A turquoise beach with white sand, surrounded by lush greenery and rocky outcrops.

Vacation Rentals in Southwest

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Our top choices for Southwest vacation rentals

1. Green Flash by the Sea

Green Flash by the Sea
Frederiksted Southeast
10.0 out of 10, Exceptional, (4 reviews)
"We love the place, we have stayed on property several times and this was our 4th condo and it was by far the best one. Loved being up on the 3rd floor and having an amazing view. Everything was well done. Keep in mind you are staying in the Caribbean so salt water tends to wear on things. Internet can be spotty but we're not there for that, water access and snorkeling is some of the best on the island and the pier is within walking distance. Will stay again. "
United States
Daniel E.
The price is ¥52,071
¥76,603 total
includes taxes & fees
Sep 27 - Sep 28
Green Flash by the Sea

2. Sunset Villas"Tecoma Stans" Glamping Tent Walking Distance to the Beach

Sunset Villas"Tecoma Stans" Glamping Tent Walking Distance to the Beach
Frederiksted Southeast
8.6 out of 10, Excellent, (8 reviews)
"Host was amazing, friendly and very informative "
United States
Zan C.
The price is ¥9,259
¥17,173 total
includes taxes & fees
Oct 5 - Oct 6
Sunset Villas"Tecoma Stans" Glamping Tent Walking Distance to the Beach

3. Windchime Estates

Windchime Estates
3.0 star property
Christiansted
9.0 out of 10, Wonderful, (33 reviews)
"The hospitality was amazing and the view from the rooms were breathtaking"
United States
Elijah
The price is ¥9,742
¥29,022 total
includes taxes & fees
Sep 29 - Sep 30
Windchime Estates

4. The Cottage at Green Cay - Walk to the Beach - King Bed - AC

The Cottage at Green Cay - Walk to the Beach - King Bed - AC
Gallows Bay
10.0 out of 10, Exceptional, (1 review)
"Everything was clean and comfortable. The beach that was walking distance was quite nice to hang out at. Our hosts were attentive and responsive. The area was quiet, scenic and a easy drive to restaurants and other beaches."
United States
Patricia F.
The price is ¥23,076
¥51,398 total
includes taxes & fees
Sep 27 - Sep 28
The Cottage at Green Cay - Walk to the Beach - King Bed - AC

5. Historic Apt in Heart of Christiansted

Historic Apt in Heart of Christiansted
3.5 star property
Christiansted Historic District
9.4 out of 10, Exceptional, (20 reviews)
"Great experience all around! Easy check in and comfortable apartment!"
United States
Cecily
The price is ¥35,719
¥40,184 total
includes taxes & fees
Oct 24 - Oct 25
Historic Apt in Heart of Christiansted

6. Sugar Apple Bed & Breakfast

Sugar Apple Bed & Breakfast
3.5 star property
Christiansted Historic District
9.2 out of 10, Wonderful, (81 reviews)
"Clean room, nice bathroom, comfortable bed"
United States
DEBORAH
The price is ¥31,124
¥35,014 total
includes taxes & fees
Sep 30 - Oct 1
Sugar Apple Bed & Breakfast

7. 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 ¥15,526
¥44,648 total
includes taxes & fees
Sep 26 - Sep 27
Your Caribbean home away from home

8. The Island Life Condo@ Long Reef with Separate Bedroom + True Ocean View

The Island Life Condo@ Long Reef with Separate Bedroom + True Ocean View
Christiansted Historic District
9.6 out of 10, Exceptional, (19 reviews)
"Omesha and Irma were very helpful and accommodating, especially because we needed to book our reservation at the last minute"
United States
Michael J.
The price is ¥17,663
¥44,403 total
includes taxes & fees
Sep 29 - Sep 30
The Island Life Condo@ Long Reef with Separate Bedroom + True Ocean View

9. Sunset Villas "Good Morning" Tiny Home Container

Sunset Villas "Good Morning" Tiny Home Container
Frederiksted Southeast
9.6 out of 10, Exceptional, (19 reviews)
"Beautiful view, very close to beaches, overall it was a great stay."
United States
Nelicia N.
The price is ¥19,800
¥30,505 total
includes taxes & fees
Sep 26 - Sep 27
Sunset Villas "Good Morning" Tiny Home Container

10. Caribbean View Style 1 Bedroom Condo by RedAwning

Caribbean View Style 1 Bedroom Condo by RedAwning
3.0 star property
Christiansted
10.0 out of 10, Exceptional, (1 review)
"Russ is great!"
United States
Matthew
The price is ¥15,843
¥78,688 total
includes taxes & fees
Oct 6 - Oct 7
Caribbean View Style 1 Bedroom Condo by RedAwning

