Holiday Rentals in Cayman Islands

2552 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Cayman Islands holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Best Holiday rentals and Airbnb offers in Cayman Islands

Best family friendly Cayman Islands holiday rentals

Among the 2552 accommodations in Cayman Islands, here are the 4 best family friendly rentals

Oceanfront: 3 King Suites, Pool, Shore Diving - Cayman Islands
9.9 82 reviews
Cayman Islands
02/01 – 07/01
£765/nighttotal: £3825 (5 )

Oceanfront: 3 King Suites, Pool, Shore Diving

1 6
apartment , West Bay
This West Bay townhouse, located in Northwest Point, boasts a direct oceanfront position next to Macabuca and Cracked Conch restaurants, and is a short walk from the Dolphin and Turtle Centres, with Seven Mile Beach approximately 1.6km away.
The three-storey property offers three en-suite bedrooms, sleeping six, a fully equipped kitchen, private patio with grill, two communal swimming pools, 65mbps Wi-Fi, and proximity to on-site diving facilities and world-class shore diving.
Starfish Paradise Beachfront Condo - Cayman Islands
9.7 138 reviews
Cayman Islands
01/08 – 31/08
£198/nighttotal: £5940 (30 )

Starfish Paradise Beachfront Condo

1 4
apartment , Rum Point
This beachfront property is located in the Kaibo district of Grand Cayman, just a short distance from Rum Point and its popular attractions. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The apartment has two bedrooms and two bathrooms, comfortably accommodating up to six guests. It features a fully equipped kitchen, a private patio, and access to a swimming pool, jacuzzi, and barbecue facilities.
The Meadows Luxury 3 Bdrm Townhouse With Pool And - Cayman Islands
10 1 review
Cayman Islands
01/07 – 31/07
£208/nighttotal: £6240 (30 )

The Meadows Luxury 3 Bdrm Townhouse With Pool And

1 2
house , West Bay
This townhome is situated within The Meadows at Batabano, a secure gated community in West Bay, Grand Cayman, offering a peaceful island escape conveniently located a short walk from the resort-style lap pool and community clubhouse.
This family-friendly residence accommodates up to six guests across three bedrooms and three bathrooms, featuring a modern kitchen with brand-new stainless steel appliances, air conditioning, a private garden, and a fitness centre, with the primary suite boasting a walk-out balcony with elevated grounds and slight ocean views.
Featherstone Estate, Cayman Brac - Cayman Islands
Cayman Islands
27/06 – 04/07
£1021/nighttotal: £7147 (7 )

Featherstone Estate, Cayman Brac

4 2
house , Cayman Brac
This beachfront Cayman Brac villa, situated in the Featherstone Estate, is 12 kilometres from Charles Kirkconnell International Airport.
The 265 square metre property offers four bedrooms, four bathrooms, three living rooms, accommodating up to 21 guests, and features a private pool, extensive outdoor space with barbecue facilities, and easy access to snorkelling, cycling, and fishing.

Best Cayman Islands holiday rentals with a pool

Among the 2552 accommodations in Cayman Islands, here are the 4 best rentals with a pool

Luxury Ocean View Oasis On 7 Mile Beach - Cayman Islands
10 36 reviews
Cayman Islands
27/06 – 04/07
£287/nighttotal: £2009 (7 )

Luxury Ocean View Oasis On 7 Mile Beach

1 2
apartment , George Town
This oceanfront apartment on Seven Mile Beach in George Town offers direct access to the beach and snorkelling, with restaurants and shops within walking distance.
The ground-floor flat features two en-suite bedrooms, sleeping up to five guests, a fully equipped kitchen, private patio, and access to a complex with a pool, BBQ area, and tennis/pickleball court; snorkel gear is provided.
Dove Retreat - Cayman Islands
9.4 93 reviews
Cayman Islands
27/06 – 04/07
£101/nighttotal: £707 (7 )

Dove Retreat

1 2
apartment , George Town
This one-bedroom apartment is located in George Town, a short drive from Smith’s Cove Beach and Smith’s Barcadere, and within walking distance of the Olympic Truman Bodden Sports Complex. It has received excellent user ratings for cleanliness and location, making it a great choice for travellers. This self-contained home offers a comfortable and independent living space for up to two guests, with amenities like a swimming pool, private entrance, and easy access to public transport and the airport.
Luxury Beachview Retreat, Cayman Island. - Cayman Islands
10 37 reviews
Cayman Islands
02/01 – 07/01
£1175/nighttotal: £5875 (5 )

Luxury Beachview Retreat, Cayman Island.

1 6
apartment , North Side
This luxurious North Side villa is situated a few kilometres from Rum Point, offering easy access to Over the Edge and Tukka restaurants, and a short ferry trip to Camana Bay.
This four-bedroom, four-bathroom property sleeps eleven guests, boasting a private pool, ocean views, a gourmet kitchen with a Big Green Egg BBQ, on-site mini-golf, water sports equipment, and a modern security system.
Green Oasis Homestay - Cayman Islands
9.5 30 reviews
Cayman Islands
17/09 – 31/10
£61/nighttotal: £2684 (44 )

Green Oasis Homestay

1 2
house , North Sound Estates
This self-contained suite in North Sound Estates offers a peaceful retreat, conveniently located near local attractions although precise distances aren't provided.
The one-bedroom, one-bathroom apartment sleeps two guests and includes a private garden, swimming pool access, a mini herb garden, and starter supplies of essentials; fresh fruit from the backyard is also provided.

Frequently asked questions about holiday rentals in Cayman Islands

  • What are the must-see places in the Cayman Islands?

    Seven Mile Beach is a must, of course. It's world-renowned for its powdery white sand and turquoise water. Stingray City, where you can snorkel or swim with southern stingrays, is another iconic experience. Then there's the Cayman Turtle Centre: Island Wildlife Encounter, a great place to learn about and see these magnificent creatures. For a bit of history, explore the Pedro St James National Historic Site, a beautifully preserved plantation house.
  • What are the best Airbnb and holiday rentals in Cayman Islands?

  • What are the typical activities to do in the Cayman Islands?

    Snorkelling and diving are hugely popular, especially around the reefs and Stingray City. You can also try stand-up paddleboarding, kayaking, or jet skiing. For a more relaxed pace, there's plenty of swimming, sunbathing, and boating. Deep-sea fishing is another big draw, as is exploring the island's many beautiful beaches.
  • What are the most popular Airbnbs in Cayman Islands?

  • Which part of the Cayman Islands offers the most pleasant climate?

    The climate is generally pleasant year-round, but the smaller islands like Little Cayman and Cayman Brac tend to be slightly less humid than Grand Cayman. However, the differences are subtle.
  • What are the best holiday rentals with a pool in Cayman Islands?

  • What airport options are there for reaching the Cayman Islands?

    Owen Roberts International Airport (GCM) on Grand Cayman is the main airport. There are also smaller airports on Cayman Brac (CYB) and Little Cayman (LYB), but they mainly serve inter-island flights.
  • What are the best rentals for families and kids in Cayman Islands?

  • Are there specific challenges to driving in the Cayman Islands that visitors should know?

    Driving is on the left-hand side of the road, which can take some getting used to. The roads can be narrow in places, and some areas have limited street lighting. Renting a car is a good way to explore, but remember to drive cautiously.
  • What are the best rentals or Airbnbs with a jacuzzi in Cayman Islands?

  • What currency is used in the Cayman Islands?

    The Cayman Islands dollar (KYD) is the official currency, but US dollars are widely accepted everywhere.
  • What are the top festivals to experience in the Cayman Islands?

    The Pirates Week Festival is a major event, usually held in November, celebrating the islands' seafaring past. Batabano, a colourful Carnival-style parade, typically takes place in May.
  • What is the best time of year to visit the Cayman Islands?

    The best time to visit is generally during the 'shoulder seasons' – April-May and September-October – when the weather is still lovely but the crowds are smaller, and prices may be more reasonable. The summer months (June-August) can be hot and humid, and hurricane season runs from June to November.
  • What are some local dishes to try in the Cayman Islands?

    Conch is a staple; try it in fritters, ceviche, or a hearty stew. Try the Cayman style jerk chicken or fish, and don't miss the local seafood. Many restaurants feature fresh, locally sourced ingredients.
  • What emergency numbers should you know in case of a medical or security issue in the Cayman Islands?

    For medical emergencies, dial 911. For police, also dial 911.
  • What etiquette tips are important when visiting the Cayman Islands?

    Being polite and respectful is always appreciated. Remember to dress modestly when visiting churches or other religious sites. Tipping is customary in restaurants and for tour guides.
  • What are the best areas to spend a week in the Cayman Islands?

    Seven Mile Beach offers a range of luxury resorts and plenty of activities. If you prefer a quieter experience, consider staying in the less developed areas of Cayman Brac or Little Cayman.
  • What are the best areas to spend a weekend in the Cayman Islands?

    Grand Cayman offers easy access to many attractions, making it ideal for a short trip. Seven Mile Beach is a good base for exploring the island's various beaches and activities.
  • What are the top shopping destinations in the Cayman Islands?

    George Town is the main shopping hub, with a mix of duty-free shops, boutiques, and art galleries. Camana Bay is a more upscale shopping and dining destination.
  • What are some off-the-beaten-path places to explore in the Cayman Islands?

    Little Cayman and Cayman Brac offer a more secluded experience than Grand Cayman. Explore the Bloody Bay Wall, a world-famous dive site, or hike to the top of the Bluff on Cayman Brac for panoramic views.

