Top 50 Old Man Bay Vacation Rentals

Condos (363)
Villas (153)
Houses (93)
Beachfront (442)
Golf rental (420)
Oceanfront (359)

Explore a selection of Old Man Bay vacation rentals

Sunsets And Ocean Front Luxury Awaits You!!!
Guests6
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$245 avg/night
2 beds
2 Bathrooms
Guests 6
21 reviews
Oceanfront Luxury, Awesome Views
Guests6
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$250 avg/night
3 beds
3 Bathrooms
Guests 6
59 reviews
5BR-Cayman Sands: Private Oceanfront Villa in Old Man Bay...
Guests14
Bedrooms5
Bathrooms5
Wonderful 5 / 5
$680 avg/night
5 beds
5 Bathrooms
Guests 14
24 reviews
Your Oceanside Retreat Awaits!
Guests6
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$237 avg/night
2 beds
2 Bathrooms
Guests 6
34 reviews
Its time to Relax! Beachfront 3BR Condo on the sea, North Side...
Guests6
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$322 avg/night
3 beds
3 Bathrooms
Guests 6
26 reviews
On The Bay #104-Tropical Treasure on the North Shore
Guests4
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$170 avg/night
2 beds
2 Bathrooms
Guests 4
4 reviews
2BR-Conched Out: Private, Caribbean-Style Cottage with Oceanfront...
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.7 / 5
$345 avg/night
2 beds
2 Bathrooms
Guests 4
6 reviews
3BR- Coral Cottage Yellow - Large Oceanfront Villa with Pool and...
Guests6
Bedrooms3
Bathrooms3
Wonderful 0 / 5
$413 avg/night
3 beds
3 Bathrooms
Guests 6
Castaway by the Sea - Cottage - "Private" Beach Getaway
Guests2
Bedroom1
Bathroom1
Wonderful 5 / 5
$279 avg/night
1 bed
1 Bathroom
Guests 2
48 reviews
YOU'VE ARRIVED! BREATHTAKING LUXURY BEACHFRONT VILLA, FROM...
Guests2
Bedroom1
Bathroom1
Wonderful 4.8 / 5
$159 avg/night
1 bed
1 Bathroom
Guests 2
67 reviews
Direct Beachfront 2 Bed Condo. Beautiful White Sand, Quiet, Safe
Guests5
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$159 avg/night
2 beds
2 Bathrooms
Guests 5
45 reviews
Cayman Reef 47🌴 King bed 🌴Bright Airy FULLY stocked down to to...
Guests4
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$225 avg/night
1 bed
1 Bathroom
Guests 4
32 reviews
Castaway by the Sea - Lodge - "Private" Beach Getaway
Guests2
Bedroom1
Bathroom1
Wonderful 5 / 5
$159 avg/night
1 bed
1 Bathroom
Guests 2
38 reviews
Oceanfront-Best Price on 7 Mile Beach-1 Bd # 21-Cayman Reef Resort
Guests4
Bedroom1
Bathroom1
Wonderful 4.7 / 5
$325 avg/night
1 bed
1 Bathroom
Guests 4
90 reviews
Beachfront 1 Br Condo On Seven Mile Beach At #20 Cayman Reef Resort
Guests2
Bedroom1
Bathroom1
Wonderful 4.8 / 5
$315 avg/night
1 bed
1 Bathroom
Guests 2
32 reviews
Fantastic 2 Bedroom, 7 Mile Beach, Plantation Village
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$165 avg/night
2 beds
2 Bathrooms
Guests 6
16 reviews
Beachfront 2 Bedroom Condo With Magnificent Caribbean View!
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$200 avg/night
2 beds
2 Bathrooms
Guests 6
38 reviews
Oceanfront 2 Bedroom Top Floor Condo for Rest and Relaxation
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$179 avg/night
2 beds
2 Bathrooms
Guests 6
41 reviews
Beachfront Beauty & Panoramic Views -The Retreat #23 - Steps out...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$297 avg/night
2 beds
2 Bathrooms
Guests 6
60 reviews
Rum Point Retreat #23-Beachfront beauty, panoramic views, 1767...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$297 avg/night
2 beds
2 Bathrooms
Guests 6
60 reviews
Bright & Cheerful Seven Mile beach condo!
Guests4
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$330 avg/night
2 beds
2 Bathrooms
Guests 4
65 reviews
Vitamin Sea - Beachfront and Ground Floor at Coral Bay Village
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$290 avg/night
2 beds
2 Bathrooms
Guests 4
18 reviews
Cayman Islands Stunning Condo On The Sand - Kaibo Yacht Club
Guests5
Bedrooms2
Bathrooms0
Wonderful 4.8 / 5
$299 avg/night
2 beds
0 Bathrooms
Guests 5
12 reviews
Newly Renovated Luxury Ground Floor Condo On Seven Mile Beach.
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$310 avg/night
3 beds
2 Bathrooms
Guests 6
14 reviews
Island vibes, ocean views, diving & beaches...
Guests5
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$257 avg/night
