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Old Man Bay Holiday Rentals

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50 rentals in Old Man Bay.
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Villa Caymanas: Caribbean Villa w/ Fabulous Snorkeling, Pool, & Panoramic, holiday rental in Old Man Bay

Villa Caymanas: Caribbean Villa w/ Fabulous Snorkeling, Pool, & Panoramic

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Cayman Sands: Secluded Beach Villa with Pool Atrium & Guest Cottage, holiday rental in Old Man Bay

Cayman Sands: Secluded Beach Villa with Pool Atrium & Guest Cottage

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Babylon Reef: Recently Renovated Villa with Backyard Snorkeling and a Crystal Bl, holiday rental in Old Man Bay

Babylon Reef: Recently Renovated Villa with Backyard Snorkeling and a Crystal Bl

0 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Villa Esprit, holiday rental in Old Man Bay

Villa Esprit

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Northern Lights #5: 2-Story Beachfront Oasis in North Side w/Pool, Dock, & Snork, holiday rental in Old Man Bay

Northern Lights #5: 2-Story Beachfront Oasis in North Side w/Pool, Dock, & Snork

0 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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YOU'VE Arrived! Beachfront 3BR condo w/ Pool-Relax... North Side near Rum Point, holiday rental in Old Man Bay

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

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Coral Cottages: Two Oceanfront Villas with Infinity Pools in a Scuba Diver's, holiday rental in Old Man Bay

Coral Cottages: Two Oceanfront Villas with Infinity Pools in a Scuba Diver's

6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Northern Lights #5: 2-Story Beachfront Oasis in North Side w/Pool, Dock, holiday rental in Old Man Bay

Northern Lights #5: 2-Story Beachfront Oasis in North Side w/Pool, Dock

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Coral Cottage Pink: Cozy Old Man Bay Cottage with Infinity Pool Perfect for, holiday rental in Old Man Bay

Coral Cottage Pink: Cozy Old Man Bay Cottage with Infinity Pool Perfect for

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Coral Cottage Yellow: A Scuba Diver's Paradise with Infinity Pool & Ocean Reef, holiday rental in Old Man Bay

Coral Cottage Yellow: A Scuba Diver's Paradise with Infinity Pool & Ocean Reef

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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CALYPSO BLUE: Modern Beachfront Villa with Pool and Beautiful Sunsets!, holiday rental in Old Man Bay

CALYPSO BLUE: Modern Beachfront Villa with Pool and Beautiful Sunsets!

6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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The Harvey Nicole: Beautiful Ocean Front Condo Grand Cayman, holiday rental in Old Man Bay

The Harvey Nicole: Beautiful Ocean Front Condo Grand Cayman

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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2BR-Sea Beauty: Cayman Style Gingerbread Cottage with 300' Private Beach, holiday rental in Old Man Bay

2BR-Sea Beauty: Cayman Style Gingerbread Cottage with 300' Private Beach

0 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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5BR-Cayman Sands: Private Oceanfront Villa in Old Man Bay - Excellent Renovation, holiday rental in Old Man Bay

5BR-Cayman Sands: Private Oceanfront Villa in Old Man Bay - Excellent Renovation

0 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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'A Mid-Winter Night's Dream' Grand Cayman Oceanfront, Quiet, Secluded, Rum Point, holiday rental in Old Man Bay

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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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WINDSONG - Beachfront w/ Private Dock & 50 ft Pool, holiday rental in Old Man Bay

WINDSONG - Beachfront w/ Private Dock & 50 ft Pool

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Gorgeous Beachfront Villa, Azure Breeze #5, holiday rental in Old Man Bay

Gorgeous Beachfront Villa, Azure Breeze #5

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Crescent Beach (Sand) at Half Moon Bay, holiday rental in Old Man Bay

Crescent Beach (Sand) at Half Moon Bay

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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4BR-Christmas Palms: Private Oceanfront Villa with Pool and Excellent Snorkelin, holiday rental in Old Man Bay

4BR-Christmas Palms: Private Oceanfront Villa with Pool and Excellent Snorkelin

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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4BR-Villa Caymanas: Luxury Oceanfront Villa, Private Pool, Oceanfront Balcony., holiday rental in Old Man Bay

4BR-Villa Caymanas: Luxury Oceanfront Villa, Private Pool, Oceanfront Balcony.

0 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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2BR-KiToCay-Sunny Oceanfront Home with Lovely Beach. Walk to Dining and Bar!, holiday rental in Old Man Bay

2BR-KiToCay-Sunny Oceanfront Home with Lovely Beach. Walk to Dining and Bar!

0 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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The peace and tranquility of this cottage works wonders on the soul...., holiday rental in Old Man Bay

The peace and tranquility of this cottage works wonders on the soul....

