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Holiday Rentals with Pools in Cayman Islands

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    Travellers to Cayman Islands are booking December dates now. Secure your holiday home today, and have the perfect trip.
    586 Matching Rentals in Cayman IslandsView all 778 rentals
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    Fully Renovated 1 Bedroom On Seven Mile Beach Cayman Reef Resort #11 / 26
    (55)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    5 bedroom Ocean Front Private Villa1 / 39
    (26)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    Awesome Beach Condo on Perfect Seven Mile Beach!  Super Summer/Fall Specials!1 / 26
    (149)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    'Everything about this place is first class!'1 / 42
    (21)Excellent
    3 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Spot Bay, Cayman Brac
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 8
    Sandbar Beach Island House , steps from Rum Point, FREE kayaks, bikes, WIFI1 / 48
    (28)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Rum Point, Grand Cayman
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Beachfront Sunset Silver Suite at The Retreat at Rum Point (#33)1 / 50
    (20)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Rum Point, Grand Cayman
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    YOU'VE ARRIVED! BREATHTAKING LUXURY BEACHFRONT VILLA, FROM $99.99/nt1 / 35
    (119)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    North Side, Grand Cayman
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Oceanfront 3BR w/Amazing Views, Snorkeling and Shore Diving -- 5 mins to SMB!!1 / 24
    (16)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    West Bay, Grand Cayman
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 7
    NEWLY RENOVATED 7 MILE BEACHFRONT W/ SUNSET VIEW! NEAR EVERYTHING !1 / 22
    (30)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    George Town, Grand Cayman
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Oceanfront condo at SMB, sleeps 6, just paradise!1 / 24
    (22)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Grand Cayman, Cayman Islands KY1 1201
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Avail Mar 18-25!!  Cayman Reef 47 One bed with King lots of extras1 / 44
    (59)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    George Town, Grand Cayman KY1 1208
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Bright & Cheerful Seven Mile beach condo!1 / 47
    (14)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Seven Mile Beach, Grand Cayman 00000
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Little Cayman: Dive, Fish, Relax1 / 23
    (17)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Little Cayman, Cayman Islands KY
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Luxury groundlevel beachfront condo on 7 mile beach1 / 39
    (17)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    George Town, Grand Cayman
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Romantic Walks on the Beach, Beautiful Sunsets from Any Balcony.1 / 24
    (14)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    George Town, Grand Cayman KY1 1301
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Rum Point, Grand Cayman
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Villa Bellagio- Beautiful Beach Home1 / 29
    (18)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Rum Point, Grand Cayman KY1 1000
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Seven Mile Beach, Grand Cayman KY1 1204
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    CoCoCOndo - Your 3br Home Away from Home in the Caribbean1 / 24
    (47)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    West Bay, Grand Cayman
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Beach Front Paradise Home.  Luxurious Funishings!1 / 30
    (26)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Cayman Brac, Cayman Islands KY2 2001
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Contemporary open house, oceanfront, private pool, sweet sunsets.1 / 35
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    West End, Cayman Brac
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Prime Residence #6 on 7 Mile Beach, High-End Ground Floor Beachfront Condo1 / 37
    (67)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    George Town, Grand Cayman KY1 1205
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Caribbean Paradise - Private Villa with Beachfront Deck & Resort Amenities1 / 22
    (23)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    George Town, Grand Cayman
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Sensational Beachfront View, 41 Discovery Point Club, Seasonal Special Offers.1 / 24
    (30)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    West Bay, Grand Cayman KY1 1302
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Huge Porch! 3Bedroom-Oceanfront Condo1 / 26
    (27)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Seven Mile Beach, Grand Cayman
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    ** SUPERB LOCATION** FAMILY FRIENDLY **SLICE OF PARADISE1 / 26
    (29)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    West Bay, Grand Cayman
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Cayman Islands Divers Paradise with Direct Oceanfront1 / 27
    (33)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    West Bay, Grand Cayman 34471
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    WYNDHAM REEF RESORT Beachfront Condo- TOP FLOOR/END UNIT/PRIVATE/QUIET/RELAXING!1 / 50
    (15)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Grand Cayman, Cayman Islands
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Tranquil setting close to everything,  Come relax, dive, sight see and explore.1 / 24
    (13)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    West Bay, Grand Cayman KY 1003
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Closest Ocean Front Condo on 7-Mile beach-Cayman Reef 311 / 22
    (52)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    George Town, Grand Cayman KY1 1208
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Newly renovated ocean view & pool side 2B condo for a perfect vacation1 / 48
    (112)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Seven Mile Beach, Grand Cayman
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    **Special Offers** Cayman Reef 57 * 3 Bedroom COMPLETELY RENOVATED!! On SMB1 / 42
    (32)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    George Town, Grand Cayman KY1 1203
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    West Bay, Grand Cayman
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Your Dream Vacation is Affordable! 2BR-2bath Oceanfront Condo Seasonal Discount!1 / 24
    (66)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Seven Mile Beach, Grand Cayman KY1 1107
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Private Oceanfront Home W/Large Lanai, Pool and Cabana1 / 50
    (36)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Spot Bay, Cayman Brac BWI KY1 1104
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    37 Steps To The Ocean!   Quiet, Ocean View, No-Crowd Beach1 / 23
    (15)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    West Bay, Grand Cayman
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Beachfront Luxury Living Directly On Palm-Lined Cove - kayaks and bikes included1 / 47
    (34)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Rum Point, Grand Cayman KY1 1701
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    3 Bdr condo on 7 Mile Beach : 15 % reduced rate until Dec 15 20191 / 41
    (46)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Grand Cayman, Cayman Islands 143H28
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Beachfront 1 Br Condo On Seven Mile Beach At #20 Cayman Reef Resort1 / 25
    (73)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Seven Mile Beach, Grand Cayman KY1 1204
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    George Town, Grand Cayman KY1 1110
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Kid friendly
    Smoking allowed
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    North Side, Grand Cayman
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    5BR-Ocean Kai: Newly Built Oceanfront Villa in Cayman Kai with Private Pool.1 / 27
    (14)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
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    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 January 2017
    The Ocean Kai is a beautiful house to stay in...We had 5 adults, 2 children, ages 8 & 12. They provide absolutely everything a family would need. Top of the line...
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    Grand Cayman, Cayman Islands
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Relax, Rejuvenate and Refresh Your Body, Mind & Soul at Kaibo B131 / 32
    (35)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Grand Cayman, Cayman Islands KY1 1007
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Beachfront Beauty & Panoramic Views -The Retreat #23 - Steps out to Two Beaches1 / 32
    (51)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    North Side, Grand Cayman 00000
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    OCEAN FRONT, 7M BEACH, PLANTATION VILLAGE #281 / 37
    (48)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    George Town, Grand Cayman
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    East End, Grand Cayman
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    * Brand New Construction - Sun Serenity Villa in Private Cayman Kai *1 / 41
    (24)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    Location Information
    Rum Point, Grand Cayman
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
    Oceanview/Poolside------'THE BEST'  see Guest  Comments1 / 30
    (187)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Seven Mile Beach, Grand Cayman 0000
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Gorgeous 4 Bedroom Oceanfront Condo on Seven Mile Beach1 / 26
    (62)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
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    Pet friendly
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    Smoking allowed
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    Location Information
    Camana Bay, Grand Cayman
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Location Information
    Savannah, Grand Cayman KY1
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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