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

Lesser Antilles Holiday Rentals

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Our top choices for Lesser Antilles holiday rentals

1. Coconut Breeze Villas

Coconut Breeze Villas
2.5 star property
Cane Garden Bay
9.4 out of 10, Exceptional, (37 reviews)
"An absolutely amazing place to stay"
United States
Julian
The price is NZ$437
includes taxes & fees
11 Aug - 12 Aug
Coconut Breeze Villas

2. Dickenson Bay Cottages

Dickenson Bay Cottages
3.0 star property
Dickenson Bay
9.0 out of 10, Wonderful, (342 reviews)
"Overall great stay and staff was very nice — I would recommend."
United States
Camilo
The price is NZ$301
includes taxes & fees
11 Aug - 12 Aug
Dickenson Bay Cottages

3. July Apartments

July Apartments
3.0 star property
Madame's Estate
9.0 out of 10, Wonderful, (251 reviews)
"Great stay"
United States
Drunisha
The price is NZ$160
includes taxes & fees
22 Aug - 23 Aug
July Apartments

4. Simpson Bay Suites

Simpson Bay Suites
3.5 star property
Simpson Bay
7.2 out of 10, Good, (161 reviews)
"AC worked well the room was cleaned daily and the staff was always friendly and made great suggestions for dinning and places to see."
United States
Michael
The price is NZ$231
includes taxes & fees
11 Aug - 12 Aug
Simpson Bay Suites

5. Dickenson Bay Oasis Antigua Village

Dickenson Bay Oasis Antigua Village
3.0 star property
Dickenson Bay
8.8 out of 10, Excellent, (100 reviews)
"Great location friendly staff beautiful grounds"
Canada
Brittany
The price is NZ$402
includes taxes & fees
12 Aug - 13 Aug
Dickenson Bay Oasis Antigua Village

6. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (719 reviews)
"The view, the accommodation, the staff were all superb. I always stay there when I visit the Island."
United States
Janice
The price is NZ$422
includes taxes & fees
8 Sept - 9 Sept
Bluebeard's Castle Resort

7. 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, (1,264 reviews)
"It was a great stay"
United States
Shawn
The price is NZ$314
includes taxes & fees
25 Aug - 26 Aug
Hilton Vacation Club Royal Palm St. Maarten

8. Anne's Apartments

Anne's Apartments
2.0 star property
Osbourn
8.4 out of 10, Very good, (6 reviews)
"Clean room and courteous staff"
United States
Gachelle Latoya
The price is NZ$216
includes taxes & fees
11 Aug - 12 Aug
Anne's Apartments

9. Aurela Residences

Aurela Residences
2.0 star property
St. John's
The price is NZ$327
includes taxes & fees
20 Aug - 21 Aug
Aurela Residences

10. South Coast Horizons

South Coast Horizons
3.0 star property
Cades Bay
8.0 out of 10, Very good, (63 reviews)
"Great place to stay , friendly staff and good service all around"
United States
Justin
The price is NZ$206
includes taxes & fees
12 Aug - 13 Aug
South Coast Horizons

11. Chez Mango Villas

Chez Mango Villas
3.5 star property
Old Towne
7.6 out of 10, Good, (32 reviews)
"A place to stay in Montserrat, kitchen, pool and garden to relax"
United States
Audrey
The price is NZ$312
includes taxes & fees
11 Aug - 12 Aug
Chez Mango Villas

12. MIDTOWN MOTEL SXM

MIDTOWN MOTEL SXM
2.5 star property
Downtown Philipsburg
7.4 out of 10, Good, (70 reviews)
"All in all it was a great experience. Close to the beach. Clean environment. Kind staff"
United States
James
The price is NZ$148
includes taxes & fees
20 Aug - 21 Aug
MIDTOWN MOTEL SXM

13. The Breeze

The Breeze
2.0 star property
ST Thomas
The price is NZ$1,292
includes taxes & fees
11 Aug - 12 Aug
The Breeze

14. Lord Nelson Hotel & Residences

Lord Nelson Hotel & Residences
3.0 star property
Osbourn
8.4 out of 10, Very good, (61 reviews)
"Lord Nelson Hotel & Residences is an excellent place for a large group! My staff, family, and I thoroughly enjoyed our stay. The apartments were spacious and comfortable, and having a fully equipped kitchen was extremely convenient, especially for a group our size, as we were able to prepare and enjoy our own meals together. We had a wonderful experience and would definitely recommend Lord Nelson to families and large groups looking for a comfortable and convenient place to stay."
United States
Charlyn
The price is NZ$381
includes taxes & fees
30 Aug - 31 Aug
Lord Nelson Hotel & Residences

15. Whale Tails Island Suites & Villas

Whale Tails Island Suites & Villas
4.0 star property
Oranjestad
8.0 out of 10, Very good, (5 reviews)
"We very much enjoyed our stay. The room was big clean, and well equipped, with views of The Quill from the back, the ocean and St Kitts from the front. Very calm, quiet and relaxing. Rob, the owner, was extremely friendly and kind, very supportive. Picked us up from the ferry port and dropped us off at the airport. If you like peace and quiet, like to watch the watch the ocean and read books and like to cook for yourself, this place is great. Be aware, it is out of the way, so you will need a...
United Kingdom
Justin
Whale Tails Island Suites & Villas

16. Belvedere Holiday Home

Belvedere Holiday Home
4.0 star property
St. John's
9.8 out of 10, Exceptional, (9 reviews)
"Everything was good, excellent view"
United States
Clinton
The price is NZ$227
includes taxes & fees
5 Sept - 6 Sept
Belvedere Holiday Home

17. The Greenside Cottages - Private Tropical Garden - Residential area 5 mins from the beach

The Greenside Cottages - Private Tropical Garden - Residential area 5 mins from the beach
3.0 star property
St. John's
9.2 out of 10, Wonderful, (42 reviews)
"Amazing stay, convenient location, superb hospitality. Enjoyed my short stay at this serene property. Nice stay for solo travel, couples, or small family. Plan to relax and unwind with a much needed break from the every day hustle."
United States
Tenishia
The price is NZ$328
includes taxes & fees
11 Aug - 12 Aug
The Greenside Cottages - Private Tropical Garden - Residential area 5 mins from the beach

18. Antigua Village Beach Resort

Antigua Village Beach Resort
3.0 star property
Dickenson Bay
8.8 out of 10, Excellent, (458 reviews)
"Clean room, friendly staff, very quiet area, beautiful beach. Great accommodations."
United States
sylvia
The price is NZ$544
includes taxes & fees
11 Aug - 12 Aug
Antigua Village Beach Resort

19. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (162 reviews)
"Comfortable room and ac was a welcome after a hot day."
United States
Maria
The price is NZ$463
includes taxes & fees
11 Aug - 12 Aug
The Hills Residence

20. LambLion Holiday Apartments

LambLion Holiday Apartments
2.5 star property
Freemans Village
9.2 out of 10, Wonderful, (34 reviews)
"Excellent check in process, nice property, very clean, great AC in the bedroom. Very quiet and secluded, really reminded me of a cottage. Not much around that you can walk to but overall it was a really nice spot with excellent hosts."
Canada
Abdul
The price is NZ$230
includes taxes & fees
11 Aug - 12 Aug
LambLion Holiday Apartments
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Lesser Antilles holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Lesser Antilles. 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 Lesser Antilles. 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 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 holiday 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 Lesser Antilles short-term rentals, that won’t be hard to do.