Old Man Bay Rentals

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388 Houses

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23

Christmas Palms by Grand Cayman Villas and Condos

Grand Cayman / Old Man Bay

Old Man Bay house

4 10 min stay varies

4 bedrooms
sleeps 10
min stay varies

Swimming pool
Child Friendly
Air conditioning

“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

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Map

Price per night from

$802

Price per night from

$802

31

Villa Caymanas by Grand Cayman Villas and Condos

Grand Cayman / Old Man Bay

Old Man Bay house

4 8 min stay varies

4 bedrooms
sleeps 8
min stay varies

Swimming pool
Child Friendly
Air conditioning

“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

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Map

Price per night from

$813

Price per night from

$813

12

Truly Oceanfront luxury in Grand Cayman

Grand Cayman / Old Man Bay

Old Man Bay apartment

3 6 5 nights min

3 bedrooms
sleeps 6
5 nights min

Beach / lakeside relaxation
Swimming pool
Child Friendly

“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!

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Map

Price per night from

$258

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$258

Details

23

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

Grand Cayman / Old Man Bay

Old Man Bay condo

3 6 4 nights min

3 bedrooms
sleeps 6
4 nights min

Swimming pool
Child Friendly
Air conditioning

Map

Price per night from

$327

Responds fast!
avg. 1 hour 52 minutes

Price per night from

$327

Details

23

Coral Cottage Pink by Grand Cayman Villas and Condos

Grand Cayman / Old Man Bay

Old Man Bay house

3 6 min stay varies

3 bedrooms
sleeps 6
min stay varies

Swimming pool
Child Friendly
Air conditioning

Map

Price per night from

$457

Price per night from

$457

24

Northern Lights No. 5 by Grand Cayman Villas and Condos

Grand Cayman / Old Man Bay

Old Man Bay condo

3 8 min stay varies

3 bedrooms
sleeps 8
min stay varies

Swimming pool
Child Friendly
Air conditioning

Price per night from

$258

Price per night from

$258

27

Cayman Sands by Grand Cayman Villas and Condos

Grand Cayman / Old Man Bay

Old Man Bay house

5 14 min stay varies

5 bedrooms
sleeps 14
min stay varies

Swimming pool
Child Friendly
Air conditioning

“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

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Map

Price per night from

$974

Price per night from

$974

24

Coral Cottage Yellow by Grand Cayman Villas and Condos

Grand Cayman / Old Man Bay

Old Man Bay house

3 6 min stay varies

3 bedrooms
sleeps 6
min stay varies

Swimming pool
Child Friendly
Air conditioning

Map

Price per night from

$457

Price per night from

$457

26

Grand Cayman Northern Lights Beachfront Villa

Grand Cayman / Old Man Bay

Old Man Bay condo

2 6 min stay varies

2 bedrooms
sleeps 6
min stay varies

Beach / lakeside relaxation
Swimming pool
Child Friendly

“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

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Map

Price per night from

$250

Price per night from

$250

29

Coral Cottages by Grand Cayman Villas and Condos

Grand Cayman / Old Man Bay

Old Man Bay house

6 12 min stay varies

6 bedrooms
sleeps 12
min stay varies

Swimming pool
Child Friendly
Air conditioning

Map

Price per night from

$911

Price per night from

$911

24

Villa Spirit

Grand Cayman / Old Man Bay

Old Man Bay house

3 6 min stay varies

3 bedrooms
sleeps 6
min stay varies

Swimming pool
Child Friendly
Air conditioning

Map

Price per night from

$415

Price per night from

$415

Great rentals within 20 miles that match your search

Distance approx 13.8 km from Old Man Bay

43

3 Bed Condo with Huge Patio on Seven Mile Beach

Grand Cayman / Seven Mile Beach

Seven Mile Beach apartment

3 6 min stay varies

3 bedrooms
sleeps 6
min stay varies

Beach / lakeside relaxation
Nearest beach 0 mi
Swimming pool

“Excellent Condo With Very Attentive Owner” This is an excellent condo with wonderful view and large terrace. Its spacious and well worth the climb of three stairs. The apartment was probably the best equipped rental we have EVER stayed in (and we have

