Windward Islands Holiday Rentals, Caribbean: Private House Rentals

A tropical beach with palm trees, clear blue water, and rocky outcrops.

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Our top choices for Windward Islands hotels

A covered outdoor patio with a fountain, palm trees, and a view of the sea.

A framed picture of a woman in a tropical dress with the word "Cuba" on it, hanging on a wall in a hallway with wooden paneling and hanging lanterns.

A white building with multiple balconies and a garden area with palm trees.

A pool area with lounge chairs and umbrellas, a staircase, and a building with a white facade and balconies.

1. Grenadine House

Kingstown

James

Rp2.694.141

Rp3.043.427 total

includes taxes & fees

6 Oct - 7 Oct

A modern hotel lobby with multiple seating areas, including tables and chairs, and a coffee station.

A hotel room with a large bed, a TV mounted on the wall, a wardrobe, and a bathroom visible through an open door.

A modern hotel lobby with a large dining area, a flat-screen TV, and large windows offering a view of the outside.

A covered patio area with stone walls, a pergola structure, and outdoor seating.

2. Holiday Inn Express & Suites St. Vincent - Grenadines by IHG

Diamond

Olajide

Rp1.716.672

Rp2.130.104 total

includes taxes & fees

2 Nov - 3 Nov

A resort with a pool, lounge chairs, umbrellas, and a mountain view.

An aerial view of a beach with thatched umbrellas, palm trees, and sun loungers.

A corridor with a wooden ceiling and walls, featuring a stone pathway and wall-mounted lights.

A poolside area with lounge chairs, a dining table with a tray of food and drinks, and a view of the pool and mountains.

3. Sugar Beach, A Viceroy Resort

Soufrière

yaser

Rp22.352.945

Rp27.941.145 total

includes taxes & fees

6 Oct - 7 Oct

A pool area with lounge chairs and a view of the ocean.

A couple dining by a pool with a view of the sea.

A blue building with a white roof, surrounded by lush greenery and parked cars.

A spacious bedroom with a large bed, a desk, and a television.

4. Beachcombers Hotel

Villa

Michelle

Rp2.903.858

Rp3.566.599 total

includes taxes & fees

6 Oct - 7 Oct

A row of wooden buildings with balconies, surrounded by lush greenery and ferns.

An outdoor restaurant with tables set for dining, a mountain view in the background, and a wooden fence separating the dining area from the landscape.

A bar with shelves of bottles and a sign reading "THE CACAO BAR".

5. Rabot Hotel from Hotel Chocolat

Soufrière

Benda

Rp7.266.887

Rp8.716.939 total

includes taxes & fees

26 Oct - 27 Oct

A clear blue sky, a swimming pool, and palm trees.

An aerial view of a resort with multiple buildings, a beach, and a pool area.

A banquet setup with tables and chairs, decorated with floral arrangements and white drapes.

A beachside resort with sun loungers, umbrellas, and a palm tree.

6. Royalton Saint Lucia, An Autograph Collection All-Inclusive Resort

Cap Estate

Shayna Larissa

Rp6.208.630

Rp6.208.630 total

includes taxes & fees

26 Oct - 27 Oct

A beach with clear waters, boats, and thatched-roof huts.

A swimming pool surrounded by palm trees and lounge chairs.

A seaside patio with lounge chairs and a table, overlooking the ocean.

A hotel room with a large bed, wooden headboard, two bedside tables with lamps, a small bedside table with a lamp, a window with vertical blinds, and a view of greenery outside.

7. Young Island Resort

Villa

Bayan

Rp5.909.643

Rp7.203.599 total

includes taxes & fees

6 Oct - 7 Oct

A swimming pool surrounded by palm trees and a gazebo.

A wooden house with a porch, surrounded by lush greenery and flowering plants.

A covered porch with a pool, green chairs, and a view of lush greenery.

A wooden staircase leading to a covered area with a white lattice railing, surrounded by lush greenery.

8. Fond Doux Eco Resort

Soufrière

Kevin

Rp3.000.743

Rp3.425.379 total

includes taxes & fees

12 Oct - 13 Oct

A beach at dusk with a row of candles on the sand, palm trees, and a small structure with lights.

