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

Lesser Antilles Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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, (1,310 reviews)
"The staff was very friendly"
United States
Carmelle,
The price is CA $156
CA $201 total
includes taxes & fees
Oct 11 - Oct 12
Hilton Vacation Club Royal Palm St. Maarten

2. Denyse Home Cottage

Denyse Home Cottage
3.0 star property
St. John's
9.2 out of 10, Wonderful, (95 reviews)
"Very clean , quite, close to shops"
United States
Theodore
The price is CA $122
CA $151 total
includes taxes & fees
Oct 5 - Oct 6
Denyse Home Cottage

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 $192
CA $253 total
includes taxes & fees
Oct 5 - Oct 6
Dickenson Bay Cottages

4. Turtles Nest Beach Resort 

Turtles Nest Beach Resort 
3.0 star property
West End Village
9.4 out of 10, Exceptional, (222 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 

5. Paradise Suite

Paradise Suite
4.0 star property
Cotton Ground
9.6 out of 10, Exceptional, (7 reviews)
"Excellent place."
United States
Edgardo
The price is CA $282
CA $433 total
includes taxes & fees
Oct 5 - Oct 6
Paradise Suite

6. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (878 reviews)
"Good place to stay especially during off season"
United States
Jason
The price is CA $263
CA $325 total
includes taxes & fees
Nov 3 - Nov 4
Bluebeard's Castle Resort

7. July Apartments

July Apartments
3.0 star property
Madame's Estate
9.0 out of 10, Wonderful, (253 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 5 - Oct 6
July Apartments

8. 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, (184 reviews)
"This place was amazing. Perfect experience"
United States
Kenneth
The price is CA $365
CA $512 total
includes taxes & fees
Oct 6 - Oct 7
Mullet Bay Suites: Your Luxury Stay Awaits

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 5 - Oct 6
Sunny 1 bedroom in Esperanza close to everything

10. Dickenson Bay Oasis Antigua Village

Dickenson Bay Oasis Antigua Village
3.0 star property
Dickenson Bay
8.8 out of 10, Excellent, (119 reviews)
"Truly enjoyed my stay"
United States
Nyah
The price is CA $215
CA $324 total
includes taxes & fees
Oct 5 - Oct 6
Dickenson Bay Oasis Antigua Village

11. Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
9.4 out of 10, Exceptional, (42 reviews)
"View was amazing . Unit itself was very unique"
United States
Zach Ezekiel Azurus
The price is CA $103
CA $688 total
includes taxes & fees
Oct 11 - Oct 12
Villa Island Paradise

12. 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, (255 reviews)
"We had an amazing time. It's highly recommended"
United States
Camierre
The price is CA $86
CA $353 total
includes taxes & fees
Oct 5 - Oct 6
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

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 5 - Oct 6
Ocean View Villa

14. The Perch at Hawk Hill

The Perch at Hawk Hill
2.0 star property
St. Thomas
The price is CA $245
CA $490 total
includes taxes & fees
Oct 5 - Oct 6
The Perch at Hawk Hill

15. 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)
"We LOVED our stay and would recommend it to anyone going to St. Thomas. The location was unbeatable, and the property was equipped with everything we needed and more!"
United States
Alessandra C.
The price is CA $86
CA $353 total
includes taxes & fees
Oct 5 - Oct 6
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!

16. 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 $250 total
includes taxes & fees
Oct 5 - Oct 6
Casa San Juan entire apartment in downtown Vieques

17. Tiny house on an acre with ocean view and private infinity pool.

Tiny house on an acre with ocean view and private infinity pool.
Vieques
9.8 out of 10, Exceptional, (38 reviews)
"Clean and secluded"
United States
Heather
The price is CA $241
CA $380 total
includes taxes & fees
Oct 5 - Oct 6
Tiny house on an acre with ocean view and private infinity pool.

18. 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

19. Antigua Village Beach Resort

Antigua Village Beach Resort
3.0 star property
Dickenson Bay
8.8 out of 10, Excellent, (464 reviews)
"Staff was very friendly, excellent location, close to downtown. The property was well kept. This is my first choice in Antigua to stay. Thanks to Tim at the front desk, very professional."
United States
sylvia
The price is CA $357
CA $468 total
includes taxes & fees
Oct 5 - Oct 6
Antigua Village Beach Resort

20. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (170 reviews)
"Very good"
United States
Alyssia
The price is CA $241
CA $406 total
includes taxes & fees
Oct 5 - Oct 6
The Hills Residence
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Lesser Antilles Hotel Reviews

Find out more about Lesser Antilles

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Lesser Antilles. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.