Photo by Bill Dillard

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Our top choices for Lesser Antilles vacation homes

1. Philips Scott House Calinago

Philips Scott House Calinago
3.0 star property
Downtown Philipsburg
2.0 out of 10, (1 review)
The price is ¥21,992
¥34,377 total
includes taxes & fees
Nov 20 - Nov 21
Philips Scott House Calinago

2. Zeus townhouse,

Zeus townhouse,
St. John's
9.2 out of 10, Wonderful, (27 reviews)
"My husband and I enjoyed our stay here. The place is really nice and spacious and clean . "
Canada
Heather L.
The price is ¥13,575
¥16,450 total
includes taxes & fees
Nov 16 - Nov 17
Zeus townhouse,

3. Sophisticated Beach Condo-Ocean View-Sapphire

Sophisticated Beach Condo-Ocean View-Sapphire
Smith Bay
9.0 out of 10, Wonderful, (46 reviews)
"Clean room, AC worked great, pool is very close. Overall, a really cool place to stay."
United States
Michael
The price is ¥25,729
¥51,944 total
includes taxes & fees
Nov 16 - Nov 17
Sophisticated Beach Condo-Ocean View-Sapphire

4. Lovely room in a nice villa , close to Friars bay and happy bay

Lovely room in a nice villa , close to Friars bay and happy bay
Saint-martin
9.0 out of 10, Wonderful, (11 reviews)
"Great place to stay. Will definitely be staying again next year! "
United States
Kurt
The price is ¥12,323
¥17,780 total
includes taxes & fees
Nov 23 - Nov 24
Lovely room in a nice villa , close to Friars bay and happy bay

5. Home a way from home in the Unspoiled queen of the Caribbean.

Home a way from home in the Unspoiled queen of the Caribbean.
Saba
10.0 out of 10, Exceptional, (4 reviews)
"The house was amazing we will be back again… Thank you Michael!"
United States
Tim L.
The price is ¥63,884
¥69,474 total
includes taxes & fees
Dec 1 - Dec 2
Home a way from home in the Unspoiled queen of the Caribbean.

6. La Iguana Morada: A/C, WiFi, BioBay, walk to Ferry

La Iguana Morada: A/C, WiFi, BioBay, walk to Ferry
Isabel II
9.4 out of 10, Exceptional, (3 reviews)
"Loved our stap...easy to get around either with car or on foot"
United States
Pam H.
The price is ¥12,745
¥33,392 total
includes taxes & fees
Nov 16 - Nov 17
La Iguana Morada: A/C, WiFi, BioBay, walk to Ferry

7. Cozy one bedroom studio

Cozy one bedroom studio
Sea Rocks
9.8 out of 10, Exceptional, (10 reviews)
"Loved both the property and the Hosts. The location was amazing, very convenient and the place was spotless, spacious, beautiful and fully equipped. Had everything needed for a super comfortable and relaxing stay. Hosts were responsive and caring, treated me as part of their Family. Also very thankful to them for taking the time and sharing their local knowledge and favorite spots in the Anguilla Paradise :) Loved my stay here, highly recommend and will come back for sure !!!"
United States
Daymara
The price is ¥22,359
¥29,386 total
includes taxes & fees
Nov 16 - Nov 17
Cozy one bedroom studio

8. Quiet Vieques Escape Private and Central

Quiet Vieques Escape Private and Central
Vieques
The price is ¥15,388
¥34,171 total
includes taxes & fees
Nov 16 - Nov 17
Quiet Vieques Escape Private and Central

9. SPECTACULAR Ensenada View @ Villa Ilusion Villa 3 - Punta Aloe #1

SPECTACULAR Ensenada View @ Villa Ilusion Villa 3 - Punta Aloe #1
Culebra
9.0 out of 10, Wonderful, (66 reviews)
"Perfect place for my family. Had what we needed. Location and everything we need to enjoy our vacation. "
United States
Adriana G.
The price is ¥33,379
¥58,666 total
includes taxes & fees
Nov 16 - Nov 17
SPECTACULAR Ensenada View @ Villa Ilusion Villa 3 - Punta Aloe #1

