Photo by Paul Shaffer -Dee

Old Man Bay vacation rentals

We found 344 vacation rentals — enter your dates for availability
Discover a selection of 9 homes and other vacation rentals in Old Man Bay that are perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll find the amenities you need and want, such as WiFi and cable TV. Whatever you're looking for, you're sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Old Man Bay

Showing deals for:Dec 11 - Dec 18

Dining area
View from the Master bedroom
View from the couch
Property grounds
Exceptional
(80 reviews)

BEAUTIFUL 3 BEDROOM VILLA LOCATED DIRECTLY ON THE BEACH, EXCELLENT SNORKELING

North Side

10% off
CA $404
CA $3,712 total
BEAUTIFUL 3 BEDROOM VILLA LOCATED DIRECTLY ON THE BEACH, EXCELLENT SNORKELING
Dining Area (incl beach towels and cooler for shopping)
Living Area
Kitchen and Living Area
2nd Bedroom
Exceptional
(53 reviews)

Cozy Cayman Beach Front Cottage - Emerald Sea House , 2 Bdrm 2 bath

North Side

5% off
CA $853
CA $7,590 total
Cozy Cayman Beach Front Cottage - Emerald Sea House , 2 Bdrm 2 bath
Screen Lanai
View From Condo
Guest Bedroom
View from Bedroom
Exceptional
(94 reviews)

Paradise Found Oceanfront Condo - Flexible Cancellation

North Side

10% off
CA $385
CA $3,269 total
Paradise Found Oceanfront Condo - Flexible Cancellation
The lanai, a unique place to enjoy without much of the sun
Days full o flight and color
Condo’s lanai, deck, pool, and beach, what a bundle for island living enjoyment
Outside deck looking straight at the beach for private and complete relax
Exceptional
(10 reviews)

BEACH and POOL at Rum Point - North Side in most secluded and tranquil area

North Side

5% off
CA $466
CA $4,169 total
BEACH and POOL at Rum Point - North Side in most secluded and tranquil area
Property The Retreat
Starfish Point  2 miles away from condo
Kaibo restaurant/beach bar/coffee shop/water taxi/boat marina located amile away
Pool at The Retreat for guests
Exceptional
(37 reviews)

2023 Renovated The Retreat 17 Oceanview ground floor condo steps to ocean/beach

North Side

10% off
CA $429
CA $3,901 total
2023 Renovated The Retreat 17 Oceanview ground floor condo steps to ocean/beach
...or marvel at the beauty of native plants in the nearby botanical garden
...with an infinity pool...
Prepare your morning coffee overlooking tranquil waves
Primary suite with exit to patio/beach, king bed, blackout curtains for privacy
Exceptional
(95 reviews)

Beachfront 1st Floor Condo - Step off your patio and into paradise!

East End

10% off
CA $461
CA $4,166 total
Beachfront 1st Floor Condo - Step off your patio and into paradise!
6 panel sliding door opens onto the private pool deck, fully screened in
Living area
Property grounds
Updated appliances, fully equipped kitchen
Exceptional
(59 reviews)

Nature's View: Cayman Style Tranquility at Pools of the Kai #2

North Side

5% off
CA $689
CA $6,043 total
Nature's View: Cayman Style Tranquility at Pools of the Kai #2
Interior
Living area
Pool
Living area
Exceptional
(68 reviews)

Escape to Paradise – Beautiful & Budget-Friendly Condo!

North Side

10% off
CA $364
CA $3,090 total
Escape to Paradise – Beautiful & Budget-Friendly Condo!
Room
Exterior
Interior
Living area
Exceptional
(24 reviews)

SAVE 10% – Coco Sands – 2 bed, 2 bath beachfront condo with sea view, Rum Point

North Side

5% off
CA $387
CA $3,486 total
SAVE 10% – Coco Sands – 2 bed, 2 bath beachfront condo with sea view, Rum Point

Find out more about Old Man Bay

Why visit Old Man Bay

  • Pristine Beaches: Relax on the beautiful, unspoiled beaches perfect for sunbathing and swimming.
  • Outdoor Adventures: Enjoy hiking trails and explore engaging outdoor activities amidst stunning natural beauty.
  • Historic Landmarks: Visit the impressive blowhole and the historic lighthouse for a taste of local culture.
  • Cayman Kai Public Beach: Unwind at this popular beach, ideal for soaking up the sun and enjoying the scenery.
  • Local Culture: Discover nearby towns to experience the vibrant island life and hospitality.

Popular types of accommodation in Old Man Bay

If you're planning a getaway to Old Man Bay, you'll find a variety of appealing accommodation options to suit your needs. The most sought-after types of holiday rentals in this stunning location include condos, private holiday homes, and villas, all offering breathtaking ocean views. Embrace the beauty of the Cayman Islands with a holiday home that ensures transparency, savings, and peace of mind during your stay.

