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, (1,303 reviews)
"Perfect location."
United States
Andre
The price is CA $201
CA $248 total
includes taxes & fees
Oct 4 - Oct 5
Hilton Vacation Club Royal Palm St. Maarten

2. 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 $116
CA $694 total
includes taxes & fees
Oct 11 - Oct 12
Villa Island Paradise

3. Turtles Nest Beach Resort 

Turtles Nest Beach Resort 
3.0 star property
West End Village
9.4 out of 10, Exceptional, (220 reviews)
"One of the best stays we have ever had!"
United States
Rayna
The price is CA $483
CA $569 total
includes taxes & fees
Oct 15 - Oct 16
Turtles Nest Beach Resort 

4. 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 $120
CA $148 total
includes taxes & fees
Sep 22 - Sep 23
Denyse Home Cottage

5. 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 $441
CA $485 total
includes taxes & fees
Sep 22 - Sep 23
Ocean View Villa

6. 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 $347
CA $491 total
includes taxes & fees
Oct 5 - Oct 6
Mullet Bay Suites: Your Luxury Stay Awaits

7. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (169 reviews)
"Very good"
United States
Alyssia
The price is CA $216
CA $377 total
includes taxes & fees
Oct 7 - Oct 8
The Hills Residence

8. 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 $147
CA $220 total
includes taxes & fees
Sep 22 - Sep 23
Sunny 1 bedroom in Esperanza close to everything

9. Four Diamonds Park Villas

Four Diamonds Park Villas
4.0 star property
Anegada
The price is CA $441
CA $529 total
includes taxes & fees
Sep 22 - Sep 23
Four Diamonds Park Villas

10. The Breeze

The Breeze
2.0 star property
ST Thomas
The price is CA $184
CA $1,046 total
includes taxes & fees
Oct 3 - Oct 4
The Breeze

11. Yepton Estate Cottages

Yepton Estate Cottages
3.0 star property
Five Islands Village
10.0 out of 10, Exceptional, (123 reviews)
"The cottage was quiet and super relaxing. The staff and owners were very accommodating"
United States
Andrew
The price is CA $278
CA $367 total
includes taxes & fees
Sep 30 - Oct 1
Yepton Estate Cottages

12. Dickenson Bay Oasis Antigua Village

Dickenson Bay Oasis Antigua Village
3.0 star property
Dickenson Bay
8.8 out of 10, Excellent, (115 reviews)
"Truly enjoyed my stay"
United States
Nyah
The price is CA $197
CA $303 total
includes taxes & fees
Oct 21 - Oct 22
Dickenson Bay Oasis Antigua Village

13. Lameshur Cottage's Guest House

Lameshur Cottage's Guest House
St John
10.0 out of 10, Exceptional, (141 reviews)
"Amazing place! Great host!!Close to Salt Pond."
United States
Shawn C.
The price is CA $301
CA $510 total
includes taxes & fees
Oct 10 - Oct 11
Lameshur Cottage's Guest House

14. 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, (30 reviews)
"Very cozy and quiet host was excellent 👍 View incredible"
United States
Eduardo
The price is CA $125
CA $229 total
includes taxes & fees
Sep 22 - Sep 23
Studio en suite, king/twin beds sleep 3, multi-deck views, early access bag drop

15. 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 $170
CA $233 total
includes taxes & fees
Oct 12 - Oct 13
Neem View Apartments Antigua

16. 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 $130
CA $136 total
includes taxes & fees
Sep 24 - Sep 25
July Apartments

17. 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 $188
CA $248 total
includes taxes & fees
Sep 22 - Sep 23
Dickenson Bay Cottages

18. Casa Paradise Palms! Beautiful views from the rooftop. Walk to ferry/beach.

Casa Paradise Palms! Beautiful views from the rooftop. Walk to ferry/beach.
Bravos de Boston
9.8 out of 10, Exceptional, (31 reviews)
"We stayed one night and it was perfect for what we needed! The property is great, the location is a bit out of the way from everything, but getting a taxi to take us to and from was no issue at all. "
United States
Ashley H.
The price is CA $240
CA $510 total
includes taxes & fees
Sep 22 - Sep 23
Casa Paradise Palms! Beautiful views from the rooftop. Walk to ferry/beach.

19. Getaway Homes

Getaway Homes
4.0 star property
Basseterre
The price is CA $152
CA $170 total
includes taxes & fees
Sep 22 - Sep 23
Getaway Homes

20. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (850 reviews)
"Bluebeards is one of my favorite places to stay when I am on the island."
United States
Erica
The price is CA $258
CA $319 total
includes taxes & fees
Oct 20 - Oct 21
Bluebeard's Castle Resort
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.