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Water Island Holiday Rentals

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Our top choices for Water Island holiday rentals

Flamboyan on the Bay Resort and Villas

Flamboyan on the Bay Resort and Villas
3.5 star property
St. Thomas
8.6 out of 10, Excellent, (807)
"location nice pool "
United States
Gary
The price is NZ$283
includes taxes & fees
25 Dec - 26 Dec
Flamboyan on the Bay Resort and Villas

Lameshur Bay Glamping Site with AC

Lameshur Bay Glamping Site with AC
St John
10.0 out of 10, Exceptional, (24)
"The location is amazing, the space was clean, and the kitchen area, shower, and snorkeling/beach gear were much appreciated!"
United States
Ann
The price is NZ$431
includes taxes & fees
31 Dec - 1 Jan 2026
Lameshur Bay Glamping Site with AC

Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
9.2 out of 10, Wonderful, (7)
"Very safe and secure place! Also very clean! Just uphill from cruz bay "
United States
Tyler
The price is NZ$1,251
includes taxes & fees
25 Dec - 26 Dec
Villa Island Paradise

Lameshur Cottage's Guest House

Lameshur Cottage's Guest House
St John
10.0 out of 10, Exceptional, (133)
"Absolutely would stay here again. We had zero issues with our stay. "
United States
Mark P.
The price is NZ$720
includes taxes & fees
31 Dec - 1 Jan 2026
Lameshur Cottage's Guest House

Family Glamping Site with AC

Family Glamping Site with AC
St John
10.0 out of 10, Exceptional, (30)
"Overall great property only semi complaint which is more needy than anything is the tent will get a bit stuffy and hot when the fans die. "
United States
Will C.
The price is NZ$471
includes taxes & fees
31 Dec - 1 Jan 2026
Family Glamping Site with AC

The Landmark Apartment

The Landmark Apartment
2.5 star property
St. Thomas
8.8 out of 10, Excellent, (15)
"I loved the historic nature of the building. It had an interesting layout, but it was very spacious and clean, and had a wonderful location for walking around downtown and seeing the sights."
United States
Mercy
The price is NZ$649
includes taxes & fees
17 Jan - 18 Jan 2026
The Landmark Apartment

Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!

Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!
St. Thomas
9.6 out of 10, Exceptional, (179)
"This room was absolutely perfect for my stay in St Thomas. It had everything I needed and was convenient to all the places I had to visit during my stay. A short walk to the beach, plenty of very good on site restaurants, nice pools, incredible views every day. As far as the room the bed was comfortable. It had a nice big TV, small kitchen with big frig, blender and Pod Coffee maker. I liked that they even supplied snorkeling gear, coolers, beach chairs, sunscreen lotion, bug spray, aloe and...
United States
Paul
The price is NZ$471
includes taxes & fees
15 Jan - 16 Jan 2026
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!

Sophisticated Beach Condo-Ocean View-Sapphire

Sophisticated Beach Condo-Ocean View-Sapphire
Smith Bay
9.0 out of 10, Wonderful, (32)
"Me and my gf’s loved staying here! Best part was having close beach access! "
United States
Maria
The price is NZ$544
includes taxes & fees
11 Jan - 12 Jan 2026
Sophisticated Beach Condo-Ocean View-Sapphire

Salt Pond Bay Glamping Site With AC

Salt Pond Bay Glamping Site With AC
St John
The price is NZ$407
includes taxes & fees
31 Dec - 1 Jan 2026
Salt Pond Bay Glamping Site With AC

Tropical Oasis 🇻🇮Stunning ocean view, minutes drive to Brewers Beach!🇻🇮🏝

Tropical Oasis 🇻🇮Stunning ocean view, minutes drive to Brewers Beach!🇻🇮🏝
St Thomas
10.0 out of 10, Exceptional, (39)
"Clean home, accurate check-in instructions, splendid view!"
United States
Jeffrey
The price is NZ$421
includes taxes & fees
19 Jan - 20 Jan 2026
Tropical Oasis 🇻🇮Stunning ocean view, minutes drive to Brewers Beach!🇻🇮🏝

The Breeze St Thomas

The Breeze St Thomas
2.0 star property
St. Thomas
The price is NZ$853
includes taxes & fees
1 Jan - 2 Jan 2026
The Breeze St Thomas

Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!

Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!
St. Thomas
9.6 out of 10, Exceptional, (152)
"Condo was everything it was advertised to be - Sudi’s was the cherry on top"
United States
John A.
The price is NZ$584
includes taxes & fees
1 Jan - 2 Jan 2026
Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!

The Peter Bay 1BR Penthouse Suite at St John's Most Prestigious Address

The Peter Bay 1BR Penthouse Suite at St John's Most Prestigious Address
Maho Bay Quarter
9.6 out of 10, Exceptional, (27)
"Beautiful property with gorgeous views! Tommy was very quick to answer any questions or just give us information!"
United States
Amy G.
The Peter Bay 1BR Penthouse Suite at St John's Most Prestigious Address

Shibui Cove

Shibui Cove
2.0 star property
St. Thomas
10.0 out of 10, Exceptional, (1)
"I had a great stay here. The view was absolutely stunning. Being up on the side of the mountain was great. Very private but less than 5 min away from town. I will definitely stay again. "
United States
Adam R
The price is NZ$653
includes taxes & fees
2 Jan - 3 Jan 2026
Shibui Cove

Little Indigo Apartments

Little Indigo Apartments
3.5 star property
St. Thomas
8.4 out of 10, Very good, (22)
"Amazing views, very nice people"
United States
Ramie
The price is NZ$575
includes taxes & fees
2 Jan - 3 Jan 2026
Little Indigo Apartments

Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
St. Thomas
9.4 out of 10, Exceptional, (222)
"Clean, quiet, convenient location. Perfect stay!!!"
United States
Glenda
The price is NZ$341
includes taxes & fees
30 Dec - 31 Dec
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

Caribbean Escape just steps from Sapphire Beach!

Caribbean Escape just steps from Sapphire Beach!
St Thomas
9.8 out of 10, Exceptional, (78)
"Very clean unitGood restaurant on siteOcean view with boat dockShort walk to the beach"
United States
Ade Gabriel S.
The price is NZ$567
includes taxes & fees
26 Dec - 27 Dec
Caribbean Escape just steps from Sapphire Beach!

Suite St. John at Gallows Point Resort

Suite St. John at Gallows Point Resort
4.0 star property
St. John
8.6 out of 10, Excellent, (95)
"Amazing property and helpful staff. "
United States
Joseph
The price is NZ$1,855
includes taxes & fees
18 Jan - 19 Jan 2026
Suite St. John at Gallows Point Resort

Lazy Loft: Tiny Room Loft Queen w Pool

Lazy Loft: Tiny Room Loft Queen w Pool
St. Thomas
10.0 out of 10, Exceptional, (11)
"Awesome Laid Back Island Asthethics"
United States
Ryan
The price is NZ$312
includes taxes & fees
23 Jan - 24 Jan 2026
Lazy Loft: Tiny Room Loft Queen w Pool

Oceanfront Condo with Balcony, Pool & Fast Wi-Fi – Near Red Hook

Oceanfront Condo with Balcony, Pool & Fast Wi-Fi – Near Red Hook
St. Thomas
9.8 out of 10, Exceptional, (17)
"Great location and a very nice 1BR condo overlooking the ocean. We walked to nearby spots for food and drinks. Really liked this place and would stay again. "
United States
David
Oceanfront Condo with Balcony, Pool & Fast Wi-Fi – Near Red Hook
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 Water Island Hotel Reviews

Find out more about Water Island

Everything you need to know about Water Island 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 Water Island 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 Water Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Water Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Water Island. 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 Water Island 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 Water Island holiday rentals we have selected for you start as low as NZ$283 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Water Island rentals

At Expedia, we put the best Water Island 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 Water Island 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 Water Island 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 Water Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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