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With resort season quickly approaching, it totally doesn’t hurt to start browsing beautiful vacation homes and begin planning that dreamy island Airbnb getaway for the upcoming holiday break. Retiring to an island feels like the ultimate fantasy during the cold/winter months. Who doesn’t want to escape to a white sand beach as the temperature plummets—and stays—below freezing? (The “Winter Blues,” after all, is a medically recognized term, whereas its more extreme cousin, “Seasonal Affective Disorder,” is a medical diagnosis.)
Vogue has rounded up a few island rentals—from Curaçao to Costa Rica to St. Barths to Barbados—that boast idyllic tropical retreats. These are totally some of the best island Airbnbs on offer, and until you manifest that majestic retreat of your own this forthcoming winter, for now, you can live vicariously through your screen.
Batts Rock Beach | Saint Michael, Barbados
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The Portobello Villa promises a chic and contemporary stay, furnished with a modern interior complemented by natural lighting washing over the entire villa. Start the day with a seaside breakfast, soak up some sun in the lounging area, play a round of table tennis, then finish the night with a dip in the infinity pool.
Rooms: 4 bedrooms, 4 bathrooms
Amenities: private chef + butler, ping pong table, housekeeping included
Location: Near Greenridge Road, Batts Rock Beach, Bahamas
Limin’ da Coconut | Anguilla
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If you have the urge to splurge, retire with friends to this luxurious retreat tucked away off the lovely Anguillan coast. Equipped with everything you need for long-term lodging – this stunning rental home has a full-service kitchen, a dining area for 10 people, an outdoor lounging area, and a private pool—not to mention ocean views from every room. The island’s capital, as well as Crocus Cay Beach, is also a short drive away.
Rooms: 6 bedrooms, 6 bathrooms
Amenities: private pool, patio/balcony, outdoor dining area, housekeeping included
Location: Little Harbor, near Jeremiah Gumbs Highway, Anguilla
Cul de Sac, St. Martin
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For a serene island escape, retreat to this picturesque villa off the coast of St. Martin. The interior of the villa also has a super artful and minimalistic design accompanied by beautiful woodworking details. Relax in the heated pool while immersing in views of the mountainous coast, then take a kayak for a spin (which is also provided by the villa) or retreat to the beach, which is minutes away.
Rooms: 4 bedrooms, 5 bathrooms
Amenities: infinity pool, mountain view, breakfast bar, watersports equipment
Location: Near Rue de Terrasse d Cul de Sac, Saint Martin
Saint George, Grenada
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This massive coastal estate houses a party of 50 people comfortably, incredibly—in three individual villas surrounded by seven acres of lush greenery. Indulge in exquisite meals during your retreat whipped up by your private chef, treat yourself to a spa session, and lounge by the pool with scenic views of the Grenada coast.
Rooms: 15 bedrooms, 15 bathrooms
Amenities: infinity pool, spa, fire pit, beach access, gym, housekeeping included
Location: Reef View Drive, Lance aux Epines, Saint George, Grenada
Guanacaste, Costa Rica
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Designed by California-based architect Steve Adams, this luxurious rental home is intended for the modern-day aesthete. Its beautiful interior exudes a very pure and minimalist ambiance with both traditional and contemporary elements. The villa is also surrounded by a beautiful naturescape with gorgeous greenery. Tamarindo Beach is also a short walk away, and the downtown area with shopping, bars, and restaurants is also close by.
Rooms: 5 bedrooms, 5.5 bathrooms
Amenities: infinity pool, sauna, breakfast + housekeeping included, water sports equipment
Location: Ruta Nacional Secundaria 152, Tamarindo, Guanacaste, Costa Rica
Villa Square, Bonaire
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Take a voyage to the ABC islands and retreat to beautiful Bonaire to explore this stunning newly built beachfront villa. This rental home just oozes luxury, from its modern architectural façade to its interior, thoughtfully and meticulously designed with artful décor and an open-air layout to maximize views of Esmerelda Beach. Kralendijk is also just a short 10-minute drive away, with bustling bars, restaurants, and shopping.
