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Old Man Bay Rentals

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Price range

Per night

$10 - $500

Old Man Bay Rentals

403 Houses

New Listing - 3 Bedroom Ocean Front - Tranquil, Peaceful Location! Snorkeling!

Old Man Bay condo

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 55 minutes

Price per night from

$275

1 / 34

Christmas Palms by Grand Cayman Villas and Condos

Old Man Bay house

4 bedrooms / 4 bathrooms / sleeps 10

“Wedding Week Stay” In a rare occurrence these days, Christmas Palms actually exists as it is portrayed in both photos and video. Everything aspect of our rental was as we hoped for and expected and would have no reservation in staying there again. T

Responds fast! avg. 3 hours 41 minutes

Price per night from

$700

1 / 24

Villa Caymanas by Grand Cayman Villas and Condos

Old Man Bay house

4 bedrooms / 5 bathrooms / sleeps 8

“A perfect vacation!” The second spring time vacation we had at villa caymanas. When arriving, the view entering the front door blows me away each time I arrive. Property is well maintained and everything was super clean. Private ocean side back y

Responds fast! avg. 3 hours 41 minutes

Price per night from

$710

1 / 31

Truly Oceanfront luxury in Grand Cayman

Old Man Bay apartment

3 bedrooms / 3 bathrooms / sleeps 6

“Beautiful location” Beautiful view of the ocean and great location right on the beach in a quiet area of cayman. Condo has lots of amenities and a nice-sized swimming pool. We had a great time!

Responds fast! avg. 2 hours 19 minutes

Price per night from

$225

1 / 12

Ocean Front Villa -New on the Market Available Christmas- New Years -High Season

Old Man Bay house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 55 minutes

Price per night from

$500

1 / 20

Your Oceanside Retreat Awaits!

Old Man Bay apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Peace and tranquility” This is a lovely complex of just 12 apartments. We were there over Christmas, probably the islands busiest time, but it was still very quiet at this spot (until our 3 boys arrived??!). The apartment has lovely views of the poo

Price per night from

$265

1 / 17

YOU'VE Arrived! Beachfront 3BR condo w/ Pool-Relax... North Side near Rum Point

Old Man Bay condo

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 36 minutes

Price per night from

$285

1 / 23

Coral Cottage Pink by Grand Cayman Villas and Condos

Old Man Bay house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 41 minutes

Price per night from

$399

1 / 23

Northern Lights No. 5 by Grand Cayman Villas and Condos

Old Man Bay condo

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 41 minutes

Price per night from

$225

1 / 28

Cayman Sands by Grand Cayman Villas and Condos

Old Man Bay house

5 bedrooms / 5 bathrooms / sleeps 14

“A wonderful, relaxing paradise” I recently stayed at Cayman Sands with my husband, my in-laws, and our 2 young girls, ages 4 and 6. This home is everything we could have asked for - as gorgeous as the pictures, but even fresher (the larger bedrooms h

Responds fast! avg. 3 hours 41 minutes

Price per night from

$850

1 / 27

Grand Cayman Northern Lights Beachfront Villa

Old Man Bay condo

2 bedrooms / 3 bathrooms / sleeps 6

“A piece of heaven in the Carribean” We arrived at Northern Lights after a long, cold, snowy winter to find a place that exceeded our expectations. Many times during the week, we spoke about how happy we were that we chose Northern Lights. The settin

Price per night from

$250

1 / 26

Coral Cottages by Grand Cayman Villas and Condos

Old Man Bay house

6 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 3 hours 41 minutes

Price per night from

$775

1 / 28

Coral Cottage Yellow by Grand Cayman Villas and Condos

Old Man Bay house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 41 minutes

Price per night from

$399

1 / 25

Villa Spirit

Old Man Bay house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$415

1 / 23

Great rentals within 20 miles that match your search

Three Little Birds -2BR+ Villa, Private Beach

Rum Point house

2 bedrooms / 2 bathrooms / sleeps 6

“Gorgeous, peaceful- perfect island setting!” We rarely saw any other guests while staying at Three Little Birds. The place is well appointed, clean, comfortable, with a fully stocked kitchen; lovely sitting room overlooking the little beach. Swimming

Responds fast! avg. 3 hours 56 minutes

Price per night from

$309

1 / 32

Ocean Pearl Beachfront Townhome Vacation Rental

North Side house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$249

1 / 27

Cayman Stead, 2 BR, 2 bath,BEACH condo,sleeps 6

North Side apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect paradise” This was perfect for my family of 2 teenage girls, my wife and I. We wanted the hot Caribbean vacation without the resort. We dove and explored everyday. This condo had everything we needed, pool, right on the sea, internet, full kit

Price per night from

$249

1 / 13

OCEANFRONT 3 BR 2 BATH VILLA ON PRIVATE, SANDY BEACH & AMAZING SNORKELING!!

