Southwest Holiday Rentals

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Our top choices for Southwest holiday rentals

Windchime Estates

Windchime Estates
3.0 star property
Christiansted
9.0 out of 10, Wonderful, (28 reviews)
"The hospitality was amazing and the view from the rooms were breathtaking"
United States
Elijah
The price is NZ$371
includes taxes & fees
5 Apr - 6 Apr
Windchime Estates

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 NZ$651
includes taxes & fees
7 Apr - 8 Apr
Romey's Villa in Gated Community

Large & Comfortable 1 Bed/Bath Guest Room on St. Croix

Large & Comfortable 1 Bed/Bath Guest Room on St. Croix
Christiansted
8.8 out of 10, Excellent, (8 reviews)
"Nice quiet place to stay in a great walking neighborhood. Nice central location."
United States
Anthony B.
The price is NZ$341
includes taxes & fees
16 Apr - 17 Apr
Large & Comfortable 1 Bed/Bath Guest Room on St. Croix

Your Caribbean home away from home

Your Caribbean home away from home
Christiansted
9.2 out of 10, Wonderful, (20 reviews)
"great place in st. croix. Our host Russell made it very easy and accommodating"
United States
jeffrey b.
The price is NZ$544
includes taxes & fees
12 Apr - 13 Apr
Your Caribbean home away from home

STUDIO APT. a/c - stable wifi - filtered tap water - 5 min. to the boardwalk

STUDIO APT. a/c - stable wifi - filtered tap water - 5 min. to the boardwalk
Christiansted
9.4 out of 10, Exceptional, (69 reviews)
"Owner was fabulous, attentive and friendly, great washer and dryer also "
United States
Frankie
The price is NZ$284
includes taxes & fees
16 Apr - 17 Apr
STUDIO APT. a/c - stable wifi - filtered tap water - 5 min. to the boardwalk

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 NZ$313
includes taxes & fees
6 Apr - 7 Apr
Buck Island Views on North Shore: Windsors Rest

Private & Cozy 1 Bed/1 Bath Apartment

Private & Cozy 1 Bed/1 Bath Apartment
Christiansted
9.8 out of 10, Exceptional, (7 reviews)
"When I arrived the owner came out and showed me exactly where to go. The apartment was small but just what I needed. It was clean, smelled nice, and I appreciate the nice touch of having gentle music and scenery on the TV monitor. Great stay. A couple of unexpected, but friendly dogs were nearby, eager for a pat on the head. All good!"
United States
Sean D.
The price is NZ$418
includes taxes & fees
12 Apr - 13 Apr
Private & Cozy 1 Bed/1 Bath Apartment

Best Buck Island Views on North Shore: The View

Best Buck Island Views on North Shore: The View
Northcentral
8.2 out of 10, Very good, (13 reviews)
"Beautiful location, property and the owner was a great wealth of information so very friendly! Would love to visit again!"
United States
Lori C.
The price is NZ$384
includes taxes & fees
6 Apr - 7 Apr
Best Buck Island Views on North Shore: The View

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
9.6 out of 10, Exceptional, (5 reviews)
"The location was just perfect with a 9 hole golf course, Ollie’s a terrific quick breakfast/lunch place and Duggins one of the best restaurants on the island. The owners are very responsive and friendly. The views are magnificent. I wouldn’t stay anywhere else."
United States
Lou S.
The price is NZ$1,024
includes taxes & fees
16 Apr - 17 Apr
Beautiful 2-bd condo w/ views walking distance to beach in amazing Christiansted

Luxury 2 bedroom home next to Buccaneer Resort

Luxury 2 bedroom home next to Buccaneer Resort
St Croix
8.8 out of 10, Excellent, (3 reviews)
"Excellent place, I would stay again please fix the water pressure only complain slow water pressure."
United States
Racquel F.
The price is NZ$788
includes taxes & fees
5 Apr - 6 Apr
Luxury 2 bedroom home next to Buccaneer Resort

"Spectacular Ocean Views" at Calypso Castillo!

"Spectacular Ocean Views" at Calypso Castillo!
Sion Farm
10.0 out of 10, Exceptional, (5 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 NZ$619
includes taxes & fees
12 Apr - 13 Apr
"Spectacular Ocean Views" at Calypso Castillo!

