Hawaii beach woman relaxing swimming in bikini in idyllic ocean of lost paradise remote island tropical getaway. Wanderlust and adventure lifestyle banner panorama.

Search Holiday Rentals in Estate Little Saint James Island

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Estate Little Saint James Island holiday rentals

Lameshur Cottage's Guest House

Lameshur Cottage's Guest House
St John
10.0 out of 10, Exceptional, (141 reviews)
"Amazing place! Great host!!Close to Salt Pond."
United States
Shawn C.
The price is £272
includes taxes & fees
22 Jun - 23 Jun
Lameshur Cottage's Guest House

Peter Bay Gatehouse

Peter Bay Gatehouse
4.0 star property
Maho Bay Quarter
8.4 out of 10, Very good, (20 reviews)
"Staying at the gate house was wonderful. Walk to beach was a little longer than expected because of the sharp incline. Very nice place to stay!! "
United States
jonathan
The price is £659
includes taxes & fees
11 Jul - 12 Jul
Peter Bay Gatehouse

The Breeze

The Breeze
2.0 star property
ST Thomas
The price is £620
includes taxes & fees
4 Jul - 5 Jul
The Breeze

The Westin St. John Resort Villas

The Westin St. John Resort Villas
4.5 star property
St. John
8.2 out of 10, Very good, (491 reviews)
"Great unit, clean, updated and comfortable. Laundry and coffee were a plus. The resort is beautifully maintained and landscaped."
United States
Lindsay
The price is £620
includes taxes & fees
5 Jul - 6 Jul
The Westin St. John Resort Villas

Good Vibes Only Waterfront Villa /Private Pool/Modern/Sun Decks/Majestic Views!

Good Vibes Only Waterfront Villa /Private Pool/Modern/Sun Decks/Majestic Views!
St Thomas
10.0 out of 10, Exceptional, (100 reviews)
"Wonderful VRBO with amazing views and amenities!We could not have asked for better communication from our host Ryan & Roxy!"
United States
Lori L.
The price is £802
includes taxes & fees
4 Jul - 5 Jul
Good Vibes Only Waterfront Villa /Private Pool/Modern/Sun Decks/Majestic Views!

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

The Peter Bay 1BR Honeymoon Suite at St. John's Most Prestigious Address
Maho Bay Quarter
9.8 out of 10, Exceptional, (28 reviews)
"The property was wonderful and the check in process was seamless with Tommy there to greet us. Don’t look elsewhere, just rent this one!"
United States
Chris B.
The price is £799
includes taxes & fees
11 Jul - 12 Jul
The Peter Bay 1BR Honeymoon Suite at St. John's Most Prestigious Address

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

Tropical Oasis 🇻🇮Stunning ocean view, minutes drive to Brewers Beach!🇻🇮🏝
St Thomas
9.8 out of 10, Exceptional, (55 reviews)
"One of my favorite vrbo stays, place felt very serene and relaxing, if you love being immersed in nature I would definitely book this place."
United States
Ishjah S.
The price is £209
includes taxes & fees
29 Jun - 30 Jun
Tropical Oasis 🇻🇮Stunning ocean view, minutes drive to Brewers Beach!🇻🇮🏝

Breathtaking Views from Sapphire Village

Breathtaking Views from Sapphire Village
ST THOMAS
9.4 out of 10, Exceptional, (111 reviews)
"Great place to stay for the night."
United States
Kyle E.
The price is £259
includes taxes & fees
2 Jul - 3 Jul
Breathtaking Views from Sapphire Village

Suite St. John at Gallows Point Resort

Suite St. John at Gallows Point Resort
4.0 star property
St. John
8.8 out of 10, Excellent, (105 reviews)
"Everything was just first class!!! Amazing place and great people!"
United States
Grady
The price is £553
includes taxes & fees
13 Jul - 14 Jul
Suite St. John at Gallows Point Resort

Octopus Den Glamping Site with AC

Octopus Den Glamping Site with AC
St John
10.0 out of 10, Exceptional, (8 reviews)
"Emily & Bill are great hosts & have the wonderful ability to be attentive to guests while providing a peaceful & relaxed atmosphere where you know they’re on property, yet giving everyone their personal space. "
United States
William C.
The price is £177
includes taxes & fees
22 Jun - 23 Jun
Octopus Den Glamping Site with AC

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, (246 reviews)
"We were impressed with the room and its location. Had everything we needed for our brief stay. Appreciated the king sized bed after several days of much smaller ones. In great walking proximity to Sapphire Bay Beach and its restaurants and coffee shop."
United States
Roxanne
The price is £226
includes taxes & fees
2 Jul - 3 Jul
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

🌴 Sapphire Beachfront New Renovated Villa Perfect for Family WiFi ★★★★★

🌴 Sapphire Beachfront New Renovated Villa Perfect for Family WiFi ★★★★★
St Thomas
10.0 out of 10, Exceptional, (29 reviews)
"Everything! Can’t wait to return"
United States
Matt M.
The price is £570
includes taxes & fees
17 Jul - 18 Jul
🌴 Sapphire Beachfront New Renovated Villa Perfect for Family WiFi ★★★★★

