamelaRating, 5 stars5 days ago
I love love this place. What a beautiful peaceful house. I rented the house for me and my daughters, we had an amazing time there. The house comes with everything you need for a getaway. It’s close to so many beaches, restaurants, shopping and grocery stores. Only 15 min away from my favorite beach which is Lido Beach. Erinn is a lovely host, communicating immediately and extremely friendly. I would definitely stay here again :).
Guest favorite
An aerial view captures the expansive Siesta Key coastline, showcasing a stretch of sandy beach meeting calm blue waters. Nearby buildings and lush greenery punctuate the landscape, highlighting the serene environment just minutes away from the cottages.
Cottage in Sarasota
4.77 out of 5 average rating, 132 reviews

Siesta Key Cottages Crescent 1B Beach/Pool/Hot Tub

ElbaRating, 5 stars1 day ago
Marc and Dave made our stay incredible. Their response was always fast and helpful. Great location and amenities.
Top guest favorite
A spacious, heated pool is surrounded by tall trees and located within a manicured community. Comfortable lounge chairs are arranged around the pool, inviting relaxation under the clear blue sky. Sunlight reflects off the water's surface, creating a serene atmosphere.
Home in Sarasota
4.92 out of 5 average rating, 48 reviews

3655 White Pine Ct, Sarasota, FL 34238

AlbenaRating, 5 stars1 month ago
Our family of four had a fantastic time. The villa was spotlessly clean, had all that one might need to cook meals and was in a beautiful complex with a large and also spotlessly clean pool. The location is perfect to get to all the beaches in no time and a short driving distance to Anna Maria Island, St. Petersburg and Tampa with all they have to offer. The hosts were very responsive and even recommended some activities in the area , which ended up being great. All in all , a great place that we hope to return to.

Family- and pet-friendly home rentals

Guest favorite
A private tropical heated pool is framed by lush greenery and palm trees. A lounge chair with a colorful towel rests beside the tranquil blue water. The inviting pool area is enclosed in a screened area, enhancing privacy and comfort.
Home in Bradenton
4.95 out of 5 average rating, 259 reviews

Paradise Retreat

TeresaRating, 5 stars1 week ago
Maggie’s place is perfect!! So convenient to everything you need!! Everything in house that you would need and also everything you need to go to the beach!!! Maggie is very fast to responding to any questions you have!! 5 star for sure!!
Guest favorite
A warm and welcoming room showcases a blend of natural wood paneling and vibrant artwork. Seating is provided by three bamboo stools, while a desk and lamp create an inviting workspace. A blue quilted bed and framed photos enhance the cozy atmosphere.
Home in Holmes Beach
4.97 out of 5 average rating, 135 reviews

Twin Palms: Big House Steps to Beach w/Lush Pool

BrandonRating, 5 stars1 week ago
Staying a this Airbnb on Anna Maria island was nothing short of amazing. From the moment we arrived, everything exceeded our expectations. The location was unbeatable, just a short stroll to the beach, where we spent our mornings. The home itself was spotless, beautifully maintained, and had everything we needed. The private pol was a dream-crystal clear and perfect for relaxing after a day at the beach. It truly felt like our own personal oasis. What really made the experience stand out was the host. Communication was prompt, friendly, and thoughtful from start to finish. They went above and beyond to make sure we felt welcome and had everything we needed to enjoy our stay. If you're looking for a peaceful, beachside retreat with all the comforts at home- and then some- this is the place. Anytime we travel to this island this is the first place I will check to see if it is available.
Superhost
A bright and inviting bedroom features two twin beds adorned with a coastal-themed bedspread. Large windows allow natural light to fill the space, framed by turquoise curtains. A bedside table with lamps sits between the beds, complemented by cheerful nautical decorations on the walls.
Villa in Sarasota
4.76 out of 5 average rating, 127 reviews

Aloha Villa Pet Friendly 3 miles to Siesta Key #2

AwildaRating, 5 stars2 months ago
I visited Sarasota with my family from the state of Rhode Island from April 4 to April 7 and we stayed at Jason’s & Laura house and it was an amazing experience. The house was very clean and organized. The house is located on a great neighborhood, super safe and great amenities. The house was stocked with beach supplies like beach chairs, beach towels, a boogie board and a beach cooler that was so nice. The house was exactly what we were expecting, I would recommended to everyone. Thank you Josh and laura.
Guest favorite
An oversized private pool is surrounded by lush tropical plants and palm trees, offering a serene atmosphere. The pool features a gently curving shape and a tiled edge, with comfortable lounge chairs positioned nearby for relaxation.
Home in Bradenton
4.77 out of 5 average rating, 258 reviews