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Crescent Beach (Sky) at Half Moon Bay, holiday rental in Old Man Bay

Crescent Beach (Sky) at Half Moon Bay

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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2BR-Conched Out: Private, Caribbean-Style Cottage with Oceanfront Pool, holiday rental in Old Man Bay

2BR-Conched Out: Private, Caribbean-Style Cottage with Oceanfront Pool

0 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Reef Romance: Ultimate Friendcation Getaway w/ Outdoor Bar, Private Pool, holiday rental in Old Man Bay

Reef Romance: Ultimate Friendcation Getaway w/ Outdoor Bar, Private Pool

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Beach Plum Villa, holiday rental in Old Man Bay

Beach Plum Villa

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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SUMMER/FALL RATES DISCOUNTED!/OCEANFRONT VILLA ON PRIVATE SANDY BEACH!!, holiday rental in Old Man Bay

SUMMER/FALL RATES DISCOUNTED!/OCEANFRONT VILLA ON PRIVATE SANDY BEACH!!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Suncoast # 4, holiday rental in Old Man Bay

Suncoast # 4

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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4BR-Mahogany Cove: Private Oceanfront Villa with Excellent Snorkeling, holiday rental in Old Man Bay

4BR-Mahogany Cove: Private Oceanfront Villa with Excellent Snorkeling

0 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Mahogany Point 5: 3 BR / 3 BA villa in North Side, Sleeps 6, holiday rental in Old Man Bay

Mahogany Point 5: 3 BR / 3 BA villa in North Side, Sleeps 6

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Castaway Cove: Tropical Beachfront Villa with Superb Snorkeling and Coastal, holiday rental in Old Man Bay

Castaway Cove: Tropical Beachfront Villa with Superb Snorkeling and Coastal

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful White Sandy Beach. Specials: Stay 7 nights pay only for 6 nights, holiday rental in Old Man Bay

Beautiful White Sandy Beach. Specials: Stay 7 nights pay only for 6 nights

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cayman Dream: Rum Point Beach Bungalow with Pool for Oceanfront Living, holiday rental in Old Man Bay

Cayman Dream: Rum Point Beach Bungalow with Pool for Oceanfront Living

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Blue Serenity: Breezy Beach House with Backyard Snorkeling, holiday rental in Old Man Bay

Blue Serenity: Breezy Beach House with Backyard Snorkeling

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Coconut Beach: Secret Garden Oasis with Palm-Shaded Beach and Spectacular, holiday rental in Old Man Bay

Coconut Beach: Secret Garden Oasis with Palm-Shaded Beach and Spectacular

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Ocean Paradise # 4 Green - Affordable Luxury Home w/ pool, holiday rental in Old Man Bay

Ocean Paradise # 4 Green - Affordable Luxury Home w/ pool

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Perfect Large Apartment for your Grand Cayman Vacation - Unit #3, holiday rental in Old Man Bay

Perfect Large Apartment for your Grand Cayman Vacation - Unit #3

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Babylon Reef: Recently Renovated Villa with Backyard Snorkeling and a Crystal, holiday rental in Old Man Bay

Babylon Reef: Recently Renovated Villa with Backyard Snorkeling and a Crystal

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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KiToCay: Modern Beach House w/Over-the-Water Sun Deck & Private Beach Lot, holiday rental in Old Man Bay

KiToCay: Modern Beach House w/Over-the-Water Sun Deck & Private Beach Lot

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Conched Out: Island Chic Bungalow w/ Lush Tropical Landscaping,Pool & Backyard, holiday rental in Old Man Bay

Conched Out: Island Chic Bungalow w/ Lush Tropical Landscaping,Pool & Backyard

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Ocean Paradise # 3 Blue - Affordable Luxury Home w/ pool, holiday rental in Old Man Bay

Ocean Paradise # 3 Blue - Affordable Luxury Home w/ pool

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Ocean Paradise # 1 Cream - Affordable Luxury Home w/ pool, holiday rental in Old Man Bay

Ocean Paradise # 1 Cream - Affordable Luxury Home w/ pool

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Ocean Paradise # 2 Peach - Affordable Luxury Home w/ pool, holiday rental in Old Man Bay

Ocean Paradise # 2 Peach - Affordable Luxury Home w/ pool

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious, Fully Furnished Family Friendly 2 bed Apt. with Ocean View  - Unit #4, holiday rental in Old Man Bay

Spacious, Fully Furnished Family Friendly 2 bed Apt. with Ocean View - Unit #4

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Very Spacious Ocean View 2 Bed 2 Bath  - Unit #1, holiday rental in Old Man Bay

Very Spacious Ocean View 2 Bed 2 Bath - Unit #1

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Casa Tortuga, holiday rental in Old Man Bay

Casa Tortuga

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Frenchie’s Haven 3 bedroom Eco Friendly House located in Frank Sound, holiday rental in Old Man Bay

Frenchie’s Haven 3 bedroom Eco Friendly House located in Frank Sound

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mahogany Point 2, holiday rental in Old Man Bay

Mahogany Point 2

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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CORAL VISTA - Infinity Pool, Arcade, Private Cabana, Beachside Firepit, holiday rental in Old Man Bay

CORAL VISTA - Infinity Pool, Arcade, Private Cabana, Beachside Firepit

10 bedrooms
8 bathrooms
Sleeps 26
Match: Sleeps
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Beachfront Villa Vacation in the Cayman Islands, holiday rental in Old Man Bay

Beachfront Villa Vacation in the Cayman Islands

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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