Grand Cayman Rentals with Pools

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142 condos in Grand Cayman with pools

SMB-Grand 32. Beachside condo with pool. Remote work from Paradise.

Seven Mile Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$334

2 BR MoonLight Kai condo at Kaibo Yacht Club, ph.2

Rum Point apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Paradise” We stayed at MoodLight Kai condo the first week of april 2014. It was a magical experience being in Cayman Island for the first time. The condo is very modern and comfortable with a beautiful beach view right from the living room couch. There was no excessive noise or biting insects, the beach is very close and if you are feeling too lazy to go anywhere you can just lounge on the beach in front of the condo or soak in the jacuzzi. We had an excellent time and would definitely go back for another family vacation.

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Price per night from

$284

Laguna del Mar: Prime Seven Mile Beach location ground floor beachfront

Seven Mile Beach condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,248

"A Mid-Winter Night's Dream" Grand Cayman Oceanfront, Quiet, Secluded, Rum Point

North Side apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Loved it” We loved the Rum Point area. The condo was clean. Pool area was clean. We enjoyed the area enough for us to do. When we wanted to do more drove 45 minutes to Seven Mile Beach. Just a great location

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Price per night from

$275

Coconut Beach: Rum Point Beach House w/Pool, Beach Cabana, & Spectacular

Rum Point house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 12 minutes

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Price per night from

$925

2 BR condo on Seven Mile Beach with ocean views

Seven Mile Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$454

Villa Caymanas: Caribbean Villa w/ Fabulous Snorkeling, Pool, & Panoramic

Old Man Bay house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“A perfect vacation!” The second spring time vacation we had at villa caymanas. When arriving, the view entering the front door blows me away each time I arrive. Property is well maintained and everything was super clean. Private ocean side back yard made it great for relaxing. House has everything you need and some extras. We drove most days to Rum Point Beach( 10 minute drive) to relax, great beach. Spent a few days never leaving the property as we grilled fish we bought from local fisherman at the docks. With the big group we had, the villa suited us perfectly as there was plenty of room inside and out. I liked best the privacy and location of the house, we enjoy getting away from it all and this place gave us that. Worst part about the house is saying good bye.

Responds fast! avg. 3 hours 12 minutes

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Price per night from

$617

Cayman Beachfront at 22 Villas Pappagallo

West Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$264

“Paradise Found” This was our first time to Grand Cayman Island. We were very excited to go as a family for the first time to the Caribbean. We usually like to vacation at destinations that are not too “touristy” so we decided to stay away from the seven mile beach strip, since we heard that was very busy. We are so grateful that we found this wonderful townhome at Rum Point. Starboard Kai was very tastefully decorated, really clean and very well stocked. They even had a complimentary water cooler for us which were so helpful. They had three kayaks with life jackets, bikes (which we never got a chance to use), laundry in the unit (just make sure you bring your own HE laundry detergent), dvd player (I am not sure if we saw any dvds, but we hardly watched any TV since were had full days), coffee maker, spices, pool towels, beach toys. The only thing we needed was food, that’s how well stocked this place was. It was so nice to be right across from a Rum Point where our boys could play in the water, without worrying about waves. The location is superb, since you have the beach right in front of the condo and the beautiful bioluminescent bay in the back. It was so nice to lounge in the lanai and see the bay. From the living room and office you had nice views of the ocean of Rum Point. Many beautiful parrots, roosters and iguanas to see here, which was really neat! We did venture towards Seven mile beach and other areas of interest but wished we had just spent more time at our home base Starboard Kai. We checked out all the top beaches on the island and found our location to be #1. Janice the owner was a delight to work with; she really goes above and beyond to accommodate her guests. We also found Bob Wagner, the property manager very helpful as well. They truly excel in customer service and were very responsive to any issue we had. We loved going to the recommended restaurants. Loved our day at Sting Ray city, with Red Sail Sports which to sign up is right across the street and leaves from Rum Point’s pier. We really liked the blue iguana sanctuary nearby. We also have great memories of feeding the ‘Pirate’ Frigate birds at Tukka, a restaurant on the east end. Going to get sticky toffee pudding and seeing the Tarpons at Calypso Grill was fantastic as well. Would highly recommend this to others and have. When we got back we showed my friends and family and were amazed how beautiful everything was. Hoping to go back soon!

