Find Vacation Homes in Cayman Islands from $399

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Top Cities in Cayman Islands

Compare 254 Vacation Homes in Cayman Islands with updated reviews, rates, and availability.

Coco Kai Beach Front Villa with Heated Pool and Private Dock
10.0 out of 10, Exceptional, 76 reviews
"Nothing can beat the beautiful ocean views right outside your back door. We enjoyed this property with our 5 kids and 3 grandchildren (ages 1-3). Everyone had the option of going from the beach to the pool, to the kitchen for snacks, to the bed for naps all right there. The house is well equipped with most everything you need. We snorkeled around the north side and decided the snorkeling right out back was some of the best! This gave those antsy people something to do and what beautiful marine...
Coco Kai Beach Front Villa with Heated Pool and Private Dock
The peace and tranquility of this cottage Works Wonders on the soul....
10.0 out of 10, Exceptional, 48 reviews
"We thoroughly enjoyed our stay. The property is well located and affords privacy will still be close to various attractions. The pool and beach were wonderful, and we enjoyed kayaking and paddle boarding. Would definitely stay again!"
The peace and tranquility of this cottage Works Wonders on the soul....
SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point
9.8 out of 10, Exceptional, 47 reviews
"My husband and I and 7 friends stayed here for our 30th wedding anniversary. We love the quieter side near Rum Point and this house did not disappoint! The layout was incredible with an amazing beach at our fingertips. The pool and outside seating was perfect!!! The table with the automatic lazy Susan was a huge plus. The house was clean and so open and bright. We had the most amazing time and would recommend this property to anyone. This property and the beach made our vacation!"
SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point
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Caymanian Style Home w/ Pool, Pickle Ball Court, Optional Private Bar,
9.8 out of 10, Exceptional, 34 reviews
"The house and grounds are very clean and well maintained. The kitchen is well stocked and having the extra kitchen downstairs was wonderful. We really enjoyed every minute"
Caymanian Style Home w/ Pool, Pickle Ball Court, Optional Private Bar,
Ocean Paradise
4.0 star property
9.6 out of 10, Exceptional, 37 reviews
"This is a super cute little group of homes with a pool on the water. Here are the things you won't know from the advertisement although you're on the water you can't swim it's covered in rocks and coral. Bring aquasocks if you plan on trying to go out on the water. The furniture in unit two in the living room needs to be replaced you sit on the couch or love seat and you sink in. Beds and pillow are very good. Ac is good. Dishwasher needs updating. If you dont know grand cayman this is a 40...
Ocean Paradise
Beach Front Paradise Home. Luxurious Funishings!
10.0 out of 10, Exceptional, 52 reviews
"Lovely home with gorgeous sunsets. Oceanside pool was awesome to cool off in afternoon after a day of exploring. Restaurants near by on this small island. Our two favs were Captains Table and Star Island. Came to island to scuba and chill. After the sun set the porch was great to star gaze and enjoy a glass of wine. Entry into the water was a bit rocky, we didn’t use the kayaks. On site washer and dryer was a welcome amenity. Communication with property manger using WhatsApp was excellent."
Beach Front Paradise Home. Luxurious Funishings!
Fun Family Home! *Private pool, Walk to the Beach *
10.0 out of 10, Exceptional, 21 reviews
"We rented this property with 2 families (6 people) with kids ranging from 8-12 for a week. We rented a car to get around which is a must for this property. Close to 7 mile beach but far enough away from the crowd. There was more than enough space for everyone to come together to watch tv, hang out at the pool, and cook in the kitchen. When we wanted to wind down after being out and about, we could retreat back to our own rooms while the kids played on the xbox, watched tv in their own rooms,...
Fun Family Home! *Private pool, Walk to the Beach *
Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!
9.4 out of 10, Exceptional, 18 reviews
"This house was just as stated. We had 10 people and everything was amazing. We all enjoyed the pool, beach, and large living areas. The bedrooms were ideal for 5 couples. We will definitely plan to stay again."
Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point
9.8 out of 10, Exceptional, 151 reviews
"We had an incredible week! House, pool, beach and ocean are exactly as pictured - beautiful. The house is well supplied with everything we needed: snorkeling gear, pool floats, beach towels, plenty of dinnerware and kitchen supplies. We enjoyed the non-touristy Northside area and it was easy to explore the whole island from there. The surf is natural with short seagrass with bare sand areas interspersed. We took the kayaks out to the reef area for snorkeling and were amazed with all the wildlife...
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point
Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point
10.0 out of 10, Exceptional, 26 reviews
"We were very impressed with the home and location. The kayaks and snorkeling gear were a nice bonus. We would definately stay again!!"
Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point
Blue Vista Villa - Oceanfront 4 Bedroom Pool Home on Northside
9.4 out of 10, Exceptional, 15 reviews
"Our stay here was just what we needed. It was perfect for 2 families to unwind, spread out and enjoy the sound of the waves. We loved the quiet location. Just minutes from everything we wanted to do involving kids, ages 9-16. So close to go diving and the snorkeling was superb. Highly recommended if you like to stay away from tourist traps. Thank you so much!"
Blue Vista Villa - Oceanfront 4 Bedroom Pool Home on Northside
PROMO: Waterfront Villa on Private Beach at Rum Point, 3 Free Kayaks, 4 bikes
9.8 out of 10, Exceptional, 57 reviews
"My friends and I stayed at the Barefoot Lagoon this past week and couldnt have asked for a better place to be in Grand Cayman. It was so much quieter than George Town and we loved every minute. The Bio Bay in the backyard was a highlight! It felt like a once in a lifetime experience. Rum Point was a 30 second walk and made for some nice relaxing evenings for drinks, dinner, and a sunset. Starfish Point and Kaibo were super close too. It was so nice having the three bathrooms, and we all spent a...
PROMO: Waterfront Villa on Private Beach at Rum Point, 3 Free Kayaks, 4 bikes
Sea Orchard Retreat: Gated Micro-Resort Near Seven Mile Beach w/Private Pool & Heated Spa
9.8 out of 10, Exceptional, 12 reviews
"We booked this property for a family reunion and we were all blown away. Coming from Canada, we knew we had booked something special, but the location, the units, the grounds and the staff were all above and beyond our expectstions! We all fell in love with Cayman because of our special stay. I would not hestitate to book The Sea Orchard Retreat again in the future!"
Sea Orchard Retreat: Gated Micro-Resort Near Seven Mile Beach w/Private Pool & Heated Spa
Parrot-ise 4 Bedroom Oceanfront Villa in Cayman Kai
10.0 out of 10, Exceptional, 43 reviews
"Loved the location- away from the busy areas and get easily accessible to everything."
Parrot-ise 4 Bedroom Oceanfront Villa in Cayman Kai
Luxury 3bd Beach Front, # 5 Yellow, Stunning Views
10.0 out of 10, Exceptional, 57 reviews
"Loved the house. 3 comfortable bedrooms with queen or king beds and 3 bathrooms plus a 4th room for kids. Our family of 8 was very comfortable. Pool area was great and we unexpectedly enjoyed some swimming and snorkeling on the beach out front, Chisholm's grocery a few miles down the road had all the essentials and we enjoyed dinners at Kaibo’s, Tukkas East End, and especially La Casita (brunch burrito was delicious). Especially enjoyed hanging out at Rum Point Club’s lovely beach (public is...
The price is $399
$909 total
includes taxes & fees
Jun 27 - Jun 28
Luxury 3bd Beach Front, # 5 Yellow, Stunning Views
Neptune's Nest by the Sea, East End
10.0 out of 10, Exceptional, 12 reviews
"A wonderful villa with everything you could need. Lots of water toys, pool towels, kitchen appliances and cookware, spices etc. The pools are great and Trish is a wonderful hostess, even taking time to teach our girls a domino train game which is a new family favorite! Trish shared lots of great information about grocery options prior to our arrival as these are limited as you get out to the East End. Within walking distance of Ocean Frontiers dive shop and Eagle Rays, as well as Eastern Star...
Neptune's Nest by the Sea, East End
Pools of the Kai 3 - Beautiful Island House with Indoor Pool
9.8 out of 10, Exceptional, 8 reviews
"The property was amazing! It was well laid out and so gorgeous. We had a great time."
Pools of the Kai 3 - Beautiful Island House with Indoor Pool
Ritz-Carlton Deckhouse #1: Seven Mile Beach Villa w/Pool, Boathouse, + Resort Privileges
8.0 out of 10, Very Good, 1 review
"Property is well furnished and quite comfortable for large groups with all the necessary amenities. Great views and close to tennis/pickleball courts. It is located some distance from resort and the golf cart commute (5 minutes) is not the most scenic. Just wish the pool would have been heated as it was too cold to utilize."
Ritz-Carlton Deckhouse #1: Seven Mile Beach Villa w/Pool, Boathouse, + Resort Privileges
White Dahlia: Modern Villa on Bio Bay w/ Pool, Spa + Kiddie Splash Pool.
10.0 out of 10, Exceptional, 4 reviews
"This was a perfect house for small, multi-gen family with young child. Very clean, neat, with recent updated everything. Great big pool, kiddie pool and hot-tub. Everyone loved it. Nice, well tended area on Rum point, walk to beaches. The dock made boating convenient and easy. Definitely get the kayaks to paddle around, especially at night on the luminescent waters!"
White Dahlia: Modern Villa on Bio Bay w/ Pool, Spa + Kiddie Splash Pool.
Bit of Heaven: Perfect Beachfront Home w/Free Kayaks!
10.0 out of 10, Exceptional, 1 review
"This place was wonderful. Location was pretty far from the hustle and bustle of the city and 7 mile beach, it was PERFECT for quiet and peaceful get-a-way. The beach was perfect for the small children in the family with NO waves and undertow. Safe, beautiful place. Loved the place!!"
Bit of Heaven: Perfect Beachfront Home w/Free Kayaks!
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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.

