Photo by Paul Shaffer -Dee

Old Man Bay vacation rentals

We found 344 vacation rentals — enter your dates for availability

Welcome to Old Man Bay, where azure waters meet pristine beaches, and the gentle sound of waves creates an inviting atmosphere for relaxation. Explore the charm of the traditional fishing village, marvel at the captivating blowhole, or dive into vibrant coral reefs teeming with marine life. Ideal for groups and families, our diverse vacation rentals—from cozy condos to luxurious villas—offer the comforts and amenities of home, ensuring a memorable getaway filled with adventure and tranquility.

Holiday rentals with weekly discounts - Old Man Bay

Showing deals for:Nov 6 - Nov 13

Guest Bedroom
View From Condo
View from Bedroom
Screen Lanai
Exceptional
(94 reviews)

Paradise Found Oceanfront Condo - Flexible Cancellation

North Side

9% off
$229
$1,603 for 7 nights
All fees included
Paradise Found Oceanfront Condo - Flexible Cancellation
Room
patio view
Pool looking South-West
Interior
Exceptional
(31 reviews)

Beachfront Kaibo Condo

North Side

6% off
$388
$2,714 for 7 nights
All fees included
Beachfront Kaibo Condo
Property The Retreat
Starfish Point 2 miles away from condo
Master Bedroom King bed, nightstands with storage/ceiling fan/blackout curtains
Pool at The Retreat for guests
Exceptional
(37 reviews)

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

North Side

8% off
$374
$2,618 for 7 nights
All fees included
2023 Renovated The Retreat 17 Oceanview ground floor condo steps to ocean/beach
Another view of the beach bar
The middle pool at the Wyndham Resort. Here's where you'll find the kiddies pool
Castaways' Cove Pool and hot tub
View of the primary bedroom and balcony
Exceptional
(24 reviews)

East End Dream, RESORT LIVING WITHOUT ANY EXTRA FEES!

East End

8% off
$308
$2,154 for 7 nights
All fees included
East End Dream, RESORT LIVING WITHOUT ANY EXTRA FEES!
Private kitchen
View from screened lanai over beach and cove
Pool looking out over dock and Cove.
Dining
Exceptional
(150 reviews)

Dream Kai -Island House #15

North Side

9% off
$371
$2,596 for 7 nights
All fees included
Dream Kai -Island House #15
Prepare your morning coffee overlooking tranquil waves
...with an infinity pool...
...or marvel at the beauty of native plants in the nearby botanical garden
Primary suite with exit to patio/beach, king bed, blackout curtains for privacy
Exceptional
(93 reviews)

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

East End

8% off
$361
$2,525 for 7 nights
All fees included
Beachfront 1st Floor Condo - Step off your patio and into paradise!
Living area
Pool
Living area
Living area
Exceptional
(68 reviews)

Escape to Paradise – Beautiful & Budget-Friendly Condo!

North Side

9% off
$299
$2,091 for 7 nights
All fees included
Escape to Paradise – Beautiful & Budget-Friendly Condo!

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Old Man Bay

Why visit Old Man Bay

  • Beautiful Beaches: Old Man Bay boasts stunning beaches perfect for relaxation and sunbathing.
  • Unique Blowhole: Explore the fascinating blowhole, a natural wonder that captivates visitors.
  • Charming Fishing Village: Experience the quaint atmosphere of a traditional fishing village.
  • Excellent Diving Spots: Discover vibrant marine life and coral reefs at nearby diving locations.
  • Botanical Garden Strolls: Enjoy a peaceful walk through lush botanical gardens filled with exotic plants.

Popular types of accommodation in Old Man Bay

Planning your getaway to Old Man Bay? You're in for a treat. This stunning destination offers a variety of vacation rentals to suit every traveler. From cozy condos and houses to luxurious villas, you'll find the perfect spot to unwind. Enjoy breathtaking oceanfront views, relax by the outdoor pool, or experience the charm of a local guesthouse. Start exploring Old Man Bay vacation rentals for an unforgettable stay.

  • Condos: The top choice for vacation rentals in Old Man Bay, offering modern amenities and breathtaking views.
  • Houses: A close second, perfect for families or groups seeking privacy and comfort.
  • Villas: Ideal for those looking for luxury accommodations with spacious living areas and private pools.
  • Apartments: A practical option for travelers wanting a cozy space with essential amenities.
  • Cottages: Charming and quaint, these provide a unique and homely atmosphere for your stay.**

Top attractions near Old Man Bay

Old Man Bay in the Cayman Islands offers the perfect setting for beach and outdoor adventures. Visitors can enjoy beautiful beaches, explore the unique blowhole, and stroll through the botanical garden. The area is known for its charming fishing village atmosphere, excellent diving spots, and the iconic Old Man Bay itself, making it an ideal destination for travelers seeking thrilling and relaxing experiences alike.

  • Grand Cayman Blow Holes: Witness the natural spectacle of water shooting through coral rock formations. Located 5 miles from Old Man Bay, this secluded spot offers a serene atmosphere, perfect for relaxation and recreation while enjoying the ocean's force.
  • Rum Point Beach: A picturesque beach located 6 miles away, Rum Point Beach is known for its soft sands and tranquil waters, ideal for sunbathing and swimming. The laid-back vibe makes it a perfect spot for a relaxing day by the sea.
  • Queen Elizabeth II Botanic Park: Just 2 miles from Old Man Bay, this beautiful botanical garden features lush landscapes and vibrant flora, providing a romantic and family-friendly experience. It's a great place for leisurely strolls and appreciating nature's beauty.