A bathroom with a wooden vanity, a white sink, a mirror, and a view of greenery through the window blinds.

A spacious room with a large bed, wooden furniture, and a ceiling fan.

A breakfast table with tropical fruits, coffee, and juice, overlooking a mountainous landscape with palm trees.

9. Anse Chastanet Resort

Soufrière

Rich

Rp9.835.100

Rp11.802.120 total

includes taxes & fees

6 Oct - 7 Oct

A wooden deck with lounge chairs and a view of the sea.

A pond with lily pads and a stone bridge.

A balcony with a view of the sea and a distant island.

An aerial view of a resort with a swimming pool, lounge chairs, and palm trees.

10. BodyHoliday - All inclusive

Cap Estate

Rumi

Rp16.463.957

Rp17.831.018 total

includes taxes & fees

6 Oct - 7 Oct

A modern hotel with a large pool, multiple balconies, and a bar area.

A beachfront dining setup with white tablecloths, bamboo chairs, and floral centerpieces.

A couple seated at a table with a view of the sea and a bar area in the background.

11. Royalton Hideaway Saint Lucia, An Autograph Collection All-Inclusive Resort - Adults Only

Cap Estate

Nicole Y

Rp6.609.187

Rp6.609.187 total

includes taxes & fees

26 Oct - 27 Oct

A beachfront patio with lounge chairs, a potted plant, and a view of the sea with boats.

A sunset over a calm sea with a silhouette of a tree on the right.

A person seated at a table with a drink and a fruit.

A spacious outdoor dining area with wicker chairs and a glass-top table, leading to an indoor living space with sofas and a television.

12. Sunset Shores Beach Hotel

Villa

Jacques

Rp2.031.882

Rp2.511.508 total

includes taxes & fees

6 Oct - 7 Oct

A rooftop pool with lounge chairs and a hot tub, surrounded by glass railings.

A compact hotel room with a bed, a kitchenette, a microwave, and a ceiling fan.

A hotel lobby with a checkered floor, a chandelier, and a sign reading "MII MYAHT'S HOTEL".

A multi-story hotel with balconies, named "MYAH'S SUITES," surrounded by lush greenery and flowering plants.

13. Myah's Luxury Suites Hotel

Diamond

Terrence

Rp2.703.758

Rp3.670.674 total

includes taxes & fees

6 Oct - 7 Oct

A beachside area with palm trees, a sandy beach, and a building with outdoor seating.

A reception area with a modern design, featuring a marble wall and a light-colored reception desk.

A modern restaurant with white furniture, large windows, and a view of palm trees.

A poolside area with lounge chairs and umbrellas, overlooking a clear blue sea and a rocky coastline.

14. LA Vue Boutique Hotel & Beach Club

Villa

Shannon

Rp4.264.857

Rp5.213.408 total

includes taxes & fees

6 Oct - 7 Oct

A swimming pool with a sunset view, surrounded by palm trees and thatched umbrellas.

A room with a large window, a bed, a chair, and a small round table.

A thatched-roof outdoor bar area with wooden chairs and a bar counter.

A covered outdoor dining area with tables and chairs, a view of the ocean, and a pergola structure.

15. Secrets St. Lucia Resort & Spa All Inclusive Adults Only

Gros Islet

Andrew

Rp14.287.360

Rp14.287.360 total

includes taxes & fees

26 Oct - 27 Oct

A resort with multiple buildings, a central pool, and a beach area.

A grand lobby with a high ceiling, multiple balconies, and a grand piano.

A beach with clear turquoise water, palm trees, and a distant mountain range.

An aerial view of a beach with rows of blue umbrellas and white lounge chairs, surrounded by palm trees and a swimming pool.

16. The Landings Resort & Spa

Gros Islet

Sarah

Rp6.904.240

Rp8.292.545 total

includes taxes & fees

17 Oct - 18 Oct

A wooden deck with two lounge chairs, each with a dark towel and a flower. Two glasses of champagne are on the deck, and a tropical view of the ocean is visible in the background.

A wooden fence with a wooden post and a metal showerhead.

A bedroom with a bed, a balcony with a view of the ocean, and a dining area with a table and chairs.

A boat on a clear turquoise beach surrounded by dense green forest.

