Guest house holiday rentals in Caribbean
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Top-rated guest house rentals in Caribbean
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for guest house rentals in Caribbean
Family-friendly guest house rentals
Guest house in Sarasota, Florida, US
4.93 out of 5 average rating, 455 reviewsLa Casetta: "the little house" near to the beaches
12–19 Aug
Guest house in Rockley, Barbados
4.97 out of 5 average rating, 147 reviewsFootsteps to the beach
8–15 Apr
Guest house in Coral Gables, Florida, US
4.85 out of 5 average rating, 301 reviewsStudio #1 hot jacuzzi Miami Center Beach
22–29 Oct
Guest house in Barrio Rio Grande, Puerto Rico
4.95 out of 5 average rating, 368 reviewsClean & Breezy Solar Casita :: POOL AC WIFI GRILL
9–16 Feb
Guest house in Miami, Florida, US
4.93 out of 5 average rating, 521 reviewsArtsy Cottage. Cute patio. LittleHavana & Brickell
1–8 Feb
Guest house in Fort Myers, Florida, US
4.98 out of 5 average rating, 621 reviewsHints of Key West in Fort Myers' Historic District
20–27 Mar
Guest house in Punta Cana, Dominican Republic
4.9 out of 5 average rating, 242 reviewsLa casita guesthouse
25 Sept – 2 Oct
Guest house in Sarasota, Florida, US
4.97 out of 5 average rating, 233 reviewsCasita Lantana, a 1925 cottage in a Tropical Oasis
20–27 Sept
Guest house rentals with a patio
Guest house in Sarasota, Florida, US
5.0 out of 5 average rating, 100 reviewsMagical Guesthouse 1 mi from SRQ airport
22–29 Sept
Guest house in Toa Alta, Puerto Rico
4.9 out of 5 average rating, 153 reviewsUnder Sea Guest House.
23–30 Sept
Guest house in Bradenton Beach, Florida, US
5.0 out of 5 average rating, 121 reviewsBradenton Beach Sunsets 1, Anna Maria Island, FL
12–19 Jan
Guest house in Lauderhill, Florida, US
4.97 out of 5 average rating, 115 reviewsGuest House Oasis
8–15 Aug
Guest house in Miami, Florida, US
4.98 out of 5 average rating, 237 reviewsChic Miami Studio - Near Everything Trendy
19–26 Jul
Guest house in Fort Lauderdale, Florida, US
4.86 out of 5 average rating, 116 reviewsTrendy Studio in FLL - Private entrance & bathroom
12–19 Aug
Guest house in Herradura, Costa Rica
4.89 out of 5 average rating, 103 reviewsCabina Bamboo - Cozy studio cabina with A/C & pool
7–14 Jun
Guest house in Miami Gardens, Florida, US
4.88 out of 5 average rating, 113 reviewsCozy remodeled private guest house.
8–15 Oct
Guest house rentals with a washing machine and dryer
Guest house in Fort Lauderdale , Florida, US
4.92 out of 5 average rating, 130 reviewsVilla with Heated Pool, Laundry, Ping Pong & More
17–24 Jan
Guest house in Saint Martin, Guadeloupe
4.88 out of 5 average rating, 173 reviewsBungalow aux terres basses
30 Nov – 7 Dec
Guest house in North Miami, Florida, US
4.89 out of 5 average rating, 148 reviewsStylish North Miami Guesthouse w/Parking-King bed
19–26 Jul
Guest house in Naples, Florida, US
4.8 out of 5 average rating, 297 reviewsWaterfront Sea Cottage
8–15 Dec
Guest house in Tamarindo, Costa Rica
4.97 out of 5 average rating, 190 reviewsPool side Deluxe Cottage
20–27 Jun
Guest house in Turrialba, Costa Rica
4.91 out of 5 average rating, 228 reviewsNebliselva 500 Mb optical fiber. Telework or relax
30 Aug – 6 Sept
Guest house in Sarasota, Florida, US
4.83 out of 5 average rating, 190 reviewsCozy Cottage by the Bay
11–18 Sept
Guest house in Fort Myers, Florida, US
4.98 out of 5 average rating, 191 reviewsLil's Lane Farm
24 Jun – 1 Jul
Destinations to explore
- House rentals Cuba
- Guest house rentals Cuba
- Nature eco lodge rentals Caribbean
- Ski-in/ski-out rentals Caribbean
- Rentals with outdoor seating Caribbean
- House rentals Caribbean
- Beach house rentals Caribbean
- Earth house rentals Caribbean
- Holiday home rentals Caribbean
- Motorhome rentals Caribbean
- Rentals with a firepit Caribbean
- Smoking-friendly rentals Caribbean
- Rentals with a washing machine and dryer Caribbean
- Beachfront rentals Caribbean
- Bungalow rentals Caribbean
- Townhouse rentals Caribbean
- Container rentals Caribbean
- Farm stay rentals Caribbean
- Boutique hotel rentals Caribbean
- Rentals with lake access Caribbean
- Rentals with breakfast Caribbean
- Rentals with beach access Caribbean
- Loft rentals Caribbean
- Family-friendly rentals Caribbean
- Wheelchair-accessible rentals Caribbean
- Cabin rentals Caribbean
- Cottage rentals Caribbean
- Bed and breakfasts Caribbean
- Chalet rentals Caribbean
- Rentals with pools Caribbean
- Rentals with an EV charger Caribbean
- Island rentals Caribbean
- Boat rentals Caribbean
- Hostel rentals Caribbean
- Luxury rentals Caribbean
- Serviced apartment rentals Caribbean
- Rentals with an accessible-height bed Caribbean
- Rentals with a balcony Caribbean
- Rentals with a patio Caribbean
- Houseboat rentals Caribbean
- Rentals with a hot tub Caribbean
- Rentals with a kayak Caribbean
- Villa rentals Caribbean
- Pet-friendly rentals Caribbean
- Apartment rentals Caribbean
- Hotel rentals Caribbean
- Flat rentals Caribbean
- Rentals with an accessible-height toilet Caribbean
- Rentals with a cinema Caribbean
- Rentals with a sauna Caribbean
- Fitness-friendly rentals Caribbean
- Monthly Rentals Caribbean
- Tent rentals Caribbean
- Waterfront rentals Caribbean
- Treehouse rentals Caribbean
- Rentals with a fireplace Caribbean
- Aparthotel rentals Caribbean
- Private suite rentals Caribbean
- Resort rentals Caribbean
- Campsite rentals Caribbean
- Family-friendly rentals Caribbean
- Tiny house rentals Caribbean
- Guest house 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
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- Big House Rentals United States
- 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
- 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