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Old Man Bay Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Old Man Bay vacation rentals

A two-story house with a beige facade, large windows, and a brick driveway.

1. Casa de Bells 3

Casa de Bells 3
Patricks Island
The price is ￥24,032
￥44,299 total
includes taxes & fees
Sep 3 - Sep 4
Casa de Bells 3
A coastal view with a beach, palm trees, and a gazebo.

2. Relax and Unwind at our cozy 1-bedroom Apt, within mins away from the beach

Relax and Unwind at our cozy 1-bedroom Apt, within mins away from the beach
Bt
9.4 out of 10, Exceptional, (10 reviews)
"Had a great stay"
United States
Annette
The price is ￥14,237
￥31,320 total
includes taxes & fees
Sep 10 - Sep 11
Relax and Unwind at our cozy 1-bedroom Apt, within mins away from the beach
A beach with clear turquoise water, a sandy path, and dense green foliage on the right.

3. Pease Bay House Cayman Islands

Pease Bay House Cayman Islands
Grand Cayman
10.0 out of 10, Exceptional, (1 review)
"The house itself was absolutely beautiful and the location on the beach with both sunrise and sunset views was incredible. We have 4 children and had another family joined us with their 2 children and we had the best time. Lots of clean sandy beach area to play, plus fun coral area to explore. Be sure to bring water shoes to make it easy to explore. Host was super helpful with recommendations and response time was very quick. We truly enjoyed our stay!"
United States
Aileen R.
The price is ￥623,181
￥924,545 total
includes taxes & fees
Sep 10 - Sep 11
Pease Bay House Cayman Islands

4. Country Road, Take me Home- your own Island Cottage!

Country Road, Take me Home- your own Island Cottage!
Savannah
9.2 out of 10, Wonderful, (16 reviews)
"Great location’"
Canada
Renee M.
The price is ￥17,623
￥28,838 total
includes taxes & fees
Sep 3 - Sep 4
Country Road, Take me Home- your own Island Cottage!
A building with a pink facade, a well-maintained garden with artificial grass and potted plants, and a palm tree.

5. Beautiful one bedroom apartment

Beautiful one bedroom apartment
Savannah
9.6 out of 10, Exceptional, (17 reviews)
"The location is in a quiet neighborhood in the middle of the island, so easy to get to anywhere. Also close to Spotts Beach for snorkeling. The hosts were very friendly and helpful. "
United States
Stephanie H.
The price is ￥22,830
￥42,781 total
includes taxes & fees
Sep 3 - Sep 4
Beautiful one bedroom apartment
A two-story house with a swimming pool in the foreground.

6. Casa de Bells 2 - Studio apartment with pool, gazebo, private entrance & parking

Casa de Bells 2 - Studio apartment with pool, gazebo, private entrance & parking
George Town
9.8 out of 10, Exceptional, (71 reviews)
"The host was really nice and the stay was perfect"
United States
luis M.
The price is ￥24,032
￥44,299 total
includes taxes & fees
Sep 3 - Sep 4
Casa de Bells 2 - Studio apartment with pool, gazebo, private entrance & parking
A modern two-story house with a well-lit entrance, a small front yard, and a driveway.

7. Charming 1-bedroom apartment in enchanting Savannah, Cayman Islands

Charming 1-bedroom apartment in enchanting Savannah, Cayman Islands
Savannah
9.8 out of 10, Exceptional, (11 reviews)
"Excellent stay! "
United States
Emma
The price is ￥17,303
￥33,004 total
includes taxes & fees
Sep 12 - Sep 13
Charming 1-bedroom apartment in enchanting Savannah, Cayman Islands

8. Slice of Paradise- 2 mins from Spotts Beach!

Slice of Paradise- 2 mins from Spotts Beach!
Patricks Island
8.4 out of 10, Very Good, (31 reviews)
"Quiet and convenient, was exactly what we needed for a nights stay!!!!"
United States
Matt D.
The price is ￥22,429
￥27,556 total
includes taxes & fees
Sep 3 - Sep 4
Slice of Paradise- 2 mins from Spotts Beach!
A paved pathway with palm trees and dense foliage.

