Villa holiday rentals in Cinnamon Bay

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Popular amenities for villa rentals in Cinnamon Bay

Private villa rentals

Top guest favourite
Villa in Coral Bay
5 out of 5 average rating, 57 reviews

Memory Daze

BlakeRating, 5 stars3 weeks ago
This is the greatest place we’ve ever stayed. It had a breathtaking view, was well appointed, quiet, peaceful, and tranquil. Memory Daze is a dream and we will be coming back. The hosts were supper communicative and helpful and the house had everything we needed to have a great vacation. I literally teared up when we were about to leave because it was such a happy place for my wife and I. If you are reading this and contemplating a vacation here in St. John, do it! Book this place now. You won’t regret it.
Guest favourite
Villa in Coral Bay
5 out of 5 average rating, 34 reviews

Water View, 2 King Primary Suites, pool, private

JasonRating, 5 stars3 weeks ago
This place was amazing. The property was very well maintained and clean. Everything worked and it had everything we needed. The location is close to hiking, beaches, grocery and food. Kim was a great host we will be back for sure.
Guest favourite
Villa in Tortola
4.96 out of 5 average rating, 24 reviews

Sand Dollar- overlooking Long Bay Beach

CindyRating, 5 stars3 weeks ago
Loved our stay. The view was amazing! The owners had paid much attention to detail. It was so nice to have beach towels to use and the drying lines in the bathroom as well as the drying racks. The beds were huge and very comfortable. It was just a short drive to our favorite beach - Smugglers. It was very hard to leave!
Top guest favourite
Villa in St. John
4.98 out of 5 average rating, 54 reviews

Just Peachy - Pool Villa + Bronco + WE’RE SOLAR!

JoshuaRating, 5 stars3 months ago
Absolutely Perfect Stay at Just Peachy! Our stay at Just Peachy in St. John was nothing short of incredible! From the moment we arrived, we were blown away by the stunning views of the mountains and ocean—it truly felt like paradise. The villa itself was immaculate, beautifully designed, and had everything we needed for a comfortable and relaxing vacation. Melissa, our host, was phenomenal! She was incredibly responsive, always just a message away, and went above and beyond to make sure our stay was perfect. Whether it was providing great local recommendations, answering any questions we had, or simply ensuring we felt at home, her hospitality was unmatched. Waking up to breathtaking sunrises, lounging on the patio with the cool island breeze, and enjoying the peaceful surroundings made this trip unforgettable. If you're looking for the perfect getaway in St. John, Just Peachy is the place to be. We can’t wait to come back! Thank you, Melissa, for making our trip so special!
Superhost
Villa in Cruz Bay
4.92 out of 5 average rating, 39 reviews

The Tile House

CateRating, 5 stars6 days ago
Chirag was so kind and responsive! His place is gorgeous. The pool felt amazing after a long day at the beach or a hike. The place looked just as pictured. I would definitely come back!
Top guest favourite
Villa in Charlotte Amalie
4.99 out of 5 average rating, 81 reviews

Tropical Modern Loft | SoHo Style | Concierge

LevyRating, 5 stars1 week ago
Zack was an excellent host. Very responsive and proactive communicator with suggestions for restaurants, etc. I can't say enough great things about his place itself. It's an incredibly hip and modern vibe and in a great walkable location to shopping and restaurants. VERY unique. We loved it. Centrally located on the island and he connected us with someone to rent a jeep. He made it so easy. The whole experience was great! We would definitely stay here again and highly recommend his place to anyone staying in St. Thomas!
Guest favourite
Villa in White Bay
4.94 out of 5 average rating, 16 reviews

Ocean View Villas, 1 Bedroom- (Seascape)

JohnRating, 5 stars1 month ago
We stayed in the two bedroom villa for a few days in April and it was wonderful. We really enjoyed the large patio and amazing views. The beds were very comfortable and bathrooms super clean and nice. Kitchen was well stocked and again very clean. Overall it was such a peaceful retreat and a wonderful stay. Nigel and Karen were wonderful hosts.
Top guest favourite
Villa in Tortola
5 out of 5 average rating, 32 reviews

Gorgeous 4 bed villa with pool and amazing views

ScottRating, 5 stars1 month ago
Excellent communication with the host. Quickest responses from any other host I have ever dealt with. Gave some info on possible additions to the stay for future guests and was well received. Most spectacular view looking at St John and Jost Van Dyke. Great sunsets and very convenient to West end of Tortola for dining and beaches. Thank you so much!!