2 beds
2 Bathrooms
Guests 5
12 reviews
Windsong 3 Gorgeous condo-Balcony -Desirable Area SMB - $269...
Guests6
Bedrooms3
Bathrooms0
Wonderful 4.9 / 5
$387 avg/night
3 beds
0 Bathrooms
Guests 6
65 reviews
Charming Oceanfront Sea Lodge in Delightful Cayman Kai
Guests2
Bedroom1
Bathroom1
Wonderful 4.7 / 5
$186 avg/night
1 bed
1 Bathroom
Guests 2
64 reviews
ESCAPE TO BEACHFRONT PARADISE! FROM $99.00/NT BEST VALUE...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$148 avg/night
2 beds
2 Bathrooms
Guests 6
71 reviews
Windsong 1 Spacious Luxury-Beautiful Serene Area SMB - $269...
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$334 avg/night
3 beds
2 Bathrooms
Guests 6
51 reviews
Sunset Cove 2 Bed/2Bath Condo on Seven Mile Beach with Discounted...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$281 avg/night
2 beds
2 Bathrooms
Guests 6
28 reviews
Remodeled Family Friendly Condo in the Heart of Seven Mile Beach
Guests5
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$245 avg/night
2 beds
1 Bathroom
Guests 5
28 reviews
BEACHFRONT Condo -- Retreat at Rum Point #33 - 7th Night Free
Guests6
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$317 avg/night
2 beds
2 Bathrooms
Guests 6
90 reviews
Cayman Islands Divers Paradise 1st Floor Oceanfront Condo
Guests8
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$177 avg/night
2 beds
2 Bathrooms
Guests 8
57 reviews
Luxurious 4BR Chateau-Pool, Family-Friendly, near Spotts Beach...
Guests12
Bedrooms5
Bathrooms3
Wonderful 4.9 / 5
$440 avg/night
5 beds
3 Bathrooms
Guests 12
11 reviews
Cozy Cayman Beach Front Cottage - Emerald Sea House
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$398 avg/night
2 beds
2 Bathrooms
Guests 4
10 reviews
Beachfront 3br Condo On Seven Mile Beach At #44 Cayman Reef Resort
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.8 / 5
$475 avg/night
3 beds
2 Bathrooms
Guests 6
17 reviews
Stop Your Search-paradise Found! Caribbean Paradise-600 Ft. of...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$259 avg/night
2 beds
2 Bathrooms
Guests 6
25 reviews
Complete RENOVATION Sept 2017! Best value on Seven Mile Cayman...
Guests4
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$225 avg/night
1 bed
1 Bathroom
Guests 4
38 reviews
Oceanfront, Tortuga Kai Condo At Kaibo Yacht Club, Cayman Kai
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$150 avg/night
2 beds
2 Bathrooms
Guests 6
36 reviews
'Cayman Breeze' Luxury Beachfront Condo located at Rum...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$200 avg/night
2 beds
2 Bathrooms
Guests 6
40 reviews
Oceanfront condo at SMB, sleeps 6, just paradise!
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$425 avg/night
3 beds
2 Bathrooms
Guests 6
22 reviews
Pay 6 stay 7 thru Oct 2017! - Ocean Front Condo Cayman Kai Rum...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.7 / 5
$194 avg/night
2 beds
2 Bathrooms
Guests 6
52 reviews
Cayman Islands Divers Paradise with Direct Oceanfront
Guests8
Bedrooms3
Bathrooms3
Wonderful 4.9 / 5
$215 avg/night
3 beds
3 Bathrooms
Guests 8
29 reviews
7BR “Tatenda,” a Luxury Cayman Villas Signature Property
Guests20
Bedrooms7
Bathrooms7
Wonderful 4.5 / 5
$1,925 avg/night
7 beds
7 Bathrooms
Guests 20
12 reviews
Oceanview/Poolside Condo on Seven Mile Beach
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.7 / 5
$250 avg/night
2 beds
2 Bathrooms
Guests 6
23 reviews
NEWLY RENOVATED 7 MILE BEACHFRONT W/ SUNSET VIEW! NEAR EVERYTHING...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.7 / 5
$225 avg/night
2 beds
2 Bathrooms
Guests 6
18 reviews
Kaibo Vacation 50ft From The Water
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$190 avg/night
2 beds
2 Bathrooms
Guests 6
35 reviews
Discovery Point #15 – The Beachfront Spot You’ll Want to Claim
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.7 / 5
$400 avg/night
2 beds
2 Bathrooms
Guests 6
6 reviews
The Pink Beach House - Private House and Pool on Beach, Rum Point
Guests6
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$551 avg/night
3 beds
3 Bathrooms
Guests 6
56 reviews
Grand Cayman Slice-of-heaven/Azure Breeze #3 ***
Guests6
Bedrooms3
Bathrooms3
Wonderful 4.9 / 5
$347 avg/night
3 beds
3 Bathrooms
Guests 6
38 reviews