Rooms: 6 bedrooms, 7 bathrooms
Amenities: infinity pool, hot tub, patio/balcony, BBQ grill
Location: Near EEG Boulevard, Kralendijk, Bonaire
Willemstad, Curaçao
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Escape to the delightful Dutch Caribbean island of Curaçao for your next vacation—enjoy the gorgeous Caribbean coast from this beautiful and spacious villa, set atop the highest point for the best scenic views. Jan Thiel Beach is a short 5-minute drive away, and the heart of the capital, Willemstad, is also a 15-minute drive from the villa—where you can indulge in stunning street art, history museums, local shopping, and delectable dining options.
Rooms: 5 bedrooms, 4.5 bathrooms
Amenities: pool, patio/balcony, ping pong + pool table, exercise equipment, private backyard
Location: Jan Sofat N, Willemstad Curaçao
Case Baronesa, Galapagos Islands
For an intimate island vacation, retreat to Casa Baronesa in Puerto Villamil. This comfy beachfront home has plenty of room to lounge around and unwind. It will truly feel like you and your friends have the beach all to yourself too—get cozy on the villa’s hammock, relax on the porch whilst reading by the coast, then explore the island filled with restaurants and bars a short walk and/or ferry ride away.
Rooms: 4 bedrooms, 3 bathrooms
Amenities: hot tub, backyard, indoor fireplace, hammock, BBQ grill
Location: Near Antonio Gil and Los Flamingos, Puerto Villamil, Galapagos Islands, Ecuador
Villa Jocapana, Saint Barthélemy
Gaze out onto Gustavía and its port from Villa Jocapana, a well-appointed home built into the hillside of Lurin. There s an infinity pool, an outdoor deck perfect for entertaining, and an outdoor shower for each bedroom. A brief drive to the center of town, it s also in the perfect location. This writer can attest that the West Indies sunsets viewed from your balcony are so beautiful, they will stay in your mind long after you leave.
Rooms: 4 bedrooms, 4 bathrooms
Amenities: housekeeping included, breakfast bar, patio/balcony
Location: Near Lurin, St. Barts, St. Bathlélemy
Kūono at Volcano National Park, Hawaii
On the cusp of the Big Island’s Volcano National Park is this spectacular modern cabin nestled in an expanse of Ohia trees. There’s a hot tub, a fire pit, and a private lanai—or, a covered porch—perfect for enjoying Hawaii’s tropical climate.
The real draw here is its immersion in nature, given its location in Volcano, Hawaii, a quaint village surrounded by a rainforest reserve. There’s a local winery, an orchid farm, a Volcano art center (the area is home to many local artisans), and every Sunday, a farmers market where fresh local produce abounds. The national park is a mere five-minute drive away.
Rooms: 2 bedrooms, 1 bathroom
Amenities: hot tub, patio/balcony, backyard,
Location: Liona Street, Volcano, Hawaii
Neomodernist Villa in Turks and Caicos
Fully indulge in island time with this beachfront neo-modernist villa on Grace Bay, complete with an infinity pool and sun loungers arranged right in the sand. Thanks to a folding glass wall, the living room can turn into an al-fresco space any time of the day, and the interiors are adorned with bright, tropical, yet not-cheesy accents. Plus, the deck—complete with a barbecue—is absolutely perfect for outdoor dining.
Rooms: 2 bedrooms, 2.5 bathrooms
Amenities: beach access, patio/balcony, infinity pool, outdoor shower, breakfast bar
Location: Near Coconut Rd, Grace Bay, Providenciales, Turks Caicos Islands
Grand Tiki Suite
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Designer Rosie Assoulin previously shared her adoration of this floating Tiki Hut Airbnb in Key West—and we have to agree. Only accessible via boat, the aqua-home comes with two stand-up paddleboards, snorkel gear, and a swim ladder that makes jumping in and out of the ocean that much easier.
Rooms: 1 bedroom, 1 bathroom
Amenities: ocean view, private patio/balcony, beach essentials included
Location: Key West, Florida
Whale Tale Hale, Waimea, Hawaii
Why is this Big Island villa named Whale Tale Hale? Because during the sea creatures’ migration period, you can hear—and see—them pass by. All the amenities you could dream of are there: infinity pool, fire pit, an outdoor dining area, and even a Steinway piano. The interiors are decorated with bright pops of tropical oranges and blues, as well as teak furniture.
Rooms: 3 bedrooms, 3.5 bathrooms
Amenities: private pool, outdoor shower, firepit, private patio/balcony
Location: Near Umaumalei Pl, Waimea, Hawaii