Luxury villa rentals

Superhost
Villa in Cruz Bay
4.64 out of 5 average rating, 25 reviews

Villa Belvedere Oceanfront Suites

CourtneyRating, 5 stars1 month ago
Our group had an amazing time staying at Joys place. We are a very outdoorsy active group and after a day of snorkeling or hiking it was always nice coming back to her place for the amazing sunsets. You're super close to grocery stores restaurants equipment rentals shopping. Would absolutely recommend. Her and Chris were very quick and responsive with anything we needed.
Superhost
Villa in St John
4.86 out of 5 average rating, 66 reviews

Coconut Breeze, Mesmerizing Views, Generator

IanRating, 5 stars1 month ago
Coconut Breeze was as good as advertised. The home was comfortable, well stocked and had spectacular views, absolutely perfect for our group of 6. Definitely get a 4 wheel drive vehicle as the roads leading up are steep and a bumpy, but hey it’s St John and that’s what you signed up for. While the home is tucked into the private, lush jungle hillside it’s also conveniently located a short drive away from multiple restaurants, grocery stores etc. We had an issue with an AC unit in the cottage, but it was promptly resolved by our host. The cottage porch was not screened in, but maybe this is something that will be done in the future. If you are staying in Coral Bay Coconut Breeze is the way.
Guest favourite
Villa in VG
4.98 out of 5 average rating, 51 reviews

Stunning Limeberry Villa, a designer's dream.

JimRating, 5 stars3 months ago
Great host and property. Unique,great view,comfortable,well equipped. Great pool. 5 star across board except star on location as represented due to advertising of "short walk to beach ". Was short drive to multiple beautiful beaches,Smugglers Cove most beautiful secluded beach ever
Guest favourite
Villa in Northside
4.83 out of 5 average rating, 48 reviews

Minutes to Magens Bay - POOL - Views - Dining

JasonRating, 5 stars1 week ago
The view is amazing, plenty of room and very spacious. AWD is a must for the driveway, pool are is very nice. No complaints at all. We loved our week here !!!!
Guest favourite
Villa in Ballast Bay
4.91 out of 5 average rating, 65 reviews

Villa Almondeen- Peaceful 2bedroom villa with pool

NatalieRating, 5 stars2 weeks ago
Janice and her family are absolutely amazing! From the moment we arrived, she went above and beyond to make our stay seamless and welcoming. She provided clear instructions on where to meet and was incredibly flexible with our check-in time. Janice even personally drove us to the villa, gave us a full tour, and made sure we knew where everything was. As a thoughtful touch, she welcomed us with a fresh bowl of mangoes picked right from the tree on her property—such a lovely gesture! The villa itself is private, peaceful, and perfectly located. We were no more than 20 minutes away from everywhere we wanted to go on the island, including all the ferry ports. Each evening, we relaxed by the pool and watched the sunset—truly a breathtaking experience. We felt completely at home and safe throughout our stay. Without a doubt, we’ll be returning to Tortola—and when we do, we can’t imagine staying anywhere else!
Superhost
Villa in St. John
4.86 out of 5 average rating, 65 reviews

Stunning Views Villa Catalina. Full Generator!

EddieRating, 5 stars3 weeks ago
Claudia was great and very responsive. Also gave helpful info for the ferry and jeep rentals. Curtis, the property manager was also great and helped us with a jeep and fishing & snorkel charter recommendations. Just good people that took good care of us. I'd highly recommend Claudia.
Guest favourite
Villa in Long Bay
4.99 out of 5 average rating, 82 reviews

Luxury LongView Villa with Stunning Sea views

BruceRating, 5 stars4 months ago
There's not much to add as a review of Nick's wonderful home that hasn't been said already. We just spent 10 days there for the third year in a row, and this is our third review. Because of the 4 king bed rooms (two on each side of the center living area), his place can certainly accommodate four couples with plenty of privacy (our trips have been just my wife and myself), each bedroom and a number of outdoor dining and relaxing spots all having world class views of the Carribean from about 200 feet above the sea. Being right above a nice beach provides a constant sound of waves hitting the beach that adds to the ambience of the villa. The villa is well equipped (we cooked every meal there), clean and comfortable. Has WiFi and TV's for those who need or want Internet access and entetainment. Nick (the owner) and Jon and Jude (the on island management team) are terrific people and very accommodating. We hope to be back again to our personal favorite vacation spot on the planet.
Superhost
Villa in Cruz Bay
4.87 out of 5 average rating, 15 reviews

Mandavilla Rose - SuperHost/Generator/Starlink

RebeccaRating, 5 stars3 weeks ago
This was our second stay at Mandavilla Rose. It was a great base for our long weekend in St. John. We loved coming back to the pool after a day at the beach and our Friends of the Park Power Swim. And perhaps our favorite time was sitting around the large dining table after dinner with wine, playing the conversation card game that we found on the shelf. We hope to return next year.

