Holiday Homes in Cayman Islands

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Featured Holiday Homes in Cayman Islands

Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point
Beach | On the beach, sun-loungers, beach towels
Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point
10.0 out of 10, Exceptional, (25)
"We love the area...close to Rum Point and Kaibo Beach. We have stayed in this unit twice now and it is always immaculate with all of the necessities of home. Checking in and out very easy, with the agent easily and always accessible. We highly recommend this unit."
Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point
Coco Kai Beach Front Villa with Heated Pool and Private Dock
A heated pool
Coco Kai Beach Front Villa with Heated Pool and Private Dock
10.0 out of 10, Exceptional, (76)
"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...
The price is £1,098
per night
4 May - 5 May
Coco Kai Beach Front Villa with Heated Pool and Private Dock
Nautilus One – A Beachfront Condo on Seven Mile Beach
On the beach
Nautilus One – A Beachfront Condo on Seven Mile Beach
10.0 out of 10, Exceptional, (28)
"It was just as pictured or even better. The deck was so well landscaped and shaded with palm and almond trees, beautiful spot to sit in between snorkeling sessions. The most popular reef is directly out back door, no tour guide boat needed. Great beach house, wonderful property manager. Will be back!"
Nautilus One – A Beachfront Condo on Seven Mile Beach
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Carolina Kai - NEWLY BUILT luxury villa, private beach in Rum Point / Cayman Kai
Outdoor pool, a heated pool, pool loungers
Carolina Kai - NEWLY BUILT luxury villa, private beach in Rum Point / Cayman Kai
10.0 out of 10, Exceptional, (18)
"Our group had a great time at Carolina Kai. The space is wonderful with everything you need to enjoy your stay at the property!"
Carolina Kai - NEWLY BUILT luxury villa, private beach in Rum Point / Cayman Kai
Crystal Waters: Luxe Villa w/Private Pool, Dock and Barefoot Beach Lounge - Walk to The Kaibo!
Terrace/patio
Crystal Waters: Luxe Villa w/Private Pool, Dock and Barefoot Beach Lounge - Walk to The Kaibo!
10.0 out of 10, Exceptional, (11)
"Beautiful beach location and comfortable for our group. Lots of starfish on the beach and even some lionfish under the dock! The sunsets were amazing and we were withing walking distance to Kaibo and a short drive to Rum Point! 10/10"
Crystal Waters: Luxe Villa w/Private Pool, Dock and Barefoot Beach Lounge - Walk to The Kaibo!
Beach Front Paradise Home. Luxurious Funishings!
Pool
Beach Front Paradise Home. Luxurious Funishings!
10.0 out of 10, Exceptional, (51)
"We've been to several islands in the Caribbean, but keep coming back to Cayman Brac. As busy Americans always with a to do list that's longer than we can complete, we like coming to a place where there's not much to do and it forces us to relax. No beaches means no crowds, there's no traffic, the snorkeling is great (including right from the house, once we found a path free of urchins), and the pool and shaded screened porch make lounging all day so comfortable. LaRonda's place was everything we...
Beach Front Paradise Home. Luxurious Funishings!
Villa Esprit – 3 Bedroom Beachfront Villa in North Side
Property grounds
Villa Esprit – 3 Bedroom Beachfront Villa in North Side
10.0 out of 10, Exceptional, (73)
"My husband and I loved our stay at Villa Esprit. It was very relaxing and had amazing views. The house was just as it looked in the photos. We absolutly loved our stay. Pros: Private location Great kitchen with everything you need Sunrise in the morning was beautiful Morning coffee and views from the living room/dining room, kitchen, bedroom just perfect Cons: Far drive from most attractions - good dining, seven mile beach, shopping etc is about 45-55 min drive Beach by the house - this...
Villa Esprit – 3 Bedroom Beachfront Villa in North Side
Pool, 5 bdrm, sandy beach, sunsets, quiet, cabana w/hammocks, bikes, well kept
On the beach
Pool, 5 bdrm, sandy beach, sunsets, quiet, cabana w/hammocks, bikes, well kept
10.0 out of 10, Exceptional, (72)
"We rented all 3 units & worked well for the whole family"
Pool, 5 bdrm, sandy beach, sunsets, quiet, cabana w/hammocks, bikes, well kept
Villa Olea - Grand Harbour
Interior
Villa Olea - Grand Harbour
10.0 out of 10, Exceptional, (1)
"Lovely property and owner, fantastic stay thank you. Great communication. Great area close to shops and restaurants. Wonderful pool, waterside location."
The price is £1,116
per night
3 May - 4 May
Villa Olea - Grand Harbour
White Dahlia: Modern Villa on Bio Bay w/ Pool, Spa + Kiddie Splash Pool.
Outdoor pool
White Dahlia: Modern Villa on Bio Bay w/ Pool, Spa + Kiddie Splash Pool.
10.0 out of 10, Exceptional, (4)
"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!
Property grounds
Bit of Heaven: Perfect Beachfront Home w/Free Kayaks!
10.0 out of 10, Exceptional, (1)
"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!
Faroway Oceanfront Luxury Villa in South Sound
On the beach
Faroway Oceanfront Luxury Villa in South Sound
10.0 out of 10, Exceptional, (13)
"Love staying at this house. Wish I could buy it."
Faroway Oceanfront Luxury Villa in South Sound
Ultimate Comfort: Newly Renovated Townhouse on Seven Mile Beach!
Pool
Ultimate Comfort: Newly Renovated Townhouse on Seven Mile Beach!
10.0 out of 10, Exceptional, (1)
"This place has it all - great layout, beautifully remodeled, 2 minute walk from beach and local food options, and perfect for our group of 6 (including our 2 small children, under three years old). While the place itself was worth it all, the gracious host team was a "cherry on top". They went above and beyond to make us comfortable during our stay. If you're traveling with a small group of folks, or even just a couple trying to get away for a bit - I couldn't be happier to recommend this place...
Ultimate Comfort: Newly Renovated Townhouse on Seven Mile Beach!
The peace and tranquility of this cottage Works Wonders on the soul....
Property grounds
The peace and tranquility of this cottage Works Wonders on the soul....
10.0 out of 10, Exceptional, (48)
"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....
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point
Pool
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point
9.8 out of 10, Exceptional, (150)
"Everything was clean, linens were soft and comfortable, there were kayaks and snorkel equipment aplenty ~ The pool was fantastic and the beach was perfect. Loved all aspects and will definitely return!"
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point
Sea Orchard Retreat: Gated Micro-Resort Near Seven Mile Beach w/Private Pool & Heated Spa
Property grounds
Sea Orchard Retreat: Gated Micro-Resort Near Seven Mile Beach w/Private Pool & Heated Spa
9.8 out of 10, Exceptional, (12)
"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
SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point
Pool | Outdoor pool
SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point
9.8 out of 10, Exceptional, (46)
"We all had a wonderful stay!"
SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point
Caymanian Style Home w/ Pool, Pickle Ball Court, Optional Private Bar,
Beach nearby, beach towels
Caymanian Style Home w/ Pool, Pickle Ball Court, Optional Private Bar,
9.8 out of 10, Exceptional, (34)
"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,
Serenity On The Bay2 - Two Bed Apt On The Beach!
Beach nearby, beach towels
Serenity On The Bay2 - Two Bed Apt On The Beach!
9.8 out of 10, Exceptional, (12)
"Great place, awesome sunsets and location! BBQ needs a little attention."
Serenity On The Bay2 - Two Bed Apt On The Beach!
Lone Palm: Oceanfront Pool, 2 Free Kayaks, & Wide Beachfront.
Pool
Lone Palm: Oceanfront Pool, 2 Free Kayaks, & Wide Beachfront.
9.8 out of 10, Exceptional, (17)
"Beautiful place in a great location. Would recommend."
Lone Palm: Oceanfront Pool, 2 Free Kayaks, & Wide Beachfront.
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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.

