50 Best Cayman Islands Vacation rentals on Holiday Lettings - Condos

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Cayman Islands

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275 Vacation rentals

(1) Excellent 

37

Rum Point Vacation home rental

Grand Cayman / Rum Point

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
Ocean Paradise is perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations yet is conveniently located near world-famous Sting …see more

from $259 / night

$1,813 / week

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from $259 / night

31

Rum Point Vacation home rental

Grand Cayman / Rum Point

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
Ocean Paradise is perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations yet is conveniently located near world-famous Sting …see more

from $219 / night

$1,533 / week

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from $219 / night

(5) Excellent 

29

Vacation condo with shared pool in Cayman Islands

Grand Cayman / Seven Mile Beach

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
Our beach-front vacation home offers guests a luxury standard of vacation accommodation, with incredible views across the bay and over the pristine sands of Seven Mile Beach. Large luxury condos like those at Sea Breeze are hard to find on Grand Cayman, sleeping up to …see more

from $750 / night

$6,825 - $16,000 / week

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from $750 / night

(2) Excellent 

16

Vacation villa in East End

Grand Cayman / East End

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our rental villas are situated in the quaint community of East End on Grand Cayman, away from all the noise and congestion of Georgetown and 7-mile beach. Parking is a HUGE problem in Georgetown and on 7 mile beach -- there are very few public parking lots, and many s …see more

from $238 / night

$1,666 - $4,026 / week

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from $238 / night

(1) Excellent 

13

Vacation villa with shared pool in Rum Point

Grand Cayman / Rum Point

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Ocean Paradise is perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations yet is conveniently located near world-famous Sting …see more

from $259 / night

$3,423 / week

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from $259 / night

59

Vacation condo with shared pool in Cayman Islands

Grand Cayman / Seven Mile Beach

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Located on a beautiful pristine section of Seven Mile Beach, Sea Breeze is a boutique condo development of just nine luxury corner condos with incredible ocean views. Condo 3 is located on the second floor and can sleep up to 10 guests in comfort (and can be rented alon …see more

from $1,000 / night

$12,250 / week

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from $1,000 / night

5

Vacation villa with shared pool, golf nearby in East End

Grand Cayman / East End

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Premier Morritt's Tortuga Club resort offers a luxury beach front paradise atmosphere, with 2 pools a waterfall and swim up cocktail bar. Each air conditioned apartment has a balcony and a fully equipped kitchen. The property's restaurant serves gourmet food and ther …see more

from $480 / night

$3,360 / week

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from $480 / night

(7) Very Good 

21

Vacation guest house in Seven Mile Beach

Grand Cayman / Seven Mile Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Your own private Seven Mile Beach area 2 bed / 2 bath 'home away from home', with the best snorkeling on all of SMB within 2 blocks of your door step! From us$100/ night..."Cayman's Best Value!" Close to everything yet away from the crowds! Please take a look at our …see more

from $160 / night

$995 - $1,895 / week

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from $160 / night

54

Vacation condo rental

Grand Cayman / West Bay

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Condo 4 at Sea Breeze is a superbly appointed and furnished four-bedroom oceanfront condo on Seven Mile Beach. Located on the second floor, and with beautiful views of the Caribbean Sea and the pristine beach, it is perfectly located for a Grand Cayman vacation. The fou …see more

from $1,000 / night

$11,000 - $16,000 / week

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from $1,000 / night

(1) Good 

10

George Town Vacation guest house rental

Grand Cayman / George Town

4 14 1 night min

  • 4 bedrooms
  • Sleeps 14
  • 1 night min
  • Nearest beach 8 mi
  • Child friendly
  • Air conditioning
Right at the Historical center of Santiago de Cuba, Casa "Don Carlos" offers the best host in the city, we speak fluent English and some French, Italian and Portuguese. Feel the warmt of a Cuban family, and enjoy the city of Santiago as never before, at a walkable dista …see more

from $36 / night

$199 / week

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from $36 / night

(1) Very Good 

18

Cottage rental in Cayman Islands

Grand Cayman / East End

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
Both beds are QUEEN sized. The Cottage provides basic accommodation, nothing fancy, no marble foyer nor granite countertops, but it does give you spotlessly clean accommodation literally steps from a powdery - white sand beach. We also have a large HOT TUB. O …see more

