Guesthouse vacation rentals in Caribbean
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Caribbean
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Caribbean guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Sarasota, Florida, US
4.93 out of 5 average rating, 456 reviewsLa Casetta: "the little house" near to the beaches
Aug 12 – 19
Guesthouse in Rockley, Barbados
4.97 out of 5 average rating, 147 reviewsFootsteps to the beach
Apr 13 – 20
Guesthouse in Coral Gables, Florida, US
4.85 out of 5 average rating, 300 reviewsStudio #1 hot jacuzzi Miami Center Beach
Oct 22 – 29
Guesthouse in Barrio Rio Grande, Puerto Rico
4.95 out of 5 average rating, 368 reviewsClean & Breezy Solar Casita :: POOL AC WIFI GRILL
Apr 10 – 17
Guesthouse in Miami, Florida, US
4.93 out of 5 average rating, 521 reviewsArtsy Cottage. Cute patio. LittleHavana & Brickell
Feb 4 – 11
Guesthouse in Fort Myers, Florida, US
4.98 out of 5 average rating, 620 reviewsHints of Key West in Fort Myers' Historic District
Jul 17 – 24
Guesthouse in Punta Cana, Dominican Republic
4.9 out of 5 average rating, 242 reviewsLa casita guesthouse
Jun 8 – 15
Guesthouse in Sarasota, Florida, US
4.97 out of 5 average rating, 233 reviewsCasita Lantana, a 1925 cottage in a Tropical Oasis
Nov 11 – 18
Guest house rentals with a patio
Guesthouse in Sarasota, Florida, US
5.0 out of 5 average rating, 100 reviewsMagical Guesthouse 1 mi from SRQ airport
Sep 3 – 10
Guesthouse in Toa Alta, Puerto Rico
4.9 out of 5 average rating, 153 reviewsUnder Sea Guest House.
Jan 4 – 11
Guesthouse in Bradenton Beach, Florida, US
5.0 out of 5 average rating, 120 reviewsBradenton Beach Sunsets 1, Anna Maria Island, FL
Jan 9 – 16
Guesthouse in Lauderhill, Florida, US
4.96 out of 5 average rating, 113 reviewsGuest House Oasis
Aug 8 – 15
Guesthouse in Miami, Florida, US
4.98 out of 5 average rating, 237 reviewsChic Miami Studio - Near Everything Trendy
Jul 19 – 26
Guesthouse in Fort Lauderdale, Florida, US
4.86 out of 5 average rating, 115 reviewsTrendy Studio in FLL - Private entrance & bathroom
Sep 18 – 25
Guesthouse in Herradura, Costa Rica
4.9 out of 5 average rating, 102 reviewsCabina Bamboo - Cozy studio cabina with A/C & pool
Mar 31 – Apr 7
Guesthouse in Miami Gardens, Florida, US
4.88 out of 5 average rating, 112 reviewsCozy remodeled private guest house.
Nov 18 – 25
Guest house rentals with a washer and dryer
Guesthouse in Saint Martin, Guadeloupe
4.88 out of 5 average rating, 173 reviewsBungalow aux terres basses
Jan 9 – 16
Guesthouse in North Miami, Florida, US
4.89 out of 5 average rating, 148 reviewsStylish North Miami Guesthouse w/Parking-King bed
Aug 27 – Sep 3
Guesthouse in Naples, Florida, US
4.8 out of 5 average rating, 296 reviewsWaterfront Sea Cottage
Dec 8 – 15
Guesthouse in Tamarindo, Costa Rica
4.97 out of 5 average rating, 190 reviewsPool side Deluxe Cottage
Jun 20 – 27
Guesthouse in Turrialba, Costa Rica
4.91 out of 5 average rating, 228 reviewsNebliselva 500 Mb optical fiber. Telework or relax
Aug 28 – Sep 4
Guesthouse in Sarasota, Florida, US
4.83 out of 5 average rating, 190 reviewsCozy Cottage by the Bay
Jul 19 – 26
Guesthouse in Fort Myers, Florida, US
4.98 out of 5 average rating, 191 reviewsLil's Lane Farm
Apr 13 – 20
Guesthouse in Fort Myers, Florida, US
4.92 out of 5 average rating, 107 reviewsGet Away to the Mango Cottage
Nov 3 – 10
Destinations to explore
- Guesthouse rentals Cuba
- House rentals Cuba
- Rentals with breakfast Caribbean
- Condo rentals Caribbean
- Rentals with a fire pit Caribbean
- Smoking-friendly rentals Caribbean
- Rentals with an EV charger Caribbean
- Family-friendly rentals Caribbean
- Wheelchair accessible rentals Caribbean
- Campsite rentals Caribbean
- Bungalow rentals Caribbean
- Townhouse rentals Caribbean
- Kid-friendly rentals Caribbean
- Tiny house rentals Caribbean
- Rentals with a balcony Caribbean
- Cottage rentals Caribbean
- Bed and breakfasts Caribbean
- Rentals with a washer and dryer Caribbean
- Chalet rentals Caribbean
- Vacation home rentals Caribbean
- Rentals with an accessible height bed Caribbean
- Boutique hotel rentals Caribbean
- Rentals with beach access Caribbean
- Loft rentals Caribbean
- Rentals with a fireplace Caribbean
- Cabin rentals Caribbean
- Nature eco lodge rentals Caribbean
- Treehouse rentals Caribbean
- Fitness-friendly rentals Caribbean
- Resort rentals Caribbean
- Boat rentals Caribbean
- Luxury rentals Caribbean
- Rentals with an accessible height toilet Caribbean
- Monthly Rentals Caribbean
- Rentals with a patio Caribbean
- RV rentals Caribbean
- Rentals with a sauna Caribbean
- Rentals with a home theater Caribbean
- House rentals Caribbean
- Rentals with lake access Caribbean
- Villa rentals Caribbean
- Pet-friendly rentals Caribbean
- Rentals with outdoor seating Caribbean
- Houseboat rentals Caribbean
- Hostel rentals Caribbean
- Beach house rentals Caribbean
- Earth house rentals Caribbean
- Private suite rentals Caribbean
- Tent rentals Caribbean
- Waterfront rentals Caribbean
- Shipping container rentals Caribbean
- Serviced apartment rentals Caribbean
- Rentals with a hot tub Caribbean
- Rentals with a kayak Caribbean
- Rentals with pools Caribbean
- Aparthotel rentals Caribbean
- Hotel rentals Caribbean
- Apartment rentals Caribbean
- Island rentals Caribbean
- Farmstay rentals Caribbean
- Beachfront rentals Caribbean
- Guesthouse rentals Trinidad
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom