Cottage holiday rentals in Cayman Islands

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Top-rated cottage rentals in Cayman Islands

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Guest favourite

Cottage in East End

4.97 out of 5 average rating, 59 reviews

PIECE of MINE, Beachfront Villa # 1

BEACHFRONT Cottage offers all the conveniences. Large Bedroom, oversized chair & ottoman, Closet, office space, chair, KAYAKs, Swimming, SNORKEL GEAR, FLY-FISHING from our beach. Relax in a daybed on SCREENED PORCH, Beach chairs, and beautiful SUNSETS. Hammocks throughout the property. Full bathroom glass enclosure shower, Towels, and bathrobe. FULL KITCHEN, Keurig & reg coffee maker, Blender, Toaster, smart TVs. Enjoy paradise experience well-maintained facilities & True Caymanian Hospitality!

14–21 May

$663 SGD per night

Superhost

Cottage in East End

4.54 out of 5 average rating, 26 reviews

Cayman Cottage by the Sea

Just 50 steps away from a powdery white, sandy beach the 2 bedroom cottage provides basic, spotlessly clean accommodations. Located in the peaceful East End of Grand Cayman: Great Diving, snorkelling, kiteboarding and windsurfing. A 5 minute drive from the grocery store, restaurants & the Morritts & Reef Resorts. Free use of kayaks and paddleboards. 13% Accommodation tax is added to rate. MINIMUM STAY: 5 Days High season, 4 days/low. NOTE: Christmas bookings are a minimum of 7 days.

18–25 Apr

$393 SGD per night

Guest favourite

Cottage in East End

5.0 out of 5 average rating, 11 reviews

Miss Annie's @ E'scape

E’scape, nestled in the idyllic seaside village of East End, is the ideal setting for a quick getaway or extended vacation. Whether visiting as a couple, group or family, its sweeping beachfront view invites tranquility, relaxation and rejuvenation. Incorporating touches of Cayman heritage and culture in the décor of both houses, two-bedroom “Ms. Annie’s”, sleeps four and reflects the charm of yesteryear. Larger and more modernly designed “The Isaac”, sleeps up to eight. Book your stay today.

1–8 Dec

$353 SGD per night

Guest favourite

Cottage in East End

5.0 out of 5 average rating, 79 reviews

Hidden Gem at Grapetree Cove

Hidden Gem is a Traditional Cayman Style cottage located at Grapetree Cove on a beautiful beach area in sleepy fishing village of East End. The property is filled with trees that gives it a dreamy Island ambiance. The Cottage has been fully renovated with modern amenities that makes is very comfortable and homey. Hidden Gem offers a unique CaymanKind experience from a Caymanian host that knows the area well. Located minutes away from local dinning places and many key attractions in the area.

24–31 Aug

$381 SGD per night

Guest favourite

Cottage in West Bay

4.95 out of 5 average rating, 37 reviews

Luxury Cottage, 2bd/2ba on 7 Mile Strip

Our Family Cottages are part of the Botanica collection of charming island style cottages which won the coveted 2021 Governor's Award for Excellence in Design and Construction. Our focus is casual luxury with dreamy details and high end amenities. Amenity highlight includes a resort style pool with a heated spa set in a tropical oasis with ample space to hang out and enjoy some family time. Be sure to check out our other listings under my profile. Non Smoking Complex.

2–9 Mar

$1,186 SGD per night

Guest favourite

Cottage in West Bay

5.0 out of 5 average rating, 173 reviews

Luxury Cottage, 1bd/1ba steps to Pool+7 Mile Beach

Our Queen Cottages are part of the Botanica collection of charming island style cottages which won the coveted 2021 Governor's Award for Excellence in Design and Construction. Our focus is casual luxury with dreamy details and high end amenities. Amenity highlight includes a resort style pool with a heated spa set in a tropical oasis with ample space to hang out and enjoy some down time. Be sure to check out our other listings under my profile. Non Smoking Complex.

7–14 Jul

$640 SGD per night

Guest favourite

Cottage in West Bay

5.0 out of 5 average rating, 63 reviews

Luxury Cottage, 1bd/1ba, desk | Pool+7 Mile Beach

Our King Cottages are part of the Botanica collection of charming island style cottages which won the coveted 2021 Governor's Award for Excellence in Design and Construction. Our focus is casual luxury with dreamy details and high end amenities. Amenity highlight includes a resort style pool with a heated spa set in a tropical oasis with ample space to hang out and enjoy some down time. Be sure to check out our other listings under my profile. Non Smoking Complex.

3–10 Aug

$743 SGD per night

Cottage in Cayman Brac

4.85 out of 5 average rating, 27 reviews

Blue Karma - Luxury Beachfront Cottage Cayman Brac

Vacation your way on one of the best island destinations in the Caribbean! With Blue Karma, you get a spacious 2,000 SQ. FT., 2 bedroom house with a private beach. With fold-away beds you can sleep 8 people comfortably. Check-in is at 3:00PM and Check-out is at 12:00PM. At $200.00 per night you can enjoy swimming, snorkeling, scuba diving, hiking rock climbing and much more. Or just relax on the beach during the day and dine away at night. Your vacation, your way!

14–21 Feb

$384 SGD per night

Guest favourite

Cottage in KY

5.0 out of 5 average rating, 7 reviews

Humble and Polite Little Cayman

Relax with the whole family at this peaceful oasis. Situated on private acreage in Preston Bay, on the West End of Little Cayman, this 3-bedroom cottage has absolutely everything you need. Unobstructed views of the Caribbean Sea with a one-of-a-kind edge salt water pool and jacuzzi set on a raised deck with cool-to-touch stone tiles, it’s easy to enjoy being surrounded by nature and comfortable breezes. Great for couples, families, or a small group retreat.

24–31 May

$773 SGD per night

Guest favourite

Cottage in East End

4.99 out of 5 average rating, 95 reviews

Piece of Mine, Beachfront Villa #3

BEACHFRONT Cottage offers all the conveniences of a luxury home. KAYAKS and SNORKELING GEAR, daybed & smart TV on the SCREENED PORCH, beach chairs, beach swing, and beautiful SUNSETS. Hammocks throughout the property. Modern walk-in Shower, Towels, and bathrobe. Full Kitchen, Keurig & regular coffee maker & Blender, Extra-large bedroom, Antique four post bed, Desk + smart TV. Enjoy paradise & experience "True Caymanian Hospitality!!"

12–19 Aug

$529 SGD per night

Guest favourite

Cottage in Savannah

4.97 out of 5 average rating, 132 reviews

John John's Hideaway

Cozy 1 bedroom cottage with en-suite bathroom, sitting area, full kitchen, washer and dryer. Located in a quiet neighbourhood, a 2 minute walk away from Pedro St. James Castle. 3 minute drive from a supermarket and local restaurants. 5 minute drive to snorkel at the picturesque Spotts Beach. 20 minute drive from other popular destinations, including shopping centres and other local attractions.

12–19 Jan

$212 SGD per night

Guest favourite

Cottage in Grand Cayman

5.0 out of 5 average rating, 28 reviews

PIECE of MINE, Beachfront Villa #2

BEACHFRONT VILLA offering all conveniences of a luxury home. Enjoy KAYAKING, Swimming, SNORKELING GEAR, Beach chairs, and beautiful SUNSETS. Hammocks throughout the property. Modern walk in Shower, Towels & Bath Robes. Full Kitchen, Keurig & regular coffee maker, Blender, Extra-large bedroom, Desk, two smart TV's (bedroom/Living room). Enjoy paradise & experience "True Caymanian Hospitality!!"

18–25 Mar

$560 SGD per night