Booking Tips to Find the Best Cayman Islands Vacation Homes


How much does it cost to rent a vacation home in Cayman Islands?

You can find incredible Cayman Islands vacation homes for all types of budgets: between $399 and $399 per night. The more amenities the rental has, and its proximity to popular places, the higher the price.


What is the best time to stay in a vacation home in Cayman Islands?

If you are looking for a great deal on your vacation home in Cayman Islands, consider visiting in , when prices are usually cheaper.


How many vacation homes are available for rent in Cayman Islands?

There are 254 rental houses to choose from for your trip. You’ll find holiday homes located throughout the city, near sightseeing spots, and close to local nature areas.


How do I find the best deal for a vacation home in Cayman Islands?

Begin by entering your trip dates to see what type of Cayman Islands rental houses are available. Use the map to zoom closer into the areas or zoom out to include more locations. Use the filters on the left side of your search results to narrow down by star rating, price, number of bedrooms, amenities, and more—Expedia makes it easy to score the best deal for your budget.


Why should I rent a vacation home in Cayman Islands?

Booking Cayman Islands vacation home rentals is the perfect way to spend a vacation because of the privacy, variety of amenities, and comfort you’ll have in your own space.


What amenities are available in a private vacation home?

When thinking about what you want in your Cayman Islands rental house, dream big! Depending on your budget and the area, you’ll find amenities like a private pool, hot tub, free parking, fully-equipped kitchen, in-home washer and dryer, Wi-Fi, and a beautiful view or easy access to local sightseeing spots. You can even filter your search results by accessibility to ensure that everyone in your party will be comfortable.


Why should I book a vacation home with Expedia?

Expedia has some of the best selection and deals on available vacation homes in the area—and all in one place. We reward you with members points back on every booking and ensure you get the right accommodation for the best price. And you’ll save big when you bundle your travel together, like booking a car rental in Cayman Islands along with your vacation property, into a Cayman Islands vacation package.


Can I cancel my vacation home with Expedia?

Some accommodations are free to cancel and refundable if done so by a specific date, while others may be non-refundable. To make sure that you can get your money back on cancellations, use the “free cancellation” filter during your search. Contact our customer service portal if you need help.

Cayman Islands Vacation Homes information

Number of reviews
589
Accommodation
254 Vacation Homes
Lowest Price
$399
Highest Price
$399

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