A beach with yellow lounge chairs, palm trees, a boat, and a pier.

Lesser Antilles Vacation Rentals

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Our top choices for Lesser Antilles vacation rentals

1. Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten
4.0 star property
Simpson Bay
9.0 out of 10, Wonderful, (1,315 reviews)
"The staff was very friendly"
United States
Carmelle,
The price is CA $205
CA $252 total
includes taxes & fees
Oct 22 - Oct 23
Hilton Vacation Club Royal Palm St. Maarten

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

Studio en suite, king/twin beds sleep 3, multi-deck views, early access bag drop
Culebra
9.4 out of 10, Exceptional, (32 reviews)
"Very cozy and quiet host was excellent 👍 View incredible"
United States
Eduardo
The price is CA $127
CA $233 total
includes taxes & fees
Oct 15 - Oct 16
Studio en suite, king/twin beds sleep 3, multi-deck views, early access bag drop

3. Dickenson Bay Cottages

Dickenson Bay Cottages
3.0 star property
Dickenson Bay
9.0 out of 10, Wonderful, (344 reviews)
"Overall great stay and staff was very nice — I would recommend."
United States
Camilo
The price is CA $165
CA $221 total
includes taxes & fees
Nov 5 - Nov 6
Dickenson Bay Cottages

4. July Apartments

July Apartments
3.0 star property
Madame's Estate
9.0 out of 10, Wonderful, (254 reviews)
"The property was no frills and the staff super helpful. Would stay again!"
United States
JoyAnn Carolyn
The price is CA $132
CA $139 total
includes taxes & fees
Oct 12 - Oct 13
July Apartments

5. Fountain Anguilla

Fountain Anguilla
3.5 star property
Shoal Bay
9.0 out of 10, Wonderful, (79 reviews)
"Amazing, close to shoal bay beach, paradise"
United States
Thomas
The price is CA $236
CA $892 total
includes taxes & fees
Nov 1 - Nov 2
Fountain Anguilla

6. Denyse Home Cottage

Denyse Home Cottage
3.0 star property
St. John's
9.2 out of 10, Wonderful, (96 reviews)
"Very clean , quite, close to shops"
United States
Theodore
The price is CA $122
CA $151 total
includes taxes & fees
Oct 12 - Oct 13
Denyse Home Cottage

7. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (891 reviews)
"Property was very clean and a beautiful place to stay."
United States
Freo
The price is CA $263
CA $326 total
includes taxes & fees
Nov 9 - Nov 10
Bluebeard's Castle Resort

8. Turtles Nest Beach Resort 

Turtles Nest Beach Resort 
3.0 star property
West End Village
9.4 out of 10, Exceptional, (223 reviews)
"One of the best stays we have ever had!"
United States
Rayna
The price is CA $492
CA $580 total
includes taxes & fees
Oct 15 - Oct 16
Turtles Nest Beach Resort 

9. Sunny 1 bedroom in Esperanza close to everything

Sunny 1 bedroom in Esperanza close to everything
Esperanza
9.8 out of 10, Exceptional, (42 reviews)
"Great place. "
United States
Erik
The price is CA $150
CA $224 total
includes taxes & fees
Oct 12 - Oct 13
Sunny 1 bedroom in Esperanza close to everything

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

Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
St. Thomas
9.4 out of 10, Exceptional, (258 reviews)
"We had an amazing time. It's highly recommended"
United States
Camierre
The price is CA $71
CA $335 total
includes taxes & fees
Oct 23 - Oct 24
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

11. Mullet Bay Suites: Your Luxury Stay Awaits

Mullet Bay Suites: Your Luxury Stay Awaits
4.0 star property
Maho
9.6 out of 10, Exceptional, (185 reviews)
"This place was amazing. Perfect experience"
United States
Kenneth
The price is CA $365
CA $512 total
includes taxes & fees
Oct 12 - Oct 13
Mullet Bay Suites: Your Luxury Stay Awaits

12. Galleon Beach Resort

Galleon Beach Resort
3.0 star property
English Harbour
10.0 out of 10, Exceptional, (13 reviews)
"Absolutely loved the beachfront . 10 steps to the water . Loved the privacy and cabanas."
United States
Natalie
The price is CA $275
CA $406 total
includes taxes & fees
Oct 12 - Oct 13
Galleon Beach Resort

13. Ocean View Villa

Ocean View Villa
3.5 star property
Jost Van Dyke
9.4 out of 10, Exceptional, (35 reviews)
"Great scenic view, Friendly owners. Comfortable in every way."
United States
Virginia
The price is CA $449
CA $494 total
includes taxes & fees
Oct 12 - Oct 13
Ocean View Villa

14. Casa San Juan entire apartment in downtown Vieques

Casa San Juan entire apartment in downtown Vieques
Isabel II
9.4 out of 10, Exceptional, (100 reviews)
"Cute little apartment! We just needed a place to sleep overnight and it was great for that."
United States
Jason
The price is CA $135
CA $251 total
includes taxes & fees
Oct 14 - Oct 15
Casa San Juan entire apartment in downtown Vieques

15. Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
9.6 out of 10, Exceptional, (41 reviews)
"View was amazing . Unit itself was very unique"
United States
Zach Ezekiel Azurus
The price is CA $150
CA $747 total
includes taxes & fees
Oct 16 - Oct 17
Villa Island Paradise

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

Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!
St. Thomas
9.6 out of 10, Exceptional, (202 reviews)
"Great place to stay and peaceful"
United States
Candice D.
The price is CA $71
CA $335 total
includes taxes & fees
Oct 16 - Oct 17
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!

17. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (171 reviews)
"Very good"
United States
Alyssia
The price is CA $242
CA $406 total
includes taxes & fees
Oct 13 - Oct 14
The Hills Residence

18. Flamingo Grove Glamping Site with AC

Flamingo Grove Glamping Site with AC
St John
9.8 out of 10, Exceptional, (30 reviews)
"Really enjoyed our stay. We felt well taken care of and loved the location!"
United States
John
The price is CA $127
CA $260 total
includes taxes & fees
Oct 12 - Oct 13
Flamingo Grove Glamping Site with AC

19. Neem View Apartments Antigua

Neem View Apartments Antigua
3.0 star property
Falmouth Harbour
9.8 out of 10, Exceptional, (24 reviews)
"The rooms are clean and spacious, with effective air con, and other helpful amenities. The pool is ideal and there is optional shade for sun lounges. The staff are polite and Collette was so helpful and did everything to ensure our stay was comfortable."
United Kingdom
Samantha
The price is CA $173
CA $237 total
includes taxes & fees
Oct 12 - Oct 13
Neem View Apartments Antigua

20. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
2.0 out of 10, (1 review)
The price is CA $218
CA $333 total
includes taxes & fees
Oct 13 - Oct 14
Philips Scott House Calinago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Lesser Antilles Hotel Reviews

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 $114 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.