Flamingo Grove Glamping Site with AC

Flamingo Grove Glamping Site with AC
St John
9.8 out of 10, Exceptional, (30 reviews)
"Really enjoyed our stay. We felt well taken care of and loved the location!"
United States
John
The price is £181
includes taxes & fees
22 Jun - 23 Jun
Flamingo Grove Glamping Site with AC

Sophisticated Beach Condo-Ocean View-Sapphire

Sophisticated Beach Condo-Ocean View-Sapphire
Smith Bay
9.0 out of 10, Wonderful, (41 reviews)
"We stayed just one night before heading over to St. John. The room was clean and suited our needs well. It was nice to have an on site restaurant, Sudi's, that provided a fun start to our trip"
United States
Marshall
The price is £207
includes taxes & fees
22 Jun - 23 Jun
Sophisticated Beach Condo-Ocean View-Sapphire

Generator! Private Pool Villa - Sapphire Beach 5min walk & Washer/Dryer WiFi 9

Generator! Private Pool Villa - Sapphire Beach 5min walk & Washer/Dryer WiFi 9
St Thomas
10.0 out of 10, Exceptional, (25 reviews)
"Easy to find location and clean. "
United States
james s.
The price is £471
includes taxes & fees
24 Jun - 25 Jun
Generator! Private Pool Villa - Sapphire Beach 5min walk & Washer/Dryer WiFi 9

The Captain and the Mermaid - Adventures in Paradise are waiting!

The Captain and the Mermaid - Adventures in Paradise are waiting!
St Thomas
9.8 out of 10, Exceptional, (229 reviews)
"Host was great! Super responsive and accommodating to our early check in needs. "
United States
Susanne M.
The price is £217
includes taxes & fees
12 Jul - 13 Jul
The Captain and the Mermaid - Adventures in Paradise are waiting!

Ocean and Magens Bay View NorthStar Escape

Ocean and Magens Bay View NorthStar Escape
St. Thomas
10.0 out of 10, Exceptional, (22 reviews)
"The host Jamila was amazing. She is available if you need anything. The condo was very clean and in great condition. We would recommend highly as our stay was wonderful. Thank you Jamila"
United States
Jeff M.
The price is £319
includes taxes & fees
22 Jul - 23 Jul
Ocean and Magens Bay View NorthStar Escape

The Cottage at Villa Indigo

The Cottage at Villa Indigo
3.0 star property
St. Thomas
8.8 out of 10, Excellent, (15 reviews)
"We got a true dose of the life experience on the island staying here. The entire experience was MAGICAL!!!! Me and my family will most definitely staying again when we come back "
United States
Oronde
The price is £344
includes taxes & fees
22 Jun - 23 Jun
The Cottage at Villa Indigo

Charming Beach Condo w/ Balcony

Charming Beach Condo w/ Balcony
Smith Bay
9.4 out of 10, Exceptional, (46 reviews)
"We spent five days at the beginning of May 2026 in this condo and couldn’t ask for a better spot for our first trip to St. Thomas! Perfect location ..close to Red Hook for shops and the ferry. Nice balcony for watching the sunrise and coffee. Pool was refreshing and maintained regularly. Local restaurant / bar, Sudi’s, located in the lower level of building. Provides laid back island vibes with great drinks and delicious food. Host was accommodating and responsive when needed. Would definitely...
United States
Catherine
The price is £232
includes taxes & fees
1 Jul - 2 Jul
Charming Beach Condo w/ Balcony

Turtle Nest Family Glamping Site with AC

Turtle Nest Family Glamping Site with AC
St John
10.0 out of 10, Exceptional, (35 reviews)
"Wonderful property and a fun experience! Would stay again."
United States
Carlee D.
The price is £262
includes taxes & fees
22 Jun - 23 Jun
Turtle Nest Family Glamping Site with AC
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Estate Little Saint James Island Hotel Reviews

Find out more about Estate Little Saint James Island

Everything you need to know about Estate Little Saint James 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 Estate Little Saint James Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Estate Little Saint James Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Estate Little Saint James Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Estate Little Saint James 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 Estate Little Saint James 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 Estate Little Saint James Island holiday rentals we have selected for you start as low as £217 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Estate Little Saint James Island rentals

At Expedia, we put the best Estate Little Saint James 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 Estate Little Saint James 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 Estate Little Saint James 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 Estate Little Saint James 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. 

Frequently asked questions

Are there holiday rentals in Estate Little Saint James Island?

Yes, there are holiday rentals close to the most popular sights in Estate Little Saint James Island, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Estate Little Saint James Island has to offer?

Gorgeous View, Beach Access, Swimming Pool, Kayaks, Quiet Privacy - the East End: This holiday home rental outside of Estate Little Saint James Island is located in the mountains, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You can relax into your holiday with a garden and a selection of games.

What can I see and do in Estate Little Saint James Island?

Get outdoors into nature at a spot like Sapphire Beach, or visit other top attractions such as Trunk Bay. In the wider area, you’ll find Magens Bay Beach and Cowpet Bay.

What’s a holiday rental in Estate Little Saint James Island like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Estate Little Saint James Island. Holiday rentals offer amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.