Luxury Beachfront Condo with Pool and Hot Tub

Luxury Beachfront Condo with Pool and Hot Tub
Christiansted
9.0 out of 10, Wonderful, (31 reviews)
"The place is amazing! It was exactly as it described. We loved our stay!!"
United States
Renee M.
The price is NZ$689
includes taxes & fees
17 Apr - 18 Apr
Luxury Beachfront Condo with Pool and Hot Tub

Sunset Villas "Good Morning" Tiny Home Container

Sunset Villas "Good Morning" Tiny Home Container
Frederiksted Southeast
9.6 out of 10, Exceptional, (16 reviews)
"Charles is a great host, property is in a great location close to beach which is a plus!! Thank you for your exceptional hospitality will definitely book again!! "
United States
Amelia G.
The price is NZ$334
includes taxes & fees
16 Apr - 17 Apr
Sunset Villas "Good Morning" Tiny Home Container

spacious 3 bd, 2 ba. wsh/dry onsite - AC - stable Wi-Fi - full kitchen

spacious 3 bd, 2 ba. wsh/dry onsite - AC - stable Wi-Fi - full kitchen
Christiansted
10.0 out of 10, Exceptional, (2 reviews)
"Very spacious, well decorated, comfy beds & couch, lots of privacy, quiet, just lovely. Only big drawback was that it was not clean, but he's hiring a new cleaning company, so that should be taken care of for the next guests."
United States
Carolyn T.
The price is NZ$645
includes taxes & fees
16 Apr - 17 Apr
spacious 3 bd, 2 ba. wsh/dry onsite - AC - stable Wi-Fi - full kitchen

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)
"the location was realky convenient and the condo had all the things we needed to make for a cozy and relaxing getaway for me and my husband. we especially loved being able to open the patio and listen to the waves crashing. the security staff was really friendly and our host was great at communicating. "
United States
Kerrie T.
The price is NZ$517
includes taxes & fees
6 Apr - 7 Apr
St. Croix Escape★ Oceanfront Oasis with Stunning Views and Serene Coastal Vibes

HOLIDAY SPECIAL! Island Oasis-Luxury condo at Pelican Cove

HOLIDAY SPECIAL! Island Oasis-Luxury condo at Pelican Cove
Christiansted
10.0 out of 10, Exceptional, (144 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 NZ$695
includes taxes & fees
16 Apr - 17 Apr
HOLIDAY SPECIAL! Island Oasis-Luxury condo at Pelican Cove

Buck Island Views on North Shore: The Mermaid

Buck Island Views on North Shore: The Mermaid
Northcentral
9.2 out of 10, Wonderful, (5 reviews)
"We enjoyed the beautiful views and breezes on the property. We wanted to get a feel for what it would be like to live on the island and it was perfect for our needs!"
United States
Amy L.
The price is NZ$369
includes taxes & fees
7 Apr - 8 Apr
Buck Island Views on North Shore: The Mermaid

Moko Jumbie House - "Guesthouse" - Cozy 1-Bedroom

Moko Jumbie House - "Guesthouse" - Cozy 1-Bedroom
Christiansted Historic District
10.0 out of 10, Exceptional, (13 reviews)
"Great place to stay. Extremely close proximity to the boardwalk. Staying at Moko Jumbie felt private."
United States
Nicole S.
The price is NZ$364
includes taxes & fees
20 Apr - 21 Apr
Moko Jumbie House - "Guesthouse" - Cozy 1-Bedroom

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, (18 reviews)
"Excellent location "
United States
Brian G
The price is NZ$348
includes taxes & fees
25 Apr - 26 Apr
Historic Apt in Heart of Christiansted

Tranquil Buck Island Views - Steps from the Beach

Tranquil Buck Island Views - Steps from the Beach
Christiansted
10.0 out of 10, Exceptional, (1 review)
"It is a lovely home. The property is immaculate and it was very smooth no complaints. The home owner is a pleasant and kind man. I highly recommend a stay here. You will not be disappointed "
United States
Benjamin C.
The price is NZ$1,085
includes taxes & fees
5 Apr - 6 Apr
Tranquil Buck Island Views - Steps from the Beach
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

Find out more about Southwest

Everything you need to know about Southwest holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southwest holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southwest holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Southwest holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southwest. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southwest holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southwest holiday rentals we have selected for you start as low as NZ$371 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Southwest rentals

At Expedia, we put the best Southwest holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Southwest rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southwest holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southwest. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.