from $175 / night

$1,225 - $3,325 / week

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from $175 / night

7

Vacation condo in Cayman Islands

Grand Cayman / Rum Point

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This beautiful 2 Bed/2 Bath condo is literally located steps away from world famous Rum Point Beach at the quaint condo development of The Island Houses. There are 17 units in The Island Houses that wrap around the northern end of the Rum Point Lagoon. The neighborhood …see more

from $250 / night

$1,925 - $2,625 / week

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from $250 / night

30

Home rental in Cayman Islands

Grand Cayman / Rum Point

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
Ocean Paradise is perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations yet is conveniently located near world-famous Sting …see more

from $239 / night

$1,673 / week

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from $239 / night

(1) Excellent 

50

Vacation villa in Seven Mile Beach

Grand Cayman / Seven Mile Beach

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to the Caribbean Club, a luxurious and exclusive beachfront paradise located directly on the famous Seven Mile Beach in Grand Cayman. GENERAL VILLA FEATURES Every kitchen has beautiful granite tops, modern fixings and appliances and is fully stocked with utens …see more

from $890 / night

$6,230 - $15,050 / week

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from $890 / night

8

Cayman Islands Vacation apartment rental

Grand Cayman / East End

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
This spacious, private 1 bedroom apartment takes up the entire ground floor level of a large 3-storey house in the East End of Grand Cayman. It walks out directly to a stunningly beautiful white, sandy beach, lush with vegetation and palm trees, right on your doorstep. …see more

from $175 / night

$1,225 - $4,025 / week

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from $175 / night

(1) Excellent 

14

Vacation home in Cayman Islands

Cayman Islands / Cayman Brac

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Air conditioning
  • Private garden
Welcome to The Breeze. We are a luxury boutique beach house Located directly on the beach in beautiful Cayman Brac, just 25 mins from Grand Cayman by air. Recently renovated, we have 2 lovely bedrooms with ensuites shower rooms. Full sitting room, dining room and kitc …see more

from $115 / night

$725 - $1,090 / week

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from $115 / night

14

Vacation villa in Cayman Islands

Grand Cayman / East End

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
This spacious, 2450 square foot villa is in a small complex of multi-coloured villas surrounding a gorgeous 5 level cascading swimming pool. All rooms in this villa (except 1 bathroom) face the ocean, allowing you to watch the most beautiful sunrises in the Caribbea …see more

from $250 / night

$1,750 - $5,250 / week

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from $250 / night

29

Cayman Islands Vacation apartment accommodation

Grand Cayman / Bodden Town

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0.1 mi
  • Child friendly
  • Air conditioning
The 'Sunset paradise apartment' is a large two bedroom, two bathroom ground floor apartment with nice sea view terrace located in the historic Bodden Town and just across the road from the beach. It's a perfect location in the middle of Grand Cayman island so you're wit …see more

from $71 / night

$1,080 - $1,818 / week

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avg. 2 hours 49 minutes

from $71 / night

24

Vacation apartment in Cayman Islands

Grand Cayman / Bodden Town

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0.1 mi
  • Child friendly
  • Air conditioning
The 'Sunset paradise' apartment is a large two bedroom, two bathroom apartment with a wonderful sea view terrace located in the historic Bodden Town and just across the road from the beach. It's a perfect location in the middle of Grand Cayman island so you're within ea …see more

from $71 / night

$1,080 - $1,818 / week

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Responds fast!
avg. 2 hours 49 minutes

from $71 / night

(1) Very Good 

15

Cayman Islands Vacation studio rental

Grand Cayman / East End

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
  • Nearest beach 1 mi
  • Child friendly
  • Air conditioning
Blue Sea Hideaway is a delightful, 550 square foot studio apartment that is steps from a white sandy beach. Newly built, it has a full size refrigerator, microwave/convection oven, ceramic cooktop and a dishwasher. There is a queen sized bed, sofa and dinette. J …see more

from $125 / night

$850 - $2,940 / week

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from $125 / night

16

Cayman Islands Vacation home rental

Grand Cayman / East End

3 7 5 nights min

  • 3 bedrooms
  • Sleeps 7
  • 5 nights min
  • Beach/lakeside relaxation
  • Child friendly
Designer decorated spacious Beach House on a gorgeous, private, white powder sand beach. Two master bedrooms with terraces overlooking the ocean, one with a King Bed, the other with a Queen and both with ensuite bathrooms. 3rd bedroom has twin beds and there is a d …see more

