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Guesthouse holiday rentals in Caribbean Sea

Find and book unique guesthouse rentals on Airbnb

Top-rated Guesthouses in Caribbean Sea

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Top Guest favourite
A private infinity pool is situated on a terrace, overlooking lush greenery and a panoramic ocean view. A vibrant rainbow arcs across the horizon, while gentle waves suggest a tranquil atmosphere. The pool's edge blends seamlessly with the surrounding landscape.
Guesthouse in Saint Thomas
5 out of 5 average rating, 114 reviews

Sunrise Cottage - Secluded, Romantic, Private

Sunrise cottage is located on the cool & breezy north side of St. Thomas. A relaxing 1 bedroom cottage with a full kitchen & living area. You can soak up the sun on the sundeck or hang out in your private soaking pool, while appreciating the breath taking view during the day & the abundance of stars at night. When venturing out you are 20 mins to Magen’s Bay Beach, 15 mins to Town, 30 mins to Red Hook. Note: The hosts live on property with 2 dogs and this cottage is adult only 18 or older.

Top Guest favourite
Guesthouse in Vieques
4.99 out of 5 average rating, 335 reviews

Artist A frame in Paradise Casa Mandala #1

Reconnect with nature at this funky unforgettable escape. This is a stand alone 10x12 A frame cabin next to my small main house. The restroom and large outdoor shower room are steps away and offer a private outdoor shower experience. Ac in room is super cold with queen bed with breathable memory foam mattress provide cozy feel. Beach chairs ,towels, and snorkel masks included. Parking on-site. Don't take my word for it read the reviews. I am also able to help out should the need arise.

Guest favourite
Clear turquoise water is seen from the edge of a boat, with gentle ripples reflecting sunlight. Surrounding mangroves provide lush greenery along the shoreline, enhancing the serene atmosphere of the natural landscape.
Guesthouse in Lajas
4.93 out of 5 average rating, 110 reviews

High Tide Guesthouse - Room #3

Welcome to High Tide Guesthouse, we are centrally located in the vibrant town of La Parguera, Puerto Rico. Our Guesthouse is a short walk from restaurants, gift shops, boutiques and much more. The area consists of the famous Keys such as Caracoles, Mata La Gata, and the Bioluminescent Bay. All of these experiences are just minutes from our newly renovated rooms. This small room is perfect for a single person or a couple for a weekend getaway. See host profile for additional rooms too!

Top Guest favourite
A refreshing swimming pool features a sparkling blue surface with fountain jets and is flanked by a shaded seating area with comfortable lounge chairs. Elegant greenery surrounds the space, enhancing the serene atmosphere of the outdoor area.
Guesthouse in Jayuya
4.97 out of 5 average rating, 253 reviews

Pradera Country House

Located in the Tierra Alta, surrounded by flora and fauna, with a panoramic view of Puerto Rico's highest mountain. Experience cool, dark nights under an impressive starry sky. During the day, enjoy the warm sun and refresh yourself in our private pool. Find nearby shops, restaurants, and tourist spots, allowing you to explore and enjoy the area. Immerse yourself in the natural beauty that surrounds us, escape the hustle and bustle of the city, and find peace in a unique environment.

Superhost
A rustic jacuzzi area is framed by wooden walls lined with green accents. Natural light filters through small arch windows, reflecting off the tiled floor and illuminating the inviting space. The glimpse of the blue pool can be seen beyond, enhancing the tranquil atmosphere.
Guesthouse in Mayagüez
4.87 out of 5 average rating, 342 reviews

Imperial Rustic

Es un penthouse rustico, la piscina y el jaccuzy son totalmente exclusivo para los huespedes, el check in 3 pm y el check out 12 pm Tiene un jaccuzy rustico y varias terazzas, donde pueden contemplar el paisaje de la naturaleza. Tiene un cuarto matrimonial y otro cuarto en el segundo nivel muy romantico para parejas, tiene una cama en el exterior, bbq, hamaca, columpio, sillas reclinables mecedoras, luces en las terrazas y en los cuartos, entre otros para su disfrute.

Top Guest favourite
A modern studio is presented with a spacious bed, accented by decorative pillows and towels. Soft lighting is provided by hanging globes, and a comfortable seating area is shown. Large glass doors open to a private balcony, allowing natural light to fill the room.
Guesthouse in Playa del Carmen
4.99 out of 5 average rating, 157 reviews

Casa Machetes Tobalá Studio .