Tropical Paradise - Private Pool - Close Beaches

DarleneRating, 5 stars3 weeks ago
Will definitely stay again if I ever come back this way. I wanted a place that had a private pool and was pet friendly. I got both. The neighborhood is peaceful. The house is very spacious and clean. One downside, there is no tv in the master bedroom but that was fine too. Don’t need to be in bed with a pool like this one. Thank you for allowing me to stay.
Top guest favorite
A rectangular swimming pool is surrounded by a paved patio featuring a round table with four metal chairs. Potted plants with various greenery decorate the area, and a small structure is visible in the background under a clear blue sky.
Guesthouse in Sarasota
4.99 out of 5 average rating, 117 reviews

Sarasota Pool House

DanRating, 5 stars2 months ago
This was our second time staying at Lubos pool house. We really enjoyed our stay and are already looking far time to escape back. Great location near restaurants, stores and beaches. Back yard and pool are a dream and very peaceful.
Guest favorite
The exterior of the home is framed by lush greenery and palm trees. A brick pathway leads to a welcoming entrance adorned with a combination of vibrant plants and trees, creating a serene outdoor environment.
Home in Palmetto
4.91 out of 5 average rating, 154 reviews

Historic Home with Boat parking 0.6M of Boat Ramp

SandyRating, 5 stars3 days ago
We loved Ben and Ann’s place. It was just as described and more. Very comfortable and inviting. The location was perfect for us with great places to go within a short walk or drive. Ben and Ann were easy to contact if needed. Their home was comfortable and had all the amenities one could ask for. We highly recommend their place and will definitely return.
Top guest favorite
A charming yellow home is set against a backdrop of palm trees, with a brick paved driveway leading to a two-car garage. Lush greenery surrounds the property, providing a sense of privacy and tranquility.
Home in Siesta Key
4.91 out of 5 average rating, 120 reviews

Siesta Key, FL - Casa Berano

DarrylRating, 5 stars1 month ago
We thoroughly enjoyed our stay. The house was a private and calm place to come home to after our long beach days. We enjoyed spending our nights out by the pool. The pool lights we a nice touch. Would recommend to those who enjoy being in a quiet area.
Guest favorite
A living room features two reclining genuine Italian leather couches arranged to face a wall-mounted 58" flat screen TV. Natural light enters through sheer curtains, highlighting the wood-burning fireplace and polished wooden flooring. A fan is centrally located above for ventilation.
Home in Sarasota
4.83 out of 5 average rating, 227 reviews

Home away from home mins to Siesta Beach!

MikeRating, 5 stars1 week ago
Melissa has a beautiful place and is a wonderful host. Extended our stay one day due to a last-minute change. Very responsive and helpful! Cannot recommend the location more - quiet, close to everything you need. Stay here while in Sarasota...unless we're there!!

Family-friendly home rentals with a pool

Top guest favorite
A comfortable living area features a neutral sofa with decorative cushions, flanked by two bedside tables with lamps. A piece of wall art depicting a beach scene adds a calming touch, while a ceiling fan provides overhead cooling. Natural light is visible through an open doorway.
Condo in Siesta Key
4.92 out of 5 average rating, 239 reviews

Sea Club 2-Relaxing Siesta Key Condo-Siesta Sky

KassandraRating, 5 stars1 week ago
Such a beautiful stay with all the amenities, clear instructions and a clean place with everything you need surrounding you. Beautiful home, I appreciate the stay!
Top guest favorite
A serene community pool is surrounded by a fence and complemented by lounge chairs positioned nearby. The pool's clear blue water reflects the sunlight, while the yellow exterior of the building provides a warm backdrop. Windows with awnings complete the inviting atmosphere of the area.
Apartment in Sarasota
4.94 out of 5 average rating, 153 reviews

Super Clean! 2/2 condo Walk to SKey!