from $350 / night

$2,375 - $2,585 / week

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from $350 / night

30

Vacation home in Cayman Islands

Grand Cayman / Rum Point

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
Ocean Paradise is perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations yet is conveniently located near world-famous Sting …see more

from $239 / night

$1,673 / week

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from $239 / night

(1) Excellent 

19

Cayman Islands Vacation cottage rental

Grand Cayman / Bodden Town

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Child friendly
On 3 acres of private property, this cottage has access to the homeowners' pool, tennis court, private dock, private beach, private golf driving range and it is a gated property. Included are the homeowners' stand-up board, windsurfer, hammock and snorkel gear. Addition …see more

from $500 / night

$3,500 / week

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from $500 / night

(39) Excellent 

29

Vacation apartment with shared pool in Cayman Islands

Grand Cayman / West Bay

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Located only steps from the shore and just five minutes north of Grand Cayman's famous Seven Mile Beach in the quiet West Bay neighborhood, Cayman Sunset is the ideal vacation condo for families or groups of friends looking for a Cayman Islands getaway. VACATION …see more

from $300 / night

$2,800 - $2,905 / week

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from $300 / night

(2) Very Good 

14

Vacation home in North Side

Grand Cayman / North Side

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Air conditioning
  • Private garden
Our piece of paradise looks onto the turquoise waters of the Caribbean Sea, where a coral reef protects this part of the island, and coral heads are scattered for several miles in both directions. Swim in the warm shallow waters and make friends with the local denizens, …see more

from $200 / night

$1,260 - $2,730 / week

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Responds fast!
avg. 1 hour 25 minutes

from $200 / night

(5) Excellent 

18

Vacation cottage in Cayman Islands

Cayman Islands / Cayman Brac

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
Named for the natural shade provided by 29 coconut palm trees on the property our beach cottage offers 2 bedrooms, fully equipped kitchen, free WI FI, cable television and local phone service. The 300 sq foot deck is literally steps from the water and always has shade …see more

from $135 / night

$850 / week

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from $135 / night

(16) Excellent 

Certificate of Excellence

11

Vacation condo in Bodden Town

Grand Cayman / Bodden Town

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
A 900+ sq foot loft condo with two full baths. King Bed upstairs. Queen pullout bed downstairs with memory foam/temper-soft mattress. 60 second walk to our favorite beach on island (Spotts Beach). Amenities appx 1 mi away, including grocery, liquor store, pharmacy, ban …see more

Certificate of Excellence

from $125 / night

$850 - $3,000 / week

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Responds fast!
avg. 3 hours 5 minutes

from $125 / night

(29) Excellent 

Certificate of Excellence

27

Vacation apartment with shared pool in Rum Point

Grand Cayman / Rum Point

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“Moonlight Kai” is a fully equipped, 2 bedroom 2 bathroom condo located in the heart of the Cayman Kai community. It is part of the Kaibo Yacht Club Phase II Complex near Rum Point on the spectacular Caribbean island of Grand Cayman. The complex sits on a pristine, wh …see more

Certificate of Excellence

from $180 / night

$1,575 / week

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from $180 / night

30

Vacation villa in Gun Bay

Grand Cayman / Gun Bay

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Fixed week rental, check in days: Fri, Sat, Sun. Studio, Sleeps 2, with Full Kitchen and/or 2-Bedrooms. Sleeps 6 are/may be also available - please inquire about rates and availability. LIVING AREA: Pull Out Sofa, Queen size, Bathtub/Shower BEDROOM: Queen Size Bed …see more

from $140 / night

$975 - $1,475 / week

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Responds fast!
avg. 2 hours 20 minutes

from $140 / night

23

Vacation home with shared pool in East End

Grand Cayman / East End

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Northern Lights is a 9-unit complex comprised of privately owned two-floor townhomes, located on the waters edge along the quiet north coast of Grand Cayman. The comfort and breathtaking views of this condo are matched only by its' surroundings: 240 feet of sandy beach, …see more

from $150 / night

$1,050 - $3,080 / week

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from $150 / night

(6) Excellent 

21

Seven Mile Beach Vacation apartment rental

Grand Cayman / Seven Mile Beach

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.11 mi
  • Child friendly
This condo is in a superb location in which to have a great vacation. This well appointed 3 bed and 2.5 bath apartment also offers covered parking and security fob access. A kingsized bed along with two double beds, the apartment sleeps 6 easily, along with a sectional …see more

