Vacation Homes in Cayman Islands

Compare and save

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Top Cities in Cayman Islands

Vacation Homes in Cayman Islands

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

10.0 out of 10, Exceptional, (66)
"We had a great time! The property and location were wonderful! The property manager was very helpful with setting up excursions. We loved everything about this trip and can’t wait to be back!"
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, (1)
"Beautiful home and in a great location. We enjoyed the pool and could still walk out to the sea for a swim! Kitchen was well stocked. Beds and linens were fantastic. We will be back! Thank you for an amazing stay."
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)
"great location, great view, spacious rooms!"
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, (73)
"This was the perfect property for a large group or family. Beautiful views, every amenity you could ask for and a beautiful home! The northside is very laid-back and quiet with lots of great options around for eating out. Nothing is more than 45 minutes away if you want to go into town to shop or visit seven Mile Beach or any of the other touristy areas. Definitely going to book this one again!"
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)
"Place was exactly what we needed for a relaxing vacation!"
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, (174)
"We just LOVED the Pink House! It was a beautiful, secluded beach and the house had everything we needed! The host was wonderful and responsive! The snorkeling right outside the house was perfect and they had so much equipment! Great A/C, hot water, kitchen stuff too cook with, just perfect !!! We had a wonderful time!"
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, (47)
"The home was exactly as advertised, we couldn't have asked for better accommodations, the property was stunning. We all enjoyed our stay and look forward to going back "
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 house is very clean and well appointed. We really enjoyed our visit. The beach is perfect and the area is wonderful for a family vacation."
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: Luxe Villa w/ Designer Pool, Private Beach & Rooftop Lounge w/ Panoramic Views

10.0 out of 10, Exceptional, (7)
"Beautiful home and wonderful location!"
Olympus: Luxe Villa w/ Designer Pool, Private Beach & Rooftop Lounge w/ Panoramic Views

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

10.0 out of 10, Exceptional, (91)
"Superb view, very nice house everything you need to rest."
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Cayman Islands Hotel Reviews