Vacation rentals with a pool in Grand Cayman

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Top-rated rentals with a pool in Grand Cayman

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

Guest favourite
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 3 – 10
$467 CAD per night
4.93 out of 5 average rating, 145 reviews
Superhost
Condo in George Town
Grandview condominium directly on 7-mile beach
This family friendly condo is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love this place because of the location, the people, the ambiance, the outdoors space, and the neighborhood. My place is good for couples, solo adventurers, business travelers as well as families with children. The property has biggest pool on Seven Mile Beach and hot tub overlooking beach with best sunsets. It also offers tennis courts and Basketball.
Sep. 4 – 11
$498 CAD per night
4.84 out of 5 average rating, 115 reviews
Guest favourite
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.
Aug. 5 – 12
$238 CAD per night
4.97 out of 5 average rating, 190 reviews

Popular amenities for Grand Cayman rentals with a pool

House rentals with a pool

Guest favourite
Home in Bodden Town
Casa Avi - Beachfront bliss & luxury in Cayman
Aug. 25 – Sep. 1
$1,284 CAD per night
5.0 out of 5 average rating, 25 reviews
Guest favourite
Home in George Town
Chilled Out Beach House
Jul. 17 – 24
$577 CAD per night
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Bodden Town
Tranquil Hideaway
Sep. 24 – Oct. 1
$133 CAD per night
4.87 out of 5 average rating, 78 reviews
Superhost
Home in Grand Cayman
Seaside Dreams by Grand Cayman Villas
Sep. 18 – 25
$573 CAD per night
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Grand Cayman
Snorkelers Beachfront Paradise - Beach Plum Villa
Sep. 3 – 10
$1,211 CAD per night
4.96 out of 5 average rating, 46 reviews
Guest favourite
Home in Grand Cayman
3 Bedroom Beach House with Pools
Nov. 20 – 27
$539 CAD per night
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in North Side
Luxury 3bd Ocean View, # 1 Cream, Stunning Views
Oct. 19 – 26
$404 CAD per night
4.89 out of 5 average rating, 63 reviews
Superhost
Home in East End
Luxury 4 Bdr Ocean View Home w/ Pool + Hot Tub
Nov. 24 – Dec. 1
$808 CAD per night
4.95 out of 5 average rating, 22 reviews
Superhost
Home in Grand Harbour
Boat Harbour House
Jun. 3 – 10
$1,069 CAD per night
5.0 out of 5 average rating, 5 reviews
Superhost
Home in North Side
Oceanfront “Dreamsicle” Villa with Kayaks
Nov. 28 – Dec. 5
$1,252 CAD per night
4.94 out of 5 average rating, 31 reviews
Guest favourite
Home in West Bay
5 Bedroom FUN Home, private pool close to Beach
Jul. 26 – Aug. 2
$1,066 CAD per night
4.95 out of 5 average rating, 20 reviews
Superhost
Home in Old Man Bay
Blue Vista Villa - Oceanfront 4 Bedroom Home
May 7 – 14
$1,077 CAD per night
4.86 out of 5 average rating, 7 reviews

Condo rentals with a pool

Guest favourite
Condo in Rum Point
Nature's View: Pools of the Kai #2
Dec. 14 – 21
$1,071 CAD per night
4.92 out of 5 average rating, 110 reviews
Guest favourite
Condo in George Town
Seven Mile Beach with Soul
Feb. 14 – 21
$845 CAD per night
4.92 out of 5 average rating, 127 reviews
Guest favourite
Condo in Grand Harbour
The Sanctuary at the Careenage, Grand Harbour
Jul. 9 – 16
$401 CAD per night
4.93 out of 5 average rating, 186 reviews
Guest favourite
Condo in West Bay
Sunset Hideaway (2)
Aug. 8 – 15
$352 CAD per night
4.96 out of 5 average rating, 50 reviews
Superhost
Condo in Savannah
Beachfront walkout with amazing patio & view
May 13 – 20
$825 CAD per night
4.95 out of 5 average rating, 62 reviews
Superhost
Condo in West Bay
Seven Mile Beachfront Condo at Discovery Point
Feb. 16 – 23
$1,348 CAD per night
4.86 out of 5 average rating, 28 reviews
Guest favourite
Condo in West Bay
Condo Kai- Awesome 1B/1B in West Bay, Grand Cayman
Jun. 5 – 12
$278 CAD per night
5.0 out of 5 average rating, 54 reviews
Guest favourite
Condo in George Town
Brand New|3 Bed|Ocean Front|Sunset Balcony|Pool
Jan. 10 – 17
$1,378 CAD per night
5.0 out of 5 average rating, 17 reviews
Guest favourite
Condo in George Town
2 Bed Condo in the Heart of Seven Mile Beach
Sep. 23 – 30
$690 CAD per night
4.91 out of 5 average rating, 23 reviews
Guest favourite
Condo in George Town
Beautiful apartment in Seven Mile Beach
Feb. 14 – 21
$799 CAD per night
5.0 out of 5 average rating, 44 reviews
Guest favourite
Condo in George Town
Oceanfront 2bed 2bath Condo Seven Mile Beach
Oct. 19 – 26
$683 CAD per night
4.95 out of 5 average rating, 56 reviews
Guest favourite
Condo in George Town
Blissful a Luxury Ocean Front Villa, Grand Harbour
Jul. 19 – 26
$662 CAD per night
4.97 out of 5 average rating, 39 reviews

Destinations to explore