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Estate Great Cinnamon Bay Holiday Rentals

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Our top choices for Estate Great Cinnamon Bay holiday rentals

10.0 out of 10, Exceptional, (134)
"Absolutely would stay here again. We had zero issues with our stay. "
United States
Mark P.
The price is AU$678
includes taxes & fees
25 Jan - 26 Jan 2026
Lameshur Cottage's Guest House
9.4 out of 10, Exceptional, (223)
"Clean, quiet, convenient location. Perfect stay!!!"
United States
Glenda
The price is AU$298
includes taxes & fees
30 Dec - 31 Dec
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
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 price is AU$2,161
includes taxes & fees
6 Jan - 7 Jan 2026
The Peter Bay 1BR Penthouse Suite at St John's Most Prestigious Address
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 AU$365
includes taxes & fees
31 Dec - 1 Jan 2026
Lameshur Bay Glamping Site with AC
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 AU$424
includes taxes & fees
31 Dec - 1 Jan 2026
Family Glamping Site with AC

Aparthotel in St. Thomas

The Landmark Apartment
2.5 star property
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 AU$568
includes taxes & fees
14 Jan - 15 Jan 2026
The Landmark Apartment

Villa in St. John

Villa Island Paradise
4.0 star property
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 AU$1,167
includes taxes & fees
6 Jan - 7 Jan 2026
Villa Island Paradise
The price is AU$353
includes taxes & fees
31 Dec - 1 Jan 2026
Salt Pond Bay Glamping Site With AC

Aparthotel in St. Thomas

The Breeze St Thomas
2.0 star property
The price is AU$647
includes taxes & fees
11 Jan - 12 Jan 2026
The Breeze St Thomas
10.0 out of 10, Exceptional, (39)
"Clean home, accurate check-in instructions, splendid view!"
United States
Jeffrey
The price is AU$370
includes taxes & fees
19 Jan - 20 Jan 2026
Tropical Oasis 🇻🇮Stunning ocean view, minutes drive to Brewers Beach!🇻🇮🏝
4.0 star property
8.6 out of 10, Excellent, (95)
"Amazing property and helpful staff. "
United States
Joseph
The price is AU$1,614
includes taxes & fees
11 Jan - 12 Jan 2026
Suite St. John at Gallows Point Resort

Apartment in Maho Bay Quarter

Peter Bay Gatehouse
4.0 star property
8.4 out of 10, Very good, (19)
"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 AU$1,825
includes taxes & fees
23 Jan - 24 Jan 2026
Peter Bay Gatehouse
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 AU$393
includes taxes & fees
15 Jan - 16 Jan 2026
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!
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 AU$490
includes taxes & fees
1 Jan - 2 Jan 2026
Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!
10.0 out of 10, Exceptional, (88)
"The house is perfectly positioned to capture stunning views. It was spotless, and the host was very responsive. If you’re looking for privacy and seclusion surrounded by beautiful scenery, this is the place."
United States
David C.
The price is AU$1,773
includes taxes & fees
27 Jan - 28 Jan 2026
Good Vibes Only Waterfront Villa /Private Pool/Modern/Sun Decks/Majestic Views!

Apartment in St. Thomas

Shibui Cove
2.0 star property
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 AU$568
includes taxes & fees
1 Jan - 2 Jan 2026
Shibui Cove
10.0 out of 10, Exceptional, (8)
"Nice loft with a great library in downtown Charlotte Amelie. Loved the stay, will go back if I am in the area."
United States
Kevin S.
The price is AU$1,410
includes taxes & fees
1 Jan - 2 Jan 2026
Single Night Bookings Welcome - Tropical Modern Loft - SoHo Style - Concierge

Condo resort in St. Thomas

Marriott's Frenchman's Cove
4.0 star property
9.0 out of 10, Wonderful, (189)
"the view was amazing… the room was perfect and very clean! Highly recommend! "
United States
Ron
The price is AU$1,707
includes taxes & fees
4 Jan - 5 Jan 2026
Marriott's Frenchman's Cove
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 AU$459
includes taxes & fees
11 Jan - 12 Jan 2026
Sophisticated Beach Condo-Ocean View-Sapphire

Apartment in St. Thomas

Little Indigo Apartments
3.5 star property
8.4 out of 10, Very good, (22)
"Amazing views, very nice people"
United States
Ramie
The price is AU$500
includes taxes & fees
1 Jan - 2 Jan 2026
Little Indigo Apartments
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 Estate Great Cinnamon Bay Hotel Reviews

Find out more about Estate Great Cinnamon Bay

Everything you need to know about Estate Great Cinnamon Bay 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 Great Cinnamon Bay 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 Estate Great Cinnamon Bay holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Estate Great Cinnamon Bay holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Estate Great Cinnamon Bay. 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 Estate Great Cinnamon Bay 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 Great Cinnamon Bay holiday rentals we have selected for you start as low as AU$327 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Estate Great Cinnamon Bay rentals

At Expedia, we put the best Estate Great Cinnamon Bay 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 Great Cinnamon Bay 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 Great Cinnamon Bay 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 Great Cinnamon Bay. 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

Can I find a holiday rental in Estate Great Cinnamon Bay?

Yes, there are holiday rentals close to the most popular sights in Estate Great Cinnamon Bay, 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 Great Cinnamon Bay has to offer?

The Cottage at Villa Indigo: This holiday home rental outside Estate Great Cinnamon Bay is located in the mountains, and offers a private garden, Netflix and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave.

What can I see and do in Estate Great Cinnamon Bay?

Cinnamon Bay Beach and Cinnamon Bay are a couple of lovely local spots to get outside and enjoy nature. You’ll find favourite places to visit such as Trunk Bay and Sapphire Beach in the wider area.

What are holiday rentals like in Estate Great Cinnamon Bay?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Estate Great Cinnamon Bay. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for family gatherings.