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. Dickenson Bay Cottages

Dickenson Bay Cottages
3.0 star property
Dickenson Bay
9.0 out of 10, Wonderful, (344 reviews)
"Everything was great"
United States
Sabra Platania
The price is CA $134
CA $190 total
includes taxes & fees
Nov 11 - Nov 12
Dickenson Bay Cottages

2. Royal Palms Hotel

Royal Palms Hotel
3.5 star property
South Hill
9.2 out of 10, Wonderful, (79 reviews)
"The service was excellent and staff was very accomodating and courteous. We were made to feel very comfortable."
United States
Colin
The price is CA $226
CA $287 total
includes taxes & fees
Oct 29 - Oct 30
Royal Palms Hotel

3. 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, (33 reviews)
"Very cozy and quiet host was excellent 👍 View incredible"
United States
Eduardo
The price is CA $126
CA $231 total
includes taxes & fees
Oct 20 - Oct 21
Studio en suite, king/twin beds sleep 3, multi-deck views, early access bag drop

4. 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 $211
CA $862 total
includes taxes & fees
Nov 2 - Nov 3
Fountain Anguilla

5. 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 $57
CA $311 total
includes taxes & fees
Oct 23 - Oct 24
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

6. 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 $151
CA $159 total
includes taxes & fees
Oct 20 - Oct 21
July Apartments

7. 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 $121
CA $150 total
includes taxes & fees
Oct 20 - Oct 21
Denyse Home Cottage

8. 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, (1,319 reviews)
"The staff was very friendly"
United States
Carmelle,
The price is CA $227
CA $276 total
includes taxes & fees
Nov 5 - Nov 6
Hilton Vacation Club Royal Palm St. Maarten

9. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (904 reviews)
"Property was very clean and a beautiful place to stay."
United States
Freo
The price is CA $230
CA $284 total
includes taxes & fees
Nov 18 - Nov 19
Bluebeard's Castle Resort

10. 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 $148
CA $223 total
includes taxes & fees
Oct 20 - Oct 21
Sunny 1 bedroom in Esperanza close to everything

11. 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 $176
CA $774 total
includes taxes & fees
Oct 20 - Oct 21
Villa Island Paradise

12. 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, (203 reviews)
"Great place to stay and peaceful"
United States
Candice D.
The price is CA $57
CA $310 total
includes taxes & fees
Oct 20 - Oct 21
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!

13. Dickenson Bay Oasis Antigua Village

Dickenson Bay Oasis Antigua Village
3.0 star property
Dickenson Bay
8.8 out of 10, Excellent, (125 reviews)
"The property is located on a beautiful beach!"
United States
sheralyn
The price is CA $214
CA $321 total
includes taxes & fees
Oct 23 - Oct 24
Dickenson Bay Oasis Antigua Village

14. The Hills Residence

The Hills Residence
3.0 star property
Simpson Bay
8.4 out of 10, Very good, (172 reviews)
"Very good"
United States
Alyssia
The price is CA $216
CA $363 total
includes taxes & fees
Oct 21 - Oct 22
The Hills Residence

15. 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 $488
CA $576 total
includes taxes & fees
Oct 20 - Oct 21
Turtles Nest Beach Resort 

16. 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 $126
CA $258 total
includes taxes & fees
Oct 20 - Oct 21
Flamingo Grove Glamping Site with AC

17. The Mermaid's Pearl at Sapphire Beach

The Mermaid's Pearl at Sapphire Beach
St. Thomas
9.8 out of 10, Exceptional, (164 reviews)
"Host was very courteous!! I will definitely be back!!"
United States
Tyneisha
The price is CA $150
CA $366 total
includes taxes & fees
Oct 21 - Oct 22
The Mermaid's Pearl at Sapphire Beach

18. 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 $362
CA $508 total
includes taxes & fees
Oct 20 - Oct 21
Mullet Bay Suites: Your Luxury Stay Awaits

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 $172
CA $235 total
includes taxes & fees
Oct 20 - Oct 21
Neem View Apartments Antigua

20. Your Caribbean home away from home

Your Caribbean home away from home
Christiansted
9.4 out of 10, Exceptional, (21 reviews)
"Perfect for my stay, good neighborhood, host was excellent at communicating, easy access"
United States
Breanna S.
The price is CA $139
CA $402 total
includes taxes & fees
Oct 20 - Oct 21
Your Caribbean home away from home
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 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.