Old Man Bay, Cayman Islands Vacation Rentals

Sunsets And Ocean Front Luxury Awaits You!!!

Oceanfront Luxury, Awesome Views

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

Your Oceanside Retreat Awaits!

Its time to Relax! Beachfront 3BR Condo on the sea, North Side...

On The Bay #104-Tropical Treasure on the North Shore

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

3BR- Coral Cottage Yellow - Large Oceanfront Villa with Pool and...

Castaway by the Sea - Cottage - "Private" Beach Getaway

YOU'VE ARRIVED! BREATHTAKING LUXURY BEACHFRONT VILLA, FROM...

Direct Beachfront 2 Bed Condo. Beautiful White Sand, Quiet, Safe

Cayman Reef 47🌴 King bed 🌴Bright Airy FULLY stocked down to to...

Castaway by the Sea - Lodge - "Private" Beach Getaway

Oceanfront-Best Price on 7 Mile Beach-1 Bd # 21-Cayman Reef Resort

Beachfront 1 Br Condo On Seven Mile Beach At #20 Cayman Reef Resort

Fantastic 2 Bedroom, 7 Mile Beach, Plantation Village

Beachfront 2 Bedroom Condo With Magnificent Caribbean View!

Oceanfront 2 Bedroom Top Floor Condo for Rest and Relaxation

Beachfront Beauty & Panoramic Views -The Retreat #23 - Steps out...

Rum Point Retreat #23-Beachfront beauty, panoramic views, 1767...

Bright & Cheerful Seven Mile beach condo!

Vitamin Sea - Beachfront and Ground Floor at Coral Bay Village

Cayman Islands Stunning Condo On The Sand - Kaibo Yacht Club

Newly Renovated Luxury Ground Floor Condo On Seven Mile Beach.

Island vibes, ocean views, diving & beaches...

Windsong 3 Gorgeous condo-Balcony -Desirable Area SMB - $269...

Charming Oceanfront Sea Lodge in Delightful Cayman Kai

ESCAPE TO BEACHFRONT PARADISE! FROM $99.00/NT BEST VALUE...

Windsong 1 Spacious Luxury-Beautiful Serene Area SMB - $269...

Sunset Cove 2 Bed/2Bath Condo on Seven Mile Beach with Discounted...

Remodeled Family Friendly Condo in the Heart of Seven Mile Beach

BEACHFRONT Condo -- Retreat at Rum Point #33 - 7th Night Free

Cayman Islands Divers Paradise 1st Floor Oceanfront Condo

Luxurious 4BR Chateau-Pool, Family-Friendly, near Spotts Beach...

Cozy Cayman Beach Front Cottage - Emerald Sea House

Beachfront 3br Condo On Seven Mile Beach At #44 Cayman Reef Resort

Stop Your Search-paradise Found! Caribbean Paradise-600 Ft. of...

Complete RENOVATION Sept 2017! Best value on Seven Mile Cayman...

Oceanfront, Tortuga Kai Condo At Kaibo Yacht Club, Cayman Kai

'Cayman Breeze' Luxury Beachfront Condo located at Rum...

Oceanfront condo at SMB, sleeps 6, just paradise!

Pay 6 stay 7 thru Oct 2017! - Ocean Front Condo Cayman Kai Rum...

Cayman Islands Divers Paradise with Direct Oceanfront

7BR “Tatenda,” a Luxury Cayman Villas Signature Property

Oceanview/Poolside Condo on Seven Mile Beach

NEWLY RENOVATED 7 MILE BEACHFRONT W/ SUNSET VIEW! NEAR EVERYTHING...

Kaibo Vacation 50ft From The Water

Discovery Point #15 – The Beachfront Spot You’ll Want to Claim

The Pink Beach House - Private House and Pool on Beach, Rum Point

Grand Cayman Slice-of-heaven/Azure Breeze #3 ***