Lesser Antilles Vacation Rentals from CA $42: Short-Term Rentals for 2026

A sign reading "Devil's Bay The Baths" with a beach and rocky landscape in the background.

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Our top choices for Lesser Antilles vacation rentals

A view from inside a building looking out to a beach with clear turquoise water and a distant ship.

1. MIDTOWN MOTEL SXM

Downtown Philipsburg

brenton

CA $105 total

includes taxes & fees

Dec 16 - Dec 17

A stone building with a staircase leading to an entrance, surrounded by potted plants and a clear sky.

2. Bluebeard's Castle Resort

Charlotte Amalie

James Theodore

CA $360 total

includes taxes & fees

Nov 17 - Nov 18

A resort with a view of sailboats on the water, a beach with palm trees, and a modern building with balconies.

3. Hilton Vacation Club Royal Palm St. Maarten

Simpson Bay

Prem

CA $340 total

includes taxes & fees

Dec 2 - Dec 3

A modern living room with large windows, a purple sofa, and a view of the beach and ocean.

4. Mullet Bay Suites: Your Luxury Stay Awaits

Maho

Susan

CA $443 total

includes taxes & fees

Nov 19 - Nov 20

A covered outdoor seating area with a view of the sea and a hillside.

5. Coconut Breeze Villas

Cane Garden Bay

Julian

CA $319 total

includes taxes & fees

Nov 21 - Nov 22

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

6. Beachfront Villas at Crystal Cove

St. Thomas

Olena

CA $723 total

includes taxes & fees

Nov 25 - Nov 26

A spacious balcony with a view of the ocean, a white ceiling fan, a dining table with chairs, and a patterned sofa.

7. Turtles Nest Beach Resort

West End Village

Willie

CA $581 total

includes taxes & fees

Nov 18 - Nov 19

A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

8. Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

St. Thomas

Nalbert

CA $381 total

includes taxes & fees

Nov 17 - Nov 18

A seaside property with a covered outdoor seating area, a view of the sea, and a hill in the background.

9. Studio en suite, king/twin beds sleep 3, multi-deck views, early access bag drop

Culebra

Willie F.

CA $222 total

includes taxes & fees

Nov 16 - Nov 17

A balcony with a wooden table, two chairs, and a view of the ocean and greenery.

10. Fountain Anguilla

Shoal Bay

Thomas

CA $893 total

includes taxes & fees

Nov 16 - Nov 17

11. Denyse Home Cottage

St. John's

michael

CA $151 total

includes taxes & fees

Nov 16 - Nov 17

A hotel room with a bed, a blue armchair, a small table with a lamp, and a wall-mounted radio.

12. Sunny 1 bedroom in Esperanza close to everything

Esperanza

Jodi W.

CA $232 total

includes taxes & fees

Nov 16 - Nov 17

A covered outdoor seating area with a view of the ocean and hills.

13. Ceblue Luxury Villas

The Valley

Raynaldo

CA $1,498 total

includes taxes & fees

Dec 3 - Dec 4

A woman sitting on a beach with a clear sky and palm trees in the background.

14. Antigua Village Beach Resort

Dickenson Bay

Saneka

CA $423 total

includes taxes & fees

Nov 16 - Nov 17

A beach with a clear sky, a sandy path, palm trees, and a building with a balcony.

15. Dickenson Bay Oasis Antigua Village

Dickenson Bay

Joseph

CA $315 total

includes taxes & fees

Nov 16 - Nov 17

A coastal landscape with a beach, clear blue waters, and lush greenery.

16. Villa Island Paradise

St. John

Zach Ezekiel Azurus

CA $859 total

includes taxes & fees

Nov 16 - Nov 17

A spacious living area with a sofa, dining table, and chairs, overlooking a scenic ocean view.

17. The Breeze

ST Thomas

CA $270 total

includes taxes & fees

Nov 24 - Nov 25

A resort with a large swimming pool, beach access, and palm trees.

18. Marriott's St. Kitts Beach Club

Basseterre

beverly

CA $558 total

includes taxes & fees

Nov 28 - Nov 29

A hotel room with a bed, a sofa, a small round table, and a chair. There is a bathroom visible through an open door.

19. July Apartments

Madame's Estate

JoyAnn Carolyn

CA $175 total

includes taxes & fees

Dec 16 - Dec 17

A beach with clear turquoise water, a sandy shore, and a distant island with buildings.

20. Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!

St. Thomas

Candice D.

CA $381 total

includes taxes & fees

Nov 22 - Nov 23

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Find vacation rentals that suit your style

Top Lesser Antilles Hotel Reviews

A swimming pool with lounge chairs and a table on a wooden deck, surrounded by greenery and a mountain view.

Villa Jwi Lavi Boutique Hotel

Cul de Sac

10/10 Excellent

Dawn

A modern two-story building with a flat roof, multiple balconies, and a surrounding landscape with palm trees and rocks.

Club Vieques - Adults Only Resort - LGBT Friendly

Vieques

10/10 Excellent

Yibo

A beachside resort with thatched umbrellas, lounge chairs, and a view of the ocean and distant hills.