  • Condos: These modern accommodations offer a blend of comfort and convenience, making them the top choice for visitors in Old Man Bay.
  • Private Holiday Homes: Ideal for families or groups, these spacious homes provide a home-like atmosphere with all the necessary amenities.
  • Villas: Luxurious and often featuring stunning views, villas offer an upscale experience for those seeking relaxation.
  • Apartments: Perfect for shorter stays, these self-contained units provide easy access to local attractions.
  • Cottages: Charming and quaint, cottages offer a cozy retreat amidst the natural beauty of Old Man Bay.**

Top attractions near Old Man Bay

Old Man Bay offers a delightful mix of beach and outdoor adventures, perfect for those seeking cultural experiences. Visitors can explore stunning beaches, the impressive blowhole, and a historic lighthouse. Additionally, the area features hiking trails, sights of Old Man Bay, and activities such as relaxing at Cayman Kai Public Beach, making it an ideal destination for travellers looking to enjoy nature and local attractions.

  • Grand Cayman Blow Holes: Experience the natural wonder of the blowholes, located 8km from Old Man Bay. The crashing waves create spectacular geysers, providing a serene and secluded atmosphere perfect for relaxation and contemplation.
  • Queen Elizabeth II Botanic Park: Just 3km away, this lush botanical garden offers a family-friendly environment with vibrant flora and fauna, ideal for outdoor adventures and romantic strolls amidst nature’s beauty.
  • Barefoot Beach: Located 5km from Old Man Bay, this pristine beach invites you to unwind and bask in the sun, offering a perfect spot for seaside relaxation and beachside activities.

Things to do recommended for couples

Looking for a romantic getaway in Old Man Bay? Enjoy a sunset picnic on the beach, indulge in a couple's massage at a local spa, or take a leisurely kayak tour through the serene waters. Create unforgettable memories together in this stunning paradise.

Things to do recommended for families

Families visiting Old Man Bay can explore the stunning coral reefs while snorkelling, enjoy a day at the beach building sandcastles, or take a leisurely stroll along the shoreline. Don't forget to sample local cuisine at nearby eateries, making it a delightful and memorable family holiday.

Things to do recommended for groups

Groups visiting Old Man Bay can enjoy a relaxing day at the beautiful beach, partake in snorkelling excursions to explore vibrant coral reefs, and indulge in local seafood cuisine at nearby restaurants. The laid-back atmosphere makes for an ideal setting for group bonding and unforgettable memories.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Old Man Bay

If you're planning a trip with friends, family, or pets, or if you're considering an extended stay, it's important to filter your options based on what's most important to you. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Old Man Bay with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor space for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Old Man Bay with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with having suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are fun for families.
  • Taking your pets with you to Old Man Bay: For many, a family getaway isn’t truly complete without their furry companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Old Man Bay: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider including amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Old Man Bay

Old Man Bay, located on the North Side of the Cayman Islands, offers a delightful blend of relaxation and adventure. Visitors can enjoy pristine beaches, engaging outdoor activities, and vibrant local culture. Explore the nearby towns for a taste of island life, or embark on excursions that showcase the stunning natural beauty of the area. Whether you're seeking a peaceful retreat or thrilling adventures, Old Man Bay is an ideal destination for your holiday getaway.

  • Grand Cayman: Grand Cayman is a stunning island paradise located a mere 6km from Old Man Bay. Known for its pristine beaches and vibrant family-friendly atmosphere, this destination offers a variety of outdoor experiences. Visitors can enjoy leisurely days at the beach, explore local shopping areas, and indulge in a range of dining options. Notable attractions nearby include a popular theme park and a film studio, making it an ideal spot for those seeking both relaxation and adventure.
  • East End: Situated 8km from Old Man Bay, East End is a charming district known for its serene beaches and family-oriented activities. This area boasts several shopping centres where travellers can find unique souvenirs and local crafts. Visitors can also explore local landmarks, including a historic lighthouse and various monuments, ensuring a rich cultural experience. East End is perfect for those looking to immerse themselves in both nature and history while enjoying the island's beautiful coastal scenery.
  • Breakers: Just 3km from Old Man Bay, Breakers is a quaint village that offers a delightful blend of outdoor adventures and family fun. Known for its beautiful beach access, this area invites visitors to relax by the water or embark on hiking trails that showcase the island’s natural beauty. With convenient shopping areas and a nearby marina, Breakers provides a welcoming atmosphere for tourists looking to unwind and explore the great outdoors.

