Southwest Holiday Rentals

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Top Holiday Rentals Destinations in Southwest

Cottages by the Sea

3.0 star property
Frederiksted
9.6 out of 10, Exceptional, (305)
"Beautiful beach, friendly staff and peaceful area"
United States
Joanna
Cottages by the Sea

4Br, 5Bath, 5 minutes dr to Beach AC Home

Hannah's Rest
10.0 out of 10, Exceptional, (77)
"Beautiful home , the host was fantastic, great location and price was very reasonable. Highly recommend "
United States
chad l.
4Br, 5Bath, 5 minutes dr to Beach AC Home

PARADISE COVE SECLUDED PRISTINE VILLA, "MARGARITA"

Carlton
9.8 out of 10, Exceptional, (43)
"The view is everything! We loved staying here. Gail was extremely responsive! We definitely will be back! "
United States
Diana S.
PARADISE COVE SECLUDED PRISTINE VILLA, "MARGARITA"

Sugar Apple Bed & Breakfast

3.5 star property
Christiansted Historic District
9.4 out of 10, Exceptional, (64)
"Sugar Apple BNB was an amazing stay. I will definitely be back! The morning breakfast was great and the hostess was so very friendly."
United States
Shannon
Sugar Apple Bed & Breakfast

Windchime Estates

3.0 star property
Christiansted
9.2 out of 10, Wonderful, (26)
"The hospitality was amazing and the view from the rooms were breathtaking"
United States
Elijah
Windchime Estates

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

St. Croix
10.0 out of 10, Exceptional, (3)
"“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!!"
United States
Annie D.
THIS IS IT! SEAFRONT RETREAT W/ BEACH ACCESS & POOL

Quiet hillside villa with expansive sea, beach, and mountain views...

St Croix
9.8 out of 10, Exceptional, (30)
"Great place. The view was the best. "
United States
Rick F.
Quiet hillside villa with expansive sea, beach, and mountain views...

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

Christiansted
9.8 out of 10, Exceptional, (148)
"Condo had everything we needed. It is exactly as pictured-- right on the beach, about 30 yards from the water. Hosts were very responsive to questions. Great experience! Clean/Comfortable!"
United States
T V.
Oceanfront, Beachfront, Ground Floor, Beautiful Remodeled condo with pool access

Colony Cove Beach Resort by Antilles Resorts

3.0 star property
Christiansted
7.0 out of 10, Good, (57)
"People were very nice and extremely helpful. Cleaning people did a wonderful job. Our stay was great."
United States
Michael
Colony Cove Beach Resort by Antilles Resorts

OCEANFRONT LUXURY VILLA, 4900sf, 4br, 4bth, billiards and Gym

Christiansted
9.8 out of 10, Exceptional, (168)
"Our family had an awesome stay at Villa Santa Cruz. The house and pool are beautiful and were perfect for the adults and kids. The Villa is about a 15 minute drive from the airport, Christiansted, and nice beaches. Austin was a tremendous help, and the food prepared by Chef Juliana was some of the best we’ve had anywhere!"
United States
Missi D.
OCEANFRONT LUXURY VILLA, 4900sf, 4br, 4bth, billiards and Gym

Oceanfront at Cane Bay Hideaway!

Christiansted
10.0 out of 10, Exceptional, (25)
"We had a wonderful stay! Jessie was a very responsive host and the location was a perfect getaway!"
United States
Danette H.
Oceanfront at Cane Bay Hideaway!

Beautiful Ocean Front Condo- The perfect relaxing getaway! Internet, TV. FLR A/C

ST. CROIX
9.4 out of 10, Exceptional, (81)
"The host, Tracy, was fantastic. She went out of her way to make our stay there amazing.The complex is very quiet and quaint. We loved having our morning coffee on the patio and listening to the ocean waves. Watching the sun rise over the water was also beautiful. We recommend this stay in St CroixTracy is also knowledgeable about the island and can tell you good places to see. Her suggestions on restaurants was spot on!"
United States
Ronald A.
Beautiful Ocean Front Condo- The perfect relaxing getaway! Internet, TV. FLR A/C

Club St. Croix Beach & Tennis Resort by Antilles Resorts

3.0 star property
Christiansted
8.0 out of 10, Very good, (239)
"Highly recommended "
United States
ARMANDO
Club St. Croix Beach & Tennis Resort by Antilles Resorts

Oceanfront Oasis; Fun family retreat, with private pool, snorkeling steps away.

Christiansted
9.2 out of 10, Wonderful, (35)
"Beautiful place. Will stay there again. "
United States
John
Oceanfront Oasis; Fun family retreat, with private pool, snorkeling steps away.

Paradise Exquisite Townhouse

Christiansted
9.2 out of 10, Wonderful, (13)
"It matched the picture and description, only thing that was wrong was the water being on or off and majority of the water we used was cold . Everything was smooth , the property is nice and in a quiet area , the technology is out of this world . I’ll definitely stay again !"
United States
Symone
Paradise Exquisite Townhouse

Gorgeous Ocean Views! Welcome to Bella Breeze! BeachFront 2BR 2BA

4.0 star property
Christiansted
8.6 out of 10, Excellent, (14)
"Wonderful place to stay! Easy check in needs some minor repairs but overall it is a nice place"
United States
Kelli
Gorgeous Ocean Views! Welcome to Bella Breeze! BeachFront 2BR 2BA

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

Christiansted
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."
United States
Chris M.
Private Gated Ocean Front Villa Pool&Tide Pool Cane Bay Beach Wifi Wedding Venue

Luxury Caribbean Villa 4 private suites, pool and stunning views. Judith's Fancy

Judith's Fancy
9.8 out of 10, Exceptional, (26)
"We have stayed at the property previously and this trip was just as awesome"
United States
Robert S.
Luxury Caribbean Villa 4 private suites, pool and stunning views. Judith's Fancy

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

Christiansted
9.2 out of 10, Wonderful, (96)
"Property was excellent. Little far from town but could not ask for better place. Awesome communication with owners."
United States
Charles C.
Family Friendly Private Villa,Caribbean Sea & Mountain Views With Pool

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

Frederiksted
10.0 out of 10, Exceptional, (35)
"The views were spectacular. The water was pristine, warm and full of life. Property was ideal for our group. Everyone we met on the island was helpful, pleasant and welcoming. Best vacation ever!"
United States
Michael L.
Beachfront Home with Large Deck. Walk to Restaurants. Near Downtown.
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 favourite 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 depend 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 chosen for you start as low as 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.