Independent studio with a touch of good taste, attached to Casa Machetes, have a nice common terrace to enjoy the sunsets and take a refreshing dip in the pool. The Tobala Studio has a king size bed, spacious closets, a kitchenette equipped with a refrigerator, grill, microwave, utensils, and a coffee maker. Add air conditioning, fan and a smart TV. It has a small balcony with ferns for the taste of smokers. Come and live the experience of being at Casa Machetes.

Top Guest favourite
Guesthouse in Rincón
4.85 out of 5 average rating, 155 reviews

Private Pool, Ocean View, walk to Sandy Beach

RELAX and Enjoy Island Time Located only seven houses up the road from Sandy Beach, You’ll be able to enjoy this quiet and quaint economical casita located in the heart of the well known Puntas neighborhood with it’s handful of restaurants, bars, food trucks, and other amenities like yoga, and surfboard rentals, and some of the best surf breaks. This casita is ideal for couples or solo travelers who want to get away, disconnect and enjoy Rincon at their own pace.

Superhost
Guesthouse in Rincón
4.85 out of 5 average rating, 550 reviews

Ocean-View Studio + Patio | La Casita Inn

Welcome to La Casita Inn! A private ocean-view studio designed for a memorable stay in Rincón. Wake up to views of the Caribbean Sea and enjoy your morning coffee on the private patio as the sun rises. A calm, quiet space to slow down and unwind. What you’ll love: • Peaceful location • Ocean view • Beach gear included (chairs, cooler, towels) • Free parking and self check-in Whether you’re here to explore or disconnect, La Casita Inn is the place to stay.

Superhost
A spacious circular living area features large windows surrounded by lush greenery. Rustic furnishings include a woven chair and a wooden table. Ambient lighting enhances the room, while a decorative lantern hangs overhead, contributing to a serene atmosphere connected to nature.
Guesthouse in Cabo Rojo
4.85 out of 5 average rating, 637 reviews

The Cabin in the Forest

Welcome to our place, a tranquil hideaway surrounded by lush forest in Cabo Rojo. Designed with warm wood details and open-air living, this space invites you to slow down, breathe deeply, and reconnect with nature. Enjoy peaceful mornings on the terrace, cozy evenings under soft lighting, and the soothing sounds of the forest all around you. A truly serene escape for those seeking beauty, privacy, and simplicity in a magical natural setting.

Top Guest favourite
A modern cabin is nestled among lush greenery, featuring a sleek metal exterior. A spacious balcony is visible, complemented by two chairs and a small table. Warm lighting illuminates the interior, providing a glimpse of the cozy living space within.
Guesthouse in Los Mesen
5 out of 5 average rating, 240 reviews

Unique forest cabin - Pool, river & private trails

Retreat into 10 acres of private primary rainforest! no roads, no crowds, no noise. Just toucans, streams, 3 km of private hiking trails and a river at the end. A modern, design-led cabin with A/C, a custom rain shower overlooking the San Carlos plains, full kitchen and a balcony over the forest canopy. Two pools with natural spring water and real peace, with La Fortuna, Bajos del Toro and Sarapiquí all within reach. Local owned ✌️🇨🇷

Guest favourite
The interior of the Jungle Loft features a spacious seating area with a gray sofa and a wicker chair. A hammock hangs from the ceiling, and wooden floors are complemented by rustic wooden walls. Soft lighting creates a warm ambiance throughout the space.
Guesthouse in Tunapuna/Piarco Regional Corporation
4.88 out of 5 average rating, 154 reviews

Jungle loft in the heights of Aripo

Deep into Trinidad's northern range on our little agricultural set up is the Jungle Loft. Exactly on the trailhead for the three main oilbird caves in Aripo - and the island's largest cave system, there are easy walks along the road into the rainforest. Due to the length and varying conditions of the road we’re best suited to guests looking to explore the area or looking for a retreat or if you just really love the place!

Top Guest favourite
An open living area is highlighted by floor-to-ceiling glass walls, offering expansive views of the lush valley. Natural wood furniture, adorned with nature-inspired decor, complements a spacious seating arrangement. A television is positioned near a well-equipped kitchen space, enhancing the communal atmosphere.
Guesthouse in Platanillo
5 out of 5 average rating, 225 reviews

Suave Vida Getaway - Guesthouse

The Suave Vida Getaway Guesthouse offers you its openness with window walls and valley views surrounded in Costa Rican Nature at its purest. You will feel emerged to the views of the valley in a comfortably spacious open space enriched with stylish furniture and décor themed to bring raw elements of nature inside the living area. You will find yourself in tranquility with the sounds of nature and the running streams.

Popular amenities for Caribbean Sea guesthouses

Destinations to explore