Photo by Cayman Islands Department of Tourism

Holiday Homes in Cayman Islands

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec
In one month
26 Dec - 28 Dec
In two months
23 Jan - 25 Jan

Top Cities in Cayman Islands

Holiday HomesHoliday Homes

Seven Mile Beach

Seven Mile Beach
Holiday HomesHoliday Homes

West Bay

West Bay

Featured Holiday Homes in Cayman Islands

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

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

2.0 star property
North Side
10.0 out of 10, Exceptional, (25)
"Home is as beautiful as the photos. Karen was great to work with; very quick to respond and resolve any small issues that came up.Truely a very relaxing vacation, with the Ocean right out the back door.Thank you Karen, for making our Cayman Island vacation a flawless one. We hope to return."
United States
Tom M.
Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!
Property grounds
So Serene Oceanfront Villa, Rum Point, Private Beach, Hot Tub, Kayak, Snorkeling

So Serene Oceanfront Villa, Rum Point, Private Beach, Hot Tub, Kayak, Snorkeling

Grand Cayman
9.8 out of 10, Exceptional, (19)
"We had a fantastic time at this gorgeous, peaceful property. Highly, highly recommend!"
United States
Amy W.
So Serene Oceanfront Villa, Rum Point, Private Beach, Hot Tub, Kayak, Snorkeling
Pool
Escape,Enjoy,Unwind to Kailegría, 2BR,2BA condo in Cayman Kai’s Kaibo Yacht Club

Escape,Enjoy,Unwind to Kailegría, 2BR,2BA condo in Cayman Kai’s Kaibo Yacht Club

Rum Point
Escape,Enjoy,Unwind to Kailegría, 2BR,2BA condo in Cayman Kai’s Kaibo Yacht Club
Outdoor pool, pool loungers
Ocean Paradise

Ocean Paradise

4.0 star property
North Side
9.6 out of 10, Exceptional, (38)
"Wonderful property! We enjoyed our stay very much! "
United States
Ashley
Ocean Paradise
Indoor pool, outdoor pool
CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana

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

North Side
10.0 out of 10, Exceptional, (52)
"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!"
United States
michael d.
CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana
On the beach, sun-loungers, beach towels
BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

Northside
10.0 out of 10, Exceptional, (74)
"Wonderful family vacation! The house and location were beautiful. We really enjoyed the pool and swimming and kayaking in the ocean right out the back door. The gazebo at the end of the dock was a great place to relax!"
United States
Melissa D.
BEACHFRONT w/ Private Dock-50 ft Pool-Theatre
Property grounds
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point

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

Rum Point
9.8 out of 10, Exceptional, (175)
"Perfect place to celebrate our kids graduating high school and heading off to college! Would definitely stay at the pink house again! Lounging in the hammock was the perfect start to our day!!"
United States
marie d.
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point
On the beach, sun-loungers, beach towels
Private oceanfront home with wrap-around screened porch. Unique Caymanian house.

Private oceanfront home with wrap-around screened porch. Unique Caymanian house.

North Side
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."
United States
Jean and Glenn P.
Private oceanfront home with wrap-around screened porch. Unique Caymanian house.
Property grounds
Slice of Paradise- 2 mins from Spotts Beach!

Slice of Paradise- 2 mins from Spotts Beach!

Patricks Island
8.2 out of 10, Very good, (20)
"Excellent stay. Very peaceful and easy instructions "
Canada
raymond
Slice of Paradise- 2 mins from Spotts Beach!
Pool
KAIBOSH 9 to 5 Waterfront Condo at Rum Point

KAIBOSH 9 to 5 Waterfront Condo at Rum Point

Rum Point
9.8 out of 10, Exceptional, (71)
"Great location on Bio Bay, across the street from Rum Point. Easy bike ride to Starfish Bay, and Kaibo restaurant. Clean, well equipped, comfortable beds. Great access to pool and kayaks for the bay."
United States
Sara B.
KAIBOSH 9 to 5 Waterfront Condo at Rum Point
Sun-loungers, beach towels
Country Road, Take me Home- your own Island Cottage!

Country Road, Take me Home- your own Island Cottage!

