Villa vacation rentals in Cinnamon Bay

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Popular amenities for Cinnamon Bay villa rentals

Private villa rentals

Guest favorite
Villa in VG
4.98 out of 5 average rating, 51 reviews

Stunning Limeberry Villa, a designer's dream.

JimRating, 5 stars2 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 favorite
Villa in Coral Bay
5 out of 5 average rating, 34 reviews

Water View, 2 King Primary Suites, pool, private

JasonRating, 5 stars2 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 favorite
Villa in Southside
5 out of 5 average rating, 7 reviews

NEW - open cal - Central Location - POOL Sleeps 9!

HannahRating, 5 stars2 weeks ago
This home was everything our family could have asked for on a vacation, location, views, amenities, etc. Our main purpose was to relax and slow down just a little. Meghan was super helpful and responsive no matter the time of day. I would choose this home again if we ever make it back to St Thomas.
Guest favorite
Villa in Tortola
4.96 out of 5 average rating, 23 reviews

Sand Dollar- overlooking Long Bay Beach

LukeRating, 5 stars3 weeks ago
We had an incredible stay at Sand Dollar. The location was perfect - quiet & private, yet just a short drive to Smuggler’s Cove & within walking distance to Long Bay Beach. We loved the peace at the villa; we rarely saw anyone else, which made it feel like our own little getaway. Plus, the location was super convenient for catching the ferry to Jost Van Dyke. The house itself was beautifully updated, offering both comfort & style. It was well-maintained & had everything we needed, from a fully equipped kitchen to a cozy living space. One of the highlights was the back deck with its incredible views - we even spotted flamingos in the pond one morning! Check-in was a breeze, and communication with the hosts was excellent. They took the time to walk us through the ins and outs of the island, offering local recommendations that made our trip even better. Overall, we couldn’t have asked for a better place to stay. Highly recommend this villa if you’re visiting Tortola!
Top guest favorite
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!
Top guest favorite
Villa in Charlotte Amalie
4.99 out of 5 average rating, 80 reviews

Tropical Modern Loft | SoHo Style | Concierge

LevyRating, 5 stars3 days 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 favorite
Villa in West End
4.98 out of 5 average rating, 57 reviews

Villa Morning Glory - Private Pool - Amazing Views

NiamhRating, 5 stars3 weeks ago
Everything was better than described. Wonderful stay! Host was amazing with all the recommendations!
Guest favorite
Villa in Tortola
4.97 out of 5 average rating, 37 reviews

Otis House - beach house w/ pool at Smuggler's

AnnaRating, 5 stars4 months ago
Wonderful secluded location, all you need for a perfect and lowkey getaway!

Luxury villa rentals

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

Tropical Palm Villa- Ocean Views From All Rooms!

TravisRating, 5 stars2 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.
Guest favorite
Villa in Cruz Bay
4.9 out of 5 average rating, 20 reviews

BlueWater Vista - 4 Bed Pool Villa, Amazing Views

LaraeRating, 5 stars3 weeks ago
The house was perfect for multi families, kid friendly. I was impressed how well stocked it was!
Superhost
Villa in St John
4.86 out of 5 average rating, 65 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.
Superhost
Villa in Saint Thomas
5 out of 5 average rating, 18 reviews

Paradise with Exquisite Ocean View

CathyRating, 5 stars3 weeks 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!
Guest favorite
Villa in Northside
4.83 out of 5 average rating, 48 reviews

Minutes to Magens Bay - POOL - Views - Dining

JasonRating, 5 stars4 days 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 !!!!
Superhost
Villa in Cruz Bay
4.92 out of 5 average rating, 38 reviews

The Tile House

KevinRating, 5 stars3 months ago
Exactly as advertised, host was very receptive. One bonus not really mentioned is how close the market is for coffee and anything you’ll need. Kids loved seeing the Iguanas at the tree each morning.
Guest favorite
Villa in Ballast Bay
4.91 out of 5 average rating, 64 reviews

Villa Almondeen- Peaceful 2bedroom villa with pool

michaelRating, 5 stars1 month ago
We stayed at Villa Almondeen for 21 nights. The setting is perfect for 2 couples with plenty of room and an amazing covered porch with a small pool sitting right on the oceans edge (no easy access to ocean immediately in front of house though). Quite private setting. Janice the host is amazing. So remarkably friendly and responsive. Always got back to us rather quickly. Had great advice on beaches and restaurants etc. Traveled the entire island by car over the 3 weeks----this home in Ballast Bay adjacent to Cane Garden Bay is the best area we saw. Walked over the hill to Cane Garden Bay daily. Many great restaurants within 15 min drive. The home was thoroughly cleaned prior to our arrival and at the end of each week was cleaned again---no issues. Janice made check in simple. Had the memorable chance to meet many of her family as an added bonus. We have rented many times over the years in many areas of the world----this was probably the best.
Guest favorite
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.

Villa rentals with a pool

Superhost
Villa in St. Thomas
4.81 out of 5 average rating, 57 reviews

Escape Ordinary: Villa Calvo

BonitaRating, 5 stars3 weeks ago
Enjoyed our stay. Wished it was a little warmer in the pools and definitely wanted a hot tub! But yes we enjoyed our stay!
Superhost
Villa in Water Island
5 out of 5 average rating, 4 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 stars1 week ago
Great and safe location! Right by all the action in Cruz Bay
Superhost
Villa in Northside
4.83 out of 5 average rating, 6 reviews

Luxurious Villa with Stunning Ocean Views

MarshallRating, 5 stars2 months ago
Great location, privacy, and breathtaking views! The home was more space than we needed, but we enjoyed the open layout, and spacious bedrooms and bathrooms, and beautiful views from every room. We appreciated all of the amenities as well - from everything in the kitchen to the A/C units, ceiling fans, extra towels, laundry, etc. We loved the pool area with options for sitting in the sun and shade, and really enjoyed exploring the paths around the home and the “extra” deck and chairs. Great proximity to Magens Bay and our favorite spot, the Northside Grind for coffee, smoothies and sandwiches.
Guest favorite
Villa in Southside
4.93 out of 5 average rating, 14 reviews

Villa View Caribe

MaryRating, 5 stars4 months ago
I appreciate Randall meeting near the property to provide directions and information. The house was very clean and the views are stunning from the back patio.
Guest favorite
Villa in Cruz Bay
4.95 out of 5 average rating, 20 reviews

Gorgeous ocean view penthouse! Walk to Cruz Bay!

BrookeRating, 5 stars1 month ago
This was our second time to the island and our first time at Allison’s place and I can say with confidence we will definitely stay here again! It was so great being able to walk into town so easily and yes, there is a hill, but there are hills everywhere on the island so it was no biggie for us and our two young kids. We can’t wait to come back and thank you for everything!
Guest favorite
Villa in NorthSide
4.96 out of 5 average rating, 52 reviews

Heated Pool/Views/SpaTub/Outdoor Shower/Generator

EmilyRating, 5 stars5 months ago
My family had an amazing stay at Stacie and Mark’s home. Coffee with the view, outdoor shower, and the pool were some of our favorite parts. The layout worked perfectly for us - everyone had privacy and space. We loved to adventure around the island each day and come home to a cozy and peaceful setting. It was pretty hard to leave. I highly recommend this beautiful home for your visit to St Thomas!!
Guest favorite
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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