50 Best Cayman Islands Vacation rentals on Holiday Lettings - Condos

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228 Vacation rentals

7

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 $135 / night

$999 - $1550 / week

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from $135 / night

(4) 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 $860 / night

$10200 - $15500 / week

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from $860 / night

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 …see more

from $216 / night

$1364 - $3939 / week

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from $216 / night

7

Vacation condo in Cayman Islands

Grand Cayman / Rum Point

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This newly refurbished 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 neigh …see more

from $275 / night

$1925 - $2975 / week

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from $275 / 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 $285 / night

$1800 - $5550 / week

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from $285 / night

(6) 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 0.2 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 - $2095 / week

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from $160 / night

16

Cayman Islands Vacation home rental

Grand Cayman / East End

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • 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

$2375 - $6050 / week

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from $350 / night

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 $199 / night

$1393 / week

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from $199 / 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 $199 / night

$1673 - $6293 / week

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from $199 / night

14

Vacation home in Cayman Islands

Cayman Islands / Cayman Brac

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Air conditioning
  • Private garden
Welcome to The Breeze. 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. Full sitting room, dining room and kitchen with full amenities. Enclosed porch with day be …see more

from $150 / night

$950 - $1090 / week

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Responds fast!
avg. 2 hours 41 minutes

from $150 / 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 $199 / night

$1393 / week

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from $199 / 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 1' 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 w …see more

from $170 / night

$1020 - $1350 / week

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from $170 / 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 $199 / night

$1393 / week

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from $199 / night

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 $32 / night

$180 / week

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from $32 / night

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 $750 / night

$5250 - $25200 / week

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from $750 / night

9

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 $150 / night

$1000 - $1785 / week

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from $150 / night

24

Vacation apartment in Cayman Islands

Grand Cayman / Bodden Town

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 0.1 mi
  • Child friendly
  • Air conditioning
If you're looking for a perfect holiday relaxing on white powdery sand, swimming in crystal warm Caribbean waters, enjoying fantastic food as Grand Cayman is known as the 'Culinary Capital of the Caribbean' then Gran Cayman island is the perfect island to visit. The 'S …see more

from $170 / night

$1020 - $1510 / week

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from $170 / 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

$3360 / week

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Responds fast!
avg. 1 hour 59 minutes

from $480 / 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 $199 / night

$1393 / week

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from $199 / night

6

East End Vacation apartment rental

Grand Cayman / East End

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
Stay period - (7 nights/8 days) - from December 31th, 2016 untill January 07th, 2017 Maximum capacity: 6 guests Maximum capacity with privacy: 6 guests Dimensions: 2 bedroom Kitchen: full The original Morritt’s playground! Welcoming the morning sunrise and offering unpa …see more

from $349 / night

$2443 / week

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from $349 / night

8

Cayman Islands Vacation studio rental

Grand Cayman / East End

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Blue Sea Hideaway is a 500 square foot studio apartment that offers you basic, reasonably priced accommodation with all the comforts of home. You have a full sized fridge, microwave convection oven, ceramic cooktop and a dishwasher. [SEE NOTE BELOW] There is a qu …see more

from $125 / night

$851 - $2000 / week

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from $125 / night

13

Cayman Islands Vacation apartment rental

Grand Cayman / East End

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
Stay period - (7 nights/8 days) - from December 24th, 2016 untill December 31th, 2016 Maximum capacity: 4 guests Maximum capacity with privacy: 4 guests Dimensions: 1 bedroom Kitchen: full The original Morritt’s playground! Welcoming the morning sunrise and offer …see more

from $299 / night

$2093 / week

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from $299 / night

(2) Excellent 

27

Home rental in Cayman Islands with shared pool

Grand Cayman / North Side

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
Indulge in relaxation, recreation, and romance at the “Ocean Pearl” beachfront villa. Here you can discover the natural side of Grand Cayman, escape your busy life and enjoy peace and tranquility. Part of the Northern Lights development, we are one of just nine units an …see more

from $235 / night

$1650 - $2000 / week

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from $235 / night

15

Vacation condo in Cayman Islands

Grand Cayman / North Side

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
A glorious secluded beach and the crystal clear Caribbean provide the backdrop for a dream vacation at The Haven in Cayman Kai. This lovely quiet oceanfront two bedroom, two bath sea lodge (accommodates 6) is located on the North Side of Grand Cayman near Rum Point. At …see more

from $165 / night

$1155 - $1750 / week

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from $165 / night

(1) Excellent 

5

Vacation condo with shared pool in Cayman Islands

Grand Cayman / West Bay

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
Large 3 bed 3.5 bath condo set aid lush tropical gardens on upscale ocean front development.2300 sq foot makes this a large condo with 3.5 bathrooms and an extra full size bed available to put in any of the bedrooms.Layout is queen queen twins set over 3 floors this co …see more

from $225 / night

$1650 - $2800 / week

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from $225 / night

34

Cayman Islands Vacation home rental

Cayman Islands

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning
Location, Location, Location - Beach, Restaurants and Shopping! BRAND NEW LISTING- Vacation in this newly renovated ground floor condo and enjoy both luxury and convenience. You step outside to a whirlpool tub and shallow pool and experience the Caribbean Sea, just step …see more

from $280 / night

$1960 - $2443 / week

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Responds fast!
avg. 2 hours 8 minutes

from $280 / night

(8) Excellent 

17

Vacation apartment with shared pool in Cayman Islands

Grand Cayman / West Bay

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
OCEANFRONT Ground floor one bedroom fully furnished Villa with TWO BEACHFRONT PATIOS. Twelve foot glass sliding doors out to the beautiful turquoise Caribbean sea offers a fantastic view from all rooms. Villas Pappagallo #22 is the perfect location for Honeymooners …see more