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Price per night from

$378

Responds fast!
avg. 2 hours 12 minutes

Price per night from

$378

Details

Distance approx 15.62 km from Old Man Bay

29

Cayman Islands Divers Paradise 1st Floor Oceanfront Condo

Grand Cayman / Seven Mile Beach

Seven Mile Beach condo

2 8 3 nights min

2 bedrooms
sleeps 8
3 nights min

Beach / lakeside relaxation
Nearest beach 1 mi
Swimming pool

Price per night from

$189

Responds fast!
avg. 57 minutes

Price per night from

$189

Details

Distance approx 2.24 km from Old Man Bay

21

"A Mid-Winter Night's Dream" Grand Cayman Oceanfront, Quiet, Secluded, Rum Point

Grand Cayman / North Side

North Side apartment

2 6 min stay varies

2 bedrooms
sleeps 6
min stay varies

Beach / lakeside relaxation
Swimming pool
Child Friendly

“Loved it” We loved the Rum Point area. The condo was clean. Pool area was clean. We enjoyed the area enough for us to do. When we wanted to do more drove 45 minutes to Seven Mile Beach. Just a great location

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Price per night from

$264

Responds fast!
avg. 2 hours 41 minutes

Price per night from

$264

Details

Distance approx 13.67 km from Old Man Bay

36

Spectacular Ground Floor Condo on Seven Mile Beach - Laguna del Mar

Grand Cayman / Seven Mile Beach

Seven Mile Beach condo

3 8 min stay varies

3 bedrooms
sleeps 8
min stay varies

Child Friendly

Price per night from

$691

Responds fast!
avg. 50 minutes

Price per night from

$691

Details

Distance approx 13.96 km from Old Man Bay

9

Hilton Estates, Grand Cayman

Grand Cayman / George Town

George Town house

3 6 min stay varies

3 bedrooms
sleeps 6
min stay varies

Swimming pool
Child Friendly
Air conditioning

Price per night from

$293

Price per night from

$293

Distance approx 13.72 km from Old Man Bay

34

Seven Mile Beach - Sunset Cove - Garden View

Grand Cayman / Seven Mile Beach

Seven Mile Beach condo

2 4 4 nights min

2 bedrooms
sleeps 4
4 nights min

Swimming pool
Child Friendly
Air conditioning

Price per night from

$276

Price per night from

$276

Details

Distance approx 13.66 km from Old Man Bay

68

Cayman Reef Resort 29 - Ocean Front Resort

Grand Cayman / Seven Mile Beach

Seven Mile Beach apartment

3 7 4 nights min

3 bedrooms
sleeps 7
4 nights min

Beach / lakeside relaxation
Child Friendly
Air conditioning

“Location, Location, location!!!!” Location was absolutely perfect. You could walk to most places and although we had a car, we didn't need it while at this condo. The owner was very sensitive to ensuring we had everything we needed and felt comfortabl

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Certificate of Excellence

Price per night from

$1,026

Price per night from

$1,026

Details

Distance approx 6.52 km from Old Man Bay

28

Oceanfront Ground Floor 2 bedroom 2 bathroom sleeps 4-6

Grand Cayman / North Side

North Side condo

2 6 min stay varies

2 bedrooms
sleeps 6
min stay varies

Swimming pool
Child Friendly
Air conditioning

Price per night from

$293

Price per night from

$293

Details

Distance approx 14.21 km from Old Man Bay

21

Oceanfront directly on 7 Mile Beach - Email for Specials!

Grand Cayman / Seven Mile Beach

Seven Mile Beach apartment

2 5 min stay varies

2 bedrooms
sleeps 5
min stay varies

Beach / lakeside relaxation
Swimming pool
Child Friendly

“The perfect location...Coffee in the morning on the porch with the ocean.” We just returned from a 10 night stay in Unit 11. This condo complex is away from the crowds of the big hotels but still has the perfect private stretch of 12 mile beach. Jim a

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Price per night from

$435

Price per night from

$435

Distance approx 5.64 km from Old Man Bay

38

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

Grand Cayman / East End

East End condo

1 4 7 nights min

1 bedroom
sleeps 4
7 nights min

Swimming pool
Child Friendly
Air conditioning

Price per night from

$214

Price per night from

$214

Details

Distance approx 14.06 km from Old Man Bay

18

Beach Is 37 Steps From Front Door!!!

Grand Cayman / West Bay

West Bay condo

1 4 3 nights min

1 bedroom
sleeps 4
3 nights min

Beach / lakeside relaxation
Nearest beach 0.1 mi
Swimming pool

Price per night from

$323

Responds fast!
avg. 3 hours 24 minutes

Price per night from

$323

Details

Distance approx 13.59 km from Old Man Bay

55

Cayman Reef Resort #50 - Best Value on the Beach

Grand Cayman / Seven Mile Beach

Seven Mile Beach apartment

1 4 3 nights min

1 bedroom
sleeps 4
3 nights min

Beach / lakeside relaxation
Swimming pool
Child Friendly

“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

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Certificate of Excellence

Price per night from

$528

Price per night from

$528

Details

Distance approx 13.69 km from Old Man Bay

24

On the Beach -- As Good As It Gets

Grand Cayman / George Town

George Town house

5 10 7 nights min

5 bedrooms
sleeps 10
7 nights min

Beach / lakeside relaxation
Swimming pool
Suitable for children age 5+

Price per night from

$4,186

Price per night from

$4,186

Distance approx 5.52 km from Old Man Bay

32

Morritt's Tortuga Club: Studio, Sleeps 2, Full Kitchen

Grand Cayman / East End

East End condo

1 2 7 nights min

1 bedroom
sleeps 2
7 nights min

Swimming pool
Child Friendly
Air conditioning

Price per night from

$147

Price per night from

$147

Details

Distance approx 14.82 km from Old Man Bay

18

Cayman Island Splendor at the Iron Shore House

Grand Cayman / West Bay

West Bay guest house

3 2 1 night min

3 bedrooms
sleeps 2
1 night min

Nearest beach 2 mi
Child Friendly
Air conditioning

Price per night from

$112

Responds fast!
avg. 6 minutes

Price per night from

$112

Details

Distance approx 13.66 km from Old Man Bay

49

Cayman Reef Resort #32 - Steps away from the Beach

Grand Cayman / Seven Mile Beach

Seven Mile Beach apartment

1 4 3 nights min

1 bedroom
sleeps 4
3 nights min

Beach / lakeside relaxation
Swimming pool
Child Friendly

Certificate of Excellence

Price per night from

$698

Price per night from

$698

Distance approx 13.53 km from Old Man Bay

19

Heart of Seven Mile Beach

Grand Cayman / Seven Mile Beach

Seven Mile Beach apartment

3 6 2 nights min

3 bedrooms
sleeps 6
2 nights min

Nearest beach 0 mi
Child Friendly
Car not necessary

Price per night from

$469

Responds fast!
avg. 2 hours 4 minutes

Price per night from

$469

Distance approx 14.07 km from Old Man Bay

25

Sea Jewel, 2BR, 2BA, oceanview villa

Grand Cayman / West Bay

West Bay villa

2 6 5 nights min

2 bedrooms
sleeps 6
5 nights min

Swimming pool
Child Friendly
Air conditioning

Price per night from

$381

Price per night from

$381

Distance approx 13.42 km from Old Man Bay

46

Casa Caribe penths oceanvw Condo #18 Heart of 7-Mile Beach near Ritz 15% off Apr

Grand Cayman / Seven Mile Beach

Seven Mile Beach apartment

3 7 7 nights min

3 bedrooms
sleeps 7
7 nights min

Beach / lakeside relaxation
Swimming pool
Car not necessary

“Perfectly perfect!!!” This penthouse was perfect for our 8 day vacation. The unit was beautifully decorated and set up for cooking with all the spices, pans, etc. needed. The beach was a few steps away from our unit, with views from the deck of a pe

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Price per night from

$410

Price per night from

$410

Distance approx 13.67 km from Old Man Bay

39

Magnificent Ocean Views in the Heart of 7 Mile Beach !! Fully Stocked!

