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Old Man Bay Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Old Man Bay vacation rentals

A coastal view with a beach, palm trees, and a gazebo.

1. 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 ￥14,014
￥30,357 total
includes taxes & fees
Sep 27 - Sep 28
Relax and Unwind at our cozy 1-bedroom Apt, within mins away from the beach

2. 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 ￥17,301
￥28,311 total
includes taxes & fees
Sep 28 - Sep 29
Country Road, Take me Home- your own Island Cottage!
A beach scene with a thatched umbrella and a lounge chair on the sand.

3. 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 ￥33,972
￥57,419 total
includes taxes & fees
Sep 27 - Sep 28
The Big Chill - Beach Cottage at The Sea Lodges in Cayman Kai / Rum Point
A beach view from a room with large windows, featuring palm trees, a sandy beach, and a clear blue sea.

4. 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, (19 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 ￥39,635
￥70,424 total
includes taxes & fees
Sep 29 - Sep 30
Stunning beachfront condo. Relax, Enjoy, Sunset, RumPoint, Pool & Heated Jacuzzi
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 ￥22,412
￥40,268 total
includes taxes & fees
Sep 30 - Oct 1
Beautiful one bedroom apartment

6. 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 ￥22,019
￥26,737 total
includes taxes & fees
Oct 1 - Oct 2
Slice of Paradise- 2 mins from Spotts Beach!
A resort with a central pool, palm trees, and beachfront views.

7. Newly Renovated 2 Bed Beachfront Condo w/Pool+Hot Tub

Newly Renovated 2 Bed Beachfront Condo w/Pool+Hot Tub
Rum Point
9.4 out of 10, Exceptional, (6 reviews)
"This was the perfect spot for a quiet weekend getaway."
United States
Jacob B.
The price is ￥29,569
￥71,601 total
includes taxes & fees
Oct 4 - Oct 5
Newly Renovated 2 Bed Beachfront Condo w/Pool+Hot Tub
A modern two-story house with a well-lit entrance, a small front yard, and a driveway.

8. 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 ￥16,986
￥31,928 total
includes taxes & fees
Oct 16 - Oct 17
Charming 1-bedroom apartment in enchanting Savannah, Cayman Islands
A two-story house with a swimming pool in the foreground.

9. 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 ￥23,592
￥41,601 total
includes taxes & fees
Sep 27 - Sep 28
Casa de Bells 2 - Studio apartment with pool, gazebo, private entrance & parking
A paved pathway with palm trees and dense foliage.

10. 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 ￥23,592
￥49,779 total
includes taxes & fees
Oct 15 - Oct 16
Relaxing, tastefully decorated one-bedroom unit with all modern facilities
A two-story house with a beige facade, large windows, and a brick driveway.

11. Casa de Bells 3

Casa de Bells 3
Patricks Island
The price is ￥23,592
￥41,601 total
includes taxes & fees
Sep 28 - Sep 29
Casa de Bells 3
A beach with clear turquoise water and a sandy shore.

12. 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 ￥16,613
￥31,555 total
includes taxes & fees
Oct 6 - Oct 7
Cozy Studio Steps from the Beach
A two-story building with a balcony on the upper floor, surrounded by palm trees and a landscaped garden.

13. 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 ￥11,928
￥34,947 total
includes taxes & fees
Oct 2 - Oct 3
Cozy 1-Bed, Pool + Sea and Dining close by
A beach with palm trees, lounge chairs, and a clear blue sky.

14. 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 ￥14,863
￥43,534 total
includes taxes & fees
Sep 27 - Sep 28
Minutes From 7 Mile Beach
A resort with a swimming pool, palm trees, and a view of the ocean.

15. Villas Pappagallo 17

Villas Pappagallo 17
2.0 star property
West Bay
10.0 out of 10, Exceptional, (1 review)
"I love being able to walk out of my room straight on to the beach, this place is at the most northern point on the island, you can watch the sun rise and sunset, it’s not a commercial headache, far away from the regular tourists"
United States
Andrew
The price is ￥25,129
￥62,999 total
includes taxes & fees
Sep 27 - Sep 28
Villas Pappagallo 17
A modern kitchen with white cabinets, stainless steel appliances, and a large window overlooking a balcony.

16. 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 ￥11,304
￥34,110 total
includes taxes & fees
Oct 14 - Oct 15
1BD 1.5BA Convenient and Cosy Apartment with Pool
A beach with two white lounge chairs and a blue umbrella.

17. 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 ￥84,892
￥100,173 total
includes taxes & fees
Oct 5 - Oct 6
Galleon Villas by Hello Cayman Vacation
A beach with clear blue water, a sandy shore, and a few umbrellas.

18. 2BR/2BA Peaceful Retreat, Patio, Walk to Beach

2BR/2BA Peaceful Retreat, Patio, Walk to Beach
West Bay
The price is ￥20,382
￥47,120 total
includes taxes & fees
Sep 27 - Sep 28
2BR/2BA Peaceful Retreat, Patio, Walk to Beach
A spacious living room with a large window, a ceiling fan, and a view of the ocean.

19. 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 ￥613,392
￥871,331 total
includes taxes & fees
Sep 27 - Sep 28
Pease Bay House Cayman Islands
A row of colorful houses reflecting on calm water, with a cloudy sky above.

20. Waterfront Sanctuary Serene, Grand Harbour, 2 Bed, 2 Bath, Pool, Patio

Waterfront Sanctuary Serene, Grand Harbour, 2 Bed, 2 Bath, Pool, Patio
Grand Harbour
9.8 out of 10, Exceptional, (6 reviews)
"The photos on the site do not do this condo justice. It is much nicer then the photos make it look. Really clean, had plenty of towels, quite spacious, nice little deck looking at the water, convenient to shops and restaurants and lovely pool. Would definitely stay here again! "
United States
Cynthia
The price is ￥31,896
￥48,624 total
includes taxes & fees
Oct 23 - Oct 24
Waterfront Sanctuary Serene, Grand Harbour, 2 Bed, 2 Bath, Pool, Patio
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

The Grove

The Grove

10/10 Excellent
"Amazing location"
Dylan 4-night trip
Posted less than an hour ago
The Grove

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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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?

Rum Reef, 6 bedroom house in North Side, pool, private beach, kayaks, bikes.: This vacation home rental outside of Old Man Bay is located on the beach and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a garden.

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.