Holiday houses in George Town

4.93 out of 5 average rating, 27 reviews

Home in Patricks Island

Oceanfront condo renovated w/pool & boardwalk

This extensively renovated, oceanfront 2 bed, 2.5 bath condo away from the road in a well-maintained, friendly complex offers modern island living. Step across landscaped grounds to a pool & unique boardwalk with breathtaking sunrise and sunset views over the Caribbean Sea. Grand Cayman's many activities, restaurants, beaches, and historical locations are easily reached from this perfectly located tranquil setting before you return for an ice-cold sunset drink or dip in the pool right outside.

Superhost

4.69 out of 5 average rating, 74 reviews

Where Retreat

Situated in George Town, our property is conveniently located just a 6-minute drive away from Smith's Cove Beach, also known as Smith's Barcadere. If you enjoy walking, you can take a pleasant 18-min stroll, to the Pickleball Sports Complex, where you can immerse yourself in the local culture while enjoying the sport. Also getting to and from the airport is a breeze, and it should only take you 6 mins by car. We are ready & willing to assist you with any questions or needs you may have. 🇰🇾

Apartment in Patricks Island

5 out of 5 average rating, 17 reviews

Island Inspired Homestyle Retreat

Your family will be close to everything when you stay at this centrally-located place.. walking distance to bus stop. Close to supermarket/Beaches/ restaurants/Gym. It is safe to walk at anytime. Comfortable and so peaceful. 65 inch TV for your comfort. It is home away from home. You will feel right at home..it have that kind of atmosphere. sofa beds. Can hold up to 10 persons easily. Can have meals prepared for you at a cost. No cleaning fees. Can help with arrangements if you need us to.

4.93 out of 5 average rating, 257 reviews

Condo in Grand Harbour

Sanctuary Serene | 2BR Waterfront | Porch & Pool

Cool clean contemporary Sanctuary with water views; a two bedroom/two bathroom condo with a full kitchen and living room packed with all popular amenities (wifi, cable television, Apple TV, Netflix, Playstation game console, central A/C, iron and ironing board, washer and dryer, outdoor patio, pool and free parking) - conveniently located in Grand Harbour. The Shoppes at Grand Harbour, & Harbour Walk are next door. Perfect for exploring and enjoying all that the Cayman Islands has to offer.

4.92 out of 5 average rating, 72 reviews

Loft in Patricks Island

Ocean Club Oasis

Indulge in the comfort of Ocean Club Oasis. A beautifully appointed one bed loft in oceanfront complex with incredible sea views from the seaside Boardwalk and Cabana. A two minute drive to the best snorkeling (turtles, reef fish etc) at Spotts Beach. Ten minutes to the famous Seven Mile Beach. Access to supermarket, shops and restaurants a mile away. Pickleball anyone! Steps from the unit and racquets for guest use. We welcome you to stay at Ocean Club Oasis and explore the Cayman Islands.

Superhost

Condo in George Town

4.85 out of 5 average rating, 130 reviews

Cozy Condo near Seven Mile Beach!

Welcome to the Cozy Condo, the spot for everyone coming to Grand Cayman for work, play, or a little bit of both—all at a budget-friendly price! You’ll love our prime location, just minutes from the George Town, the lively Camana Bay, and the beautiful Seven Mile Beach. Plus, you’ll find two convenient supermarkets and pharmacy within easy walking distance or a quick drive which has everything you could want, from shopping and dining to entertainment and drinks. We can’t wait to to host you!

4.98 out of 5 average rating, 237 reviews

Guest suite in Savannah

Paradise Escape-Charming Oceanfront Guest Suite

A tranquil oceanfront escape for couples and solo adventurers... Ours is a unique community with quaint freehold condo cottages on a vast tract of oceanfront land. Wake-up in bed to a lovely view of a luscious green landscape that melds with the emerald green and blue ocean, sip a hot cup of coffee on the porch, enjoy a sunset cocktail by the ocean front pool, break a sweat in a friendly game of tennis, or take a blanket out to the lawn under the palm trees for breathtaking star gazing.

4.92 out of 5 average rating, 26 reviews

Seaside Serenity at Allure

Affectionately dubbed the Seaside Chateau by owner and local fragrance designer Ted Green, Seaside Serenity at Allure is less Chateau and more contemporary island retreat that just happens to be nestled at the sea's edge of the North Sound (Caribbean Sea). A perfectly appointed and centrally located retreat. You will feel nestled away from it all, but in actuality, you're no farther than 5-10 mins from your favorite spots in South Sound, George Town, or Seven Mile Beach.

4.98 out of 5 average rating, 64 reviews

~Nim's Retreat~ Grand Cayman BWI

Nim's Retreat is a unique dwelling designed and built by the USA based architect Rufus Nims. Nim's Retreat features two bedrooms with King size beds and two baths. It is centrally located near some of the best restaurants and dive sites on Grand Cayman. Just a short trip to Smith Cove to enjoy a quick swim and beautiful sunset. Nim's Retreat can comfortably accommodate up to six persons when using the pull-out queen sleeper sofa. The property features SONOs in each room.

Guesthouse in Grand Harbour

4.98 out of 5 average rating, 160 reviews

Heavenly Suite 2 - The M @ The Edge

Heavenly Suíte #2 at The M @ The Edge is a studio apartment with sleek & modern furnishings, smart HD TV, sound bar, chandeliers, state of the art kitchenette with quartz counter-tops, Delta faucet, and under counter lights. The chic bedroom fashioned in white crisp tiles, scones and recessed lighting mimics the luxurious bath styled in porcelain & Carrera tiles, Delta faucets, mirrors. . The patio enlivened by red/white accents, greenery, bar, pergolas, and Jacuzzi.

