A cave with stalactites and stalagmites, a shallow pool of water, and rock formations.

Old Man Bay Vacation Rentals

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Old Man Bay vacation rentals

Exterior

1. 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.
$5,325 nightly
The price is $5,832
Sep 10 - Sep 11
Total with taxes and fees
Pease Bay House Cayman Islands
Beach

2. 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.
$356 nightly
The price is $384
Sep 9 - Sep 10
Total with taxes and fees
The Big Chill - Beach Cottage at The Sea Lodges in Cayman Kai / Rum Point
Beach

3. 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
$184 nightly
The price is $193
Sep 9 - Sep 10
Total with taxes and fees
Relax and Unwind at our cozy 1-bedroom Apt, within mins away from the beach
Interior

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, (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.
$442 nightly
The price is $475
Sep 14 - Sep 15
Total with taxes and fees
Stunning beachfront condo. Relax, Enjoy, Sunset, RumPoint, Pool & Heated Jacuzzi
Beach

5. 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.
$180 nightly
The price is $180
Sep 14 - Sep 15
Total with taxes and fees
Country Road, Take me Home- your own Island Cottage!
Exterior

6. 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
$206 nightly
The price is $206
Sep 12 - Sep 13
Total with taxes and fees
Charming 1-bedroom apartment in enchanting Savannah, Cayman Islands
Property grounds

7. 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
$306 nightly
The price is $324
Sep 13 - Sep 14
Total with taxes and fees
Relaxing, tastefully decorated one-bedroom unit with all modern facilities
Property grounds

8. 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.
$246 nightly
The price is $264
Sep 9 - Sep 10
Total with taxes and fees
Beautiful one bedroom apartment
Interior

9. 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.
$172 nightly
The price is $172
Sep 10 - Sep 11
Total with taxes and fees
Slice of Paradise- 2 mins from Spotts Beach!
Exterior

10. Casa de Bells 3

Casa de Bells 3
Patricks Island
$257 nightly
The price is $277
Sep 9 - Sep 10
Total with taxes and fees
Casa de Bells 3
Pool

11. 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.
$257 nightly
The price is $277
Sep 12 - Sep 13
Total with taxes and fees
Casa de Bells 2 - Studio apartment with pool, gazebo, private entrance & parking
Exterior

12. 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
$278 nightly
The price is $301
Sep 10 - Sep 11
Total with taxes and fees
Waterfront Sanctuary Serene, Grand Harbour, 2 Bed, 2 Bath, Pool, Patio
Exterior

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.
$242 nightly
The price is $242
Sep 21 - Sep 22
Total with taxes and fees
Cozy 1-Bed, Pool + Sea and Dining close by
Private kitchen

14. 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.
$285 nightly
The price is $285
Sep 11 - Sep 12
Total with taxes and fees
1BD 1.5BA Convenient and Cosy Apartment with Pool
Room

15. Family Townhouse Minutes to 7Mile Beach

Family Townhouse Minutes to 7Mile Beach
George Town
10.0 out of 10, Exceptional, (4 reviews)
"Great place - great location !! Perfect for our stay!!"
United States
Sean D.
$314 nightly
The price is $314
Sep 9 - Sep 10
Total with taxes and fees
Family Townhouse Minutes to 7Mile Beach
Beach

16. 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
$567 nightly
The price is $637
Oct 5 - Oct 6
Total with taxes and fees
Galleon Villas by Hello Cayman Vacation
House

17. The Grove 33 in Grand Cayman

The Grove 33 in Grand Cayman
2.0 star property
Seven Mile Beach
$451 nightly
The price is $514
Sep 12 - Sep 13
Total with taxes and fees
The Grove 33 in Grand Cayman
Beach

18. Modern 1BR | Pool & BBQ | Steps to 7 Mile Beach

Modern 1BR | Pool & BBQ | Steps to 7 Mile Beach
Grand Cayman
9.0 out of 10, Wonderful, (4 reviews)
"Great stay! Host was so helpful and everything was exactly as described. Loved every second and would absolutely stay again!!"
United States
Anna Emily G.
$401 nightly
The price is $426
Sep 9 - Sep 10
Total with taxes and fees
Modern 1BR | Pool & BBQ | Steps to 7 Mile Beach
Beach

19. Regal Beach Club - Fabulous 2-bedroom Apt

Regal Beach Club - Fabulous 2-bedroom Apt
George Town
10.0 out of 10, Exceptional, (2 reviews)
"This property was fantastic! The condo was updated and very clean and right on the beach. Cannot say enough good things about my stay here. Will absolutely be booking again "
Canada
Allison W.
$331 nightly
The price is $350
Sep 17 - Sep 18
Total with taxes and fees
Regal Beach Club - Fabulous 2-bedroom Apt
Room

20. Seven Mile Beach 2BR Beach walk, kayak + tennis

Seven Mile Beach 2BR Beach walk, kayak + tennis
Seven Mile Beach
$424 nightly
The price is $424
Sep 14 - Sep 15
Total with taxes and fees
Seven Mile Beach 2BR Beach walk, kayak + tennis
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Old Man Bay Hotel Reviews

The Grove

The Grove

10/10 Excellent
"The Groove was excellent enjoyed my stay will return back"
Simone 4-night trip
Posted less than an hour ago
The Grove

Find out more about Old Man Bay

Everything you need to know about Old Man Bay vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Old Man Bay vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Old Man Bay vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Old Man Bay vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Old Man Bay. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Old Man Bay in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $387 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Old Man Bay rentals

At Expedia, we put the best Old Man Bay vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Old Man Bay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Old Man Bay vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Old Man Bay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.