Southwest Holiday Rentals

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Featured Southwest Holiday Rentals

Our top choices for Southwest holiday rentals

Cottages by the Sea
Terrace/patio

Cottages by the Sea

3.0 star property
9.6 out of 10, Exceptional, (295)
"This was a great place to stay! "
Cottages by the Sea
PARADISE COVE SECLUDED PRISTINE VILLA, "MARGARITA"
Property grounds

PARADISE COVE SECLUDED PRISTINE VILLA, "MARGARITA"

9.8 out of 10, Exceptional, (43)
"The view is everything! We loved staying here. Gail was extremely responsive! We definitely will be back! "
PARADISE COVE SECLUDED PRISTINE VILLA, "MARGARITA"
Windchime Estates
Beach nearby, white sand, beach towels, 4 beach bars

Windchime Estates

3.0 star property
9.0 out of 10, Wonderful, (23)
"Amazing place to stay and what a view! "
Windchime Estates
Sugar Apple Bed & Breakfast
Terrace/patio

Sugar Apple Bed & Breakfast

3.5 star property
9.4 out of 10, Exceptional, (62)
"Very nice cozy place. Excellent to have some rest and enjoy the island."
Sugar Apple Bed & Breakfast
Private Gated Ocean Front Villa Pool&Tide Pool Cane Bay Beach Wifi Wedding Venue
Interior

Private Gated Ocean Front Villa Pool&Tide Pool Cane Bay Beach Wifi Wedding Venue

9.8 out of 10, Exceptional, (155)
"Sunrises in the morning, sunsets at night, all from the comfort of the patio and tide pool. Sea View Play is by far my favorite villa I have ever stayed in. The view is spectacular and incredibly photogenic and the fact the living room opens up to experience that makes this a must stay villa in my opinion. Rob is a fantastic host and was incredibly quick to respond and made sure we had a great time. I can't recommend this place enough! We'll be coming back for sure."
Private Gated Ocean Front Villa Pool&Tide Pool Cane Bay Beach Wifi Wedding Venue
Another Day in Paradise, Luxury Villa on the Beach with private pool !!
On the beach, sun-loungers, beach towels

Another Day in Paradise, Luxury Villa on the Beach with private pool !!

10.0 out of 10, Exceptional, (108)
"Great property and location! Very quiet and private, and the water and view were beautiful!"
Another Day in Paradise, Luxury Villa on the Beach with private pool !!
Club St. Croix Beach & Tennis Resort by Antilles Resorts
On the beach, sun-loungers, beach umbrellas, beach towels

Club St. Croix Beach & Tennis Resort by Antilles Resorts

3.0 star property
8.0 out of 10, Very good, (237)
"Beautiful place. Friendly staff. "
Club St. Croix Beach & Tennis Resort by Antilles Resorts
Castaway Dreams 20 person Villa with Boat, Pool, Tennis Court, and Sugar Mill
Beach nearby, beach towels

Castaway Dreams 20 person Villa with Boat, Pool, Tennis Court, and Sugar Mill

9.0 out of 10, Wonderful, (16)
"Beautifully, well appointed vacation rental"
Castaway Dreams 20 person Villa with Boat, Pool, Tennis Court, and Sugar Mill
Beachfront St. Croix Island, USVI
On the beach, sun-loungers

Beachfront St. Croix Island, USVI

9.6 out of 10, Exceptional, (39)
"So relaxing! I love being right on the beach and waking up to the beautiful beach and view "
Beachfront St. Croix Island, USVI
Private Beach Front Cottage
Property grounds

Private Beach Front Cottage

9.8 out of 10, Exceptional, (48)
"Our stay was wonderful. Sargassum weed was awful in May. We didn’t let us stop us from enjoying the beaches. Hope to return. "
Private Beach Front Cottage
THIS IS IT! SEAFRONT RETREAT W/ BEACH ACCESS & POOL
Outdoor pool

