Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Bungalows
Condos
Cottages
Estates
Hotels
Homes
Townhomes
Villas
Barns
Boats
Cabins
Castles
Chalets
Farmhouses
Lodges
Studios
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Cayman Islands Vacation Rentals(268)

268 Results
$275 - $420
per night
2 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(71)
$200 - $275
per night
4 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 5 night minimum stay
(25)
$225 - $625
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(53)
$215 - $295
per night
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 night minimum stay
(24)
$375 - $575
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 7 night minimum stay
(44)
$315 - $490
per night
4 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 7 night minimum stay
(65)
$195 - $375
per night
3 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 7 night minimum stay
(45)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
5 - 7 night minimum stay
(26)
$365 - $625
per night
5 - 10 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
5 - 10 night minimum stay
(16)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 7 night minimum stay
(17)
$1,064 - $1,993
per night
5 - 7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 11
5 - 7 night minimum stay
(18)
$450 - $675
per night
4 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
4 - 7 night minimum stay
(32)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 5 night minimum stay
(18)
$175 - $310
per night
1 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
1 - 7 night minimum stay
(9)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 7 night minimum stay
(17)
$150 - $220
per night
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 night minimum stay
(17)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(14)
$320 - $450
per night
5 - 6 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
5 - 6 night minimum stay
(64)
$921 - $1,707
per night
5 - 7 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 12
5 - 7 night minimum stay
(8)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 night minimum stay
(5)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
5 - 7 night minimum stay
(47)
$275 - $814
per night
1 - 5 night minimum stay
  • 4 BR,
  • 1 BA,
  • Sleeps 8
1 - 5 night minimum stay
(7)
$200 - $300
per night
5 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
5 - 7 night minimum stay
(5)
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 14
6 night minimum stay
(62)
$921 - $1,707
per night
5 - 7 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 12
5 - 7 night minimum stay
(4)
$185 - $300
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 5 night minimum stay
(7)
$225 - $400
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(10)
  • 1 BR,
  • 1 BA,
  • Sleeps 5
5 - 7 night minimum stay
(39)
  • 6 BR,
  • 4 BA,
  • Sleeps 12
5 - 7 night minimum stay
(5)
 

Recent Cayman Islands Reviews

Gorgeous Caribbean beach just outside our doors!

5 of 5
This is beyond doubt luxurious with an awesome view of the ocean at any part of the villa. The gorgeous Caribbean beach is just sitting right outside our doors. Enjoyed basking in the sun in the oceanfront deck of the infinity pool. We will definitely refer this upscale villa to friends and relatives who'd visit Cayman Islands.
  • Submitted: Sep 20, 2014
  • Stayed: Jun 2014

Amazing!!

5 of 5
What a pleasant surprise!!! When you book places like this online you get a little nervous but what a surprise. Is a beautiful place, clean apartment and safe. The view is great you can have your coffee in the morning by looking at the ocean. You can truly relax and enjoy yourself with your family. We when snorkeling every day. Just make sure you stop by the supermarket on your way because once you are in this place trust me you are not going to want to leave!!!!! Thank you Adella for being so kindand set in up my friend next to us we had a great time thanks to you!!!!! The Macchia Family Para mis hermanos hispanos este lugar es maravilloso. Creanme a veces uno se pone nervioso en separar lugares que uno no conoce pero este lugar es seguro, limpio y las personas son super amables. Las playas son espectaculares!!!!! La dueña es un amor y habla español.
  • Submitted: Sep 10, 2014
  • Stayed: Aug 2014

Serenity? Absolutely!

5 of 5
Our family (my wife, two sons, daughter-in-law and two, young grandchildren) spent a week at Serenity Now earlier this year. It was our first trip to the Cayman and we plan to return to Serenity Now next year. The house was fantastic: clean, well appointed and the location was great - private yet close to everything. Walking distance to great restaurants, groceries and pharmacy (we had several meals at Heritage Kitchen which is so close we did take out and ate back at comfort of the house). Also, the property managers, Sonya and Leif were friendly and attentive. We had a minor problem with the A/C which they resolved immediately. The ocean views, beach access, snorkeling and overall location made this a relaxing and memorable vacation.
  • Submitted: Aug 30, 2014
  • Stayed: May 2014