from $177 / night

$1,115 - $2,163 / week

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from $177 / night

27

Home rental in Cayman Brac

Cayman Islands / Cayman Brac

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Amazing 2 bedroom, 2 bath beach house on North Side of Cayman Brac, Cayman Islands. Swim, snorkel, shore dive, boat dive, kayak, bird watch, explore caves, hike the bluff, rock climb the bluff, or simply rest & enjoy the sunrises and sunsets from your living room, huge …see more

from $180 / night

$1,260 / week

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from $180 / night

22

Cayman Brac Vacation villa rental

Cayman Islands / Cayman Brac

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Be one of the first guests to relax in this BRAND NEW vacation property located in Bamboo Bay, Cayman Brac. The villa comfortably sleeps 8 in 3 master bedrooms, each with a separate ensuite bathroom. For maximum privacy, the bedrooms radiate out from the central living …see more

from $349 / night

$2,443 / week

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Responds fast!
avg. 27 minutes

from $349 / night

(1) Excellent 

32

Vacation condo in Cayman Islands

Grand Cayman / East End

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Morritt's Tortuga Club - East End, Grand Cayman, Cayman Islands: Studio, Sleeps 2, with Full Kitchen. Fixed week rental, check in days: Fri, Sat, Sun. 1-Bedroom, Sleeps 4, with Full Kitchen and/or 2-Bedrooms. Sleeps 6 are also available - please inquire about rates an …see more

from $118 / night

$825 - $1,175 / week

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Responds fast!
avg. 2 hours 20 minutes

from $118 / night

19

Vacation villa with shared pool in Cayman Islands

Grand Cayman / East End

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
2 story, 3 bedroom, 3.5 bath private villa with 4 pools just outside the slider. The beach is just across the street inside the reef. Relax under the palm with a breeze blowing in a tropical island setting. The kitchen is fully equipped for preparing your own meals, yo …see more

from $290 / night

$2,030 / week

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Responds fast!
avg. 1 hour 51 minutes

from $290 / night

10

Vacation villa accommodation

Cayman Islands / Cayman Brac

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
Our beautiful villa is located right at the tranquil Caribbean Sea. Luxury accommodations for a maximum of 4 persons. Lounge on our private beach area with romantic gazebo - the perfect place to enjoy a glass of wine as you watch the spectacular Caribbean sunsets. Sw …see more

from $180 / night

$1,200 - $1,410 / week

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from $180 / night

(21) Excellent 

37

Cayman Islands Vacation cottage rental

Cayman Islands / Cayman Brac

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This Caribbean beach home has the best location on the Brac and is the ONLY private rental home in this area. The "Golden Mile" is the ONLY area on Cayman Brac with Reef protection providing a calm lagoon. The beaches in this southside area are the only ones that do …see more

from $150 / night

$925 / week

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from $150 / night

7

Cayman Islands Vacation apartment rental

Cayman Islands / Cayman Brac

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Imagine a place where your “Personal Island Getaway” becomes a reality… Imagine a place where world-famous dive sites are found only a few hundred feet from your front door… Imagine a place where brilliant island sunsets take place outside your window every evening… …see more

from $143 / night

$1,001 / week

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from $143 / night

21

Cayman Islands Vacation condo rental

Grand Cayman / Seven Mile Beach

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
You can walk to an abundance of Restaurants, Groceries, Shopping and Water Sports Rental! Georgetown Villa #113, this 2 bedroom, 2 bath condo has been completely renovated with granite counter tops, stainless appliances, beautiful, yet comfortable furnishings, all with …see more

from $275 / night

$1,925 - $3,250 / week

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Responds fast!
avg. 3 hours 38 minutes

from $275 / night

28

Vacation apartment with shared pool in Cayman Islands

Grand Cayman / West Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Welcome to Coconut Bay #109! This is the perfect home for water lovers, divers and explores! The home is a large 2300 square foot 3 bedroom, 3.5 bath tri-level set around one of Coconut Bay’s two large swimming pools. On the ground level there is a large, open plan …see more

from $200 / night

$1,400 - $2,905 / week

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from $200 / night