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Guesthouse vacation rentals in Caribbean

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Caribbean

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

An A-frame structure features a distinct triangular design, with a white door and a small window displaying potted plants. The entrance is accented by a colorful mat, framed by lush greenery and tropical plants surrounding the area.

Guesthouse in Vieques

4.99 out of 5 average rating, 219 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.

A modern house is framed by lush greenery and set behind a sleek black fence. The structure features a combination of light and dark elements, with a flat roof and large front window that allows natural light to enter the interior.

Guesthouse in Miami

4.91 out of 5 average rating, 249 reviews

Miami “Urban Oasis” Guest (Detached Structure)

Welcome to Urban Oasis Guest House in the heart of Miami🏡 The perfect destination for those seeking a centrally located premium property at a great value. 5 min from Wynwood/Design District, 10 min from Downtown/Airport and 15 min to South Beach. Built in '21/Remodeled in '23. Bedroom boasts an amazing bed, sheets and pillows perfectly curated to offer restful nights of sleep. Queen sleeper Sofa. Full kitchen & bathroom.Private secure patio, seating & grill.Parking space inside gated property!

Top guest favorite

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

4.99 out of 5 average rating, 160 reviews

Unique & secluded forest cabin with pool & trails

Retreat to the rainforest in a cosy, confortable 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 outdoors of the property with 10 acres of primary rainforest filled 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 favorite

A tropical tiki hut features natural thatched roofing and wooden flooring, offering a relaxed seating area with a central coffee table. Surrounding greenery enhances the peaceful ambiance, while a scooter is visible in the background, suggesting a convenient way to explore the area.

Guesthouse in Biscayne Park

4.95 out of 5 average rating, 505 reviews

Cozy and charming cottage

Our cottage is located in a very quiet residential area, 15mn to the beach (Bal Harbor area).20mn from both Miami and Fort Lauderdale Airports, Located in the backyard of the main house but separate and with an independent entry. Enjoy our tropical garden and beautiful pool, in the back of our house. Share with owner only, we give priority to our guests to enjoy it! Parking available in our front yard. No kitchen but microwave and fridge. TV, cable and WIFI. It is suggested to have a car.

The first image displays a panoramic view of the beach and surrounding area, with a clear blue ocean and lush landscapes. The second image features a bedroom with natural light filtering through windows, highlighting a spacious bed. The third image shows a well-equipped kitchen area, and the final image captures the beach, showcasing soft sand and calm waters.

Guesthouse in Punta Cana

4.85 out of 5 average rating, 775 reviews

Suite with pool and beach

A 30 metros de la playa " Los Corales " pequeña suite privada de 3 metros por 3 metros con entrada individual, baño, Bien Equipada, con pequeño patio natural.. Barrio estilo Mediterráneo, Tranquilo, rodeado de vegetacion. Restaurantes, bares, Spa dentro del residencial.. Acceso a Piscina compartida del condominio . con cocina eléctrica de una hornilla , microondas, y pequeña nevera. Trasporte desde el aeropuerto 25 dolares Isla saona Los haitises Zip line Cocobongo Buggies Etc

An outdoor pool area is enclosed by a screened lanai, featuring a clear blue pool complemented by a surrounding deck. Seating areas with lounge chairs are positioned nearby, and soft curtains add a relaxed touch to the space. The main living area is visible through the open doors.

Guesthouse in Cape Coral

4.94 out of 5 average rating, 152 reviews

Pool Modern Apartment fishing paradise

Location! Location! This apartment is close distance to Deli, restaurants and supermarket . The house faces the canal with breathtaking views we have cameras facing the canal and pool area in order to protect guests. The apartment is attached to the main house but private entrance totally separate. Functional full kitchen in the Lanai area Is only for 2 persons. No children allowed. After May 2025 pool will be shared by 1 or 2 more guest. No service dogs or comfort pets allowed.

Top guest favorite

The exterior of the studio apartment is framed by lush greenery and flowering plants. An outdoor dining set with an umbrella is positioned on a blue deck. The building features large windows and light-colored walls, complemented by stone accents and manicured landscaping.

Guesthouse in Grand Harbour

4.98 out of 5 average rating, 164 reviews

Heavenly Suite 2 - The M @ The Edge

Heavenly Suíte #2 at The M @ The Edge is a studio apartment with sleek & modern furnishings, smart HD TV, sound bar, chandeliers, state of the art kitchenette with quartz counter-tops, Delta faucet, and under counter lights. The chic bedroom fashioned in white crisp tiles, scones and recessed lighting mimics the luxurious bath styled in porcelain & Carrera tiles, Delta faucets, mirrors. . The patio enlivened by red/white accents, greenery, bar, pergolas, and Jacuzzi.

An outdoor area is illuminated by string lights at dusk, showcasing a wooden structure with a spacious deck. A lap pool glimmers in the distance, framed by lush greenery and gently sloping hills, creating a serene atmosphere for outdoor relaxation.

Guesthouse in Port Antonio

4.92 out of 5 average rating, 144 reviews

Stingray, Searenity Cottages

Nestled in nature and perfectly positioned for stunning views of the Blue Mountain peak, the Port Antonio coastline, and a nearby waterfall. Enjoy frequent visits from hummingbirds to our feeders, adding a touch of nature’s charm to your stay. Conveniently located, you'll find yourself at the heart of all the attractions that the area has to offer. Searenity offers six cottages: - Starfish - Stingray - Lionfish - Jellyfish - Turtle - Octopus Your sanctuary in nature.

A modern kitchenette is visible, featuring white cabinetry and a minimalist sink area. Above the counter, decorative items create an inviting display. In the background, a cozy sleeping area is highlighted by a warm, neutral palette with a spacious bed and soft lighting.

Guesthouse in Homestead

4.97 out of 5 average rating, 146 reviews

Villa Samsara - on a beautiful 5 acre farm

When you come and stay with us, it’s a deeply immersive experience with our horses. Often you will find them in your front door or window. There is something profoundly impactful about being around horses and sharing close-quarters with them. You are in their energy field, receiving all that they have to offer. Without even realizing it, your energies are being grounded and regulated through their presence.

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

4.96 out of 5 average rating, 281 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 favorite

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, 547 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.

Top guest favorite

A natural stone jacuzzi is set in a secluded area, surrounded by lush green plants and bamboo wall accents. Soft lighting from overhead strings illuminates the space, while a pink flamingo float rests on the water, inviting relaxation and enjoyment.

Guesthouse in Homestead

4.97 out of 5 average rating, 188 reviews

Relax on HOT TUB near Florida Keys

Find solace away from the daily grind in our beautiful sanctuary. Discover serenity in our charming tiny house with a petite patio and luxurious jacuzzi. Perfect for a cozy getaway, this retreat offers a blend of comfort and relaxation. Unwind in style surrounded by nature.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Caribbean guesthouse rentals

Free parking on premises

Air conditioning

Family-friendly guest house rentals

The two-story home is illuminated at night, showcasing a spacious outdoor area. A covered patio with seating is visible, alongside a well-maintained lawn and decorative plants. Soft lighting highlights the architecture, creating a welcoming ambiance.

Guesthouse in Río Grande

4.91 out of 5 average rating, 219 reviews

🏝The White Tropical House - BEACHFRONT🏖

Top guest favorite

A private stock tank pool is surrounded by a wooden deck and lounge chairs. An umbrella provides shade over the pool area. Colorful towels and a stylish table with refreshments are visible, set amidst a landscaped courtyard with lush greenery.

Guesthouse in Sarasota

4.99 out of 5 average rating, 218 reviews

Magical Guesthouse 1 mi from SRQ airport

Top guest favorite

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

4.96 out of 5 average rating, 192 reviews

Pradera Country House

Top guest favorite

A colorful surfboard is mounted against a light-colored wall, flanked by two small square windows with glass blocks. A hose runs along the ground next to a textured mat, creating a functional outdoor space.

Guesthouse in Providenciales

5 out of 5 average rating, 133 reviews

“Sail Loft STBD”, Duplex with a Pool, Beach Access

Top guest favorite

A spacious wrap-around porch features a round table with four white chairs, inviting outdoor relaxation. Lush greenery and stunning ocean views can be seen in the distance, while bright clouds drift across the sky, enhancing the serene ambiance.

Guesthouse in Coral Bay

4.99 out of 5 average rating, 112 reviews

A House of Open Arms Cottage with AC

Vibrant bougainvillea flowers in shades of pink and deep red create a lush display against the greenery. The dense foliage adds a natural texture, while drops of water may suggest recent rainfall, enhancing the overall freshness of the scene.

Guesthouse in Key Largo

4.93 out of 5 average rating, 145 reviews

Seaside Bungalow

A pathway of stepping stones leads through a neatly manicured lawn, bordered by vibrant pink flowers. Fencing frames the entrance, guiding toward a charming cottage in the background, surrounded by palm trees and a green canopy overhead.

Guesthouse in West Palm Beach

4.95 out of 5 average rating, 264 reviews

*KING BED* Private Cottage in the heart of WPB

A shaded outdoor seating area features a comfortable couch adorned with vibrant cushions. A small dining table accompanies the seating, surrounded by lush greenery and potted plants visible in the background. Large curtains provide a soft, warm ambiance while allowing natural light to filter through.

Guesthouse in Rockley

4.97 out of 5 average rating, 176 reviews

Footsteps to the beach

Guest house rentals with a patio

A spacious terrace features a comfortable seating area with plush cushions. Lush greenery surrounds the space, offering a sense of tranquility. A staircase leads to an upper level. In the distance, a view of buildings and the sky is visible, enhancing the outdoor ambiance.

Guesthouse in Simpson Bay

4.89 out of 5 average rating, 114 reviews

White Sands Beach Studio

A spacious sleeping area features a king-sized bed with a patterned gray blanket and colorful accent pillows. A dining table with green chairs is positioned by the window, and light fixtures provide illumination. Artwork adorns the wall, enhancing the overall aesthetic.