9. Relaxing, tastefully decorated one-bedroom unit with all modern facilities

Relaxing, tastefully decorated one-bedroom unit with all modern facilities
Savannah
9.6 out of 10, Exceptional, (5 reviews)
"Was exactly how pictures show. Nice quiet relaxing location. If you dont need a pool this location for you. Plus owners are really nice and had beech chairs, umbrella and snorkel smasks in closet to use."
United States
theodor
The price is ￥23,969
￥53,290 total
includes taxes & fees
Sep 10 - Sep 11
Relaxing, tastefully decorated one-bedroom unit with all modern facilities
A beach view from a room with large windows, featuring palm trees, a sandy beach, and a clear blue sea.

10. Stunning beachfront condo. Relax, Enjoy, Sunset, RumPoint, Pool & Heated Jacuzzi

Stunning beachfront condo. Relax, Enjoy, Sunset, RumPoint, Pool & Heated Jacuzzi
Grand Cayman
10.0 out of 10, Exceptional, (18 reviews)
"Gosh, the host communicated well, we enjoyed the rum cake treat too! The condo was very clean, updated and all systems worked perfectly! We enjoyed the people that stayed around us and the beach and Kaibo resort was nice to have by. We would definitely stay in this C25 again! Very pleased!"
United States
Susie H.
The price is ￥40,267
￥75,542 total
includes taxes & fees
Sep 10 - Sep 11
Stunning beachfront condo. Relax, Enjoy, Sunset, RumPoint, Pool & Heated Jacuzzi
A two-story building with a balcony on the upper floor, surrounded by palm trees and a landscaped garden.

11. Cozy 1-Bed, Pool + Sea and Dining close by

Cozy 1-Bed, Pool + Sea and Dining close by
South Sound
10.0 out of 10, Exceptional, (1 review)
"Great room with full kitchen and bedroom. Laundry machines and dishwasher works greatPool was very refreshing and both times we used it there was no ine else in it. Short drive to seven mile and very close to grocerie store as well"
United States
brett r.
The price is ￥10,992
￥35,344 total
includes taxes & fees
Sep 8 - Sep 9
Cozy 1-Bed, Pool + Sea and Dining close by
A beach with two white lounge chairs and a blue umbrella.

12. Galleon Villas by Hello Cayman Vacation

Galleon Villas by Hello Cayman Vacation
3.5 star property
Seven Mile Beach
10.0 out of 10, Exceptional, (210 reviews)
"We loved the spacious unit and the view of the water. The beach was wonderful. Also, the recommendations provided by the host were spot on and great. We used the kitchen every morning for breakfast and the start of the day. We will definitely go back -- The only "issue" was the complex did not have a swimming pool --"
United States
Matthew
The price is ￥105,941
￥125,010 total
includes taxes & fees
Sep 5 - Sep 6
Galleon Villas by Hello Cayman Vacation
A beach scene with a thatched umbrella and a lounge chair on the sand.

13. The Big Chill - Beach Cottage at The Sea Lodges in Cayman Kai / Rum Point

The Big Chill - Beach Cottage at The Sea Lodges in Cayman Kai / Rum Point
North Side
9.6 out of 10, Exceptional, (15 reviews)
"The host was absolutely wonderful - very quick to respond and super helpful. Highly recommend for a quiet, laid-back vacation!!! "
United States
Jami G.
The price is ￥34,605
￥61,533 total
includes taxes & fees
Sep 3 - Sep 4
The Big Chill - Beach Cottage at The Sea Lodges in Cayman Kai / Rum Point
A resort with a swimming pool, palm trees, and a view of the ocean.

14. Villas Pappagallo 17

Villas Pappagallo 17
2.0 star property
West Bay
The price is ￥21,414
￥59,446 total
includes taxes & fees
Sep 3 - Sep 4
Villas Pappagallo 17
A modern kitchen with white cabinets, stainless steel appliances, and a large window overlooking a balcony.

