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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
Guesthouse in Vieques
4.99 out of 5 average rating, 315 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 structure next to small main house. The restroom and shower are outdoor but private. There is hot water in shower. Large outdoor shower room with rain and regular shower heads. Ac in room is super cold. Queen bed with foam mattress Owner lives full time on property for any needs. The reviews speak for themselves about my property have an unique experience that still feels safe peaceful and comfortable.

Top Guest favourite
A person enjoys the serene view from the edge of a plunge pool, overlooking the mountains and the Caribbean Sea. The surrounding lush greenery and the dramatic outline of the Pitons enhance the natural beauty of the setting under a clear blue sky.
Guesthouse in LC
4.96 out of 5 average rating, 186 reviews

Romantic hideaway The Lodge at Cosmos St Lucia

Magical open air Lodge for couples and nature lovers, away from busy hotels. Plunge pool and sun deck with views over the Pitons and Caribbean Sea. Studio-style accommodation with kitchen, sitting area, queen sized bed and private outdoor bathroom. Homemade continental breakfast included. Panoramic views, sustainable luxury, concierge, friendly responsive staff, housekeeping, parking. Additional services: private dining, spa treatments, private driver. 10 mins to Soufriere, beaches, activities.

Top Guest favourite
Guesthouse in Esterillos Oeste
4.95 out of 5 average rating, 155 reviews

Octopus Separate Home in Shared Villa by Ocean

This is one of two independent homes at Jumanji Villa — a handcrafted space with expressive design and a vibrant, lived-in atmosphere. Fully equipped for a comfortable stay and connected to a spacious shared patio with a pool, outdoor kitchen, and a large bath in the spa area. The ocean is just a 5-min drive away, with national parks nearby. Sauna and cold plunge sessions are available at an additional cost and offer a gentle way to end the day after exploring. Let’s slow down and simply be!

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, 113 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
A unique bedroom features natural wooden walls and flooring, with a spacious bed positioned on a raised platform. Large windows offer a view of the surrounding trees, while soft lighting highlights the room’s architectural design.
Guesthouse in Los Mesen
5 out of 5 average rating, 225 reviews

Unique & peaceful forest cabin with pool & trails

Retreat to the rainforest in a cosy, secure and modern luxury cabin, built to help you connect with nature and yourself. Enjoy your stay with a fully equipped kitchen, an amazing bathroom with a custom shower/hot tub and a one of a kind bedroom design. Explore the private trails of the property with 10 acres of primary rainforest with toucans, lapas, humming birds, butterflies and other fauna. Beware, you might not wanna leave! Located in Venecia de San Carlos, 65km from SJO airport.

Top 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, 99 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!

Guest favourite
Guesthouse in Rincón
4.86 out of 5 average rating, 542 reviews

Peaceful 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.

Guest favourite
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, 634 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
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, 219 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.

Guest favourite
A spacious bed is arranged with neatly rolled towels, positioned near large glass doors. The scene outside showcases a colorful sunset over rolling hills, providing a serene backdrop to the inviting room filled with natural light.
Guesthouse in Monteverde
4.78 out of 5 average rating, 143 reviews

Ocean View House

Ocean View House: Naturaleza, Romance y Relajación Disfruta de atardeceres inigualables con vistas al golfo y montañas en esta cabaña acogedora. Perfecta para una escapada romántica o familiar, cuenta con una tina relajante, WiFi, cocina equipada y un amplio corredor. Ubicada a solo 15 min de Monteverde, pero lo suficientemente apartada para garantizar paz total. ¡Vive la magia de la naturaleza con total comodidad!

Top Guest favourite
An exterior view of the loft reveals a modern structure with multiple levels and large glass panels. Lush greenery surrounds the terrace, which overlooks a panoramic valley view. The setting sun casts gentle light over the landscape, enhancing the serene atmosphere.
Guesthouse in Alajuela
4.97 out of 5 average rating, 402 reviews

Stylish Loft with Stunning Panoramic Views

Just 9km from SJO airport. Romantic and elegant loft for couples with stunning panoramic views. The perfect place to unwind after a long flight or before heading back home. Relax in the hot tub while enjoying the breathtaking view, and take advantage of the TV, air conditioning, and automated black-out curtains for ultimate comfort. The airbnb is located in Pilas, San isidro de Alajuela

Top Guest favourite
Lush greenery frames a serene creek, with smooth stones visible along its edge. The vibrant leaves of tropical plants create a natural border, inviting a sense of tranquility and connection with nature.
Guesthouse in Río Grande
4.96 out of 5 average rating, 612 reviews

Stay at the Yunque’s National Skirt

Recognized as one of the best community before the Yunque area. Quiet, beautiful, relaxing, good neighborhood, close to everything (zipline, Tree house restaurant, bakery, souvenirs, food, brunch, groceries and Luquillo beach). We are exactly in the Yunque’s skirt (valley). No other place can be closer.

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