MargaretRating, 5 stars1 month ago
This place was perfect for two couples and close to the beach etc The beds were comfortable and check in and check out easy. We would stay here again
Top guest favorite
A vibrant outdoor space features a heated saltwater pool surrounded by comfortable lounge chairs. Colorful shade sails provide protection from the sun, while an umbrella-shaded dining area accommodates eight. Lush palm trees complete the tropical ambiance, creating a perfect relaxation spot.
Home in Bradenton
4.99 out of 5 average rating, 101 reviews

Pickleball | Heated Pool | Game Room | 4 Min to Be

OmarRating, 5 stars1 week ago
We had a great time. Super clean, beautiful home, full of extras. The property has many things to do and keep everyone entertained. Great communication, definitely one of our favorite vacation homes. Can’t wait to stay here again!!!
Top guest favorite
A serene private pool area is framed by lush greenery and palm plants, with a view of a white fence. Two blue Adirondack chairs sit on the grass beside the pool, inviting relaxation under the sun.
Home in Siesta Key
5 out of 5 average rating, 144 reviews

Beach, Village, Dock & Private Pool! One-of-a-kind

ZacharyRating, 5 stars1 month ago
Marko’s family home was beautiful, charming, and spotlessly clean. The home is perfectly located, walkable to beautiful beaches and great restaurants and shops, including the market. Marko was extremely hospitable, ensured we were all set and gave wonderful recommendations. We loved this place and will be back again next year. Thank you!
Guest favorite
The exterior of a well-maintained condominium is displayed, featuring a two-car garage and neatly trimmed hedges. Palm trees and lush landscaping frame the entrance, while a clear blue sky enhances the tropical feel of the setting.
Home in Sarasota
4.88 out of 5 average rating, 156 reviews

5 minutes to private Siesta Key Beach + 2 pools

DonnaRating, 5 stars1 month ago
Solen was an amazing host—very responsive, friendly, and helpful throughout our stay. She even brought us a brand-new can opener when we needed one! The house was spotless, cozy, and located in a great area. We had a wonderful time and would definitely stay again!
Guest favorite
A single-story home is depicted, featuring a light-colored facade and a two-car garage. Lush green grass surrounds the property, with palm trees partially framing the view. The sky is filled with fluffy clouds, enhancing the welcoming appearance of the residence.
Home in Sarasota
4.86 out of 5 average rating, 170 reviews

The Sea is Calling

KellyRating, 5 stars4 weeks ago
This house was beautiful and we felt right at home! The pool was wonderful!! They provided everything you need for a beach/ pool vacation. We loved it, would stay again if in the area!!
Top guest favorite
A private pool area is surrounded by lush greenery, featuring a clear blue water pool and four lounge chairs positioned for relaxation. Umbrellas provide shade, enhancing the serene outdoor space. Tropical plants are situated along the edge, adding to the natural atmosphere.
Home in Sarasota
4.98 out of 5 average rating, 105 reviews

SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!

MattRating, 5 stars3 weeks ago
Great place, very clean and had everything we needed. Instructions very clear and the pie waiting for us in the fridge was much appreciated! The beach gear was a nice touch, just a pity the weather wasn’t kind to us.
Superhost
A heated pool is framed by lounge chairs, with lush tropical plants surrounding the area. The back of the home features large glass doors, providing a view into the inviting living space. A subtle sunset sky adds a soft glow to the scene.
Home in Sarasota
4.77 out of 5 average rating, 138 reviews

"Charming Pool Home 1 Mile from Siesta Key"

LoriRating, 5 stars1 week ago
The house was really great as were the hostesses. There were a few things like the air having to be set to 73 and no lower that seemed a bit odd for a summer day in Florida, but there were a ton of ceiling fans that helped keep things cool. The back yard and pool were a perfect little escape and it was a quick uber ride to some nice restaurants. If you want to be walking distance to the beach/water this may not be what you are looking for but Siesta Key is still less than a 20 minute car ride. Overall I would definitely stay with this group again. Instructions were clear and responsiveness/attentiveness was on point!

Quick stats about vacation rentals that are family-friendly in Downtown, Sarasota

  • Total rentals

    70 properties

  • Nightly prices starting at

    R177 ZAR before taxes and fees

  • Total number of reviews

    2.4K reviews

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with a pool

    20 properties have a pool

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

Destinations to explore

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