Kid-friendly holiday rentals in Caribbean

Barefoot Bliss Bungalow 10 minutes to Siesta Beach

Escape to this beach inspired bungalow with a fully equipped kitchen and a fenced yard to relax in the sunny outdoors. Only 10 minutes to Siesta Key Beach! Enjoy the Sarasota beaches, museums, parks and downtown Sarasota, all just minutes away. Centrally located to grocery stores and restaurants. From coastal decor to comfortable beds, every part of your experience was thoughtfully curated by the owners to allow you to sit back, so feel free to put your feet up and relax at Barefoot Bungalow,

Adorable private studio

Relaxing, private, peaceful and centrally-located studio. You do not share your space with anyone. Walking distance to restaurants, supermarket, bus stop, Gym and Florida International University. Conveniently close to Miami Airport, Kendall Regional Hospital, Dolphin Mall, TopGolf, Everglades Airboat Expeditions, City Place Doral with Fresh Market, shops, Movie Theaters, Comedy Club, live music and more. Eleven miles from Bayside and Wynwood Walls. The beach? A short 15-mile drive!

Cozy Oasis for 2 w/ Insta-worthy Tropical Pool*

👙 New resort-style tropical pool & hottub 🏠 Super stylish & comfortable 🌆 2 mi to beach & downtown. 🛌🏽 Westin Heavenly Bed; ultimate comfort and sleep ✅ Kitchen is fully stocked; ready for gourmet cooking 🏖️ Beach chairs, towels, & sport-brellas available for you. 🐶 Low pet fee; bring your furry friends! 💻 WFH ready - Super high speed internet. 📺 Large Smart TVs in both bedrooms & living rooms 😊 Hosts with a service heart (we’re here to make your trip perfect!)

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!

Cozy Cabin Next To Sanibel With Paddle Boards

Paddle Board Canin Stay on adventure's doorstep! 5 miles to FMB and Sanibel island (beaches, salt water fishing, paddle boarding, kayaking ). Are guests enjoy free amenities: 1. Coffee/tea/bottled water 2. Bicycles 3. SUP - inflatable paddle boards 4. BBQ gas grill 5. Beach chairs and umbrella 6. Cooler and beach towels 7. Secured Wi-Fi 8. Amazon TV, Netflix, Hulu, Disney +, ESPN+ 9. Parking 2 cars 10. Washer and dryer in house 11. Kids toys and books

Hyde Park/Southside Village Modern 5 Star Home

BEST LOCATION/BEST VALUE ON 5 STAR HOME All 5 Star Reviews! Love This Location! Recently fully remodeled home. Three blocks to Southside Village, Morton's Market, fantastic shops and restaurants. Beautiful Arlington Park is down the street with pool, tennis, walking trails and dog park. 7 Minute Drive to Siesta Key or Downtown. **We love and welcome small dogs in our home. We need them declared at the time of booking. There is a small pet fee.

Luxe 4BR Waterfront w/Htd Pool, 5min to beach

Luxurious private waterfront home minutes to gorgeous South Florida beaches, great restaurants, and much more! The home features luxury living at its finest with an open concept design, a gourmet kitchen, 4 generous bedrooms, 3 lavish bathrooms, a game room and a stunning resort yard with a kids playground, an outdoor kitchen/bar & a pool overlooking the canal.

Stylish Coastal Stay ☀ Ideal Zoom Background

50's-inspired surf shack a short walk to the beach on the barrier island. Modern amenities with 1200 Mbps unlimited wifi with direct Ethernet connection & smart TVs throughout. Spend your days basking in the sun with your cooler on wheels and beach chair backpack. Come back to a luxurious rainfall shower, fresh bathrobes, and a grill ready for cooking.

541 Seashell Cottage | Pool-Spa

Welcome to 541 Seashell Cottage! Escape to this cozy & inviting 2BD, 2BA home, perfectly situated just 5 blocks from stunning, white sand beaches. This charming home offers a serene & comfortable retreat with a private entrance, screened patio, & access to a shared pool, making it the perfect spot for beach lovers & relaxation seekers alike.