4.97 out of 5 average rating, 29 reviews

Home in Patricks Island

Seabreezes-Your Oceanside Escape

Kick back and relax in this calm, stylish loft situated in an oceanfront community- a perfect Caribbean get away for a short break or longer holiday. The central location allows for easy access by car to all the areas of this lovely holiday Island. The property offers open spaces, 5 pools, an oceanfront walkway and a Cabana. Step outside to enjoy a morning swim in the pool; a glass of wine on the porch, or a romantic evening stroll by the boardwalk.

Guesthouse in George Town

4.88 out of 5 average rating, 139 reviews

Zen Den 3, cozy private studio in George Town

Welcome to this private cozy studio in the vibrant heart of George Town! Lokated 10-15 minute walking distance to Smiths Cove Beach, this is separate unit with an independent entry. Has a bedroom, kitchenette, washer dryer, bathroom and designated parking spot. Located in George Town near hospitals, pharmacy, gas station and restaurants. Bedroom has queen bed, split A/C, smart TV and Internet. Private outside patio with seating and a hammock.

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Other great holiday rentals in George Town

Apartment in Patricks Island

4.91 out of 5 average rating, 33 reviews

Newbee! Built in 2022! Modern and stylish.

SaraiRating, 5 stars4 days ago

I had the pleasure of staying at Leon’s place, and it was exactly what I needed. Whether you’re vacationing long-term or simply need a productive workday away from the usual routine, I highly recommend it. The space is peaceful, quiet, and beautifully designed — I was able to get everything done with ease and truly enjoyed my time there. Leon was very responsive, and we were able to arrange an early check-in, which made the experience even smoother. Absolutely worth the stay!

4.8 out of 5 average rating, 15 reviews

Mini Cottage Apartment

LizRating, 5 stars1 month ago

Great spot in a tucked away place. Walkable to beaches, restaurants and the bus stops. Sara was incredibly friendly and responsive. Would stay here again

5 out of 5 average rating, 42 reviews

Condo in George Town

Regal Beach Condo #233 on Seven Mile Beach

LisaRating, 5 stars1 month ago

I had a fantastic stay at Maggie's place. The unit was exactly as described- airy, beautifully furnished, very clean and incredibly comfortable. The location could not have been better- just steps from the beautiful beach and great local restaurants. Maggie was wonderful, thoughtful and attentive, checking in to make sure everything was perfect. She went the extra mile with small touches that made the stay extra special. I highly recommend it and would only want to stay here the next time I'm in Grand Cayman. Thank you again Maggie for a wonderful experience!

5 out of 5 average rating, 6 reviews

Home in Grand Harbour

Happy Place 1 Bed/1 Bath Cayman Cottage in Red Bay

ShaziaRating, 5 stars1 month ago

If you’re looking for the authentic feel of cayman, this is the place. Vegetation, the cottage itself, the amenities - everything one may need for a vacation was there, from thermos to beach mattress, popcorn machine, bbq, all kinds of pots pans to picnic boxes, Wi-Fi to tv, beach towels…just like a home where you have every practical amenity. Rachael is a warm, caring, approachable person and genuinely cared and ensured we were comfortable. There was cold water in the fridge when we arrived, basket of local goodies. 2 min by car, or a pleasant 15min walk to the supermarket, restaurants, cafes. It is a perfect place ensuring a relaxing and comfortable stay, privacy yet in a neighborhood of houses with gardens… just one word to describe our stay: perfect. Thank you, Rachael.

Cabin in George Town

4.6 out of 5 average rating, 15 reviews

Love Shack by the Water

AnjaliRating, 5 stars5 months ago

The place was located close to beaches and activities in a quiet neighborhood. The front porch was peaceful and we spent many hours sitting outside. There was enough room for the 4 of us to spread out inside. We really enjoyed our stay.

5 out of 5 average rating, 25 reviews

Modern Oceanfront 2BD Prime Loc

DimitriosRating, 5 stars2 weeks ago

Yara’s place was really a treat. Everything was like listing and more. Very thoughtful host. Had everything, basically you just need to buy food and everything else is covered. From coffee to sun lotion - towels - dishwasher detergent- toilet paper - paper towels - salt - pepper - water in filter in fridge, oh and let’s not forget the ice that was constantly full in the freezer. That was so convenient didn’t have to go out and buy ice for drinks. The washrooms are so clean and up to date fixtures. Floors are immaculate. The balcony has a view that is so nice, it was so nice that one day we just spent the whole day on it lol. Beds are so comfortable, so much room in bedrooms and drawers and closets for hanging your clothes. Pool is out of this world, so nice and the beach chairs tables. If you are visiting the Cayman, please do yourself a favour and check Yara’s place out. Oh and let’s not forget about Yara herself, amazing host 10 ⭐️’s Thank you, Yara, your place is a gem?

5 out of 5 average rating, 5 reviews

Kings Court Villa Britannia

SilviaRating, 5 stars2 months ago

Olivia’s condo is the BEST Airbnb place I’ve ever stayed in! Beautifully decorated, very spacious and extremely clean. The location couldn’t be better either - walking distance to Camana Bay and a 5 minute drive to Governor’s public beach. Olivia responded to my questions within minutes and she was wonderful throughout our stay. I think this condo deserves 10 star review if that is an option! There is no other place we will choose next time we visit the island! If you are looking for a “home away from home” experience, O Olivia’s condo is a must! Thank you, Olivia for making our first visit to the Caymans an unforgettable one!!