Great Diamond Island holiday lettings

We found 18 holiday rentals — enter your dates for availability

Why visit Great Diamond Island

  • Stunning coastal scenery: Great Diamond Island boasts breathtaking oceanfront views, perfect for relaxation and photography.
  • Historic charm: Explore charming houses and iconic lighthouses that reflect the island's rich maritime heritage.
  • Outdoor activities: Engage in various outdoor pursuits such as hiking, biking, and beachcombing, ideal for adventure seekers.
  • Quaint village atmosphere: Enjoy a friendly local vibe, making it perfect for couples and families looking for a peaceful retreat.
  • Convenient location: Just a short ferry ride from Portland, providing easy access to both urban amenities and natural beauty.

Popular types of accommodation around Great Diamond Island

Vrbo offers a delightful selection of vacation rentals on Great Diamond Island, catering to every traveller's needs. Whether you prefer a private vacation home, a charming cottage, or a modern condo, you’ll find the perfect spot to unwind. With excellent island amenities and the opportunity to explore the natural beauty around you, Great Diamond Island is an ideal destination for your next getaway. Discover the best of Great Diamond rentals today!

  • Houses: The most sought-after option for visitors to Great Diamond Island, offering spacious and comfortable settings for families and groups.
  • Cottages: A charming choice, these quaint retreats provide a cosy atmosphere and are ideal for a relaxing getaway.
  • Condos: Popular for their modern amenities, condos offer convenience and often stunning views of the island.
  • Apartments: A practical choice for solo travellers or couples, providing essential comforts and a home-like environment.
  • Cabins: Perfect for those seeking a rustic experience, these cabins immerse you in the natural beauty of the island.**

Top attractions near Great Diamond Island

Great Diamond Island offers a delightful blend of outdoor activities and scenic beauty, making it perfect for a beach holiday. Visitors can explore historic lighthouses and charming houses while enjoying the coastal culture. The island is conveniently located near Portland, enhancing accessibility to its attractions. Whether you seek relaxation by the beach or adventurous outdoor experiences, Great Diamond Island promises an unforgettable getaway for all types of travellers.

  • Portland Head Light: This historic lighthouse, located 2.5km from Great Diamond Island, offers breathtaking views of the coastline and a glimpse into maritime history. Its picturesque setting makes it a perfect spot for photography and leisurely walks.
  • East End Beach: Situated 1.2km away, this lovely beach is perfect for sunbathing and swimming. With its soft sands and vibrant atmosphere, it's an ideal place to relax and enjoy the seaside vibes.
  • Cross Insurance Arena: Just 1.9km from the island, this entertainment facility hosts a variety of events, from concerts to family shows, making it a great destination for fun and excitement.

Things to do recommended for couples

For a romantic getaway on Great Diamond Island, consider enjoying a concert at Thompson's Point, indulging in luxury at the Portland Club, or embracing adventure with water sports at Capt Lyman Stuart. Each offers a unique atmosphere, perfect for couples seeking unforgettable experiences.

Things to do recommended for families

Families visiting Great Diamond Island can enjoy a thrilling game at Hadlock Field, explore the wonders of the Portland Observatory, and have fun at Bayside Bowl, an exciting arcade adventure zone, all within a short distance from the island.

Things to do recommended for groups

Groups visiting Great Diamond Island can enjoy a shopping spree at the Maine Mall, located 5.0km away, before experiencing a captivating performance at the Lyric Music Theater, just 1.9km from the island. Don't miss the iconic LL Bean Flagship Store, situated 11.9km away.

What do I need to keep in mind when booking a vacation around Great Diamond Island

If you're travelling with a group, as a family, bringing your pets, or seeking extended stays, be sure to filter your options according to your key priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Great Diamond Island with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Great Diamond Island with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with ensuring access to suitable facilities, such as a private swimming pool. Additionally, it's wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Great Diamond Island: For many families, a holiday wouldn’t feel complete without their furry companion by their side. If you can relate, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Great Diamond Island: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding amenities such as a parking space, a well-equipped kitchen, or even a private pool to your search criteria.

Where to stay near Great Diamond Island

Great Diamond Island, a picturesque gem off the coast of Maine, offers a delightful escape for those seeking stunning oceanfront views and outdoor adventures. This charming village is perfect for romantic getaways or secluded retreats, while its nearby urban areas provide a vibrant cultural atmosphere. Explore the island's natural beauty, relax on the beach, and enjoy the friendly local vibe, making it an ideal destination for families and couples alike.

  • Portland: Portland, located a mere 1.9km from Great Diamond Island, is a vibrant city renowned for its outdoor experiences and scenic beauty. Visitors flock here for family-friendly activities, with a plethora of venues including theatres, an arena for entertainment, and shopping centres. Explore the nearby beaches and lakes, where you can bask in the sun or enjoy a leisurely stroll. The city's lively atmosphere and diverse attractions make it an ideal destination for those seeking both relaxation and adventure.
  • South Portland: Also situated 1.9km from Great Diamond Island, South Portland offers a unique blend of family-oriented and business-themed experiences. This bustling city is perfect for those looking to shop, with a variety of shopping centres and malls to explore. Families can enjoy the local beaches and lakes, which provide excellent opportunities for outdoor fun. South Portland's welcoming vibe and accessible education facilities make it a great spot for both tourists and locals alike.
  • Downtown Portland: Just 1.9km from Great Diamond Island, Downtown Portland is a charming neighbourhood perfect for families and couples seeking a romantic getaway. With a lively arts scene, visitors can enjoy theatre performances, music concerts, and various entertainment options. The area is close to picturesque beaches and tranquil lakes, offering a perfect balance of urban excitement and natural beauty. Downtown Portland's vibrant streets and welcoming atmosphere create an unforgettable experience for all who visit.

