Guesthouse vacation rentals in Caribbean
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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, 464 reviewsLa Casetta: "the little house" near to the beaches
Guesthouse in Rockley, Barbados
4.97 out of 5 average rating, 150 reviewsFootsteps to the beach
Guesthouse in Coral Gables, Florida, US
4.85 out of 5 average rating, 303 reviewsStudio #1 hot jacuzzi Miami Center Beach
Guesthouse in Miami, Florida, US
4.93 out of 5 average rating, 527 reviewsArtsy Cottage with Cute Backyard 40% Off Tonight!
Guesthouse in Barrio Rio Grande, Puerto Rico
4.95 out of 5 average rating, 370 reviewsClean & Breezy Solar/Grid Casita : pool, ac, wifi
Guesthouse in Fort Myers, Florida, US
4.98 out of 5 average rating, 625 reviewsHints of Key West in Fort Myers' Historic District
Guesthouse in Punta Cana, Dominican Republic
4.9 out of 5 average rating, 245 reviewsLa casita guesthouse
Guesthouse in Sarasota, Florida, US
4.97 out of 5 average rating, 236 reviewsCasita Lantana, a 1925 cottage in a Tropical Oasis
Guest house rentals with a patio
Guesthouse in Toa Alta, Puerto Rico
4.9 out of 5 average rating, 156 reviewsUnder Sea Guest House.
Guesthouse in Miami, Florida, US
4.98 out of 5 average rating, 248 reviewsChic Studio - Near Everything Trendy
Guesthouse in Lauderhill, Florida, US
4.97 out of 5 average rating, 130 reviewsGuest House Oasis
Guesthouse in Bradenton Beach, Florida, US
5.0 out of 5 average rating, 127 reviewsBradenton Beach Sunsets 1, Anna Maria Island, FL
Guesthouse in Fort Lauderdale, Florida, US
4.84 out of 5 average rating, 129 reviewsTrendy Studio in FLL - Private entrance & bathroom
Guesthouse in Herradura, Costa Rica
4.9 out of 5 average rating, 106 reviewsCabina Bamboo - Cozy studio cabina with A/C & pool
Guesthouse in Miami Gardens, Florida, US
4.89 out of 5 average rating, 117 reviewsCozy remodeled private guest house.
Guesthouse in Bradenton
4.99 out of 5 average rating, 138 reviewsConch Cottage adorable one bedroom with pool.
Guest house rentals with a washer and dryer
Guesthouse in Saint Martin, Guadeloupe
4.88 out of 5 average rating, 174 reviewsBungalow aux terres basses
Guesthouse in North Miami, Florida, US
4.89 out of 5 average rating, 152 reviewsStylish North Miami Guesthouse w/Parking-King bed
Guesthouse in Naples, Florida, US
4.8 out of 5 average rating, 305 reviewsWaterfront Sea Cottage
Guesthouse in Miami, Florida, US
4.99 out of 5 average rating, 111 reviewsGuesthome w/ Heated Pool 5 mins from Miami Airport
Guesthouse in Turrialba, Costa Rica
4.91 out of 5 average rating, 230 reviewsNebliselva 500 Mb optical fiber. Telework or relax
Guesthouse in Sarasota, Florida, US
4.82 out of 5 average rating, 194 reviewsCozy Cottage by the Bay
Guesthouse in Fort Myers, Florida, US
4.98 out of 5 average rating, 195 reviewsLil's Lane Farm
Guesthouse in Englewood, Florida, US
4.86 out of 5 average rating, 294 reviewsBeach Casita. Private Beach access.
Destinations to explore
- House rentals Cuba
- Guesthouse rentals Cuba
- Rentals with breakfast Caribbean
- Rentals with a patio Caribbean
- Rentals with a sauna Caribbean
- Treehouse rentals Caribbean
- Bed and breakfasts Caribbean
- Houseboat rentals Caribbean
- Apartment rentals Caribbean
- Rentals with an EV charger Caribbean
- Boutique hotel rentals Caribbean
- Vacation home rentals Caribbean
- Cottage rentals Caribbean
- Kid-friendly rentals Caribbean
- Rentals with a washer and dryer Caribbean
- Fitness-friendly rentals Caribbean
- Hotel rentals Caribbean
- RV rentals Caribbean
- Serviced apartment rentals Caribbean
- Nature eco lodge rentals Caribbean
- Castle rentals Caribbean
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- Aparthotel rentals Caribbean
- Rentals with a fire pit Caribbean
- Rentals with pools Caribbean
- Ski-in/ski-out rentals Caribbean
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- Smoking-friendly rentals Caribbean
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- House rentals Caribbean
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- Townhouse rentals Caribbean
- Villa rentals Caribbean
- Rentals with lake access Caribbean
- Rentals with a kayak Caribbean
- Private suite rentals Caribbean
- Earth house rentals Caribbean
- Wheelchair accessible rentals Caribbean
- Hostel rentals Caribbean
- Condo rentals Caribbean
- Beach house rentals Caribbean
- Rentals with outdoor seating Caribbean
- Rentals with a home theater Caribbean
- Luxury rentals Caribbean
- Rentals with a hot tub Caribbean
- Resort rentals Caribbean
- Shipping container rentals Caribbean
- Tent rentals Caribbean
- Rentals with a fireplace Caribbean
- Tiny house rentals Caribbean
- Rentals with a balcony Caribbean
- Rentals with an accessible height bed Caribbean
- Bungalow rentals Caribbean
- Beachfront rentals Caribbean
- Chalet rentals Caribbean
- Farmstay rentals Caribbean
- Loft rentals Caribbean
- Waterfront rentals Caribbean
- Island rentals Caribbean
- Rentals with an accessible height toilet Caribbean
- Monthly 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
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- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
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- Holiday Apartments Australia
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- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
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- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
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- 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
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- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom