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Ski-in/Ski-out holiday rentals in Caribbean

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Top-rated ski-in/out rentals in Caribbean

Guests agree: these ski-in/out homes are highly rated for location, cleanliness and more.

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Guest favourite
A serene beach scene captures two individuals enjoying shallow waters near the shore. Clear blue skies enhance the peaceful atmosphere, while gentle waves lapping at a soft sandy beach emphasize the tranquility of the surroundings. Lush greenery and palm trees frame the scene in the background.
Flat in Luquillo
4.94 out of 5 average rating, 136 reviews

Luquillo Beachfront Vacation!

This place is a SANTUARY Just what we all need at this moment .Been able to breath fresh air from a clean beach ocean .Taking Sun every day walking to swim looking at amazing Sunset. Connecting with nature . The Apartment is in Punta Banderas the Best Spot in All Luquillo .because its been always like a Private Beach and at this moment is what we really need ! Its a front Beach PH apartment with a roof top for dining and relaxing after a sunny day!! I personally take care of the cleaning crew

Guest favourite
A pool area is shown with lounge chairs arranged around a clear blue pool. The deck is paved with light-colored bricks and surrounded by greenery. In the background, a covered seating area with multiple chairs can be seen, alongside colorful buildings under a sunny sky.
Apartment in Grand Harbour
4.92 out of 5 average rating, 275 reviews

Waterfront Sanctuary Serene | 2BR | Pool & Porch

Cool clean contemporary Sanctuary with water views; a two bedroom/two bathroom condo with a full kitchen and living room packed with all popular amenities (wifi, cable television, Apple TV, Netflix, Playstation game console, central A/C, iron and ironing board, washer and dryer, outdoor patio, pool and free parking) - conveniently located in Grand Harbour. The Shoppes at Grand Harbour, & Harbour Walk are next door. Perfect for exploring and enjoying all that the Cayman Islands has to offer.

Superhost
The image captures a vibrant pool area surrounded by lounge chairs and tropical plants, with a view of the water and city skyline in the background. Clear blue skies reflect over the pool, creating a serene relaxation space. Palm trees stand prominently along the waterfront.
Apartment in Miami Beach
4.84 out of 5 average rating, 124 reviews

Stunning Studio in Miami Beach: WiFi &pool

Luxury spot with stunning sunsets that can be appreciated from the pool area. Spa and restaurants and bar are among the great amenities at this beautiful location. Daily resort fees (paid upon arrival ) include: Welcome cocktail , Poolside amenities (2 chaise lounge chairs and towels)/kayaks & paddle-boards/Gym/2 hours beach cruisers/ fresh brewed coffee. EARLY CHECKING or LATE CHECKOUT MAY BE requested up on availability at $75 per request. BTR008203-11-2019 License #CND2332048

Top guest favourite
A terrace setting is displayed with a green swing and a table set for breakfast. Plates and glasses are arranged alongside a pitcher and a pink thermos. The background features a view of the mountains and fields illuminated by the warm light of sunset.
Casa particular in Vinales
4.78 out of 5 average rating, 340 reviews

KIt SOLAR PANEL Levanta (Split) 2 Rooms 8 Guests.

Unlimited Wi-Fi, places of interest, family activities, visit to a tobacco and coffee farm, enjoy the beach cayo jutias, nightlife and much more, a great adventure, the quiet place, we rent a large cozy space with good ventilation, incredible views from the terrace, in the neighborhood with many fruit trees to taste, free parking available, good advice and tranquility, my son is a horse guide speaks English, free Wi-Fi at home. (unlimited)

Guest favourite
A spacious room is presented with two beds featuring simple black frames and vibrant orange and white linens. Two small bedside lamps are placed beside the beds. The décor includes framed artwork on the walls, and a doorway leads to a bathroom.
Guest house
4.94 out of 5 average rating, 367 reviews

Villa Balcony to the Mountains Papo & Mileidys

Independent apartment with balcony overlooking the mountains of Viñales Valley with complete privacy for you and your family. Excursions on horseback and on foot are organized through the Viñales Valley. You will have parking for your car. We have our own car and we can organize excursions. We will also help you to rent bicycles if you wish to use this means of transport. There is wifi internet connection in the house.

Guest favourite
A modern kitchen area is highlighted, featuring sleek cabinetry and stainless steel appliances. A bar with high stools offers a cozy dining space. Decorative lighting fixtures add warmth, while a small indoor plant contributes a touch of greenery to the overall design.
Flat in Santiago de los Caballeros
4.94 out of 5 average rating, 117 reviews

Cozy apartment outside the city

Welcome to our cozy apartment! Perfect for a getaway or to go to the airport. It is only 10 minutes from the airport and downtown, in a quiet area. Supermarkets, health care centers, and restaurants are 5 minutes away. We offer decoration for romantic evenings, home cooking, cleaning, and transportation to the airport for an additional cost, make your reservation and enjoy the comfort everyone is looking for!

Top guest favourite
A spacious pool area features a heated saltwater pool accompanied by a jacuzzi. Comfortable lounge chairs are positioned around the pool, with lush palm trees providing shade. A modern covered terrace offers seating options for relaxation next to the scenic outdoor landscape.
Villa in Carolina
5 out of 5 average rating, 140 reviews

Luxury waterfront villa with dock and heated pool

Villa Jade is a unique luxury waterfront retreat with a heated saltwater pool, jacuzzi, and private dock to a serene lagoon. It is just 10 minutes from SJU Airport and the fabulous beaches of Isla Verde. Three spacious bedrooms with private baths. Fully remodeled. Equipped with a generator and cistern for peace of mind. As a dedicated 5-star host, I’m here to ensure a smooth, relaxing stay. Welcome!

Guest favourite
A vibrant blue house is set against a cloudy sky, surrounded by lush greenery and colorful plants. A pathway with stones leads to the entrance. An observation tower can be seen in the background, enhancing the natural ambiance of the area.
Home in Monteverde
4.86 out of 5 average rating, 205 reviews

Natural Wonders House: Where nature awaits you!

The house is walking distance of Santa Elena but secluded enough to give you the contact with nature and the privacy that is looked for when you come to Monteverde. Internet, cable tv, washer, dryer and a fully equipped kitchen and a bathtub provide all you will need to make your stay an enjoyable one. It has two rooms, where one of them has a private bath tub and bathroom.

Top guest favourite
A private jacuzzi is surrounded by lush greenery, with a vibrant red umbrella providing shade. A decorative vase filled with tropical flowers is placed nearby. Comfortable seating is arranged on a wooden deck, promoting relaxation in a tranquil outdoor setting.
Home in La Fortuna
4.95 out of 5 average rating, 212 reviews

Arenal area farm,birds, river Bukala Village Lodge

Escape to a hidden gem in La Fortuna—where adventure meets heart. Surrounded by lush nature, this cozy, family-friendly haven offers a private hot tub, a charming farm with animals, and the heartfelt care of Magdalena and Max. Start your day with fresh farm eggs, explore volcano trails, then unwind to birdsong and stars. A place where memories are made and peace finds you.

Top guest favourite
A panoramic view of rolling hills and lush green landscapes is presented, with varying shades of vegetation and a few scattered structures visible. The foreground features tall palm trees, leading to the expansive valleys that connect with distant mountains under a clear sky.
Casa particular in viñales
4.96 out of 5 average rating, 536 reviews

Casa Omar y Mayra,the best option

Casa Omar y Mayra is the best option to meet viñales in family, we have an excellent service and a beautiful rooftop 😀 to the vallerry, we have service for horses back riding tours to visit tabaco anda coffee ruts and local ron of guagua, visit to Jutias' Cay Beach in taxi colectivo and rent bicycle for all day,and the best Breakfast in Cuba.

Superhost
A modern kitchen area features stainless steel appliances, including a stove and coffee maker. Light-colored cabinets are paired with a tiled backsplash. A cozy living space includes a large television mounted on the wall and a coffee table in front of a comfortable sofa.
Flat in Humacao
4.87 out of 5 average rating, 255 reviews

Palmas View 4

Comodo apartamento para 2 o 3 personas con tv, wifi, cama queen y sofa cama. cocina equipada, aire acondicionado, calentador de aqua y estacionamiento. Cerca de la autopista #53, a minutos del complejo Turistico de Palmas Del Mar y a 5 minutos del Centro Comercial Palmas Real. Cerca de restaurantes, farmacias, gasolineria, fast food, etc.

Top guest favourite
Shipping container in La Fortuna
4.95 out of 5 average rating, 359 reviews

Rainforest Container Experience 5

💚Immerse in a beautiful rainforest Oasis close to downtown La Fortuna and popular tourist attractions. Great for couples, confortable, well decore and with all the amenities you need for a unique container experience! We are located very centrally near the hot springs near the center of town and near the La Fortuna waterfall 😃

Popular amenities for Caribbean ski-in/out rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Ski-in/out house rentals

Guest favourite
A modern single-family house is displayed with a bright yellow exterior. A white pergola extends over the front porch, providing shade. Lush tropical plants add greenery to the landscape, while clear blue skies create a vibrant background.
Home in Marathon
5 out of 5 average rating, 10 reviews

Keys Escape - It's 5 o'clock

Superhost
A modern outdoor area features a private pool and jacuzzi, surrounded by stylish seating. Cool blue water reflects the sky, while a stone wall adds texture. Plush lounge chairs invite relaxation, and a calm atmosphere is accentuated by soft, ambient lighting.
Home in Carolina
4.71 out of 5 average rating, 17 reviews

Crab view

Superhost
A serene outdoor space features a heated pool with a built-in spa and is surrounded by tropical landscaping. Comfortable lounge chairs are arranged nearby under a thatched roof structure, providing a perfect spot for relaxation by the water.
Home in Pompano Beach
4.87 out of 5 average rating, 47 reviews

Spacious Luxury Water Front, Pool & Jacuzzi, 5br

Guest favourite
A modern villa exterior is displayed, featuring a stone façade and a balcony with glass railings. Two woven chairs are positioned on a small patio, surrounded by lush green landscaping and palm trees. A stone pathway leads to the entrance.
Home in Punta Cana
4.8 out of 5 average rating, 20 reviews

Villa Lovely with Private Pool

Superhost
A serene outdoor pool area is surrounded by well-maintained greenery and modern architecture. The pool reflects soft evening light, while tall palms and decorative plants enhance the tranquil environment. White walls provide a bright backdrop, contributing to a sense of spaciousness.
Home in CARTAGENA
5 out of 5 average rating, 3 reviews

Amazing house with beach and private pool!

Superhost
A modern building features a natural stone accent wall and multiple large windows with horizontal blinds. Lush tropical greenery surrounds the structure, providing a vibrant contrast to the white exterior. The architectural design offers a contemporary yet inviting appearance.
Home in Santo Domingo
4.68 out of 5 average rating, 19 reviews

Shulywow Santo Domingo West Luxury Comfort Safe

Guest favourite
A modern home is set in a lush landscape, featuring a light-colored exterior and a distinctive turquoise front door. The well-maintained driveway leads to a spacious garage, surrounded by vibrant greenery and tropical plants that enhance the inviting curb appeal.
Home in Marco Island
4.9 out of 5 average rating, 30 reviews

5 Beds 3 BDR 2 Bath Heated Pool, Grill, Patio

Guest favourite
A clear blue swimming pool occupies the foreground, reflecting sunlight. Behind the pool, a mural depicting a natural scene is visible, surrounded by potted plants. Green chairs are situated along the pool's edge, offering a relaxing space.
Home in Monte Cristi
4.9 out of 5 average rating, 83 reviews

Elegante Moderna Villa Jayden

Family-friendly, ski-in/out home rentals

Guest favourite
An aerial view showcases the Aquarius Vacation Club, featuring multiple buildings surrounded by lush greenery. A large pool is visible in the center, alongside a private beach. Lounge chairs are positioned along the sandy shore, with umbrellas dotting the landscape for shade.
Flat in Dorado
4.76 out of 5 average rating, 62 reviews

2 beds, a swimming pool, and a beach

Superhost
A modern kitchen area features a stainless steel sink and a gas stove with an overhead pot rack displaying kitchen utensils. Light grey walls contrast with the wooden cutting board placed on the countertop, while a kettle and decorative items add functional elegance.
Flat in Kralendijk
4.77 out of 5 average rating, 44 reviews

Soant Apartment

Guest favourite
A winding staircase is framed by slender palm trees and vibrant greenery. The scene reveals a lush lawn with colorful plants, indicating a well-maintained exterior. The overall atmosphere captures a connection to nature within the apartment complex.
Flat in Carolina
4.89 out of 5 average rating, 44 reviews

Ángeles suites

Guest favourite
A simple sleeping area features a spacious bed dressed with a patterned duvet. A wall-mounted television is positioned above a small desk, while a doorway leads to an adjoining bathroom area. Light enters through an open entryway, revealing a view of the outdoor landscape.
Shipping container in Las Terrenas
5 out of 5 average rating, 7 reviews

An ideally designed space

Superhost
A cozy sleeping area features a spacious bed with a floral-patterned bedspread. Brightly colored pillows in pink and green add a cheerful touch. Two dark nightstands are positioned on either side, complementing the light blue walls and creating a welcoming atmosphere.
Guest suite
4.63 out of 5 average rating, 54 reviews

Casa Marta Domínguez 2

Guest favourite
Loft in Santa Marta
5 out of 5 average rating, 11 reviews

Suite 1207 with sea views in Pozos Colorados

Top guest favourite
A spacious bedroom is featured with a queen-size bed, complemented by a modern bedside lamp and a nightstand. A dining area with a small table and two chairs is visible. A large wall mural depicting a natural scene enhances the calming atmosphere. Air conditioning and a Smart TV are also present.
Flat in San José
4.93 out of 5 average rating, 68 reviews

Secrt Sabana | SJ | Apt 22st | AC | Paid Parking

Superhost
Flat in CARTAGENA
5 out of 5 average rating, 15 reviews

Luxurious, private beach, top view & Kayak

Ski-in/out cabin rentals

Top guest favourite
A modern two-story building is shown alongside a clear blue swimming pool. Lush green grass surrounds the pool area, with well-maintained hedges and flower beds enhancing the outdoor space. The structure features large windows that provide ample natural light.
Cabin in Juan de Acosta
5 out of 5 average rating, 15 reviews

Cabaña el Atardecer (Juan de Acosta)

Superhost
A covered porch features handcrafted wooden railings and a rustic bench, offering a comfortable space to relax. Lush greenery and a landscaped yard are visible beyond, creating a serene outdoor environment. The tiled floor adds a warm touch to the inviting area.
Cabin in La Fortuna

El Bello Amanecer cabin

Guest favourite
A wooden cabin is surrounded by greenery, featuring a red roof and large windows allowing natural light inside. The structure is elevated, with a staircase leading to the entrance. The landscape includes trees and a clear blue sky, creating a serene environment.
Cabin in Bijagua de Upala
4.87 out of 5 average rating, 98 reviews

Cedros Cabin

A single-story wooden cabana features a distinctive curved roof and large windows. Surrounded by green grass and tropical plants, the entrance is framed by a small porch. The exterior showcases natural wood tones alongside light stone accents, creating a harmonious blend with the landscape.
Cabin in La Fortuna
4.77 out of 5 average rating, 262 reviews

Habana Cabana

Superhost
A tranquil beach view is captured, with soft waves lapping at the shore. The sky displays warm hues characteristic of sunset. Palm trees gently sway in the foreground, framing the scene with a sense of relaxation and serenity, enhancing the coastal experience.
Cabin in Ciénaga

Villa oti cabin

A cozy interior features a four-poster bed with light bedding, situated behind a half-wall. A wicker armchair is positioned near a bright green table set with two plates. Natural light fills the space through multiple windows framed with sheer curtains.
Cabin in Abaco

Waterfront Cottage @ Lubbers #4

Superhost
Cabin in Bayacanes
New place to stay

Villa Merys las Velas, Picuzzi y patio Privado

A refreshing pool is bordered by a spacious patio area, featuring shaded seating and a barbecue station. Lush greenery surrounds the space, with tall trees providing natural shade. The upper level of the house is visible, showcasing a large balcony that enhances the inviting outdoor setting.
Cabin in Chomes

Villa Paraíso

Destinations to explore