Best time to go to Great Diamond Island

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.1°F (-3.3°C)Light RainMostly SunnyLowSlightly Low
February27.0°F (-2.8°C)Light RainMostly SunnyLowSlightly Low
March33.4°F (0.8°C)Light RainMostly SunnyLowSlightly Low
April43.9°F (6.6°C)Light RainMostly SunnyAverageAverage
May54.0°F (12.2°C)Light RainMostly SunnyAverageAverage
June61.9°F (16.6°C)Light RainMostly SunnyHighSlightly High
July68.9°F (20.5°C)Light RainMostly SunnyHighSlightly High
August68.5°F (20.3°C)Light RainMostly SunnyHighSlightly High
September62.2°F (16.8°C)Light RainMostly SunnyAverageAverage
October52.2°F (11.2°C)Light RainMostly SunnyAverageAverage
November41.2°F (5.1°C)Light RainMostly SunnyAverageAverage
December32.9°F (0.5°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is simple

Are you eager to save on your next getaway? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, opting for a longer stay can lead to considerable savings. To discover a Vrbo property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan exciting new journeys, pick up where you last left off, or easily view and manage your travel arrangements. You can now find the properties you've saved and booked categorised under Potential, Upcoming, or Current Trips. To explore the Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The charming area of Great Diamond Island awaits your stay

The island views and surrounding scenery provide a peaceful ambience to your holiday home in Great Diamond Island. Well known for its restaurants, shopping and kayaking, this romantic city won't disappoint. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Great Diamond Island

Are you hoping to find attractions to see in the city? Venture out of your holiday home and check out everything that makes Great Diamond Island a fun place to get away to. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Dunegrass Golf Club (14.6 mi / 23.4 km)
  • Pirate's Cove (14.7 mi / 23.6 km)
  • Funtown Splashtown USA (15.6 mi / 25.2 km)
  • Happy Wheels Skate Center (6.8 mi / 10.9 km)
  • Land's End Gift Shop (10.1 mi / 16.3 km)
  • Paddleworks (12.3 mi / 19.8 km)

Exploring the natural landscape of Great Diamond Island

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Great Diamond Island is a great spot to appreciate mother nature. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Sand Beach (1.3 mi / 2 km)
  • East End Beach (2.3 mi / 3.7 km)
  • Willard Beach (2.8 mi / 4.6 km)
  • Thompson's Point (5.1 mi / 8.2 km)
  • Higgins Beach (9 mi / 14.5 km)
  • Casco Bay (10.2 mi / 16.4 km)

Frequently asked questions

What is the most popular type of holiday rental accommodation in Great Diamond Island?
Based on our data, houses are the most popular holiday property type in Great Diamond Island. But of course, everyone's idea of an awesome stay can vary. Vrbo has holiday rentals with every shape, size and budget in mind, so you're sure to find the perfect match.
How much does it cost to rent a holiday rental in Great Diamond Island?
A range of factors can determine how much you'll pay for a holiday rental in Great Diamond Island, including the time of year, length of stay and property type. However, all Vrbo homes have something in common — unbeatable value. Simply enter your travel dates to find your home away from home.
How much does it cost to rent a beach house in Great Diamond Island?
Prices for beach houses in Great Diamond Island will vary depending on the size and type of the property and time of year you're travelling. Simply enter your travel dates into Vrbo and the number of guests to see available options and prices. From there you can use the filters to tailor your search results by ratings, nearby activities, amenities and more.
What are popular rental amenities in Great Diamond Island?
An ocean view, a fireplace and nearby museums are the most popular rental amenities in Great Diamond Island. Whether you plan to travel as a party of one, with a partner or a bunch of friends, Vrbo will help you find a holiday rental that fits your style with all the options you need.
Can I find two-bedroom holiday rentals in Great Diamond Island?
You can pick from two two-bedroom holiday rentals in Great Diamond Island. Put the kids in the second room or maybe fill it with a couple of your nearest and dearest friends. There's enough space for whoever's lucky enough to be joining in on the fun.
Are there holiday rentals with WiFi in Great Diamond Island?
Whether you'd like to keep up with the headlines, send some emails or surf social networks, there are six holiday homes with WiFi in Great Diamond Island. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How old do you have to be to rent a holiday rental in Great Diamond Island?
You'll need to check with the Great Diamond Island holiday rental you're looking at on Vrbo as the age limit differs. However, generally it's 16, 18 or 21.
How long can I rent a holiday rental in Great Diamond Island for?
It all depends on the Great Diamond Island property. To see all available options offering extended stays, simply enter your dates and guest number into Vrbo's search page. Look forward to having the whole property to yourself, along with home comforts such as air conditioning, a kitchen and an outdoor space where the kids can run and play. Be on the lookout for any long-term stays that offer weekly or monthly discounts.

More holiday ideas