50 Best Cayman Islands Vacation rentals on Holiday Lettings - Condos

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276 Vacation rentals

(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

(3) 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 $226 / night

$1,580 - $3,818 / week

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from $226 / 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 $950 / night

$6,650 - $15,050 / week

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from $950 / 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
  • 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

$1,393 / week

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from $199 / 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

(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
  • 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 $239 / night

$1,673 / week

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from $239 / night

(7) Very Good 

21

Vacation guest house in Seven Mile Beach

Grand Cayman / Seven Mile Beach

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • 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 - $1,695 / week

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from $160 / night

30

Home rental in Cayman Islands with shared pool

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 $219 / night

$1,533 / week

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from $219 / 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

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 / week

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from $250 / 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 $239 / night

$3,423 / week

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from $239 / 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

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

$7,000 - $16,000 / week

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from $1,000 / 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 $66 / night

$1,004 - $1,690 / week

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avg. 1 hour 55 minutes

from $66 / 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
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 $66 / night

$1,004 - $1,690 / week

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avg. 1 hour 55 minutes

from $66 / 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

(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 $33 / night

$185 / week

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from $33 / 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

57

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

$8,000 - $16,000 / 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

30

Vacation home with shared pool in Cayman Islands

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 $219 / night

$1,533 / week

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from $219 / night

(3) Excellent 

29

Vacation apartment in Cayman Islands

Grand Cayman / West Bay

1 3 4 nights min

  • 1 bedroom
  • Sleeps 3
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Calypso #3 "Garden View" is a very spacious 1 bdrm 1 bath apartment with a full size kitchen, Keurig coffeemaker,micro etc. A private patio with BBQ next to our Fantastic Bismark Palm tree.The apartment can sleep up to 4 guests with the queen size sofa bed in the living …see more

from $165 / night

$1,155 / week

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Responds fast!
avg. 2 hours 21 minutes

from $165 / night

(32) 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

(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

(2) Very Good 

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 $154 / night

$1,075 - $1,475 / week

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Responds fast!
avg. 3 hours 45 minutes

from $154 / night

(1) Excellent 

35

Vacation condo in Cayman Islands

Grand Cayman / East End

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Child friendly
  • Air conditioning
The Reef Resort - Grand Cayman: Studio, Sleeps 2, with Kitchenette. Fixed week - 7 nights, Fridays, Saturdays, Sundays check in only. Studio Beach Suite Our Grand Cayman Studio suite is beachfront with an area of approximately 450 square feet, including its own balcon …see more

from $154 / night

$1,075 - $1,225 / week

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Responds fast!
avg. 2 hours 39 minutes

from $154 / 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. 2 hours 41 minutes

from $125 / night

(2) Excellent 

27

Home rental in Cayman Islands with shared pool

Grand Cayman / North Side

2 6 6 nights min

  • 2 bedrooms
  • Sleeps 6
  • 6 nights min
  • 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 $250 / night

$1,750 - $2,100 / week

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from $250 / night

(1) Very Good 

38

Vacation villa in Cayman Islands

Grand Cayman / West Bay

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Villas Pappagallo is a premier rental property with a charming Spanish style located only a few miles from the world famous Seven Mile Beach on Grand Cayman Island. Our condo is a two story home with 2 bedrooms and 2 baths completely furnished with all of the comforts …see more

from $385 / night

$2,695 / week

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Responds fast!
avg. 3 hours 31 minutes

from $385 / night

(25) Excellent 

Certificate of Excellence

37

Vacation home with shared pool in Cayman Islands

Grand Cayman / Rum Point

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Beach directly out the back door and Rum Point beach steps out the front door. You are literally sandwiched between two beaches. 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 do …see more

Certificate of Excellence

from $275 / night

$1,925 - $3,850 / week

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from $275 / 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

(8) Very Good 

38

Condo rental 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
The Reef Resort - Grand Cayman: 1-BR, Sleeps 4, with Full Kitchen. Fixed week - 7 nights, Saturdays check in only. One Bedroom Executive Suite The resort's One Bedroom Suite at the Reef is among the best in the Cayman Islands. It is beachfront and sleep up to four gue …see more

from $175 / night

$1,225 - $1,775 / week

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Responds fast!
avg. 2 hours 39 minutes

from $175 / night

(2) Very Good 

27

Vacation home in Cayman Islands

Cayman Islands / Cayman Brac

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Turtle Run with WOW ocean views, gentle breezes blowing off the ocean, the perfect ending to a day on the water and at the beach. This oceanfront 1500 ft² cottage is perfect for week-long vacations, extended weekend getaways, winter retreats or temporary lodging for re …see more

from $150 / night

$1,000 / week

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from $150 / night

(1) Excellent 

14

Vacation cottage in Cayman Islands

Grand Cayman / East End

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Air conditioning
  • Private garden
“Piece of Mine” is located in “Cottage” (Frank Sound) on the southeastern coast of Grand Cayman. Enjoy the beach where you can find lots of interesting rocks, shells and other things that wash up daily. The body of water known as “Frank Sound” is protected by a coral …see more

from $250 / night

$1,750 / week

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from $250 / night

(11) 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

$1,495 - $2,555 / week

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from $215 / night

15

Vacation condo in Bodden Town

Grand Cayman / Bodden Town

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Playa Vista at MoonBay is your affordable beach vacation. This condo is tastefully furnished and impeccably clean. The unit has a fully equipped kitchen, air conditioning, cable television, wireless fibre optic internet access, local cellphone and coin operated l …see more

from $150 / night

$900 / week

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from $150 / night

(3) Excellent 

37

Vacation home rental

Grand Cayman / Rum Point

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Cayman Kai Vacations specializes in offering the "Island Houses of Cayman Kai" Tranquil Fruition, Calico Kai, Barefoot Lagoon, Summer Breeze, Toto Kai, Kai Time, Dream Kai, Casa Kai, Kai Kotch, Kai-lypso, Mango Kai, which are located in the exclusive Cayman Kai/Rum Poin …see more

from $315 / night

$2,450 / week

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Responds fast!
avg. 2 hours 57 minutes

from $315 / night

27

Vacation condo in Seven Mile Beach

Grand Cayman / Seven Mile Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
Welcome to George Town Villas Unit #218, located at the start of 7 mile beach on the beautiful island of Grand Cayman. George Town Villas consists of 54 oceanfront and ocean view condominiums in a lush garden setting overlooking the beach, coral reefs and multi-colored …see more

from $330 / night

$2,300 - $3,750 / week

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Responds fast!
avg. 2 hours 48 minutes

from $330 / night

(2) Very Good 

13

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 16 minutes

from $200 / night