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Price per night from

$454

Just For Fun: Beach Bungalow on Glowing Bio-Luminescent Bay w/ Private Pool

Rum Point house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Cayman Experience!!” We just finished our 1-week vacation at Just For Fun. The cute cottage certainly lived up to our expectations. Our family cooks three meals a day at home. The kitchen and new grilling area work perfectly. The kitchen has lots of extras that make cooking anything from a quick breakfast to a gourmet meal a breeze. Plus the wet bar with the wine fridge makes for a great flow of traffic. The outside area, with a pool, deck and a screened in porch is perfect. We ate every meal outside, either in the shade or by the pool. Plus there is a cute thatched hut with 4 showers in it for that quick rinse off after a swim in the ocean or a dive. This cottage would really be perfect for a locals getaway to the North Side. It has a great dock and it is very quiet. We will be back, Steve

Responds fast! avg. 3 hours 12 minutes

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Price per night from

$555

Great Location & Value! 7mile Beach Condo next to a Resort Hotel!

Seven Mile Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$680

Kaibo Phase 2 - A4, Grand Cayman

Rum Point apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Perfect vacation” My husband and I spent a week in this condo and found it to be perfect for us. It is very clean with nice linen and a well equipped kitchen. The location is great for walking around Kaibo. It is on a sandy beach with a restaurant right next door. We will definitely return to this spot. The beach is not good for swimming but there is a pool and hot tub. There is a beach within walking distance that is good for swimming.

Responds fast! avg. 2 hours 20 minutes

Match: Swimming pool

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Price per night from

$225

Boggy Sands Club - Parrot Penthouse on Seven Mile Beach

Seven Mile Beach condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 3 hours 32 minutes

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Price per night from

$2,270

Boggy Sands Club - Seven Mile Beach - Starfish

Seven Mile Beach condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“Best Family Vacation Ever!” We came to Grand Cayman to scuba dive as a family. Our condo was a wonderful place to relax after our dive trips because of its proximity to the beach and the pool. Boggy Sands Beach Club is within walking distance of some great local food. Heritage Kitchen, ALFresco, and Calico Bar. The owner Morne Botes was attentive to all of our needs and great to work with. We highly recommend this place and hope to return very soon.

Responds fast! avg. 3 hours 32 minutes

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Price per night from

$2,270

Oceanfront Ground Floor 2 bedroom 2 bathroom sleeps 4-6

North Side condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$447

Great Escape: Serene Cove Villa in the Quiet Neighborhood of Cayman Kai with

Rum Point house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“Best. Vacation. Ever. Amazing. Beautiful. Relaxing.” Great Escape is a beautiful home in the perfect location. A truly luxurious property with an amazing pool and a short walk to Rum Point Beach, which is fantastic. I can't say enough about the house, the pool, the beach, the island. It truly was a perfect vacation. Although it is a drive to the other side of the island, we preferred the relaxing, quiet and island feel of Cayman Kai. The photos of Great Escape are very accurate except honestly I think the pool is bigger than it looks in the photos. Grand Cayman Villas handled our reservation in a professional, timely and courteous manner. They answered all of my questions promptly. They provided lots of information about the island, the property, restaurants, car rentals, etc. Upon arrival there were a couple minor issues (not worth mentioning) but the Villa Manager answered my call immediately and things were taken care of within 20 minutes. The owners of the property were a pleasure to deal with as well. We received an email from them before our stay with helpful information about the property and the island. We spoke by phone and met in person briefly on arrival. They were nothing but helpful and friendly. Highly recommend Great Escape and Grand Cayman Villas. It might be a few years but we will definitely be back.

Responds fast! avg. 3 hours 12 minutes

Match: Swimming pool

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Price per night from

$779

Cayman Conch Quest Beachfront Condo in Rum Point

North Side apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Condo to Rent” We would agree with all of the positive reviews for this condo. We stayed a week in early January. The condo is very comfortable; it is actually even nicer than the pictures. This condo is extremely clean and well maintained. The beds are very comfortable; there are plenty of beach towels, bath towels and linens. There is a TV ( gets all kinds of channels) stereo, Ipod docking; DVD player- more than you need. The artwork in the condo is very nice. The screened in lanai is great for meals and to just watch the ocean. The pool is clean. The complex is small and is kept immaculate by the management company. It was windy the week we were there so we were not able to swim/snorkel out front. Loved having the beach chairs,mats,bags and cooler to use. Bob replyed to all of my emails thoroughly and quickly. There is detailed information Bob emails to you and there are 2 notebooks of information at the condo. It is very quiet and peaceful. The drive is approx 40 minutes from the airport. Bob recommended Marshall's car rental and we found them to be great. This was our first trip to Grand Cayman. We would without a doubt recommend this condo.