THIS IS IT! SEAFRONT RETREAT W/ BEACH ACCESS & POOL

10.0 out of 10, Exceptional, (1)
"“This is it” is absolutely amazing! We had a great time, house is very comfortable, great kitchen, very comfy beds, good showers, loved the outdoor showers!! loved the salt water swimming pool, view is breathtaking, great communication with our host Tisha! I can’t say enough good things about our stay! We want to go back!!"
THIS IS IT! SEAFRONT RETREAT W/ BEACH ACCESS & POOL
Family Friendly Private Villa,Caribbean Sea & Mountain Views With Pool
Beach nearby, sun-loungers, beach towels

Family Friendly Private Villa,Caribbean Sea & Mountain Views With Pool

9.2 out of 10, Wonderful, (96)
"This property was fantastic. We loved the location, the views, and the pool was great. The outside of the property could use some TLC but the Caribbean weather conditions are harsh and it did not distract or deter our enjoyment of the property."
Family Friendly Private Villa,Caribbean Sea & Mountain Views With Pool
Luxury Caribbean Villa 4 private suites, pool and stunning views
Terrace/patio

Luxury Caribbean Villa 4 private suites, pool and stunning views

9.8 out of 10, Exceptional, (26)
"This was a great place for our grown children and their families to all stay together. The view was wonderful!"
Luxury Caribbean Villa 4 private suites, pool and stunning views
The Villa at Rainbow Cliffs
Property grounds

The Villa at Rainbow Cliffs

9.8 out of 10, Exceptional, (32)
"We loved the place. The views alone make the trip worth it. We spent our week exploring area beaches and snorkeling. It was easy to navigate the island and there are good food/drinks/beach options just down the road from the villa. We spent every morning drinking tea on the veranda and every evening watching the sunset. Will plan to visit again in the future for sure. "
The Villa at Rainbow Cliffs
Dramatic Oceanfront House--Cane Bay Sanctuary-2025 AUG-SEPT SPECIAL!
Property grounds

Dramatic Oceanfront House--Cane Bay Sanctuary-2025 AUG-SEPT SPECIAL!

10.0 out of 10, Exceptional, (114)
"Jill is an incredible host and it was a pleasure to stay with her. "
Dramatic Oceanfront House--Cane Bay Sanctuary-2025 AUG-SEPT SPECIAL!
Oceanfront, Beachfront, Ground Floor, Beautiful Remodeled condo with pool access
On the beach, sun-loungers, beach towels

Oceanfront, Beachfront, Ground Floor, Beautiful Remodeled condo with pool access

9.8 out of 10, Exceptional, (147)
"Beautiful views and great location"
Oceanfront, Beachfront, Ground Floor, Beautiful Remodeled condo with pool access
Historic Apt in Heart of Christiansted
2 bedrooms, blackout curtains, iron/ironing board, free rollaway beds

Historic Apt in Heart of Christiansted

3.5 star property
9.4 out of 10, Exceptional, (17)
"Excellent location "
The price is HK$1,422
HK$1,600 total
includes taxes & fees
4 Oct - 5 Oct
Historic Apt in Heart of Christiansted
Beachfront Home with Large Deck. Walk to Restaurants. Near Downtown.
Outdoor dining

Beachfront Home with Large Deck. Walk to Restaurants. Near Downtown.

10.0 out of 10, Exceptional, (33)
"Has great time with family. Renter made everything easy and took good care of things. "
Beachfront Home with Large Deck. Walk to Restaurants. Near Downtown.
Oceanfront Condo - Four Steps to Beautiful Sugar Beach
On the beach

Oceanfront Condo - Four Steps to Beautiful Sugar Beach

9.6 out of 10, Exceptional, (58)
"We had a wonderful stay at this beach condo. The access to the private beach was amazing with a fun little snorkeling area right there! The condo was nice, kitchen well stocked and pool access great as well. We had some trouble getting the TV to work and it’s in need of a few more beach chairs. Great place would return! "
Oceanfront Condo - Four Steps to Beautiful Sugar Beach
Oceanfront! Saltwater Pool. Walk to Beach & Restaurants. Northshore, St. Croix
Outdoor pool

Oceanfront! Saltwater Pool. Walk to Beach & Restaurants. Northshore, St. Croix

10.0 out of 10, Exceptional, (51)
"Fantastic place to stay. Beautiful location. "
Oceanfront! Saltwater Pool. Walk to Beach & Restaurants. Northshore, St. Croix
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 Southwest Hotel Reviews