17. Tet Rouge Resort St. Lucia

Choiseul

Jean

Rp7.899.373

Rp9.512.146 total

includes taxes & fees

6 Oct - 7 Oct

A swimming pool with palm trees and lounge chairs.

A two-story building with a red-tiled roof, large windows, and a balcony.

An outdoor dining area with tables set for two, candles, and lanterns.

A resort with multiple-story buildings, palm trees, a gazebo, and a pool area.

18. StolenTime St Lucia, Adult Only All-Inclusive Boutique Resort

Castries

Junior

Rp10.009.741

Rp11.996.139 total

includes taxes & fees

6 Oct - 7 Oct

A balcony with a view of a marina, featuring boats and calm waters.

A marina with numerous boats docked, a pier, and a view of the coastline with buildings and greenery.

A beachside area with a wooden deck, a yellow chair, and a small palm tree.

A wooden dock with boats moored at the end.

19. Blue Lagoon Hotel & Marina

Ratho Mill

Melita

Rp3.256.648

Rp3.993.475 total

includes taxes & fees

9 Oct - 10 Oct

A spa area with a hot tub, seating, and large windows offering a view of the sea.

A hammock chair with a brown cushion on a wooden deck with a view of the sea.

A view through an open doorway to a pool area with a lounge chair and a view of the sea.

A wooden house with a stone staircase leading to a porch, surrounded by lush greenery and a view of the ocean.

20. Ti Kaye Resort & Spa - Adults Only

Canaries

jamie

Rp7.421.030

Rp8.897.189 total

includes taxes & fees

6 Oct - 7 Oct

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Holiday Rentals in Windward Islands

Apartment

A kitchen with wooden cabinets, a central island, a refrigerator, and a chandelier.

A kitchen with wooden cabinets, a refrigerator, a stove, and a dining table set with placemats and a vase.

A bedroom with a bed, dresser, television, and a door.

A living room with two sofas, a coffee table, and a wall-mounted fan.

Castle Berry Apartments

Brighton

"This apartment was lovely 😍 i will definitely come back...and it has amazing view"

Condo

A modern two-story house with a staircase leading to the entrance, surrounded by greenery and a clear sky.

A modern two-story building with a balcony, a staircase, and a gated entrance.

A modern kitchen with black cabinets, a stainless steel refrigerator, a microwave, and a wooden island with stools.

A modern bedroom with a large bed, a wooden headboard, a bedside table, a desk with a chair, and a mirror.

Daze Off

Vieux Fort

"This was a wonderful property with a modern design and attention to detail. It was very convenient by car to the local restaurants. While minimalist , it offered everything we needed."

Apartment

A pathway leading to a gated entrance, surrounded by lush greenery and palm trees.

A two-story building with a blue exterior, white balconies, and a garden area with various plants and a bench.

A sunset over a calm sea with boats, a yacht, and a distant coastline.

A table with a blue tablecloth, a basket, and jars of sugar and salt.

Skyblue Beach Apartments

Villa

"Felt like home. Very clean, quiet and safe."

Apartment

Two wooden Adirondack chairs facing a table with a bottle and glass, on a balcony with stone flooring and a view of a mountain.

A spacious kitchen with wooden cabinets, a built-in microwave, and a dining area with wicker chairs.

A building with a mountain in the background, surrounded by greenery.

A kitchen with wooden cabinets, a stove, and a dining area with wicker chairs and a table.

You 4 Ric Piton Suites

Soufriere

"This property is simply amazing! If you're looking for a nice quiet, peaceful and restful vacation this is place to be. Excellent views, natural environment and located close to beautiful beaches and restaurants in the town of Soufrier. I fully endorse this place and if it was possible I would give it 10 stars"

Apartment

A balcony with a view of a sunset over a cityscape.

A compact kitchen with a refrigerator, microwave, stove, and sink.

A pathway flanked by lush greenery and large leaves, leading through a garden or natural setting.

A multi-story building with balconies and a gated entrance.

Sunburst Apartments

Arnos Vale

"Great place."

Villa

A pool area with clear water, surrounded by palm trees and a building with a yellow facade.

A beach with clear water, a sandy shore, and a hill with dense vegetation.

A cozy living room with wicker furniture, a large window with curtains, and a view of the outdoors.

