Kid-friendly holiday rentals in Longboat Key

Townhouse in Holmes Beach

4.99 out of 5 average rating, 135 reviews

Steps from the Beach! Heated Pool & Spacious Deck!

Welcome to Your Dream Beach Getaway! Steps (one block!) from the sugar-white sands of Holmes Beach. We provide bikes, paddle boards, and all the other beach gear you will need for fun in the sun! Nestled in a quiet beachside community on the famed Anna Maria Island, this newly renovated home is ready for your dream vacation! Enjoy the shared HEATED pool or stroll to shops, restaurants, and the vibrant attractions of Anna Maria Island— a quick walk or trolley ride away. Perfect for families!

4.88 out of 5 average rating, 150 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.

4.97 out of 5 average rating, 101 reviews

Cottage in Bradenton

Escape to Hidden Cove #1 - Privacy with Water View

Most rentals can boast one or two, but this one has ALL THREE. Hidden Cove Cottage No. 1 features: 1) WATER VIEWS - Over 300 feet of shoreline 2) PRIVACY - Over an acre of property protected by security gate and wall 3) LOCATION - Approximately 1 mile from I-75 with all shopping and restaurant options just minutes away 3 bedroom; 2 bath home that sleeps up to 10 people. Bring your toys - RV's, boats and golf carts, plenty of space and no HOA! Golf courses and a boat ramp just steps away.

4.9 out of 5 average rating, 134 reviews

Your Slice of Paradise

20 minutes from Siesta Key, 15 minutes from Lido Beach, Within a mile from Der Dutchman and Yoders Amish Restaurant, this cozy little home is tucked back under a giant oak tree, newly remodeled with new furniture all new mattresses, new kitchen appliances February 2020, 55” Samsung Smart 4K tv screen available for streaming all your favorite shows etc. propane grill for you to use, washer and dryer free for guests, located on a quiet street 1/2 mile from Pinecraft, a very unique community.

Home in Gulfport

4.78 out of 5 average rating, 169 reviews

16 Sandals

According to City of Gulfport ordinances, this property can be rented short term less than 30 days only 3 times per 12 month calendar year, minimum night stay for those short term rentals is 3 nights. All other rentals are 30 days. Home has a private non heated pool. Disclaimer: pool is cleaned by private service every Wednesday. Owner has no control over inclement weather and will not refund any portion of rental due to any issues directly related to weather as related to pool usage.

Superhost

Home in Seminole

4.91 out of 5 average rating, 279 reviews

Beachy Home Minutes from sugary sand beaches

Sunny Florida Beach Home! 4 minutes drive to the #1 best beach in America nominated by Trip Advisor, where you will find beautiful white sand and extremely warm and clear water! Enjoy tons of top local restaurants and entertainment all minutes from your door in this relaxing, low key beach neighborhood. Super kid friendly! Games, BBQ, swing set, Apple TV, and bikes for the whole family! Enjoy the entire house that has been completely remodeled and is sparkling CLEAN!

4.99 out of 5 average rating, 233 reviews

Apartment in Dunedin

Tropical Paradise

Please visit our website Grovekeeper collective for a video of the property Private vacation rental I know if you are coming to Delightful Dunedin you know how amazing this waterfront community is, from award winning restaurants , micro breweries, one of the #1 beaches in America, 40 miles of bike trails, waterfront parks. Just bring food and clothes, we have the rest covered! This rental is for a maximum of 5 guest all our units are non-smoking and vaping

Superhost

Condo in Indian Rocks Beach

4.93 out of 5 average rating, 181 reviews

Waterfront, Harbourside, Water Park, Beach, #7720

4 FREE daily water park passes and parking for one car is included! Just a few minutes walk to the BEACH! This 2/2 condo is located at the 'Harborside@Marker 33' and 'Splash Harbour Water Park' complex. This 7th floor "end unit" has been newly renovated and has a balcony that overlooks the Intracoastal and anther one that overlooks the Water Park. A fully stocked kitchen which includes a washer/dryer makes for that perfect place to bring the whole family.

4.98 out of 5 average rating, 384 reviews

The Cottage at Central Park II

If you are looking for the perfect family home to cater to your every need, then look no further! With plenty of space to spread out, natural light that pours into every room, an expansive and private fenced in yard, screened-in porch and outfitted kitchen- this is the perfect place to entertain AND relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota in one of the areas most sought after neighborhoods you are in the middle of it all!

4.88 out of 5 average rating, 121 reviews

Home in Pinellas Park

Rustic 3BR Raised Ranch on 1.5 acre Farm !!!

Family friendly, fully furnished, 1700+ sq foot split plan home with enormous wrap around deck outside and huge living room space inside. In the middle of everything that makes the Tampa / St.Pete area a great destination, yet off the beaten path (not on a busy road) in heart of equestrian area, directly adjacent to a large community park. Toddler proofed and equipped for family recreation, with plenty of space for the kids to run and play.

Condo in Indian Rocks Beach

4.84 out of 5 average rating, 219 reviews

Waterfront, Harbourside, Water Park, Beach, #6620

4 FREE daily water park passes and parking for one car is included! 3/5 minute walk to the BEACH! This 2/2 condo is located at the 'Harborside@Marker 33' and 'Splash Harbour Water Park' complex. This 6th floor "end" unit has a balcony that overlooks the Intracoastal and another that overlooks the Water Park! Come stay in this rare unit. There is a fully stocked kitchen that even includes a stackable washer and dryer.