Things to do recommended for couples

Ready for a romantic getaway in Old Man Bay? Explore the stunning beaches, indulge in a couple's massage at a local spa, or enjoy a sunset dinner by the ocean. Don't miss the chance to snorkel together in the crystal-clear waters—perfect for creating lasting memories.

Things to do recommended for families

Families visiting Old Man Bay can enjoy a day at the beautiful beaches, perfect for swimming and building sandcastles. Snorkeling adventures nearby offer exploration of vibrant marine life, while local dining options provide delicious Caymanian cuisine that everyone will love.

Things to do recommended for groups

Explore the stunning coral reefs while snorkeling or diving in Old Man Bay. Gather your group for a relaxing day at the beach, followed by a delicious seafood feast at a local restaurant. Enjoy a guided tour of the picturesque surroundings for a memorable experience together.

*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

When you're planning a trip, whether it's with a group, your family, or even your pets, or if you're considering an extended stay, be sure to apply the right filters to meet your needs. 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 and any additional features you might want, like a full kitchen or outdoor space for group events. The good news is that you can easily use filters on Vrbo to find exactly what you need and more.
  • Traveling to Old Man Bay with young kids: Traveling with little ones can present its own set of challenges. It's important to prioritize their comfort and safety, along with seeking out age-appropriate amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Old Man Bay: For many families, a vacation wouldn’t feel complete without their furry companion. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Old Man Bay: If you're searching for vacation rentals that offer 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 rental options. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Old Man Bay

Old Man Bay in the Cayman Islands offers a serene escape for beach lovers and adventure seekers alike. With its tranquil oceanfront, stunning ocean views, and nearby beaches, it's the perfect destination for relaxation and exploration. Enjoy a day at Old Man Bay Beach, take a trip along the coast, and immerse yourself in the natural beauty that surrounds this charming village. Experience the ideal blend of recreation and leisure in this picturesque paradise.

  • Grand Cayman: Grand Cayman is a stunning island located just 4 miles from Old Man Bay. It's celebrated for its pristine beaches and vibrant family-friendly atmosphere. Visitors flock to Grand Cayman for an outdoor experience that includes diving, snorkeling, and enjoying the sun on world-renowned Seven Mile Beach. The island offers a variety of resorts and shopping areas, making it easy to unwind and indulge. Local attractions such as the Cayman Turtle Centre and the interactive Dolphin Discovery provide unforgettable experiences for families and nature lovers alike.
  • North Side: As a district where Old Man Bay is situated, North Side boasts a serene environment perfect for families and outdoor enthusiasts. Travelers to North Side are drawn to its beautiful beaches and adventurous activities, including snorkeling and diving in the crystal-clear waters. The area is dotted with shopping locales and waterfront marinas, providing access to a wealth of water sports. Don't miss the chance to explore the scenic tourist precinct, which features local dining options and shops that capture the essence of Cayman culture.
  • Breakers: Breakers is a charming village located 2 miles from Old Man Bay, known for its laid-back vibe and stunning coastal scenery. Ideal for families and outdoor lovers, Breakers offers beautiful beaches and hiking trails that showcase the island's natural beauty. Here, you can visit local stores and art galleries that highlight the creativity of the Cayman Islands. The nearby marina is a great spot for water activities, ensuring a memorable experience for visitors looking to explore the vibrant underwater world.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Also, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers an easy-to-use platform where you can plan new trips, continue from where you last stopped, or organize your travel plans. You'll have access to your saved or booked properties, neatly organized into Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/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)
  • Star Fish Point (6.5 mi / 10.5 km)
  • Rum Point Beach (6.6 mi / 10.6 km)
  • Starfish Beach (7.1 mi / 11.4 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, Cayman Islands when booking a vacation rental?
When looking for the best area to stay in Old Man Bay, the neighborhoods near the coastline are particularly appealing for vacation rentals. This area offers a serene atmosphere and stunning views of the Caribbean Sea, making it great for relaxation.One of the top attractions nearby is the beautiful beach, where you can enjoy swimming, sunbathing, and snorkeling in the vibrant coral reefs. Additionally, you'll find several local eateries that serve delicious Caymanian cuisine, providing an opportunity to experience the local culture.In terms of vacation rentals, Old Man Bay has a good selection of properties, ranging from charming cottages to more spacious villas, suiting different group sizes and preferences.
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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
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. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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 travelers 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, Cayman Islands?
In Old Man Bay, travelers can enjoy a tranquil beach experience with beautiful stretches of sand and clear turquoise waters. The area is known for its stunning snorkeling opportunities, particularly at the nearby coral reefs, which are filled with vibrant marine life. Visitors can also explore the scenic coastline, superb for leisurely strolls and relaxing by the sea.For those seeking adventure, the nearby Bioluminescent Bay offers a great experience where the water glows at night, providing a magical atmosphere for nighttime kayaking or boat tours.Additionally, the local dining scene features charming beachfront restaurants where guests can savor fresh seafood and traditional Caymanian dishes while enjoying picturesque views.
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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 as applicable. 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively. Vrbo also offers support via live chat through our Help Center, 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 organizing 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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