A pool area with clear water, surrounded by palm trees and a white pool edge.

Reef View Pavilion Villas and Condos

Lance aux Épines

"We really enjoyed our stay! Our family of six enjoyed the large 3 bedroom apartment so we could spread out! The pool was fun for the kids and refreshing for the adults. Sharon was very accommodating as a host."

Apartment

A glass table with a pitcher of water and glasses, overlooking a swimming pool with a view of a cityscape and hills.

A dining area with a round table, chairs, a TV, and a view of the outdoors.

A hotel room with a bed, a nightstand, a lamp, and a view of the outside through a door.

A balcony with wicker furniture and a table set for tea, overlooking a lush green landscape and a coastal town.

Heavenly Suites

Gros Islet

"Ms Chancella was a great host. She was very attentive and responsive and gave us many recommendations and options of places to eat and things to do. I would book again."

Apartment

A balcony with a clear view of a coastal area, including a body of water and greenery.

A spacious balcony with a view of the ocean, a dining area with chairs and a table, and a potted plant.

A modern kitchen with a large island, a dining area with a view of the sea, and a cozy seating area with a sofa and a coffee table.

A spacious living area with a large window overlooking the sea, a sofa, a coffee table, and a potted plant.

Villa Vino Lucia & Helen's Wine Cellar

Marigot Bay

"Amazing welcome by staff. Beautiful grounds and views! Very clean. Tranquil area with amazing wine."

Cottage

A beach with turquoise chairs, palm trees, and boats in the background.

An aerial view of a coastal property with multiple buildings, a marina with boats, and lush greenery.

A marina with multiple boats docked, a red building with a staircase, and a hillside in the background.

A swimming pool surrounded by palm trees and boats.

Le Phare Bleu Marina Resort

St. George's

"Very clean rooms, helpful staff, and beautiful grounds. "

Villa

A balcony with a wicker tray holding a wine bottle, a glass, and fruits.

A modern kitchen with white cabinetry, a central island with a vase of flowers, and a blue upholstered chair.

A bathroom with a white towel laid out on the floor, a blue soap dish, and two bottles of Bergman Kelly shampoo and lotion.

A living room with a dark blue sofa, patterned cushions, and a glass coffee table.

Seabliss Villa

Vieux Fort

"The Seabliss Villa on the South Coast in St Lucia, was the perfect choice and place for us to have spend our vacation this year. The breathtaking scenery, the peaceful and quiet community added to the thorough enjoyment of that place. Each room of that Villa had a story to tell, and I liked that. The place is so warm, cozy, relaxing and welcoming. Thank you Seabliss host, you did an excellent job. I will come again and again."

Apartment

A calm beach with boats, a mountain, and a clear sky.

A backyard with a thatched-roof structure, a swimming pool, and potted plants.

A hot tub with blue lighting, surrounded by a concrete edge, near a thatched structure.

A two-story house with a covered porch, a small garden, and a view of a mountainous landscape.

Diamondview

Soufrière

"Cisco was very friendly and accomodating. He helped with ideas of where to go in the area. We enjoyed our stay. "

Apartment

A wooden deck with a picnic table and wicker furniture, overlooking a scenic view with a wooden building and a red-roofed structure in the background.

An aerial view of a modern house with a swimming pool, a sun terrace, and lush surrounding vegetation.

A hotel room with a bed, a window with curtains, and two wall art pieces.

A modern room with a black sofa, a small white table with a vase of flowers, a mounted TV, and two windows with curtains.

Banbou Terrace

Vieux Fort

"The host was great and very helpful, if you’re thinking about booking, do it !"

Villa

A clear blue pool with a wooden deck and a red building in the background.

A room with large windows offering a view of the ocean and a red-roofed structure.

A window with white curtains and a view of a landscape.

A tropical garden with a thatched-roof structure, a staircase leading to a balcony, and lush greenery.

Kaye Coco

Choiseul

"This was a beautiful place to stay away from everything to just rest and relax. The property is as listed . The roads getting there are a little tricky to drive on because some are unpaved and narrow. navigate with caution and totally rent an SVU if you plan on staying in this area."

Apartment

A wooden staircase leading to a beach with clear turquoise water.

A view of a waterfront with boats, a red railing, and lush greenery.

