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
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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
Dec 13 – 20
Guesthouse in Coral Gables, Florida, US
4.85 out of 5 average rating, 301 reviewsStudio #1 hot jacuzzi Miami Center Beach
Jul 18 – 25
Guesthouse in Barrio Rio Grande, Puerto Rico
4.95 out of 5 average rating, 368 reviewsClean & Breezy Solar Casita :: POOL AC WIFI GRILL
Mar 9 – 16
Guesthouse in Miami, Florida, US
4.93 out of 5 average rating, 521 reviewsArtsy Cottage. Cute patio. LittleHavana & Brickell
Oct 1 – 8
Guesthouse in Fort Myers, Florida, US
4.98 out of 5 average rating, 621 reviewsHints of Key West in Fort Myers' Historic District
Jan 10 – 17
Guesthouse in Punta Cana, Dominican Republic
4.9 out of 5 average rating, 242 reviewsLa casita guesthouse
Jul 27 – Aug 3
Guesthouse in Sarasota, Florida, US
4.97 out of 5 average rating, 233 reviewsCasita Lantana, a 1925 cottage in a Tropical Oasis
Nov 15 – 22
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
Aug 14 – 21
Guesthouse in Toa Alta, Puerto Rico
4.9 out of 5 average rating, 153 reviewsUnder Sea Guest House.
Apr 15 – 22
Guesthouse in Bradenton Beach, Florida, US
5.0 out of 5 average rating, 121 reviewsBradenton Beach Sunsets 1, Anna Maria Island, FL
Sep 15 – 22
Guesthouse in Miami, Florida, US
4.98 out of 5 average rating, 237 reviewsChic Miami Studio - Near Everything Trendy
Jul 19 – 26
Guesthouse in Lauderhill, Florida, US
4.97 out of 5 average rating, 115 reviewsGuest House Oasis
Aug 8 – 15
Guesthouse in Fort Lauderdale, Florida, US
4.86 out of 5 average rating, 116 reviewsTrendy Studio in FLL - Private entrance & bathroom
Sep 26 – Oct 3
Guesthouse in Herradura, Costa Rica
4.89 out of 5 average rating, 103 reviewsCabina Bamboo - Cozy studio cabina with A/C & pool
Jun 8 – 15
Guesthouse in Miami Gardens, Florida, US
4.88 out of 5 average rating, 113 reviewsCozy remodeled private guest house.
Mar 13 – 20
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
Oct 28 – Nov 4
Guesthouse in North Miami, Florida, US
4.89 out of 5 average rating, 148 reviewsStylish North Miami Guesthouse w/Parking-King bed
Jul 23 – 30
Guesthouse in Naples, Florida, US
4.8 out of 5 average rating, 297 reviewsWaterfront Sea Cottage
Jul 17 – 24
Guesthouse in Turrialba, Costa Rica
4.91 out of 5 average rating, 228 reviewsNebliselva 500 Mb optical fiber. Telework or relax
Aug 31 – Sep 7
Guesthouse in Sarasota, Florida, US
4.83 out of 5 average rating, 190 reviewsCozy Cottage by the Bay
Aug 11 – 18
Guesthouse in Fort Myers, Florida, US
4.98 out of 5 average rating, 191 reviewsLil's Lane Farm
Jun 24 – Jul 1
Guesthouse in Englewood, Florida, US
4.97 out of 5 average rating, 202 reviewsShabby chic cottage with pool one mile from beach
Apr 16 – 23
Guesthouse in Fort Myers, Florida, US
4.92 out of 5 average rating, 107 reviewsGet Away to the Mango Cottage
Nov 6 – 13
Destinations to explore
- House rentals Cuba
- Guesthouse rentals Cuba
- Nature eco lodge rentals Caribbean
- Ski-in/ski-out rentals Caribbean
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- Yurt Rentals United States
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