2.0 star property
Savannah
9.0 out of 10, Wonderful, (8)
"Excellent host excellent home"
United States
Nathan
The price is AU$281
includes taxes & fees
2 Dec - 3 Dec
Country Road, Take me Home- your own Island Cottage!
Property grounds
Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!

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

Cayman Islands
9.6 out of 10, Exceptional, (44)
"We really enjoyed our stay at the Romantic Reef! The house was perfect to host our friends. The pool area/beach really made the trip! "
United States
Gina T.
Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!
Beach nearby, beach towels
Caymanian Style Home w/ Pool, Pickle Ball Court, Optional Private Bar

Caymanian Style Home w/ Pool, Pickle Ball Court, Optional Private Bar

Rumpoint
9.8 out of 10, Exceptional, (53)
"We had a great time at Seaside. It worked out very well for our family and Grand Cayman did not disappoint. "
United States
Anonymous traveller
Caymanian Style Home w/ Pool, Pickle Ball Court, Optional Private Bar
On the beach, sun-loungers, beach towels
Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point

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

Grand Cayman
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."
United States
Jamie W.
Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point
Pool
Cayman Beach House - New Swimming Pool !

Cayman Beach House - New Swimming Pool !

East End
9.6 out of 10, Exceptional, (30)
"We loved staying at this house in the Cayman Islands. The property manager was also very kind and responsive."
United States
Jaimeson E.
Cayman Beach House - New Swimming Pool !
Pool
Relax Enjoy and Play

Relax Enjoy and Play

George Town
9.6 out of 10, Exceptional, (18)
"We stayed nine days and discovered the island from this extremely clean and well-appointed apartment with pleasant interior and covered terrace with BBQ. Good AC and ceiling fans securing nice indoor ambiance. "
Austria
Jens Nicolai P.
Relax Enjoy and Play
Beach nearby
Quiet, private nature retreat with pool and ocean views.

Quiet, private nature retreat with pool and ocean views.

Old Man Bay
10.0 out of 10, Exceptional, (8)
"Spacious and well stocked house in a beautiful quiet area. Very comfortable for a party of 5.Great location off the beaten path. Thank you to our hosts for great communication and adaptability. "
United States
Maria V.
Quiet, private nature retreat with pool and ocean views.
Property grounds
Beach Cottage w/ Kayaks, Snorkeling & A/C Glass Living Room by the Ocean!

Beach Cottage w/ Kayaks, Snorkeling & A/C Glass Living Room by the Ocean!

Grand Cayman
10.0 out of 10, Exceptional, (1)
"Piece of Mine is simply an island paradise. From the moment we arrived at the property we were met by Tia who was amazing. She showed us everything about the house and the property. Tia's knowledge of the property and the island was tremendous. Tia and Harriet truly make you feel like home. The house and the beachfront property are first class and they have thought of every detail. Harriet's fruit cake was a great touch too and so delicious. The house was super clean, and the bed was uber...
United States
christopher u.
Beach Cottage w/ Kayaks, Snorkeling & A/C Glass Living Room by the Ocean!
Outdoor pool
Serene 3 Bedroom Home with Saltwater Pool & Gardens

Serene 3 Bedroom Home with Saltwater Pool & Gardens

Savannnah
10.0 out of 10, Exceptional, (10)
"We enjoyed the house and the island. Would definitely recommend this property. "
United States
Alexis O.
Serene 3 Bedroom Home with Saltwater Pool & Gardens
Outdoor pool
Minutes From 7 Mile Beach

Minutes From 7 Mile Beach

West Bay
9.8 out of 10, Exceptional, (13)
"The apartment is full of small details that made the whole stay a joy!"
United States
Norman C.
Minutes From 7 Mile Beach
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.
View all properties

Black Friday Sale

Save up to 40% on select hotels
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cayman Islands Hotel Reviews

Wyndham Reef Resort - All Inclusive

Wyndham Reef Resort - All Inclusive

10/10 Excellent
"the room and all the staff were beyond great."
Teresa 4-night trip
Posted 8 hours ago
Wyndham Reef Resort - All Inclusive

Find out more about Cayman Islands

Cayman Islands Holiday Homes information

Number of reviews
651
Accommodation
264 Holiday Homes
Lowest Price
AU$281
Highest Price
AU$281

Explore a world of travel with Expedia