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Family-friendly vacation rentals in Caribbean

Find and book unique family-friendly homes on Airbnb

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Top-rated family-friendly rentals in Caribbean

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

Guest favorite
Condo in Montego Bay, Jamaica
Jus' Beachy! Luxury Apt in a B/front Gated Cmnty.
This new beach theme apartment is located in 22 Freeport – A gated community in Freeport Montego Bay. 22 Freeport is a beach front complex on a Marina that features 24 hour security, a gym, infinity edge pool and playground; whilst the unit on the ground floor opens onto a cozy back yard space that flows into an open green space. Be sure to check out my other units in this community on my profile if your dates are not available or if you would like to book them all for your large group.
Dec 4 – 11
$195 per night
Guest favorite
Home in Havana, Cuba
Casa Colonial 1922-Entire apartment-DATA internet
Painstakingly restored Casa Colonial 1922 is a private, complete apartment with 2 bedrooms. Spread over 2 levels the home features generous outdoor spaces and refined comfort indoors. Your casa away includes a 70 ft wrap around balcony accessed through 7 doors, 16 ft ceilings, spiral stairs, roof gardens, original tile, 6 AC splits + fans, a modern kitchen, 3 full bathrooms (one en suite), laundry, Also included: A view of the busy Havana street life and Hammocks for maximum relaxation.
Nov 8 – 15
$206 per night
Guest favorite
Apartment in Miami, Florida
Luxury ICON Brickell Condo @47th Floor / POOL
This Unique and Deluxe 5-star Condo, Fully Equipped and located in the same building of the famous W Hotel, Icon Brickell, at 47th-floor with the biggest SWIMMING POOL in town. We are located on the mouth of Miami river on the sea, with amazing views of the sunrise in the morning and sunsets in the dusk. Steps from City Centre Mall, downtown, restaurants, cafés, and nightclubs. Five to six miles from Design District & South Beach. THIS IS THE PLACE TO STAY!
May 8 – 15
$257 per night

Popular amenities for Caribbean family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Apartment in Miami, Florida
Front Sea, Corner, Balcony, Luxe, Above W, Wi-Fi
Jan 7 – 14
$865 per night
Superhost
Apartment in Miami, Florida
★ FANCY 2BR/2BA CORNER UNIT | ICON BRICKELL ❤️
Apr 12 – 19
$423 per night
Guest favorite
Apartment in Miami, Florida
2BD PH W/ Top Views & Five-Star Amenities | W 49
Apr 27 – May 4
$779 per night
Superhost
Apartment in Miami, Florida
New Presidential Royale Direct Oceanfront Apt-1001
Oct 10 – 17
$715 per night
Guest favorite
Cottage in San Isidro, Costa Rica
Country house with panoramic view
Aug 3 – 10
$44 per night
Guest favorite
Apartment in Cartagena, Colombia
31 floor Sea Retreat ♥BOCAGRANDE / MORROS CITY♥
Mar 24 – 31
$178 per night
Guest favorite
Villa in La Fortuna, Costa Rica
Hummingbird Arenal Villa & private pool
Jan 18 – 25
$255 per night
Guest favorite
Home in Havana, Cuba
Water-facing relaxation
Jan 24 – 31
$354 per night
Guest favorite
Home in Punta Cana, Dominican Republic
Puntacana 3BR Modern Villa with Private Pool*****
Aug 9 – 16
$248 per night
Superhost
Apartment in Cartagena, Colombia
Casa del Colegio
Sep 15 – 22
$262 per night
Guest favorite
Home in Cartagena, Colombia
Beautiful Private Home in Centro Historico, Pool..
Jan 28 – Feb 4
$158 per night
Guest favorite
Cabin in La Fortuna, Costa Rica
Casa del Rio- Gaspar- Breakfast Included
Sep 23 – 30
$157 per night

Family- and pet-friendly home rentals

Guest favorite
Home in Hollywood, Florida
Pool House 3B/2B King Bed EV-Charger Hollywood, FL
Sep 21 – 28
$374 per night
Guest favorite
Cabin in Vinales, Cuba
The Sunset Sheet
Dec 15 – 22
$29 per night
Guest favorite
Home in Oranjestad, Aruba
Cas de Mango
Oct 26 – Nov 2
$112 per night
Guest favorite
Apartment in Palm Beach Gardens, Florida
PGA National Golf Course View Condo-Renovated 2023
Jan 13 – 20
$495 per night
Guest favorite
Apartment in Havana, Cuba
OCEAN VIEW / GREAT LOCATION
Apr 2 – 9
$92 per night
Superhost
Guest suite in San Juan, Puerto Rico
The Vintage Treehouse at La Botanica
Aug 31 – Sep 7
$304 per night
Superhost
Guesthouse in LC, St. Lucia
Romantic hideaway The Lodge at Cosmos St Lucia
Aug 25 – Sep 1
$450 per night
Guest favorite
Home in Cartagena, Colombia
Casa Bovedas - Private Pool - 3 Bedroom
Aug 4 – 11
$622 per night
Guest favorite
Apartment in Havana, Cuba
Terrace Vista Capitolio
Feb 15 – 22
$90 per night
Superhost
Condo in Montego Bay, Jamaica
Ocean View Penthouse on Hip Strip Montego Bay Wifi
Sep 9 – 16
$159 per night
Guest favorite
Apartment in Havana, Cuba
Cozy Apartment Valdés - Historic Center - Wiffi
Jan 4 – 11
$40 per night
Guest favorite
Apartment in Havana, Cuba
❤ The Lovers Place - 100m Central Park & Capitol
May 29 – Jun 5
$49 per night

Family-friendly home rentals with a pool

Superhost
Villa in Soufriere, St. Lucia
Villa Piton Caribbean Castle
Apr 9 – 16
$450 per night
Guest favorite
Apartment in Rincón, Puerto Rico
Rincón Beachfront Retreat King Master Private Balcony &pools
Apr 27 – May 4
$314 per night
Guest favorite
Home in Rincon, Puerto Rico
Casa Ensenada- Rincon Puerto Rico
Sep 14 – 21
$413 per night
Superhost
Home in Wilton Manors, Florida
Private Oasis, Pool. Walk to Dining, Entertainment
Jul 3 – 10
$272 per night
Superhost
Home in Naples, Florida
Coastal Getaway w/ Inground Heated Pool
Dec 16 – 23
$250 per night
Guest favorite
Apartment in Leeward Settlement, Turks & Caicos Islands
Romantic Apartment few steps from beach
Dec 5 – 12
$290 per night
Superhost
Townhouse in Cruz Bay, U.S. Virgin Islands
Luxury 2 Bed/2 Bath, Ocean View, Pool, Walk2Town!
May 16 – 23
$539 per night
Superhost
Condo in Carolina, Puerto Rico
Breathtaking Views, Beachfront, Remodeled!
Jan 16 – 23
$504 per night
Guest favorite
Cottage in Ocho Rios, Jamaica
"Tumbleweed Cottage"
Sep 11 – 18
$193 per night
Guest favorite
Home in Tower Isle, Jamaica
Tranquil Times Villa
Jan 22 – 29
$458 per night
Guest favorite
Guesthouse in Biscayne Park, Florida
Cozy and charming cottage
Jul 18 – 25
$135 per night
Superhost
Condo in Santo Domingo, Dominican Republic
Welcoming Studio Surrounded by Beautiful Garden
May 10 – 17
$66 per night

Destinations to explore