Guesthouse in Fort Lauderdale

4.86 out of 5 average rating, 271 reviews

Trendy Studio in FLL - Private entrance & bathroom

Top guest favorite

A charming exterior of a black wooden home is framed by lush green palm trees and shrubs. A stone pathway leads to the front entrance, with decorative plants positioned along the garden beds. Large windows invite natural light into the space.

Guesthouse in West Palm Beach

4.97 out of 5 average rating, 147 reviews

Raven Haus: Curated 2 Bedroom Guest House w/Pool

Top guest favorite

A vibrant yellow cottage is depicted with a landscaped area featuring palm trees and a gravel yard. Colorful adirondack chairs in pastel shades of pink and blue offer seating options, creating a casual outdoor space. Nearby cottages are visible, enhancing the beachfront setting.

Guesthouse in Bradenton Beach

4.99 out of 5 average rating, 180 reviews

Bradenton Beach Sunsets 1, Anna Maria Island, FL

A hammock is suspended under a wooden pergola, surrounded by lush greenery and soft drapes that gently frame the space. A textured blue rug lies beneath, enhancing the serene atmosphere. String lights provide soft illumination, creating a cozy retreat for relaxation.

Guesthouse in Miami

4.95 out of 5 average rating, 163 reviews

Cozy and private studio.

A tranquil river flows gently through a lush green landscape, with vivid blue water visible among smooth stones. Towering trees frame the scene, enhancing the natural beauty and inviting exploration of the surrounding area.

Guesthouse in Rio celeste

4.92 out of 5 average rating, 147 reviews

Tenorio’s Treasure

A modern bathroom features a sleek freestanding tub positioned against a textured wall. A wooden ladder holds towels, while a potted plant adds a touch of greenery. A natural fiber rug lays underfoot, contributing to the serene ambiance of the space.

Guesthouse in Carolina

4.91 out of 5 average rating, 135 reviews

5 minute from the airport, sleep 4, 2 Bedroom,

A bright and airy space showcases a cozy living area with a blue couch, accompanied by a small dining table and chairs. The kitchenette features modern appliances and white cabinetry. Natural light fills the room through large windows, highlighting the wood flooring and inviting atmosphere.

Guesthouse in West Palm Beach

4.94 out of 5 average rating, 154 reviews

Steps from Downtown West Palm Beach

Guest house rentals with a washer and dryer

Top guest favorite

Vibrant purple orchids are prominently displayed in the foreground, with a lush garden environment surrounding a clear swimming pool in the background. Tropical plants and trees are seen throughout the scene, contributing to a serene outdoor atmosphere.

Guesthouse in Kingston

4.95 out of 5 average rating, 150 reviews

Orchid Cottage

Top guest favorite

A natural pathway framed by lush green foliage leads towards a tranquil beach scene. The ocean's turquoise waters gently meet the shoreline under a clear blue sky, creating a serene coastal atmosphere.

Guesthouse in Jupiter

5 out of 5 average rating, 248 reviews

Jupiter Kozy Kottage- August Discounts 2.7 beach

Top guest favorite

An open-layout studio is illuminated by natural light, showcasing a comfortable queen size bed draped in white linens. Shelving units are positioned in the room, accompanied by a small dining area and kitchenette with modern appliances. A wall-mounted smart TV is visible, enhancing the living space.

Guesthouse in Sarasota

4.94 out of 5 average rating, 105 reviews

Downtown Garden Studio close to everything

Top guest favorite

The interior of the cottage features wooden walls and a spacious layout. A comfy sofa is positioned next to a well-equipped mini kitchen, which includes cabinets and countertop space. Large windows allow natural light to fill the space, complementing the warm wood tones.

Guesthouse in Osprey

4.99 out of 5 average rating, 334 reviews

Cozy Cottage by the Bay

A bright open space features a comfortable bed with neutral bedding and decorative pillows. A cozy seating area with wicker chairs and a round dining table is adjacent. Natural light streams through a window and sheer curtains, while a sleek flat-screen TV is mounted on the wall.

Guesthouse in Hollywood

4.93 out of 5 average rating, 235 reviews

La Moderna: A Private Guesthouse

Top guest favorite

A serene bedroom is designed with soft white bedding and natural light pouring in through large glass doors. A mirror reflects the room's simplicity, while a bookshelf filled with books adds a touch of character. The outdoor view reveals lush greenery and the ocean beyond.

Guesthouse in Christiansted

5 out of 5 average rating, 113 reviews

St. Croix Ocean Vista Honeymoon Cottage - Beach

Two spacious, white bean bag chairs are positioned near a turquoise pool, with a small black table holding a vibrant pink flower in between. A wooden fence provides privacy, creating a relaxing atmosphere for lounging by the water.

Guesthouse in Fort Lauderdale

4.84 out of 5 average rating, 105 reviews

Boho Retreat: Couples Oasis Near Ft. Laud. Beaches

The bright exterior of the pool house features vibrant murals against a clean wall. A heated saltwater pool is surrounded by a safety fence, with sun loungers positioned nearby on a manicured lawn. Lush greenery adds to the serene ambiance of the outdoor space.

Guesthouse in West Palm Beach

4.92 out of 5 average rating, 149 reviews

Sanctuary with Pool Perfect Location

Destinations to explore