Hotel Les Ondines Sur La Plage

Grand Cul-de-Sac

10/10 Excellent

Amber

A beach resort with palm trees, a pathway, and a view of the ocean.

Orient Beach Hotel

Orient Bay

10/10 Excellent

We had an incredible week at Orient Beach Hotel. Our immediate first impression was the genuinely warm welcome from the front desk team member, Junior. This positive energy remained through the week and was complemented by the incredible hotel manager, Myriam, and the attentive housekeeping staff. Room and views were exactly as pictured. We couldn’t have planned it any better. Thank you!! We hope to be back.

Luigi

A resort with a pool, beach, and boats in the water.

GYP SEA Saint Barth

Colombier

10/10 Excellent

Charles

A beach with clear turquoise water, sandy shore, and palm trees.

Sea Gate Hotel

Isabel II

10/10 Excellent

Daisy

A beach with clear water, palm trees, and beach chairs.

Curtain Bluff Resort - All Inclusive

Carlisle Bay

10/10 Excellent

Curtain Bluff is the most rare of places to still be found when traveling. Its design, layout,, service quality and attention to detail is hard to find anymore. From the arrival at the airport to the check-in and check-out experience the staff cannot be more helpful. Rather than see this as another all inclusive resort, think of Curtain Bluff as a fine 5 star hotel set in the Caribbean sea. From its white linen service to its extensive wine list, the dining experience is more akin to a fine...

Bill

An infinity pool with a view of the ocean, outdoor dining area with tables and chairs, and palm trees.

Le Toiny Hôtel & Beach Club

Toiny

10/10 Excellent

Adeyemi

A balcony with a view of the ocean, a bottle of champagne, two wine glasses, and a book titled "Linda Van Rijn Zoutelande".

La Vista Hotel

Pelican Key

10/10 Excellent

I stayed at the property from August 22-29. Great location, very clean, wonderful property and friendly staff. Rooms were cleaned daily, kitchen did not lack any appliances or dishes, plenty of towels daily, super comfortable bed and pillows, wifi worked wonderfully as well as the air conditioners and the pressure in the shower with hot water was amazing. Check in was quick and easy, late check out available as well as a great shower area near the pool with toiletries and towels to get ready...

Marta

A coastal resort with a swimming pool, beach access, and lush greenery.

Grand Case Beach Club

Grand Case

10/10 Excellent

WAYNE

A resort with multiple swimming pools, water slides, and sun loungers.

Aurora Anguilla Resort & Golf Club

Rendezvous Bay

10/10 Excellent

Marc-Olivier

A balcony with a view of the sea, a bed with towels, and two white wicker chairs.

Le Temps des Cerises Hotel Beach

Grand Case

10/10 Excellent

Heather

A poolside area with lounge chairs and umbrellas, a person in a white robe, and a view of the sea and hills in the background.

Christopher Hotel

Pointe Milou

10/10 Excellent

Hotel Christopher is a small and very well appointed hotel. Very clean and new with excellent room design. Reception services were excellent. Concierge was good and housekeeping very efficient. Pools staff were a bit distracted and often required reminders for orders. Car/Valet are fantastic and transfers to the airport are included which makes renting a smaller car possible with a family (much appreciated) Breakfast was quite good however selection was repeated with very little variety....

Anonymous traveller

A coastal building with a stone facade, a palm tree, and a view of the ocean.

The Waves at Cane Bay

Kingshill

8/10 Good

Robert

Find out more about Lesser Antilles

Everything you need to know about Lesser Antilles vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Lesser Antilles vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Lesser Antilles vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Lesser Antilles vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Lesser Antilles. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Lesser Antilles vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Lesser Antilles vacation rentals we have selected for you start as low as CA $42 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Lesser Antilles rentals

At Expedia, we put the best Lesser Antilles vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Lesser Antilles rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Lesser Antilles vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Lesser Antilles. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Lesser Antilles Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Lesser Antilles vacation rentals

1. MIDTOWN MOTEL SXM

2. Bluebeard's Castle Resort

3. Hilton Vacation Club Royal Palm St. Maarten

4. Mullet Bay Suites: Your Luxury Stay Awaits

5. Coconut Breeze Villas

6. Beachfront Villas at Crystal Cove

7. Turtles Nest Beach Resort

8. Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

9. Studio en suite, king/twin beds sleep 3, multi-deck views, early access bag drop

10. Fountain Anguilla

11. Denyse Home Cottage

12. Sunny 1 bedroom in Esperanza close to everything

13. Ceblue Luxury Villas

14. Antigua Village Beach Resort

15. Dickenson Bay Oasis Antigua Village

16. Villa Island Paradise

17. The Breeze

18. Marriott's St. Kitts Beach Club

19. July Apartments

20. Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!

Find vacation rentals that suit your style

Top Lesser Antilles Hotel Reviews

Villa Jwi Lavi Boutique Hotel

10/10 Excellent

Find out more about Lesser Antilles

Lesser Antilles vacation rentals: An excellent choice for every season

How to find incredible deals on Lesser Antilles rentals