15. 1BD 1.5BA Convenient and Cosy Apartment with Pool

1BD 1.5BA Convenient and Cosy Apartment with Pool
George Town
9.6 out of 10, Exceptional, (4 reviews)
"Really enjoyed it, the place was very clean and comfortable. "
United States
mauricio o.
The price is ￥20,011
￥45,737 total
includes taxes & fees
Sep 11 - Sep 12
1BD 1.5BA Convenient and Cosy Apartment with Pool
A starfish on a clear sandy beach with turquoise water and a clear sky.

16. S4 BP | Steps to Beach | Save 15% if Book Non-Refundable

S4 BP | Steps to Beach | Save 15% if Book Non-Refundable
West Bay
9.8 out of 10, Exceptional, (30 reviews)
"We were very pleased with our stay and highly recommend!"
United States
Evan E.
The price is ￥16,942
￥36,077 total
includes taxes & fees
Sep 3 - Sep 4
S4 BP | Steps to Beach | Save 15% if Book Non-Refundable
A beach with palm trees, a sandy shore, and beach chairs.

17. Minutes From 7 Mile Beach

Minutes From 7 Mile Beach
West Bay
9.8 out of 10, Exceptional, (14 reviews)
"This is a beautiful location, well maintained and very quiet."
United States
Colletta
The price is ￥21,484
￥54,076 total
includes taxes & fees
Sep 15 - Sep 16
Minutes From 7 Mile Beach
A beach with clear blue water, a sandy shore, and a few umbrellas.

18. Cozy 2-bedroom condo with sleeper in beautiful West Bay, steps from the beach

Cozy 2-bedroom condo with sleeper in beautiful West Bay, steps from the beach
West Bay
10.0 out of 10, Exceptional, (1 review)
"Absolutely loved the place. Great location. Clean. Couldn’t think of anything to complain about. Will definitely rent again when we come back this way."
United States
Summer
The price is ￥13,084
￥42,402 total
includes taxes & fees
Sep 8 - Sep 9
Cozy 2-bedroom condo with sleeper in beautiful West Bay, steps from the beach
A beach with clear turquoise water and a sandy shore.

19. Cozy Studio Steps from the Beach

Cozy Studio Steps from the Beach
West Bay
10.0 out of 10, Exceptional, (5 reviews)
"The property was clean and had plenty of amenities. It was a pleasure to stay there. Great location. The host was great-very communicative-much appreciated!"
United States
Lori
The price is ￥16,748
￥32,288 total
includes taxes & fees
Sep 15 - Sep 16
Cozy Studio Steps from the Beach
A beach with sun loungers and umbrellas, palm trees, and a clear blue sky.

20. 2 Bedroom Condo Seven Mile Beach -Sunset Cove

2 Bedroom Condo Seven Mile Beach -Sunset Cove
George Town
10.0 out of 10, Exceptional, (90 reviews)
"We loved our stay here! "
United States
Breanna D.
The price is ￥32,443
￥58,610 total
includes taxes & fees
Sep 3 - Sep 4
2 Bedroom Condo Seven Mile Beach -Sunset Cove
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.
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Top Old Man Bay Hotel Reviews

Palm Heights

Palm Heights

10/10 Excellent
"Stunning"
Alexandra 3-night trip
Posted 3 hours ago
Palm Heights

Find out more about Old Man Bay

Search for holiday rentals in Old Man Bay on Expedia! You can easily find your home rentals, villas, holiday apartments in Old Man Bay using one of the methods below:

  • View our selection of featured holiday rentals in Old Man Bay
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Look no further and take a look at our great range of rental properties in Old Man Bay!

Frequently asked questions

Are there vacation rentals in Old Man Bay?

Yes, we offer vacation rentals near top sights in Old Man Bay, or you can select a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental that Old Man Bay has to offer?

Cayman Bliss - Beachfront house private Pool & Beach Sleeps 8 Family-Friendly: This vacation home rental outside of Old Man Bay is located on the beach and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals will I find in Old Man Bay?

Choose from 9 Expedia vacation rentals in Old Man Bay for a memorable vacation.

What’s there to see and do in Old Man Bay?

Grand Cayman Beaches and Cayman Crystal Caves are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Grand Cayman Blow Holes and Starfish Point.

What’s a vacation rental in Old Man Bay like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Old Man Bay. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a family getaway.