
Vacation rentals with a pool in Cayman Brac
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Top-rated rentals with a pool in Cayman Brac
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Cayman Brac rentals with a pool
House rentals with a pool

Home in Stake Bay
5 out of 5 average rating, 15 reviewsSea Fan Meadows: Oceanfront w/ Pool
MatthewRating, 5 stars9 months ago
Have been wanting to vacation at Cha Che’s home for 15years! Finally made it - didn’t want to leave! Total privacy, peaceful, and tranquil. Watched sunrise and sunset from the pool every day. House was lovely. Ocean was a bit rough some days due to hurricane Beryl but great snorkeling on property. Pool was perfect. Kitchen was lovely. Bed was comfy. Couldn’t ask for better. Will definitely return on our next trip to Cayman as it felt like our home away from home!!!
Superhost

Home in Cayman Brac
5 out of 5 average rating, 16 reviewsFeatherstone - Upstairs Beach Front Apartment
JeffRating, 5 stars1 month ago
Coralie was great. Proactive communication. Flexible on check-in and -out. Helped right away with a minor problem Place was great. Cottage vibe, nicely decorated, comfortable Mattresses were great/comfy Kitchen (very important for me cuz we cook) was stocked with basics - right spices, good amount of condiments in the fridge, pots, pans, etc. We would stay again.

Home in Cayman Brac
4.44 out of 5 average rating, 9 reviewsSouthern Reach. "A Little Piece of Paradise
TristanRating, 5 stars39 months ago
Our second trip in only a few months - love the location for the nature and the pool is a big hit. Paul is very responsive. Looking forward to coming back soon!
Guest favorite

Home in Spot Bay
5 out of 5 average rating, 5 reviewsDan's Dive Seaside Retreat in Spot Bay with Pool
DavidRating, 5 stars2 months ago
What a quiet, peaceful and beautiful place. After traveling around the island, Spot Bay is the best and quietest part of the island. Highly recommend this cottage. It has awesome views of the Carribean, everything you need for a comfortable vacation, would most definitely stay again!
Top guest favorite

Home in Little Cayman
4.96 out of 5 average rating, 168 reviewsJust Chillin in Little Cayman
SophiaRating, 5 stars1 week ago
Another brilliant stay. This will be my go to place when going to Little. Thank you for everything!
Superhost

Home in West End
4.86 out of 5 average rating, 14 reviews2-bdm tropical beach paradise w/ pool, cabana&more
TimothyRating, 5 stars3 weeks ago
Henry’s place was the perfect place for some deep relaxation! Right on the water, with beautiful grounds and hammocks that were perfect for drifting in and out of sleep, reading, and generally soothing the days away. The location too, was perfect. Just a few minutes from “downtown” and under ten minutes to the Brac Scuba Shack. The sea was a bit choppy right in front of the house, but on calm days, you could absolutely shore dive just out the front. While we were there, the other two units were unoccupied, which meant that we had the hammocks and pool to ourselves. The interior was perfectly appointed with a great kitchen and comfy couches. Communication was impeccable. We would absolutely return!

Home in West End
4.6 out of 5 average rating, 5 reviewsVilla VanEl
AlexiaRating, 5 stars11 months ago
Such a great place! Looks just like the pictures and Derri was always very responsive and accommodating. Would love to go back again.
Guest favorite

Home in Cayman Brac
4.89 out of 5 average rating, 19 reviewsFeatherstone - The Cottage
Jayda Rating, 5 stars7 months ago
My partner and I had a lovely and peaceful experience here at featherstone. The place was very cozy and felt like at home. The scenery was beautiful, very easy accessible. Our host was great as well, she was very helpful, responsive and friendly. We plan to come again in the near future! This place was the perfect fit for our vacation.
Condo rentals with a pool

Condo in Sister Islands
4.77 out of 5 average rating, 39 reviewsBrac Sea'renity - Coastal chic oceanfront condo
BillRating, 5 stars1 month ago
Nice place. Comfy bed. Nice TV. High-end washer/dryer made life easier for 2 divers on a 15 day dive trip with just a carry on bag of clothes!
Guest favorite

Condo in Cayman Brac
5 out of 5 average rating, 9 reviewsCayman Brac, Carib Sands 221- "Stumble Inn"
BarbaraRating, 5 stars2 months ago
Really enjoyed our stay at the “Stumble Inn” . Karen was quick to respond to our inquiries and provided us with helpful suggestions - access was simple and straightforward, and the unit perfect for our visit. Great location with a nice pool and small beach - and great bird watching close by. Would definitely recommend contacting Karen if you plan on visiting Cayman Brac .
Superhost

Condo in Blossom Village
4.85 out of 5 average rating, 60 reviewsConch Club 16, Little Cayman, Cayman Islands
LeslieRating, 5 stars2 months ago
We really loved staying in this condo. It was very quiet and comfortable. We loved the view from the top floor deck and being able to bring chairs to the beach right below the condo in the afternoon. Little Cayman is really different from other islands because not that many people live here. The plane rides between the islands were a blast and we felt safe with two pilots in the front of the plane. We loved all the red footed boobies nesting in trees right along the road. We had a great time diving the Bloody Bay Wall with Little Cayman Divers. We will be back!

Condo in Sister Islands
4.33 out of 5 average rating, 3 reviewsCharming, Ocean Front Condo with Pool & Bluff View
ArminRating, 5 stars14 months ago
lovely apartment!

Condo in LITTLE CAYMAN
4.5 out of 5 average rating, 6 reviewsThe Club at Little Cayman - Luxurious Living
JaydeRating, 5 stars30 months ago
Great stay - very quiet complex located just a short walk from LCBR. Easy check in and thanks for letting us in early! Pool and beach right there with a nice sea view from the balcony! We’ll be back!
Destinations to explore
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