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Vacation rentals with a pool in Cayman Islands

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Top-rated rentals with a pool in Cayman Islands

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Guest favorite
Condo in George Town
Cayman Reef Resort on Seven Mile Beach
At the heart of Seven Mile Beach, our home is in the middle of everything and far from nothing. Extensively renovated and well maintained, the condo is designed for you to enjoy a tranquil beach getaway in a luxurious setting with all the comforts of home. Picture perfect views, top of the line amenities and our local touch provide a warm welcome and cozy stay. We are fully licenced and our rate includes the 13% tourist accommodation tax. 20% discount from list price for local residents!
May 9 – 16
$339 per night
Guest favorite
Guest suite in Savannah
Paradise Escape-Charming Oceanfront Guest Suite
A tranquil oceanfront escape for couples and solo adventurers... Ours is a unique community with quaint freehold condo cottages on a vast tract of oceanfront land. Wake-up in bed to a lovely view of a luscious green landscape that melds with the emerald green and blue ocean, sip a hot cup of coffee on the porch, enjoy a sunset cocktail by the ocean front pool, break a sweat in a friendly game of tennis, or take a blanket out to the lawn under the palm trees for breathtaking star gazing.
Jun 23 – 30
$141 per night
Guest favorite
Condo in Rum Point
Nature's View: Pools of the Kai #2
Discover the peaceful Caribbean paradise of Cayman Kai. This secluded oasis will put you at ease as soon as you walk through the door. Our beach front property features stunning views across the Caribbean Sea to an unspoiled nature reserve. The double story screened in private pool deck can't be beat. Perfect for family holidays or a romantic getaway. Savor heavenly mornings and sundowners on your master bedroom balcony. Stroll down the beach to Kaibo, true barefoot living!
Nov 11 – 18
$404 per night

Popular amenities for Cayman Islands rentals with a pool

House rentals with a pool

Guest favorite
Home in Stake Bay
Modern Oceanfront, 2Primary Suites, sleeps 6, pool
Jan 29 – Feb 5
$435 per night
Guest favorite
Home in Bodden Town
Casa Avi - Beachfront bliss & luxury in Cayman
Oct 20 – 27
$675 per night
Guest favorite
Home in George Town
Chilled Out Beach House
Jul 16 – 23
$360 per night
Guest favorite
Home in Bodden Town
Tranquil Hideaway
Jul 14 – 21
$81 per night
Superhost
Home in Grand Cayman
Lone Palm by Grand Cayman Villas
Jul 19 – 26
$840 per night
Guest favorite
Home in West End
POOL, sandy beach w/cabana, wi-fi, a/c, sunsets
Sep 21 – 28
$129 per night
Guest favorite
Home in Grand Cayman
Snorkelers Beachfront Paradise - Beach Plum Villa
Oct 21 – 28
$736 per night
Guest favorite
Home in North Side
Luxury 3bd Ocean View, # 1 Cream, Stunning Views
Oct 6 – 13
$230 per night
Superhost
Home in Grand Harbour
Boat Harbour House
Jun 2 – 9
$626 per night
Superhost
Home in North Side
Oceanfront “Dreamsicle” Villa with Kayaks
Nov 14 – 21
$507 per night
Guest favorite
Home in Grand Cayman
3 Bedroom Beach House with Pools
Jan 11 – 18
$295 per night
Superhost
Home in Old Man Bay
Blue Vista Villa - Oceanfront 4 Bedroom Home
May 7 – 14
$677 per night

Condo rentals with a pool

Superhost
Condo in George Town
Grandview condominium directly on 7-mile beach
Dec 20 – 27
$713 per night
Guest favorite
Condo in George Town
Beautiful Modern Condo on 7 Mile Beach
Aug 2 – 9
$400 per night
Guest favorite
Condo in George Town
Seven Mile Beach with Soul
May 24 – 31
$370 per night
Guest favorite
Condo in West Bay
Sunset Hideaway (2)
Dec 20 – 27
$195 per night
Superhost
Condo in West Bay
Seven Mile Beachfront Condo at Discovery Point
Jul 24 – 31
$569 per night
Guest favorite
Condo in West Bay
Condo Kai- Awesome 1B/1B in West Bay, Grand Cayman
Jun 5 – 12
$166 per night
Guest favorite
Condo in West Bay
Oceanfront penthouse: pool, diving & snorkeling
Nov 1 – 8
$436 per night
Superhost
Condo in Savannah
Beachfront walkout with amazing patio & view
Dec 29 – Jan 5
$799 per night
Guest favorite
Condo in George Town
2 Bed Condo in the Heart of Seven Mile Beach
Aug 19 – 26
$361 per night
Guest favorite
Condo in George Town
Beautiful apartment in Seven Mile Beach
Jul 25 – Aug 1
$447 per night
Guest favorite
Condo in West Bay
7 Mile Beach - Amazing Rooftop + Pool Pavilion
Sep 2 – 9
$788 per night
Guest favorite
Condo in Rum Point
Beautiful oceanfront condo in peaceful North Side
Apr 28 – May 5
$280 per night

Destinations to explore