Top regions Cayman Islands

Best Cayman Islands holiday rentals with parking

Beach Living At Island Pine Villas Blaw - Cayman Islands
9.4 36 reviews
Cayman Islands
28/11 – 05/12
£355/nighttotal: £2485 (7 )

Beach Living At Island Pine Villas Blaw

2 3
apartment , George Town
This apartment is located in George Town, just 5 km from Owen Roberts International Airport and directly on the famous Seven Mile Beach. It has excellent user, location and cleanliness ratings.
This 2-bedroom flat is 79 square metres and has a fully equipped kitchen, air conditioning, a swimming pool, a terrace and a garden. It also includes free Wi-Fi, parking and is non-smoking.
Luxury 1 Bed Apartment Near Seven Mile Beach At The Grove - Villa Gypsy Soul - Cayman Islands
9.7 14 reviews
Cayman Islands
06/08 – 16/08
£276/nighttotal: £2760 (10 )

Luxury 1 Bed Apartment Near Seven Mile Beach At The Grove - Villa Gypsy Soul

1 3
apartment , Upper Land
This Upper Land apartment is a 2-minute walk from Seven Mile Beach and 7km from Owen Roberts International Airport.
The 63-square-metre flat offers one bedroom, one bathroom, a fully equipped kitchen, air conditioning, a balcony, and private parking, perfect for couples seeking a self-catering stay near Grand Cayman's most famous beach.
Britannia 7 Mile Beach Condo - Cayman Islands
9.5 2 reviews
Cayman Islands
20/07 – 29/07
£410/nighttotal: £3690 (9 )

Britannia 7 Mile Beach Condo

3 6
house , Upper Land
This three-bedroom, three-bathroom house in Upper Land is situated a 19-minute walk (approximately 1.5km) from Seven Mile Beach and 6km from Owen Roberts International Airport.
This 242 square metre property boasts a private swimming pool, Jacuzzi, and balcony with sea views, accommodating up to 15 guests and including free Wi-Fi, private parking, and a fully equipped kitchen.
Crescent Point #9: 3bed Condo - Cayman Islands
8.0 1 review
Cayman Islands
20/07 – 29/07
£570/nighttotal: £5130 (9 )

Crescent Point #9: 3bed Condo

3 6
house , Seven Mile Beach
This three-bedroom condo in Crescent Point, Grand Cayman, is a short walk from Seven Mile Beach and 5km from Owen Roberts International Airport.
The 173 square metre property boasts three bathrooms, a private balcony with sea views, a swimming pool, free Wi-Fi, and parking, comfortably accommodating up to 11 guests.

Best Cayman Islands holiday rentals with a balcony

Pools Of The Kai 10 - Cayman Islands
10 1 review
Cayman Islands
24/12 – 01/01
£952/nighttotal: £7616 (8 )

Pools Of The Kai 10

2 4
apartment , Driftwood Village
Pools of the Kai 10 apartment in Driftwood Village is an 8-minute walk from Water Cay Public Beach and 2.9km from Rum Point Beach.
This one-bedroom self-catering flat, sleeping seven, boasts two bathrooms, a private pool, terrace, and parking, plus all the kitchen appliances you need for a comfortable stay.
Rum Point Resort 405 - Cayman Islands
Cayman Islands
01/07 – 31/07
£682/nighttotal: £20460 (30 )

Rum Point Resort 405

1 2
apartment , Driftwood Village
Rum Point Resort 405, a two-bedroom apartment in Driftwood Village, boasts direct access to Rum Point Beach and is 2.1 kilometres from Water Cay Public Beach.
This 194 square metre property offers a spacious layout sleeping up to 11 guests, featuring a fully equipped kitchen with microwave and dishwasher, air conditioning, a private terrace, swimming pool access, parking, and free Wi-Fi.
Featherstone Cottage, Cayman Brac - Cayman Islands
9.2 5 reviews
Cayman Islands
25/07 – 06/08
£256/nighttotal: £3072 (12 )

Featherstone Cottage, Cayman Brac

1 2
house , Cayman Brac
Featherstone Cottage is situated in Cayman Brac, a 12km drive from the Charles Kirkconnell International Airport.
The one-bedroom cottage offers a private pool, a fully equipped kitchen, air conditioning, free Wi-Fi, and parking, ideal for a group of up to seven guests.
Regal Beach Club - 2bed Luxury Unit - Cayman Islands
Cayman Islands
26/11 – 02/12
£325/nighttotal: £1950 (6 )

Regal Beach Club - 2bed Luxury Unit

1 2
apartment , Grand Cayman
This Grand Cayman apartment is located in the Seven Mile Beach district, just a short walk from the famous Seven Mile Beach and 5 kilometres from Owen Roberts International Airport.
This 111 square metre flat offers accommodation for up to nine guests, featuring two bathrooms, air conditioning, a fully equipped kitchen, complimentary high-speed Wi-Fi, and a private balcony.
©2026 cozycozy.com