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Old Man Bay Vacation Rentals

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Our top choices for Old Man Bay vacation rentals

1. 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 CA $349
CA $654 total
includes taxes & fees
Sep 14 - Sep 15
Stunning beachfront condo. Relax, Enjoy, Sunset, RumPoint, Pool & Heated Jacuzzi

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.
The price is CA $299
CA $538 total
includes taxes & fees
Sep 4 - Sep 5
The Big Chill - Beach Cottage at The Sea Lodges in Cayman Kai / Rum Point

3. 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 CA $152
CA $249 total
includes taxes & fees
Sep 4 - Sep 5
Country Road, Take me Home- your own Island Cottage!

4. 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 CA $123
CA $269 total
includes taxes & fees
Sep 4 - Sep 5
Relax and Unwind at our cozy 1-bedroom Apt, within mins away from the beach

5. 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 CA $907
CA $1,073 total
includes taxes & fees
Sep 13 - Sep 14
Galleon Villas by Hello Cayman Vacation

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 CA $194
CA $236 total
includes taxes & fees
Sep 4 - Sep 5
Slice of Paradise- 2 mins from Spotts Beach!

7. Casa de Bells 3

Casa de Bells 3
Patricks Island
The price is CA $208
CA $380 total
includes taxes & fees
Sep 4 - Sep 5
Casa de Bells 3

8. 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 CA $198
CA $449 total
includes taxes & fees
Sep 7 - Sep 8
Relaxing, tastefully decorated one-bedroom unit with all modern facilities

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 CA $208
CA $380 total
includes taxes & fees
Sep 4 - Sep 5
Casa de Bells 2 - Studio apartment with pool, gazebo, private entrance & parking

10. 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 CA $197
CA $367 total
includes taxes & fees
Sep 4 - Sep 5
Beautiful one bedroom apartment

11. 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 CA $150
CA $285 total
includes taxes & fees
Sep 12 - Sep 13
Charming 1-bedroom apartment in enchanting Savannah, Cayman Islands

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
The price is CA $368
CA $558 total
includes taxes & fees
Sep 4 - Sep 5
Waterfront Sanctuary Serene, Grand Harbour, 2 Bed, 2 Bath, Pool, Patio

13. 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 CA $5,404
CA $8,035 total
includes taxes & fees
Sep 4 - Sep 5
Pease Bay House Cayman Islands

14. Luxurious Oceanfront Villa El Oceano with Ocean views

Luxurious Oceanfront Villa El Oceano with Ocean views
Grand Harbour
9.4 out of 10, Exceptional, (8 reviews)
"This was a very nice property, well maintained, appropriately furnished, comfortable, clean. I would recommend this place for a family."
United States
Jay S.
The price is CA $1,933
CA $3,280 total
includes taxes & fees
Sep 4 - Sep 5
Luxurious Oceanfront Villa El Oceano with Ocean views

15. Cayman Wind and Sea!

Cayman Wind and Sea!
West Bay
10.0 out of 10, Exceptional, (18 reviews)
"Place was beautiful!"
United States
Anonymous traveller
The price is CA $348
CA $868 total
includes taxes & fees
Sep 4 - Sep 5
Cayman Wind and Sea!

16. BE WHERE THE CRUISE SHIP CROWDS CAN'T GO! Oceanfront resort on Seven Mile Beach

BE WHERE THE CRUISE SHIP CROWDS CAN'T GO! Oceanfront resort on Seven Mile Beach
George Town
9.8 out of 10, Exceptional, (110 reviews)
"The pool area was nice! And we loved the swim up bar. The condo was clean and it was very quiet! Our host responded quickly to all of our questions and was very accommodating. "
United States
Mary M.
The price is CA $414
CA $679 total
includes taxes & fees
Sep 4 - Sep 5
BE WHERE THE CRUISE SHIP CROWDS CAN'T GO! Oceanfront resort on Seven Mile Beach

17. 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 CA $147
CA $315 total
includes taxes & fees
Sep 4 - Sep 5
S4 BP | Steps to Beach | Save 15% if Book Non-Refundable

18. Cayman Luxury Rentals at Lighthouse Point Residences

Cayman Luxury Rentals at Lighthouse Point Residences
3.5 star property
Northwest Point
9.4 out of 10, Exceptional, (3 reviews)
"A very perfect place!"
United States
Kirk Thomas
The price is CA $709
CA $1,061 total
includes taxes & fees
Sep 4 - Sep 5
Cayman Luxury Rentals at Lighthouse Point Residences

19. 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 CA $186
CA $472 total
includes taxes & fees
Sep 17 - Sep 18
Minutes From 7 Mile Beach
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

Find out more about Old Man Bay

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Old Man Bay. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.