A beach with clear turquoise water, a sandy shore, and lush greenery.

A beachfront property with a two-story building, a balcony, and a rocky shoreline.

Sea Glass Place

Grand Anse

"Elvis and Jane were truly wonderful hosts and made us feel so welcome from the moment we arrived. They took great care of us and made sure we had everything we needed. The accommodation was lovely—just steps from a small, peaceful, secluded beach—and the view from our room was absolutely breathtaking. One of the little things we really appreciated was how easy it was to get around. Local taxis pass right by the property, and all you have to do is wave one down for a $1 ride into town. We had...

Apartment

A balcony with curtains, a view of a lush landscape, and a building in the background.

A residential area with a paved driveway leading to a house with a red roof and a balcony.

A bedroom with a bed, two bedside tables with lamps, a chair, and a door leading to another room.

A room with wicker chairs and a round table, a vase with flowers, and curtains.

Dalys Luxury Apartments

Choppins

"I visited the property shortly after the hurricane and the property manager went above and beyond to ensure we had everything needed given the current conditions. "

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Stay near popular Windward Islands attractions

A beach with two surfboards leaning against a post, a clear blue sky, and calm sea with boats in the distance.

Grand Anse Beach

9.6/10 (1,447 reviews)

If a restful holiday is part of your travel plans, Grand Anse Beach might be the perfect place to visit during your trip to Grand Anse. Make time to visit the area's shops or simply enjoy its top-notch restaurants.

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A coastal town with colorful houses, a mountain, and a rainbow over the sea.

Gros Piton

9.6/10 (803 reviews)

Explore one of the most famous sites in Soufrière, a gigantic volcanic peak rising from the sea that attracts visitors from all over the world.

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A beach with clear turquoise water, boats, and a distant mountain.

Reduit Beach

9.0/10 (1,288 reviews)

Ride a Jet Ski, laze on the sand and enjoy a cool drink at the bar on this scenic beach set against a backdrop of verdant hills.

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A coastal landscape with a prominent mountain peak, lush green hills, and calm blue waters.

Anse Chastanet Beach

9.2/10 (538 reviews)

Enjoy a pleasant Caribbean beach day surrounded by abundant natural beauty. Relax sunbathing on dark sand and snorkeling in crystal-clear waters.

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A beach at sunset with waves, palm trees, and a silhouette of a person walking.

Sandy Beach

7.8/10 (211 reviews)

If a restful holiday is part of your travel plans, Sandy Beach might be the perfect place to visit during your trip to Vieux Fort. While in this romantic area, you can savour the top-notch restaurants.

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A coastal marina with sailboats, surrounded by lush greenery and a hillside with buildings.

Marigot Bay

8.8/10 (598 reviews)

Commune with nature and explore the great outdoors at Marigot Bay during your travels in Marigot Bay. While in this relaxing area, you can savour the top-notch restaurants.

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Pointe du Bout Beach

8.4/10 (376 reviews)

If a restful holiday is part of your travel plans, Pointe du Bout Beach might be the perfect place to visit during your trip to Pointe du Bout.

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Learn more about Windward Islands

Explore attractions like Kingstown Market and Indian Bay as you discover things to see and do in Windward Islands.

See all hotels in Windward Islands

A lush green landscape with a prominent mountain peak in the background and a body of water in the foreground.

Top Windward Islands Hotel Reviews

Bay Gardens Hotel

10/10 Excellent

"Great people with great customer service they go above and beyond to make sure your taken care of and all your needs are met"

True Blue Bay Resort

8/10 Good

"Lovely staff and property however needs some refurbishment."

BodyHoliday - All inclusive

10/10 Excellent

"Everyone in this resort comes back."

Royalton Saint Lucia, An Autograph Collection All-Inclusive Resort

10/10 Excellent

"AMAZING HOTEL!!!! FOOD, ROOMS AND POOLS"

Royalton Hideaway Saint Lucia, An Autograph Collection All-Inclusive Resort - Adults Only

10/10 Excellent

"Very good resort. Food was excellent and staff was friendly. It was an excellent trip all around. Excursions are a must. Drinks were also not watered down"

Bel Jou Hotel – Adults Only – All Inclusive

10/10 Excellent

"Its a wonderful place to relax and feel the luxury of service, I would recommend anyone who needs a vacation away from the busy life schedule to make a reservation to enjoy the comfort and luxury that is Bel jou"

Sugar Beach, A Viceroy Resort

10/10 Excellent

"Absolutely amazing! Can’t wait to go back."