Responds fast! avg. 3 hours 52 minutes

Match: Swimming pool

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Price per night from

$199

Cayman - SAND at Crescent Beach - Luxurious Tranquility

East End apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$337

Responds fast! avg. 3 hours 12 minutes

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Price per night from

$602

Ocean front Villa Grand Cayman

West Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$432

Cayman Reef Resort #33 - Personal Lanai Overlooking Beach & Ocean

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Wonderful Stay, Beautiful Condo and Grounds, Easy to Work With” Condo is beautiful and exactly as described in the listing and in all communications with Marc. Very close to beach and water. Even closer than looks in pictures. Literally few steps out the door. Also close walk to great restaurants, stores and Camana Bay. Unit well equipped with towels, umbrella. Beach is gorgeous with beautiful turquoise warm water. Pool and grounds immaculate. Well maintained. Pretty landscaping. Enjoyed the screened porch with ceiling fan for morning coffee. Most gorgeous sunsets on the island right outside of the door. Marc was easy to work with ..... from the time of booking and throughout our stay. He touched base by email and phone upon our arrival to ensure we were doing ok. We would not hesitate to book again .... amazing experience.

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Price per night from

$555

Hidden Cove: Family Hideaway w/Free Kayaks & Bikes, Private Pool and Dock

Rum Point house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

“Beautiful house/location...but erroneous charges from owner not” This is a truly wonderful vacation rental...beautifully decorated and well situated in the cove allowing both privacy and easy access to the ocean. We had a large group and I can easily say we all agreed it was a magical spot worth returning to...especially given the bioluminescene right in our cove which we enjoyed every night! Our other concern was access to the grocery store which turned out to be a shorter drive than expected (maybe 20 mins). All was well until we checked out and the owners slammed us with erroneous charges for missing items! We were never given an innitial inventory, yet we received a massive bill and automatic charge from the owner. They even charged us for items they admitted were missing before we arrived. It was a ridiculous ending to a wonderful trip and it left us all with a bitter taste in our mouths. If you're a strong negotiator, perhaps this rental is worth your trouble.I would certainly recommend getting an inventory pre-visit and writing into the contract that you would only be held accountable for those items listed.

Responds fast! avg. 3 hours 12 minutes

Match: Swimming pool

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Price per night from

$891

Cayman - SKY at Crescent Beach - Luxurious Tranquility

East End apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$341

First Floor Oceanfront Condo in Top Location!

West Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$297

Responds fast! avg. 3 hours 12 minutes

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Price per night from

$331

Fischer's Reef: Spacious, Luxury Beach Villa w/ Heated Infinity Pool & Amazing

Rum Point house

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 20

Responds fast! avg. 3 hours 12 minutes

Match: Swimming pool

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Price per night from

$3,866

Cayman Dream: Rum Point Beach Bungalow with Pool for Oceanfront Living

Rum Point house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Cayman Dream” We rented Cayman Dream in early June of 2013. We were very happy with the house. It's exactly as the pictures show. The kitchen is very well appointed and the grounds are kept very nicely. It's located in a nice quiet area with very little traffic. Our only complaint with the house was the phone/wifi. It was out for three of the six days that we were there and even after it had been fixed we had to constantly reset while we used it. With our children back in the states, we felt really out of touch. We truly enjoyed our stay and would recommend staying there.

Responds fast! avg. 3 hours 12 minutes

Match: Swimming pool

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Price per night from

$477

Wyndham Reef Resort: Studio, Sleeps 2, with Kitchenette

East End condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$219

Responds fast! avg. 3 hours 12 minutes

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Price per night from

$1,283

Lone Palm: Oceanfront Pool, 2 Free Kayaks, & Wide Beachfront.

East End house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 12 minutes

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Price per night from

$682

Responds fast! avg. 3 hours 12 minutes

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Price per night from

$1,564

Boggy Sands Club- Stingray Penthouse on Seven Mile Beach

Seven Mile Beach condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“Heaven on Earth in Grand Cayman” The reviews and pictures don't begin to do this Boggy Sand Road property justice! We rented the ground floor unit,which was absolutely spotless, elegant, roomy, well-equipped and only a few steps to the most beautiful beach. The area is residential, private and quiet - like we had somehow privately rented Seven Mile Beach! The grounds of the property were garden-like and the pool was lovely and clean. Our rental car was nice to have but not necessary - there is a Foster's Market within a short walk of the condo, as well as a few great little restaurants (Alfresco's, Timbuctuu and Heritage Kitchen). The bus service is great - more like hailing a cab with pick-up right at the foot of the driveway. But back to the beach...the unit is equipped with 2 kayaks and a paddle board, which we enjoyed tremendously on the calm, crystal-clear waters. Cemetery Beach is right next door for some of the best snorkeling we had ever experienced. The Kittiwake Shipwreck is directly off shore for another fantastic snorkeling experience. We even enjoyed swimming with our own resident sea turtle every day! The condo unit itself was spacious and fully equipped with everything you need - beach towels, chairs, umbrella, rafts and cooler;fully-equipped, gorgeous kitchen with granite counter tops, beautiful and spacious bathrooms, and super-comfortable beds. Although our "kids" were 15, the unit would be wonderful for families with smaller children as well. I must say, the absolute best part, however, was our gracious host Morne, who made us feel like pampered family members visiting from out of town. He picked us up from the airport, made sure we had everything we needed, made great recommendations for activities and restaurants, was never intrusive but always available for anything we needed. I would (and will) vacation here again in a heartbeat, and make the highest recommendation to anyone to enjoy the vacation of a lifetime at this property! Just please don't take the week I want! ;)

