Southwest Holiday Rentals

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Top Holiday Rentals Destinations in Southwest

Cottages by the Sea

3.0 star property
9.6 out of 10, Exceptional, (300)
"Great location right on the beach. Perfect for our stay"
Cottages by the Sea

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"

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

10.0 out of 10, Exceptional, (2)
"“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

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

9.2 out of 10, Wonderful, (35)
"Overall the stay was amazing. The condo was accurately described. The pool area and beach was amazing. I would stay here again. "
Oceanfront Oasis; Fun family retreat, with private pool, snorkeling steps away.

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

Windchime Estates

3.0 star property
9.2 out of 10, Wonderful, (25)
"Amazing place to stay and what a view! "
Windchime Estates

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

Tropical one bedroom condo steps from pool.

10.0 out of 10, Exceptional, (53)
"This condo was everything advertised. It was perfect for my wife and I, well stocked and well located, an easy drive to anywhere on the island. The pool was a great place to cool off and meet people. Lucas was very good at communicating and making sure we had everything. We would definitely book it again!"
Tropical one bedroom condo steps from pool.

Luxurious Oceanfront Honeymoon Cottage - as seen on HGTV - Gated Subdivision

10.0 out of 10, Exceptional, (192)
"This is a beautiful location right on the ocean and very central to activities on the island. Chad and Emily were there to greet us, offered us great suggestions as to how to enjoy the island, and even made us delicious cookies upon our arrival.The cottage is well-appointed and very clean. The space is very private and separate from the main house. We enjoyed golfing, snorkeling and hiking on the island, and we would certainly recommend this cottage to couples who just want to get away! Enjoy...
Luxurious Oceanfront Honeymoon Cottage - as seen on HGTV - Gated Subdivision

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

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

10.0 out of 10, Exceptional, (34)
"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.

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

9.8 out of 10, Exceptional, (155)
"Sprawling Hacienda with spectacular views and wonderful outdoor areas . Room for everyone! Great Host and Property Manager. Great place ! "
Private Gated Ocean Front Villa Pool&Tide Pool Cane Bay Beach Wifi Wedding Venue

Beachfront St. Croix Island, USVI

9.6 out of 10, Exceptional, (41)
"We had a great time staying here. The condo was very clean and had everything we needed. Good location close to Christiansted. We spent a lot of time sitting on the patio enjoying the beach. "
Beachfront St. Croix Island, USVI

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

Historic Apt in Heart of Christiansted

3.5 star property
9.4 out of 10, Exceptional, (17)
"Excellent location "
The price is NZ$368
includes taxes & fees
29 Oct - 30 Oct
Historic Apt in Heart of Christiansted

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

4.0 star property
8.6 out of 10, Excellent, (13)
"Great stay "
Gorgeous Ocean Views! Welcome to Bella Breeze! BeachFront 2BR 2BA

Colony Cove Beach Resort by Antilles Resorts

3.0 star property
7.0 out of 10, Good, (57)
"The property was in a great location, easy to get to town, grocery and around the island. Complex was quiet and clean. Beach area was nice and kept clean."
Colony Cove Beach Resort by Antilles Resorts

Oceanfront Condo - Four Steps to Beautiful Sugar Beach

9.6 out of 10, Exceptional, (59)
"We wanted to spend a relaxing week by the beach and enjoying the local food. This condo was perfect! Everything you could need for a family of four to make your own meals and enjoy the beach without schlepping everything over the sand. Perfect stay and we greatly appreciate it!"
Oceanfront Condo - Four Steps to Beautiful Sugar Beach

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

Convenient, clean, private, spacious and ready for your large group or family!

9.6 out of 10, Exceptional, (55)
"Amazing view, friendly animals next door, great communication. Also, it is a must to add in Mike's Catamaran (Sandy Toes sailing) to top it all off. Mike does a great job with taking us around on the Catamaran. The restaurant right down the hill, KD,s is a great place for adults and kids. "
Convenient, clean, private, spacious and ready for your large group or family!
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

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$368 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.