Ti Kaye Resort & Spa - Adults Only

10/10 Excellent

"We went in with high expectations and were blown away by how amazing our experience was. Can’t recommend this place enough!"

Coconut Bay Beach Resort & Spa All Inclusive

10/10 Excellent

"Friendly staff"

More cheap stays in Windward Islands

Relax Inn Grenada West Indies

Calliste Hill St. George's Grenada

Rp1.448.442

Rp1.593.286 total

6 Oct - 7 Oct

includes taxes & fees

Seaview Apartel

John Compton Highway Castries Castries

Rp1.314.506

Rp1.621.182 total

7 Oct - 8 Oct

includes taxes & fees

Aupic Paradise

Aupicon Vieux Fort

Rp1.537.852

Rp1.752.436 total

11 Oct - 12 Oct

includes taxes & fees

Samfi Gardens

Colombette Drive Soufrière

Rp2.503.480

Rp2.929.072 total

6 Oct - 7 Oct

includes taxes & fees

La Haut Resort

West Coast Road, West Indies Soufrière

Rp3.621.105

Rp4.451.277 total

6 Oct - 7 Oct

includes taxes & fees

Caldera Villas

Upper Fond Benier Soufrière

Get rates

10/10 Exceptional! (76 reviews)

Find hotels in Windward Islands from Rp1.541.608

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Windward Islands

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Windward Islands hotels

1. Grenadine House

2. Holiday Inn Express & Suites St. Vincent - Grenadines by IHG

3. Sugar Beach, A Viceroy Resort

4. Beachcombers Hotel

5. Rabot Hotel from Hotel Chocolat

6. Royalton Saint Lucia, An Autograph Collection All-Inclusive Resort

7. Young Island Resort

8. Fond Doux Eco Resort

9. Anse Chastanet Resort

10. BodyHoliday - All inclusive

11. Royalton Hideaway Saint Lucia, An Autograph Collection All-Inclusive Resort - Adults Only

12. Sunset Shores Beach Hotel

13. Myah's Luxury Suites Hotel

14. LA Vue Boutique Hotel & Beach Club

15. Secrets St. Lucia Resort & Spa All Inclusive Adults Only

16. The Landings Resort & Spa

17. Tet Rouge Resort St. Lucia

18. StolenTime St Lucia, Adult Only All-Inclusive Boutique Resort

19. Blue Lagoon Hotel & Marina

20. Ti Kaye Resort & Spa - Adults Only

Holiday Rentals in Windward Islands

Castle Berry Apartments

Daze Off

Skyblue Beach Apartments

You 4 Ric Piton Suites

Sunburst Apartments

Reef View Pavilion Villas and Condos

Heavenly Suites

Villa Vino Lucia & Helen's Wine Cellar

Le Phare Bleu Marina Resort

Seabliss Villa

Diamondview

Banbou Terrace

Kaye Coco

Sea Glass Place

Dalys Luxury Apartments

Stay near popular Windward Islands attractions

Grand Anse Beach

Gros Piton

Reduit Beach

Anse Chastanet Beach

Sandy Beach

Marigot Bay

Pointe du Bout Beach

Learn more about Windward Islands

Top Windward Islands Hotel Reviews

Bay Gardens Hotel

True Blue Bay Resort

BodyHoliday - All inclusive

Royalton Saint Lucia, An Autograph Collection All-Inclusive Resort

Royalton Hideaway Saint Lucia, An Autograph Collection All-Inclusive Resort - Adults Only

Bel Jou Hotel – Adults Only – All Inclusive

Sugar Beach, A Viceroy Resort

Ti Kaye Resort & Spa - Adults Only

Coconut Bay Beach Resort & Spa All Inclusive

More cheap stays in Windward Islands

Relax Inn Grenada West Indies

Seaview Apartel

Aupic Paradise

Samfi Gardens

La Haut Resort

Caldera Villas

Go further with the Expedia app