Family-friendly vacation rentals in Downtown, Sarasota

4.98 out of 5 average rating, 174 reviews

A serene backyard features a large saltwater pool surrounded by lush greenery and tropical plants. Comfortable loungers are positioned near the pool, inviting relaxation under clear blue skies.

Home in Bradenton

Sunshine Retreat with heated saltwater pool

A beautiful 4 bedroom 2 bath home in a very quiet neighborhood in NW Bradenton. Quiet hours from 9pm to 7am. This ideal location is minutes away from the beautiful beaches of Anna Maria Island and IMG academy. Less than a mile to grocery stores, restaurants and shopping. The house has WIFI and cable TV. Fully stocked kitchen: Pots, pans, utensils, new stainless steel appliances, coffee maker, Keurig, etc.). New saltwater pool and privacy fenced in back yard. Two stall garage for parking.

Superhost

A light and airy kitchen space features modern cabinetry and stainless steel appliances. A glass dining table is surrounded by four upholstered chairs. Natural light streams in through large sliding doors, revealing an outdoor patio area adorned with greenery.

Townhouse in Siesta Key

4.86 out of 5 average rating, 145 reviews

"Relax Here" -Royal Palm Suite- Siesta Key Beach

The pampering begins HERE: 3 bed/ 2.5 baths townhouse, sqft 1,850, 2 kings & 1 queen bed, an enchanting loft bedroom with it's own balcony and incredible Gulf / Beach views All 3 balconies have Gulf views!! Imagine sitting on your patio and watching people at the beach. Gumbo Limbo Rentals is a mini resort, 60 steps to the beach with only 2 duplexes sharing a black bottom lagoon pool which is heated during the colder winter months. Free: Wifi, beach chairs & sun umbrellas, 2-3 parking spaces

Apartment in Holmes Beach

A charming cottage is surrounded by lush palm trees and tropical landscaping. A white picket fence frames the property, with a sandy pathway leading up to the entrance. Bright sunlight enhances the inviting atmosphere of the outdoor space.

4.97 out of 5 average rating, 191 reviews

Crows Nest at Spinnakers Vacation Cottages

Close to the beach, family-friendly activities, nightlife, and the free AMI trolley. You’ll love the location, the ambiance, and the high ceilings. Located in the lush tropical paradise of Spinnakers Vacation Cottages. Offers a spacious living area, with the bedroom and bathroom on the living floor with a spiral staircase leading to a loft with two twin beds. Great for couples, families and dogs (with small pet fee) Great private deck for star gazing! Spa maintains same temperature as pool

A white gazebo is surrounded by lush greenery, featuring a round table and four chairs with bright green cushions. The flooring is concrete, and the structure offers a shaded retreat, providing an inviting space for relaxation and conversation.

4.93 out of 5 average rating, 110 reviews

Sunny Sarasota Vacation Home - VR2400236

Quiet Neighborhood - Single Private Home, Great Location! This beautiful home includes 3 bedrooms, 2 bathrooms and sleeps up to 10 people. Near #1 Rated SIESTA KEY BEACH & LIDO KEY BEACH. Come and relax in this newly renovated home. Large living room, dining room and lanai to accommodate your friends & family. 5 TV's, DVD players, Cable, Internet. Fully equipped kitchen & laundry. Bus stops, grocery stores & restaurants are near by. Base rate covers 6 guests; $20.00/night/additional guest.

A cozy living area is highlighted by a soft, textured chair and a light wooden console holding a large television. A view into the adjacent bedroom is visible, featuring a spacious bed and bedside tables, while natural light cascades in through the windows.

4.88 out of 5 average rating, 153 reviews

5 minutes to private Siesta Key Beach + 2 pools

Best getaway, beach vacation, and staycation! The luxurious condo is on the 1st. floor and located on Siesta Key in a tropical setting. It is kid-friendly and has private access to its private beach on Siesta Key Beach within 5 minutes of walking distance (the Best Beach in the U.S.A.) with crystal white sand and turquoise waters of the Gulf of Mexico. There are two heated pools, barbeque areas, lighted pickleball and tennis courts, a fishing pier, a gym, and a sauna, all for your enjoyment.

