Find Vacation Homes in Cayman Islands

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Vacation Homes in Cayman Islands

The peace and tranquility of this cottage Works Wonders on the soul....

10.0 out of 10, Exceptional, (66)
"Great location away from Hustle and Bustle of Georgetown. The amenities were great and the house is beautiful! It really Worked Wonders on our souls! "
The peace and tranquility of this cottage Works Wonders on the soul....

Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.

10.0 out of 10, Exceptional, (2)
"The Pool was large and the pool deck was gigantic! The inside of the house is absolutely gorgeous with tons of amenities, kitchen aid, blenders, espresso maker, everything you could think of for serving many people. The private beach was absolutely serene! The family can't wait to go back! Bikes, kayaks, snorkeling heard float toys, I could go on and on! Waking up in the large master looking over the deck at the glowing blue water every morning was certainly a highlight. PS5 for the kids on...
Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.

Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!

9.6 out of 10, Exceptional, (41)
"We were here for a family wedding. We had a very nice time. Everything was as "
Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!

BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

10.0 out of 10, Exceptional, (74)
"This was one of our best vacations yet. I have been gifting my family with a surprise family vacation for christmas for 10 years instead of stuff.The house was great. It was well stocked, we needed nothing. Location? Perfect. The kids loved the pool and the kayaks and the fire pit where we did the s'mores that were in a basket for us upon arrival. Management was one of the best we have dealt with. We will be back for sure. "
BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

Coco Kai Beach Front Villa with Heated Pool and Private Dock

10.0 out of 10, Exceptional, (90)
"Excellent place for extended family gathering. The house is spacious, well equipped, and really had no limitations in how to enjoy a beachside vacation. The manager was super-responsive to requests/questions. We had a great time there!"
Coco Kai Beach Front Villa with Heated Pool and Private Dock

The Pink Beach House - Private House and Pool directly on the Beach, Rum Point

9.8 out of 10, Exceptional, (175)
"Such a great home to stay at. Location is very convenient to Rum Point, Kaibo and Starfish point. Home is equipped for cooking any meal you want. The hammock out back is a crowd pleaser. Just amazing!"
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point

Relax at Coconut Bay!

10.0 out of 10, Exceptional, (30)
"We loved our condo unit in coconut bay. Really nice propery and pool. Had a nice snorkel out fromt when the waves calmed down. "
Relax at Coconut Bay!

SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point

9.8 out of 10, Exceptional, (72)
"It was everything we had hoped it would be and more! House was clean and spacious. Perfect for a family of 8 Great snorkeling off the beach. Minutes from Rum Point "
SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point

Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!

2.0 star property
10.0 out of 10, Exceptional, (24)
"The property was wonderful. Beautiful location and all as described! We look forward to returning. Snorkeling was amazing just off property and we often felt we had the beach to ourselves. "
Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!

FREE Night in 2025! Private, quiet oceanfront home, wrap-around screened porch.

10.0 out of 10, Exceptional, (28)
"My husband and I along with our two adult children stayed at this property for 7 nights. Our trip was centered around scuba diving. We like to stay on the North side for the quiet and access to diving. This place is perfect for that, but it’s also so comfortable and well-maintained. We really felt like we ere alone in our own little paradise."
FREE Night in 2025! Private, quiet oceanfront home, wrap-around screened porch.

Nautilus Two – A Beachfront Condo on Seven Mile Beach - by Cayman Villas

9.6 out of 10, Exceptional, (38)
"We had the best, most relaxing time in the Grand Cayman! The property was beautiful, clean, and in the best location. We will definitely be back!!"
Nautilus Two – A Beachfront Condo on Seven Mile Beach - by Cayman Villas

Beach Front Paradise Home. Luxurious Funishings!

10.0 out of 10, Exceptional, (64)
"We thoroughly enjoyed our 2 week stay at Paradise Found. The home was well equipped, clean and very comfortable. The screened in porch was a plus. We have vacationed on Cayman Brac many times and Paradise Found is now one of our favorites."
Beach Front Paradise Home. Luxurious Funishings!

CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana

10.0 out of 10, Exceptional, (49)
"We have stayed in houses all around the world, and Coral Vista is the best house ever! The pool was tremendous, as was the arcade and movie room. The beds were comfortable, and the owner thought of everything, including air freshener in the bathrooms. Everything was perfect!"
CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana

Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point

10.0 out of 10, Exceptional, (47)
"This property was even more beautiful than the pictures. The beach area was quiet and serene, and we loved taking the kayaks out every morning. The property comes with everything you need, including snorkel gear, bikes, and various beach floats. The home itself is beautifully decorated and welcoming. We’re looking forward to coming back soon."
Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point

Kai Baby Waterfront Cottage Private Pool Cabana Kayaks Paddleboards & Bikes!

10.0 out of 10, Exceptional, (39)
"This was an easy and relaxing stay. Communication was excellent with the owners. The home had all we needed and more! "
Kai Baby Waterfront Cottage Private Pool Cabana Kayaks Paddleboards & Bikes!

THE YELLOW HOUSE OF SEACLIFF RESORT HOMES

9.8 out of 10, Exceptional, (41)
"We loved staying at the Yellow House. It is away from the hustle and bustle of the "tourist area" which we found to be perfect for us. Heritage Beach is rght across the street and made for beautiful sunsets. We would love to visit again! "
THE YELLOW HOUSE OF SEACLIFF RESORT HOMES

Neptune's Nest by the Sea, East End

10.0 out of 10, Exceptional, (20)
"This home was perfect for the 5 of us. It's a very nice quiet area. Plenty of space and had everything we needed. The pools outside were great to relax amd cool off. The owner Trish was very helpful with information on where to shop, places to eat, and things to do. Very responsive with any questions we had. She keeps the home stocked with so many supplies that were very helpful. We would definitely stay here again!"
Neptune's Nest by the Sea, East End

Olympus Villa by Grand Cayman Villas

10.0 out of 10, Exceptional, (7)
"Beautiful home and wonderful location!"
Olympus Villa by Grand Cayman Villas

Villa Esprit – Stunning 3 Bedroom Beachfront Villa in North Side with pool!

10.0 out of 10, Exceptional, (91)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Beautiful home with stunning views!! Perfect location for relaxing!"
Villa Esprit – Stunning 3 Bedroom Beachfront Villa in North Side with pool!

Oceanfront Oasis Home with cottage & pool

Oceanfront Oasis Home with cottage & pool
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 Cayman Islands Hotel Reviews

Find out more about Cayman Islands

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 and 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 269 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

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269 Vacation Homes
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