11. Quiet and cozy 2-bedroom house

Quiet and cozy 2-bedroom house
Downtown Frederiksted
The price is ¥15,827
¥23,741 total
includes taxes & fees
Sep 29 - Sep 30
Quiet and cozy 2-bedroom house

12. BEACH FRONT! Island Oasis-Luxury condo at Pelican Cove

BEACH FRONT! Island Oasis-Luxury condo at Pelican Cove
Christiansted
10.0 out of 10, Exceptional, (145 reviews)
"We enjoyed our stay at Island Oasis, with an excellent location, a good apartment, and an amazing breakfast view from the balcony."
United States
Lucci S.
The price is ¥28,489
¥62,913 total
includes taxes & fees
Sep 26 - Sep 27
BEACH FRONT! Island Oasis-Luxury condo at Pelican Cove

13. Romey's Villa in Gated Community

Romey's Villa in Gated Community
Christiansted
9.4 out of 10, Exceptional, (3 reviews)
"Great home, clean, plenty of towels, host was great to communicate."
United States
Kert S.
The price is ¥22,253
¥59,222 total
includes taxes & fees
Sep 27 - Sep 28
Romey's Villa in Gated Community

14. "Spectacular Ocean Views" at Calypso Castillo!

"Spectacular Ocean Views" at Calypso Castillo!
Sion Farm
10.0 out of 10, Exceptional, (6 reviews)
"Their property was very nice and clean and loved the area where it was located at"
United States
Stephen M T.
The price is ¥22,949
¥56,048 total
includes taxes & fees
Sep 26 - Sep 27
"Spectacular Ocean Views" at Calypso Castillo!

15. Beautiful 2-bd condo w/ views walking distance to beach in amazing Christiansted

Beautiful 2-bd condo w/ views walking distance to beach in amazing Christiansted
Teagues Bay
9.8 out of 10, Exceptional, (6 reviews)
"Location, host responses, plenty of amenities. Great visit. Will do it again. "
United States
Brian N.
The price is ¥35,611
¥88,513 total
includes taxes & fees
Sep 26 - Sep 27
Beautiful 2-bd condo w/ views walking distance to beach in amazing Christiansted

16. Cozy Retreat by Chenay Bay

Cozy Retreat by Chenay Bay
Chenay Bay
9.6 out of 10, Exceptional, (14 reviews)
"Everything was neat, all the necessary details to have a wonderful stay."
United States
Monica V.
The price is ¥17,805
¥45,037 total
includes taxes & fees
Sep 26 - Sep 27
Cozy Retreat by Chenay Bay

17. Buck Island Views on North Shore: Windsors Rest

Buck Island Views on North Shore: Windsors Rest
Northcentral
9.6 out of 10, Exceptional, (10 reviews)
"beautiful location and great people"
United States
Tom M.
The price is ¥11,906
¥26,095 total
includes taxes & fees
Sep 29 - Sep 30
Buck Island Views on North Shore: Windsors Rest

18. Sea Views•Stargazing Nights•Hilltop Privacy

Sea Views•Stargazing Nights•Hilltop Privacy
Christiansted
9.8 out of 10, Exceptional, (74 reviews)
"Wonderful Stay . Highly Recommend "
United States
Sali K.
The price is ¥32,050
¥80,846 total
includes taxes & fees
Sep 26 - Sep 27
Sea Views•Stargazing Nights•Hilltop Privacy

19. St. Croix Escape★ Oceanfront Oasis with Stunning Views and Serene Coastal Vibes

St. Croix Escape★ Oceanfront Oasis with Stunning Views and Serene Coastal Vibes
Christiansted
9.8 out of 10, Exceptional, (7 reviews)
"This is a fantastic place to stay! Beautiful ocean view, great access to Christianstead and owner quickly responds and has wonderful communication. Definitely would stay here again on a return trip. "
United States
Rebecca G.
The price is ¥25,467
¥58,812 total
includes taxes & fees
Sep 28 - Sep 29
St. Croix Escape★ Oceanfront Oasis with Stunning Views and Serene Coastal Vibes

20. Lookout Point @ Coakley Bay

Lookout Point @ Coakley Bay
Christiansted
7.4 out of 10, Good, (3 reviews)
"This condo is perfectly situated on the east end and has stunning a stunning view. Sitting on the porch to watch the sunsets was lovely. Communication was quick and very helpful! We will be back"
United States
Erin P.
The price is ¥24,928
¥58,432 total
includes taxes & fees
Sep 26 - Sep 27
Lookout Point @ Coakley Bay
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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