Responds fast! avg. 3 hours 32 minutes

Match: Swimming pool

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Price per night from

$2,270

Cayman Reef Resort #50 - Best Value on the Beach

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Excellent Long Term Stay” Unit 50 was very suitable for my wife and me for a four week visit. We thought the overall experience was excellent and it provided excellent value for our money. We would definitely recommend Unit 50 and we plan to return. Don't expect luxury, but do expect comfort, convenience and a relaxing place to stay. The owner, Marc, is very well organized, responsive, a good communicator and a pleasure to deal with. There were no surprises. Marc's information packages were clear with all the information we needed for our stay in the condo plus he provided helpful information about the island. The resort is clean and well maintained with a good pool, on a non-crowded section of the beach with plenty of beach chairs for all. The resort staff were very helpful. The resort is very well located on Seven Mile beach within easy walking distance to restaurants, grocery stores and Camana Bay shopping. If loaded down with groceries, we took a taxi back. We did not need a car, although we rented one for a couple of days to explore the island farther afield, which I would recommend. If you dive, the resort is an easy walk along the beach to the Red Sail Sports locations at the Grand Cayman Beach Suites (GCBS) or the Marriott. If you own and don't rent, you can store your gear in lockers at GCBS so there is no need to lug it back and forth. The apartment is spacious and is comfortably furnished. We cooked and ate four to five dinners/lunches per week in the condo and ate at restaurants the other times. The electric barbeque works well but takes longer to heat up and to cook than a gas one, so we had to learn to plan accordingly. We took advantage of the option to have the apartment cleaned half-way through our stay. Our unit was at the back of the property overlooking the pool with a view of the sea in the distance. It was generally quiet, although there is construction on the adjacent property to the south and we could hear the backhoe from the pool area. Sometimes the Royal Palms Beach Club, three units north, plays music loudly when the cruise ship passengers are in or there is a special event. This is a benefit or a curse depending on your point of view. In summary, we found Unit 50 to be a good place to stay and we recommend it to others.

Match: Swimming pool

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Price per night from

$505

Cayman Reef Resort #32 - Steps away from the Beach

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$667

Cayman Reef Resort #1 - Renovated Seven Mile Beach

Seven Mile Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Excellent 1BR on SMB” My wife and I just spent six night in this great one bedroom condo on SMB. It was our first stay in the Caymans. The unit was exactly as advertised. Ample towels were provided, including beach towels. The unit has a full kitchen, with every appliance that you could ever want. The screened in patio, which was great for dinners, also has a nice electronic grill that I used to cook a beautiful red snapper that I purchased from a local fisherman in downtown George Town. The bed was comfortable, the bathroom large, the hot water VERY hot and plentiful, and the AC worked very well. The unit is reasonably stylish, with several nice finishes throughout. The condo building has a mix of vacationers and residents. The pool isn't huge, but more than adequate if you want to take a quick dip. There is a tennis court in very good condition in front of the building. The private beach has several recliners and umbrellas. We never had to fight anyone for use of these, but that may be different during peak travel times. The location of the unit was IDEAL. The resort is on the beach, which is obviously a big plus. Additionally, there are TONS of great food options within a quick 5 minute walking radius. To quickly name a few, Chicken Chicken, Al La Kebab, and several restaurants at Camana Bay were all excellent. We rented a car, which we found useful to get to the grocery store several times. In hindsight, could we have done this by taking cabs or buses? Yes. But we liked the flexibility. The owners provided us with ample suggestions and guides to help make our first stay on island more pleasant. Marc was very responsive to emails and was on top of everything. All in all, the unit worked out great. We didn't spend a whole lot of time there, as we were out every day diving. But the time that we did spend there was very pleasant. We would certainly consider renting this unit again.

Match: Swimming pool

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Price per night from

$555

Responds fast! avg. 3 hours 12 minutes

Match: Swimming pool

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Price per night from

$1,121

Northern Lights #5: 2-Story Beachfront Oasis in North Side w/Pool, Dock

Old Man Bay condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 12 minutes

Match: Swimming pool

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Price per night from

$331

Cayman Islands Kaibo Yacht Club Condo - Rum Point

Rum Point condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$443

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