Best time to go to Old Man Bay

If you're planning a trip to Old Man Bay, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from January to March, while off-peak times, like August to October tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January78.4°F (25.8°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
February78.4°F (25.8°C)No Rain (Dry)Mostly SunnyModerately HighAverage
March78.4°F (25.8°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
April80.2°F (26.8°C)No Rain (Dry)Mostly SunnyAverageAverage
May81.7°F (27.6°C)Light RainMostly SunnyAverageAverage
June82.9°F (28.3°C)Light RainMostly SunnyAverageAverage
July83.8°F (28.8°C)Light RainMostly SunnyAverageAverage
August84.4°F (29.1°C)Light RainMostly SunnyModerately LowSlightly Low
September84.2°F (29.0°C)Light RainMostly SunnyModerately LowSlightly Low
October83.1°F (28.4°C)Moderate RainMostly SunnyModerately LowSlightly Low
November81.3°F (27.4°C)Light RainMostly SunnyAverageAverage
December79.9°F (26.6°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is simple

Are you hoping to cut down on costs for your upcoming adventure? Being flexible with your travel dates can really help, as prices can vary quite a bit. Additionally, if you opt for a longer stay, you often unlock some substantial savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of holiday rental. Happy travels.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers an easy-to-use platform where you can plan new adventures, continue from where you last stopped, or manage your travel arrangements. You’ll see your saved or booked properties neatly organized under Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Find the perfect vacation rental for your Old Man Bay getaway

Learn about the unique charm of Old Man Bay with a stay in a private vacation home. There's no shortage of things to see and do in the area.With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Old Man Bay

Are you hoping to find things to do during your stay? Venture out of your vacation home and check out everything that makes Old Man Bay a fun place to get away. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • North Sound Golf Course (12.3 mi / 19.8 km)
  • Britannia Golf Course (13.2 mi / 21.2 km)

Exploring the natural landscape of Old Man Bay

Whether you're looking for fun outdoor activities or just want to take in the scenery, Old Man Bay is a great place to get out in nature. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Grand Cayman Beaches (3.3 mi / 5.3 km)
  • Grand Cayman Blow Holes (4.7 mi / 7.6 km)
  • Starfish Point (6.5 mi / 10.5 km)
  • Rum Point Beach (6.6 mi / 10.6 km)
  • Spotts Beach (10.2 mi / 16.5 km)
  • Governor's Beach (13.4 mi / 21.5 km)

How to get to and around Old Man Bay

Fly into Owen Roberts Intl. Airport (GCM), the closest airport, located 12.3 mi (19.8 km) from the city center.

Frequently asked questions

What is the best area to stay in Old Man Bay when booking a vacation rental?
When considering a vacation rental in Old Man Bay, the area offers a delightful mix of tranquillity and natural beauty, making it an excellent choice for a relaxing getaway. This coastal neighbourhood is renowned for its stunning beaches and crystal-clear waters, superb for those looking to indulge in water sports or simply unwind by the sea.You'll find a variety of properties available, ranging from beachfront villas to charming cottages, suiting different tastes and budgets. One top attraction in the vicinity is the picturesque Rum Point, which provides a fantastic spot for swimming and enjoying local cuisine at beachfront eateries. Additionally, the nearby bioluminescent bay offers a unique opportunity to experience the magic of glowing waters on a night-time kayak tour.Old Man Bay is an ideal base for exploring the natural wonders of the Cayman Islands while also enjoying the peaceful atmosphere that this area provides.
How much does it cost to rent a vacation home in Old Man Bay?
Prices for vacation rentals in Old Man Bay vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Old Man Bay to more spacious homes.
Are there any discounts for Old Man Bay vacation house rentals?
You can find great discounts on house rentals in Old Man Bay on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I find long-stay vacation rentals in Old Man Bay?
A long-stay vacation rental in Old Man Bay is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any Old Man Bay vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Old Man Bay with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
How early should I book a Old Man Bay vacation rental?
Book your Old Man Bay vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Old Man Bay?
In Old Man Bay, visitors can enjoy a laid-back atmosphere and stunning natural beauty. The beach itself is a major attraction, offering soft sands and clear turquoise waters, superb for swimming and sunbathing. Nearby, the secluded cove at Rum Point provides a lovely spot for water sports and relaxation, with opportunities for kayaking and paddleboarding.For those interested in local culture, the nearby district of North Side features the Cayman Crystal Caves, where guests can take guided tours to explore the fascinating rock formations and learn about the island's geology.Additionally, the area is within a short drive to the famous Stingray City, where visitors can interact with friendly stingrays in their natural habitat, making for an unforgettable experience.
Can I change or cancel my Old Man Bay home rental booking on Vrbo?
To find Old Man Bay vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Old Man Bay vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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