Villa rentals with a pool

Top guest favourite
Villa in East End
4.96 out of 5 average rating, 50 reviews

Tropical Palm Villa- Ocean Views From All Rooms!

TravisRating, 5 stars3 months ago
We had an amazing week at the Tropical Palm Villa!! Spencer was extremely helpful and always quick to respond to any questions we had. Mason met us and made us feel right at home while checking us into the villa. The views from villa are incredible! The place was perfect for my family of five to enjoy St. Thomas and all it has to offer. We were especially grateful for the amenities that made cooking and grilling a breeze. We also enjoyed the beach gear that was provided, including chairs, beach umbrella, and snorkel gear. The location of the house is perfect, offering easy access to the beach, or a quick drive into Red Hook for restaurants, groceries, and the ferry to St. John. Overall, we had a tremendous week and hope to make it back soon.
Superhost
Villa in St. Thomas
4.8 out of 5 average rating, 59 reviews

Escape Ordinary: Villa Calvo

SarahRating, 5 stars6 days ago
The place was amazing! Best vacation we have ever been on. Beautiful views of the water. Snorkel gear and chairs come in handy! My advice would be to rent a car, so you can explore multiple beaches. We felt very at home at Ryan’s place. We were sad to leave.
Superhost
Villa in Saint Thomas
5 out of 5 average rating, 18 reviews

Paradise with Exquisite Ocean View

CathyRating, 5 stars1 month ago
I cannot say enough about how beautiful this house and location is. A beautiful view of the water in almost every location in the home. Very clean and the ere was plenty of room for 5 of us. We loved the spacious dining room with a huge dining table to seat a large group. When on the deck, you are almost directly above the water-feels like you are on a cruise ship! Andrew responded immediately whenever we had a question. I would definitely recommend this home!
Superhost
Villa in Water Island
5 out of 5 average rating, 5 reviews

Seagrape Villa on Water Island

CodyRating, 5 stars3 months ago
From start to finish, April made our stay one of our most memorable vacations. Having visited the island multiple times, we knew exactly what we wanted—and this property checked all the boxes. Anything we needed or requested was promptly addressed by either April or her property managers. This property is truly one of a kind, offering both stunning sunrise and sunset views. The ocean breeze is strong but refreshing, keeping you cool throughout the day. We also opted to have April provision our groceries, and she went above and beyond—everything was neatly put away upon our arrival. Water Island has always held a special place in our family’s heart, and staying here made it even more unforgettable. We can’t recommend it enough!
Superhost
Villa in Cruz Bay
4.82 out of 5 average rating, 33 reviews

Aqua Bay Villa #3~A' La Plage~1 BR~Ocean View~Pool

AlexRating, 5 stars3 weeks ago
Great and safe location! Right by all the action in Cruz Bay
Guest favourite
Villa in Cruz Bay
4.95 out of 5 average rating, 21 reviews

Gorgeous ocean view penthouse! Walk to Cruz Bay!

JordanRating, 5 stars1 week ago
We really enjoyed this condo on St. John!! It was so comfortable and had everything we needed. We loved sitting out on the covered balcony, enjoying the view, both in the morning while having our coffee and in the evening watching the sunset! The location was fantastic! We walked to town for restaurants & groceries, and we walked to the taxi area to get a ride to the beautiful beaches! There was a steep hill walking back to the condo, but it was worth it for the condo and its location! It was just right for us and our two teenagers:)
Guest favourite
Villa in NorthSide
4.96 out of 5 average rating, 53 reviews

Heated Pool/Views/SpaTub/Outdoor Shower/Generator

AnabellaRating, 5 stars3 weeks ago
I’ve had staying in many airbnbs before, and Stacie’s place has been one of the best I’ve stayed at. It had everything we needed and wanted plus more. Don’t even think twice to book this place! It’s beautiful. Also bathrooms were recently remodeled and they’re both beautiful. I will say that this home is not for children under or the elderly.
Guest favourite
Villa in Southside
4.95 out of 5 average rating, 65 reviews

Frenchman's View Villa 2 BD/2.5 BA w/ Pool

StephenRating, 5 stars1 month ago
I would absolutely recommend this place for anyone! Everything was as advertised the views were stunning the home was absolutely beautiful and sabrina was an excellent host. My favorite part was that it wasn't dead in the center of town nor was it too far away from Charlotte Amalie or anything else, really 10/10 on all fronts.

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