from $215 / night

$1750 / week

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from $215 / night

(3) Very Good 

26

West Bay Vacation apartment rental

Grand Cayman / West Bay

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This condo at Bonnie's Arch condominiums is on the second floor and has direct access to the pool and ocean. The crystal clear turquoise water, pristine sandy beach, lush tropical vegetation and dramatic sunsets are all part of the backdrop for this tropical paradise. T …see more

from $185 / night

$1295 - $2485 / week

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Responds fast!
avg. 3 hours 48 minutes

from $185 / night

31

Home rental in Cayman Islands

Cayman Islands

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning
Location, Location, Location - Beach, Restaurants and Shopping! BRAND NEW LISTING- Vacation in this newly renovated ground floor condo and enjoy both luxury and convenience. You step outside to a whirlpool tub and shallow pool and experience the Caribbean Sea, just step …see more

from $309 / night

$2163 - $2933 / week

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Responds fast!
avg. 2 hours 8 minutes

from $309 / night

11

Vacation condo with shared pool in Seven Mile Beach

Grand Cayman / Seven Mile Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This newly listed penthouse condo has everything for your perfect vacation. Enjoy stunning views of the sun setting over the Caribbean Sea from your private balcony. Located in a resort style complex with a great amenities. The space This top floor unit offers stunnin …see more

from $250 / night

$1750 / week

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Responds fast!
avg. 3 hours 39 minutes

from $250 / night

(3) Excellent 

18

Vacation villa in Cayman Islands

Grand Cayman / Bodden Town

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Air conditioning
  • Private garden
If you are loooking to de-stress, relax and spend some quality time with your loved one, Castaway Cottage is just what you need. Wake to breathtaking sunrises while enjoying breakfast on the spacious deck overlooking the sea. Stroll the beach searching for the quintesse …see more

from $179 / night

$1253 / week

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Responds fast!
avg. 2 hours 23 minutes

from $179 / night

8

Vacation apartment in Cayman Islands

Grand Cayman / West Bay

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
Fully refurbished 1200 sq foot 2 bedroom, 2 bathroom condo set up upscale private complex set amid lush tropical gardens nestled by the ocean.Linga Longa at coconut bay is a perfect destination for those looking to explore and enjoy the Cayman Islands.The condo has just …see more

from $200 / night

$1650 - $2800 / week

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from $200 / night

(3) Excellent 

11

Vacation home in Cayman Islands

Cayman Brac / West End

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Hear and see the ocean in this beautiful, newly remodeled 1500 Sq. Ft, two bedroom beach front home features an open floor plan enabling you to interact with others easily. It has free stateside calls, central air, three sitting areas, all new kitchen appliances, bott …see more

from $140 / night

$875 - $1100 / week

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Responds fast!
avg. 1 hour 27 minutes

from $140 / night

(23) Excellent 

65

Vacation home with shared pool in Cayman Islands

Cayman Islands / Grand Cayman

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Away from busy Seven Mile Beach, with a peaceful palm-lined cove directly out the back door and Rum Point Beach steps away from the front door, Starboard Kai has the perfect location for your vacation. Whether you prefer to relax by the pool or on the beach, stroll in …see more

from $280 / night

$1960 - $3500 / week

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from $280 / night

(5) Excellent 

7

Vacation apartment in Cayman Brac

Cayman Islands / Cayman Brac

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night 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 $129 / night

$903 / week

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from $129 / night

(8) Excellent 

Certificate of Excellence

23

Vacation apartment with swimming pool in Cayman Islands

Grand Cayman / East End

3 7 5 nights min

  • 3 bedrooms
  • Sleeps 7
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Crescent Beach offers very secluded, private and peaceful ocean-front living in a marine park with coral gardens. The beach is semi-private and a home for nesting turtles. The two luxury apartments are called Sky (upper) and Sand (ground). Each apartment accommodates …see more

Certificate of Excellence

from $225 / night

$1575 / week

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from $225 / night

(11) Very Good 

14

Vacation apartment with shared pool in Seven Mile Beach

Grand Cayman / Seven Mile Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Ideally located condo on the renowned 7 mile beach. This spacious condo, on the ground floor, has 2 bedrooms, and 2 full bathrooms, with a sofa bed in the living room. This air-conditioned unit, with fitted wardrobes, Wi-Fi, safety deposit box, fully equipped kitchen, T …see more

from $175 / night

$1225 / week

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Responds fast!
avg. 1 hour 50 minutes

from $175 / night

33

Home rental in Cayman Islands

Cayman Islands

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning
Location, Location, Location - Beach, Restaurants and Shopping! BRAND NEW LISTING- Vacation in this newly renovated ground floor condo and enjoy both luxury and convenience. You step outside to a whirlpool tub and shallow pool and experience the Caribbean Sea, just step …see more

from $280 / night

$1960 - $2443 / week

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Responds fast!
avg. 2 hours 8 minutes

from $280 / night

(1) Excellent 

5

Vacation cottage accommodation

Cayman Brac / West End

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Hear and see the ocean in this beautiful, newly remodeled 670 Sq. Ft, one bedroom ocean view cottage features an open floor plan enabling you to interact with others easily. It has free stateside phone calls, central air, living room areas, all new kitchen with gorgeo …see more

from $100 / night

$600 - $771 / week

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Responds fast!
avg. 1 hour 27 minutes

from $100 / night

(5) Excellent 

18

Vacation cottage in Cayman Islands

Cayman Islands / Cayman Brac

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 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

$851 / week

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from $135 / night

1