
Guesthouse vacation rentals in Caribbean
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Top-rated guesthouses in Caribbean
Guests agree: these guesthouses 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 guesthouses
Family-friendly guesthouses

Casita Linda (Cute Little House)
Mel and Jeff are great. We were actually in the bigger house so I will review that. The location is perfect. Great day trips to beaches, waterfalls, lighthouse and wonderful restaurants! We had everything we needed in the house. Clean, comfortable beds and everything you need. It was a wonderful week. Thank you Mel & Jeff!

Private studio with stunning ocean views
Majestic place and gold-value hosts. Every minute is enjoyed at this location.

CAMPOCOSTA: private property w/pool, near beach
I had an exceptional stay at this lovely Airbnb just steps away from the beach. The location is ideal—close to excellent restaurants and offering stunning views that made the entire trip feel special. The property is spacious, clean, and well-maintained—perfect for a family gathering or group getaway. It had everything we needed for a comfortable and relaxing stay. The host was incredibly friendly, responsive, and made sure we felt welcome from start to finish. I highly recommend this place and would gladly return in the future. One area for improvement would be the outdoor space directly in front of the rooms. It could benefit from more regular upkeep, as there were some stains, scattered leaves, and occasional dog waste that took away from the otherwise beautiful surroundings. That said, it didn’t take away too much from the overall experience, and I would still highly recommend this property. I’d gladly return in the future!

La casita guesthouse
Adorable and beautiful place, Jahel and Karim are very welcoming... We recommend this place very clean and close to all amenities. We'll be back for a future stay...

Country Life Guest house with pool
Peaceful, comfortable place with friendly hosts and animals; many places for walks, bike rides, and rollerblading (wish I'd brought mine); close drive to stores, restaurants and attractions; definitely would stay again; the cats were our favorites

Sarasota guest house only 8 miles to Siesta Key
Our stay at Paulett's guest house was perfect. Her guest house exceeded our expectations. Clean, comfortable, well stocked with everything we needed. It was also easy to maintain while we were there. She had plenty of cleaning supplies, vacuum and a washer/dryer. The neighborhood was quiet and well maintained as well. We enjoyed the private outside space in the back of the house as well. It was a serene place relax after a day at the beach and visiting with family. We would highly recommend Paulett's guest house. We can't wait to return!

Clean & Breezy Solar/Grid Casita : pool, ac, wifi
10/10, a beautiful tranquil stay! Thank you very much Vivienne and Ricardo!

Sandee's Cottage
Our stay here was memorable. The location is perfect-walkable to the beach, restaurants, and the neighborhood. The yard at the cottage is fenced in so my little guy could run around and chase lizards freely. The cottage itself had all the necessary items you would find yourself needing for a few days near the beach. The items you would need to make a few meals for yourself. And the ability to do laundry is so useful, especially with kiddos. There were toys and puzzles for my kiddo too! The cottage reminded me of camping when I was a kid. Nothing fancy, just what you needed. We would definitely recommend this space!
Guesthouses with a patio

Poolhouse Haven
Lesley's place was excellent and very clean. The pool house was very comfortable and private. Lesley and Chris were incredible hosts and made me feel right at home. I highly recommend this place.

Bungalow with Putting Green, Hot Tub, & Garden
Adam was very responsive and the accommodations were centrally located to all types of local activities.

Pradera Country House
Beautiful property, lovely clean home, really cool area in the rain forest, refreshing pool, easy check in.

Under Sea guest house.
We came to “Under the sea” because of my birthday. First I want to say this was a last minute book and we nailed it choosing this place! Right when we arrive we were amazed on how Omar and his wife brought the concept of “Under the Sea” to life. The entrance, the patio, the bathroom, the bedroom, the sounds, I mean everything. Me and my wife love the ocean so, this was the perfect place. If you want somewhere close to everything, peaceful, if you want attention to detail, this is the place. #UndertheSea

The RoofTop House Loft
Breathtaking views and location! Perfect for a holiday escape!

City Garden Cottage
Small yet very cute house, enough for too people. Very well placed :)

Guesthouse on Resort Style Site2
The studio space has everything you need. The terrace was wonderful to have. The kitchenette was well stocked. The pool was fantastic, and a great place to spend the afternoon. You can walk about a km to the Main Street with all the shops and restaurants. Ronette provided lots of tips for the area. Walk up to the Mirador, it’s a great hike. The air conditioning worked well. All the comforts of home.

Escape to Peace.
We stayed at Kashka's property for 4 days. The land surrounding the cottage is stunning and the cottage itself has plenty of space and beautiful custom wood work. We saw green monkeys and horses in the neighboring properties. Kashka is friendly and around when you need him. We recommend this spot to anyone wanting to enjoy a peaceful and nature-driven stay.
Guesthouse rentals with a washer and dryer

Perfect Getaway‼️ 2 Miles from MIA & 8 To UR Cruise
Pedro & Eva are great hosts! Their hosted house looks new and very clean. They have the most complete amenities and supplies in the kitchen that we have seen in Airbnb. They also have two beach chairs, umbrella, and coolers for use. Washer and driers are in the unit and they provide everything you need for laundry. They are extremely responsive and we always get their replies in 5 min. They offer us great privacy and wash the grill for us after our first use. Great host and highly recommend!!

Breeze Villa 1
This is our second time staying at Janet's place and we absolutely love it. The place is clean, spacious, and cozy. It is very close to the airport and only a few minutes away from our favorite beach crash boat. We'll definitely be back.

Palm Tree Paradise Guest House
great place and marvin was wonderful & accommodating

Guest House central to Anna Maria and St Pete
A beautiful home away from home. Very quiet & peaceful neighborhood. Very convenient to every things.

Pompano Beach Guesthouse on the ocean
Our 3rd visit to the Guest House. We enjoy the “Old Florida Bungalow” feel of the place while it’s fully modern & very comfortable inside. Access to the beach directly from the property is such a treat. A nice shaded deck between the Guest house & Main house is great for outdoor dining or coffee. Pompano is a busy place but the Guest House feels very quiet & relaxing.

Cozy 1-Bedroom Private Guesthouse
We had a great time staying at the place. There was everything we needed,also for cooking, and the location was good, for example, to supermarkets or even the center of Miami. the property is located in a quiet area and is great for two people and several days stay. George was a super host always friendly and responsive to our messages. George is a great host. We felt very comfortable.

Gables gated private guesthouse free parking wifi
Great Airbnb would stay there again

Charming SoSo Apartment: Walk to Intracoastal
This was the first time that my husband ever stayed in an Air B & B and it was a great experience for us. The unit was super clean, tastefully decorated with comfortable furniture. It is in a very quiet residential neighborhood which is what we wanted. There are very helpful extras like bikes, helmets, beach towels and toys and even a beach bag. There is a small but super clean and efficient kitchen. I enjoyed my morning coffee at the kitchen table. - The host leaves great instructions about the TV and my husband figured it out pretty easily. I really enjoyed using the bikes and you can easily ride along the intercoastal. The bike ride to the beach is decent but not impossible. You can easily drive to several nearby beaches and I highly recommend having at least one meal at Benny's on the Beach. The hosts were very responsive but not intrusive at all. We stayed in the end of April. The AC worked perfectly . It was a comfortable, private and quiet unit and we would love to come back.
Destinations to explore
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