Grand Cayman / Seven Mile Beach

Seven Mile Beach condo

2 4 1 night min

2 bedrooms
sleeps 4
1 night min

Swimming pool
Child Friendly
Air conditioning

“A Peaceful Place In Paradise” Where do I begin ~ My first trip to Grand Cayman Islands and staying at "Regal Beach" in the beautiful, bright, clean, two-bedroom Condo in paradise was truly amazing! The condo not only has a beautiful view of the Car

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Price per night from

$296

Responds fast!
avg. 2 hours 54 minutes

Price per night from

$296

Details

Distance approx 14.32 km from Old Man Bay

29

Sea Breeze - A Luxury 4br + den SMB Condo

Grand Cayman / Seven Mile Beach

Seven Mile Beach condo

4 10 7 nights min

4 bedrooms
sleeps 10
7 nights min

Beach / lakeside relaxation
Nearest beach 0.1 mi
Swimming pool

Price per night from

$922

Price per night from

$922

Details

Distance approx 14.67 km from Old Man Bay

21

GCAYMAN: Your Very Own Private Seven Mile Beach Area Tropical Blue Guest Home

Grand Cayman / Seven Mile Beach

Seven Mile Beach guest house

2 6 min stay varies

2 bedrooms
sleeps 6
min stay varies

Beach / lakeside relaxation
Nearest beach 0.1 mi
Child Friendly

“Cayman Relaxed” What a great place. Away from the congestion of seven mile beach. Two good restaurants, beach and a grocery store within walking distance. We made good use of the two outdoor hammocks. Nicely appointed kitchen although we just used

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Price per night from

$235

Price per night from

$235

Details

Distance approx 5.69 km from Old Man Bay

24

Grand Cayman: large 2 bedroom,2 bedroom apartment with a sea view terrace

Grand Cayman / Bodden Town

Bodden Town apartment

2 4 min stay varies

2 bedrooms
sleeps 4
min stay varies

Nearest beach 0.1 mi
Child Friendly
Air conditioning

Price per night from

$76

Responds fast!
avg. 59 minutes

Price per night from

$76

Distance approx 6.47 km from Old Man Bay

37

Cos Kai - 5 Bedrooms at Rum Point - Book Now

Grand Cayman / Rum Point

Rum Point villa

5 15 5 nights min

5 bedrooms
sleeps 15
5 nights min

Child Friendly

Price per night from

$1,229

Price per night from

$1,229

Distance approx 13.94 km from Old Man Bay

20

Sea Breeze 5 luxury 4 bedroom on SMB

Grand Cayman / Seven Mile Beach

Seven Mile Beach condo

4 10 min stay varies

4 bedrooms
sleeps 10
min stay varies

Beach / lakeside relaxation
Swimming pool
Ask about children

Price per night from

$1,024

Price per night from

$1,024

Distance approx 5.44 km from Old Man Bay

14

Tequila Sunrise Villa

Grand Cayman / East End

East End villa

3 10 min stay varies

3 bedrooms
sleeps 10
min stay varies

Child Friendly

Price per night from

$352

Responds fast!
avg. 2 hours 58 minutes

Price per night from

$352

Distance approx 13.43 km from Old Man Bay

33

Mora - 7 Bedrooms at South Sound - Book Now

Grand Cayman / George Town

George Town villa

7 18 min stay varies

7 bedrooms
sleeps 18
min stay varies

Child Friendly

Price per night from

$1,945

Price per night from

$1,945

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