A modern kitchen features dark wood cabinetry and a granite countertop. Stainless steel appliances, including a refrigerator and dishwasher, are included. A doorway leads to a bright living area where natural light filters through a window, illuminating a cozy seating arrangement.

4.96 out of 5 average rating, 236 reviews

The Key Lime Cottage 2 miles from Siesta Key Beach

Great location. 2 miles from the # 1 rated Beach in America , Siesta Key . The cottage is near several other beaches as well. Close to restaurants and shopping. 1 hour from Tampa and 2 hours from Orlando. The Key Lime Cottage is totally updated with new stainless steel & granite in the kitchen . There are two new beds ..... one is a queen size and the other is a full size. (URL HIDDEN) Linens & towels are all new. New tile and wood floors throughout. Quite neighborhood for walking .

4.92 out of 5 average rating, 294 reviews

❤ Villa & Garden in Downtown ~ 5 Min to Beaches

Our bright and contemporary Heart Villa offers the quintessential Sarasota downtown and beach experience. It is nestled among tropical trees in a charming cul-de-sac in historic Laurel Park – right in the heart of downtown with loads of restaurants, boutiques, and sights on offer. Several fantastic beaches are just 5-mins ride away! And the villa's private garden is the perfect place to enjoy alfresco dining! We’ve poured our hearts & souls into this villa, it's our family business.

5 out of 5 average rating, 140 reviews

A charming cottage is depicted with light blue wooden siding and white accents. The front yard is gravelled, surrounded by landscaping featuring mature trees and shrubs. A welcoming porch with a railing leads to the main entrance, enhancing the property's inviting look.

Home in Siesta Key

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

FULLY RESTORED POST HURRICANE! HERE IT IS! This “one of a kind” property is uniquely situated between the beach, canal, village with a private heated pool & dock, one of the best spots on Siesta Key! This charming 1,500 sq. ft. cottage beach home is being offered for the 1st time and post hurricane updates! If you want a cute, private original bungalow style beach cottage home all to yourself without the shared wall feel of a condo, then you are in the right spot!

4.91 out of 5 average rating, 297 reviews

A modern game room features a foosball table at its center, surrounded by bar stools. Two flat-screen TVs are mounted on the walls, and pendant lights illuminate the open kitchen area, which includes a spacious countertop and sleek appliances.

Home in Bradenton

Palm Retreat Gold: Luxury Edition of #1 Rental

High end, luxury 3/2 pool home! 7 4k TVs w/ Netflix and cable (75" in living room), SONOS throughout house/pool, wifi, PS5, private heated salt water pool/Spa, putt putt, foosball, beach gear, Pack & Play, Game room (board games, billiards, shuffle board, arcade), massive kitchen/bar, washer & dryer, garage parking-- all in a quiet and safe neighborhood. Just 5 miles to the best beaches and restaurants. Entire home with no shared amenities!

Superhost

The bathroom features modern tile walls and flooring, with a compact toilet and a sink against a stone backdrop. Fresh towels hang nearby, and a small wooden storage unit holds linens. A patterned shower curtain adds a touch of color to the space.

Apartment in Bradenton Beach

4.86 out of 5 average rating, 369 reviews

Las Palmas Beach Rentals unit 2

Unit 2 Ground floor;800 sq ft; patio; limited beach view . Steps to the white sandy beach across the street Free parking to registered guest. Fully equipped kitchen with markets nearby, Restaurants and shopping, within walking or hop free trolly. Trolly stop nearby. Linens and basic supplies are included. Overnight guest are welcome to arrive early to adventure the island, stay parked until after sunset on departure day.

4.9 out of 5 average rating, 101 reviews

A single-story house is framed by a large pine tree and colorful landscaping. The brick exterior is complemented by white walls and red accents around the windows and doors. A fenced area is visible in the background, providing a sense of privacy.

Home in Bradenton

Large Sparkling Clean Pool Home West Bradenton

3 Bedrooms, 2 Baths, Whole House all to yourselves. Huge sparkling clean blue pool and deck with table and grill. Fenced private backyard. Great for families and kids. Fully equipped kitchen. Everything you need for a fun vacation! Close to Beaches, IMG, Restaurants, Shopping. Why stay in a tiny hotel? Why not have a peaceful vacation?