Cayman Islands Holiday Homes: Find the Perfect Place


What is the best time to enjoy a holiday home in Cayman Islands?

It might be best to get a rental house in when the weather is ideal for enjoying local surroundings. If you go during the off-season months, there might be fewer tourists and often lower rates, like in .


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

Choose from 343 beautiful holiday homes in Cayman Islands for your getaway.


How much is a holiday home in Cayman Islands?

You can find perfect holiday homes in Cayman Islands for as low as £1,098 per night. Holiday home prices vary depending on what time of year you visit, whether the home is in the city centre or near popular sightseeing spots, and what kinds of amenities it offers.


How can I get the best deal on a holiday home in Cayman Islands?

Find the best deals on Cayman Islands holiday homes by entering dates and the number of travellers in the search bar. You can use the map feature to view prices and more specific locations of several accommodations all at once. Or filter your search results by star rating, price, number of bedrooms, types of amenities, and accessibility features—Expedia offers incredible deals for every budget.


Why should I book a holiday home in Cayman Islands?

There’s no better way to spend your well-earned holiday than in a private, cosy Cayman Islands holiday home. You’ll be able to fit all travellers in your group and have a place to call home while you explore Cayman Islands.


What amenities are available in a private holiday home?

Depending on your budget and the neighbourhood you choose, you’ll find amenities like a private pool, hot tub, free parking, a full-service kitchen or kitchenette, in-home laundry and WiFi. Your Cayman Islands holiday won’t be complete without a beautiful view and easy access to popular activities, use our filter to browse our offers.


Why should I book a holiday home with Expedia?

With Expedia, you’ll earn points on every booking and get incredible deals and member prices. Choose from a vast inventory of holiday homes in Cayman Islands—and book all your travel in one place. Save even more when you bundle your bookings together. Add a Cayman Islands car hire to your holiday property into a holiday package.


What are the cancellation and flexibility options?

We suggest using the “free cancellation” filter during your search to make sure your booking is flexible. Some accommodations accept and refund cancellations within a specific timeframe, while others may be non-refundable. Before you book, check your rental terms, or reach out to our customer service portal for further assistance.

Cayman Islands Holiday Homes information

Number of reviews
577
Accommodation
343 Holiday Homes
Lowest Price
£1,098
Highest Price
£1,116

Cayman Islands Hotel Reviews
Expedia verified reviews

Kimpton Seafire Resort + Spa, an IHG Hotel

Kimpton Seafire Resort + Spa, an IHG Hotel

5/5 Excellent
"exceeded our expectations."
A verified traveller stayed at Kimpton Seafire Resort + Spa, an IHG Hotel
Posted 10 hours ago
Kimpton Seafire Resort + Spa, an IHG Hotel

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