Rum Point villa

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 10 minutes

Price per night from

$175

1 / 24

Luxury Condo centrally located - Park Place (17)

Seven Mile Beach apartment

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$177

1 / 21

Direct Beachfront Condo,quiet,with pool and tennis

George Town apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$199

1 / 21

10 feet from the beach, Grandview has a grand view

George Town apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$309

1 / 32

First Floor Oceanfront Condo in Top Location!

West Bay apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 29 minutes

Price per night from

$224

1 / 21

Cayman Reef Resort #33 - Personal Lanai Overlooking Beach & Ocean

Seven Mile Beach apartment

1 bedroom / 1 bathroom / sleeps 4

“Wonderful Stay, Beautiful Condo and Grounds, Easy to Work With” Condo is beautiful and exactly as described in the listing and in all communications with Marc. Very close to beach and water. Even closer than looks in pictures. Literally few steps ou

Responds fast! avg. 3 hours 48 minutes

Price per night from

$493

1 / 10

The Reef Resort - Grand Cayman: 1-BR, Sleeps 4,

East End condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 0 minutes

Price per night from

$175

1 / 38

Cayman Reef Resort #50 - Best Value on the Beach

Seven Mile Beach apartment

1 bedroom / 1 bathroom / sleeps 4

“Excellent Long Term Stay” Unit 50 was very suitable for my wife and me for a four week visit. We thought the overall experience was excellent and it provided excellent value for our money. We would definitely recommend Unit 50 and we plan to retu

Responds fast! avg. 3 hours 48 minutes

Price per night from

$448

1 / 55

Beachfront Retreat, just off Spotts Beach - ONLY 10 minutes from George Town

Bodden Town condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$394

1 / 7

Cayman Reef Resort #32 - Steps away from the Beach

Seven Mile Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 48 minutes

Price per night from

$593

1 / 49

Westpoint townhome

West Bay townhouse

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$189

1 / 18

Cayman Islands Kaibo Yacht Club Condo - Rum Point

Rum Point condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 2 minutes

Price per night from

$394

1 / 31

Beachfront Winter Getaway at Resplendent Kaibo

North Side apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Heaven on Earth” My husband and myself have stayed at Kaibo Yacht Club B-13 several times a year for the past 8 years. The condo is wonderful, fully furnished, excellant condition and right on the beach. Walk out the back door into the pool. We lov

Price per night from

$145

1 / 25

Your Paradise Pointe of View

West Bay apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$130

1 / 33

Cayman Reef Resort 56 - Luxury on Seven Mile Beach

Seven Mile Beach apartment

3 bedrooms / 2 bathrooms / sleeps 7

“Fantastic Condo on a fantastic beach” This condo was more than we could have hoped for. Modern, new, clean and extremely well stocked with kitchen ware, towels and bed linens. Two screened in patios with a view of the sunset. A very clean pool just of

Responds fast! avg. 3 hours 48 minutes

Price per night from

$872

1 / 79

Morritt's Tortuga Club: 1-BR, Sleeps 4, Full Kitchen

East End condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 52 minutes

Price per night from

$176

1 / 31

Beautiful 7 Mile Beach Oceanfront Condo

Seven Mile Beach apartment

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 1 hour 16 minutes

Price per night from

$427

1 / 28

Mediterranean Villa

West Bay villa

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 12 minutes

Price per night from

$248

1 / 7

Ultimate Oceanfront Penthouse W Unbeatable Views!!

Seven Mile Beach apartment

3 bedrooms / 2 bathrooms / sleeps 7

“Absolutely fabulous!!!” All I can say is we were spoiled! The condo was huge and comfortable, kitchen had everything. We enjoyed the pools and beach also. I would definitely recommend this place to anyone with a family or 3 couples. There were alw

Responds fast! avg. 57 minutes

Price per night from

$568

1 / 29

Island Houses - Tranquility

Rum Point condo

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$274

1 / 7

Luxury Home near Rum Point w/ Beachfront Pool, Spectacular Views, # 4 Green

North Side villa

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$298

1 / 7
Viewing 38 of 403
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