10. To complete

To complete
Cul-de-Sac
10.0 out of 10, Exceptional, (1 review)
"Jamal is very helpful, great communication."
Canada
Abdal M.
The price is ¥7,922
¥8,802 total
includes taxes & fees
Nov 22 - Nov 23
To complete

11. Vieques Home Base | Beaches & Bio Bay

Vieques Home Base | Beaches & Bio Bay
Vieques
The price is ¥22,569
¥50,723 total
includes taxes & fees
Nov 16 - Nov 17
Vieques Home Base | Beaches & Bio Bay

12. Captivating 1-bed Cottage in Codrington

Captivating 1-bed Cottage in Codrington
2.5 star property
Codrington
The price is ¥22,540
¥34,278 total
includes taxes & fees
Nov 17 - Nov 18
Captivating 1-bed Cottage in Codrington

13. To complete

To complete
Grand Case
The price is ¥21,126
¥22,886 total
includes taxes & fees
Nov 26 - Nov 27
To complete

14. SPECTACULAR Ensenada View @ Villa Ilusion Villa 4 - Punta Aloe #1

SPECTACULAR Ensenada View @ Villa Ilusion Villa 4 - Punta Aloe #1
Culebra
6.0 out of 10, (2 reviews)
"Amazing view and deck! The deck was such a great feature and great use of space. Everything was neat and tidy. Would highly recommend!!"
United States
trisha h.
The price is ¥27,790
¥43,023 total
includes taxes & fees
Nov 16 - Nov 17
SPECTACULAR Ensenada View @ Villa Ilusion Villa 4 - Punta Aloe #1

15. Spacious Home with Beach Gear and Outdoor Space

Spacious Home with Beach Gear and Outdoor Space
Esperanza
9.8 out of 10, Exceptional, (38 reviews)
"Cute property. Walking distance to town and a little market. Nice to have the beach chairs and beach towels. Washer and dryer were a must with beach days and snorkeling. Host was very responsive. Would stay again."
United States
Oona C.
The price is ¥33,031
¥55,251 total
includes taxes & fees
Nov 30 - Dec 1
Spacious Home with Beach Gear and Outdoor Space

16. SPECTACULAR Ensenada View @ Villa Ilusion Villa 2 - Punta Aloe #1

SPECTACULAR Ensenada View @ Villa Ilusion Villa 2 - Punta Aloe #1
Playa Sardinas II
9.0 out of 10, Wonderful, (29 reviews)
"Excellent view quiet peaceful very relaxing cold air inside had a blast "
United States
Randall
The price is ¥27,790
¥43,023 total
includes taxes & fees
Nov 16 - Nov 17
SPECTACULAR Ensenada View @ Villa Ilusion Villa 2 - Punta Aloe #1

17. Quiet and cozy 2-bedroom house

Quiet and cozy 2-bedroom house
Downtown Frederiksted
The price is ¥15,971
¥22,679 total
includes taxes & fees
Nov 18 - Nov 19
Quiet and cozy 2-bedroom house

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)
"Was very clean and host was very responsive and respectful!!! Will definitely stay here again!!"
United States
Adilene Y.
The price is ¥31,143
¥60,717 total
includes taxes & fees
Nov 16 - Nov 17
Casa Paradise Palms! Beautiful views from the rooftop. Walk to ferry/beach.

19. Treehouse - The Observatory

Treehouse - The Observatory
Christiansted Historic District
The price is ¥23,957
¥41,805 total
includes taxes & fees
Nov 30 - Dec 1
Treehouse - The Observatory

20. Playa Negra--Luxury Container Home--Casa NoSe'

Playa Negra--Luxury Container Home--Casa NoSe'
Vieques
10.0 out of 10, Exceptional, (5 reviews)
"Fantastic location and setup. We spent so much time chilling in the outdoor area that we almost didn’t want to step out. "
United States
Anurag D.
The price is ¥22,280
¥40,227 total
includes taxes & fees
Nov 19 - Nov 20
Playa Negra--Luxury Container Home--Casa NoSe'
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.

Learn more about Lesser Antilles

Island views, boating, and popular sights from Maho Beach to Sapphire Beach—explore Lesser Antilles, a seaside destination also known for its beaches.

A sign reading "Devil's Bay The Baths" with a beach and rocky landscape in the background.
Photo by Bill Dillard
Open Photo by Bill Dillard