Family-friendly vacation rentals in Siesta Key

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Top-rated family-friendly rentals in Siesta Key

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Home

4.98 out of 5 average rating, 170 reviews

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

Home

4.87 out of 5 average rating, 118 reviews

IMG golf & close to AMI- Ocean View | Slt Wtr Pool

Welcome to The Beachview @ Bayside in beautiful Bradenton, Florida—a true slice of paradise with stunning views of the inner coastal waterway, Longboat Key, and Anna Maria Island! This spacious beach retreat offers 3 main-level bedrooms and an exclusive Master/Family Suite upstairs, providing the perfect setup for families or groups of friends. Comfort & Relaxation Await Each of the three main bedrooms features a private deck, ideal for sipping your morning coffee or enjoying a sunset cockta

Guest favorite

Rental unit

4.97 out of 5 average rating, 189 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

Guest favorite

Home

4.96 out of 5 average rating, 119 reviews

5 Star! Walk/Bike DTN ~ 5 mi to Lido Beach Pets Ok

Central, Quiet Downtown Neighborhood on Legacy bike trail in Sarasota. 1 mi to Main St dining, theatres & shops. 2 mi to Bayfront waterfront dining, Marina boat trips. 1.6 mi to Bobby Jones golf course. 5 mi to Lido Beach. Near free trolley to St Armands & Lido Beach. Updated comfy, open, clean & bright 3 bedroom/2 bath home with coastal decor. Screened in back lanai porch & large fenced yard. Pets ok. Near Siesta Key, Selby Gdns, Ringling museum, WIFI, SmartTV, BBQ, beach gear, washer/dryer.

Guest favorite

Home

4.88 out of 5 average rating, 145 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.

Guest favorite

Home

4.96 out of 5 average rating, 224 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 .

Guest favorite

Home

4.92 out of 5 average rating, 284 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.

Guest favorite

Home

4.93 out of 5 average rating, 115 reviews

Great shape after Milton -Gorgeous Pool! - os

Great news! We've quickly reopened after Milton! Restaurants, stores, our beach access & Historic downtown-all now open! Beautifully decorated 3 bedrooms, 2 bathrooms, attractive family room & open concept kitchen with breakfast room overlooking private pool. On desirable Island of Venice, “Villa Sorrento” is only 8 minute walk to beach. Near Historic Venice Avenue's unique shops, restaurants. Low-key quiet vacationers only. 2 car max. no visitor parking. No pets. No smoking

Guest favorite

Home

4.91 out of 5 average rating, 288 reviews

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!

Guest favorite

Cottage

4.94 out of 5 average rating, 159 reviews

Cozy Cottage L-Steps to Riverwalk/Close to Beaches

Beautiful cottage style duplex located in Old Downtown West Bradenton in Historic Point Pleasant neighborhood - steps from Riverwalk! Close to beaches!!! Visit RealizeBradenton website for a listing of monthly events , Comfortably sleeps 4 - 1 bedroom with king size bed ,Living area has queen sleeper sofa, Kitchen: well equipped • Guest must disclose if they are bringing a pet and the pet breed • $50 per each 2-7 day stay - per pet

Guest favorite

Home

5 out of 5 average rating, 137 reviews

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

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. 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!

Guest favorite

Rental unit

4.88 out of 5 average rating, 350 reviews

Las Palmas Beach Rentals unit 2

No HOT TUB or Washer/Dryer due to flooding. Unit 2 Ground floor;800 sq ft; patio; limited beach view . Steps to the white sandy beach across the street. Fully equipped kitchen with markets nearby, Restaurants and shopping within walking or hop on the free trolly. Trolly stop nearby. Outdoor open air patio with Caldera Spa and screen porch for outside enjoyment. Linens and basic supplies are included.