Five Islands holiday lettings

We found 757 holiday rentals — enter your dates for availability

Discover a selection of 5 homes and other holiday rentals in Five Islands that are perfect for your trip. Holiday rentals provide the amenities that you need and want for your family, friends or furry companion, such as parking and a washer and dryer. What you'll find is a property to rent for everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

Why visit Five Islands

  • Scenic Coastal Exploration: Discover the breathtaking beauty of Five Islands and its surrounding areas, perfect for outdoor adventures.
  • Charming Marina Vibes: Enjoy the picturesque marina, ideal for leisurely strolls and soaking in the coastal atmosphere.
  • Botanical Serenity: Visit the delightful botanical garden, offering a tranquil escape amidst vibrant flora.
  • Local Culinary Delights: Savor fresh seafood at the renowned Islands Lobster Co, a must-try for food enthusiasts.
  • Welcoming Community: Experience the friendly locals and rich cultural charm that enhance your holiday experience.

Popular types of accommodation in Five Islands

If you're wondering about the best accommodation options in Five Islands, look no further. Our most sought-after choices include Houses, charming Cottages, and comfortable Apartments. Whether you're searching for Five Islands hotels or delightful vacation rentals, we provide transparent information to help you make the right choice. Don't miss out on the local experience, including the renowned Islands Lobster Co in Maine, as you enjoy a memorable stay in one of our lovely vacation homes.

  • Houses: The top choice for visitors in Five Islands, offering spacious and comfortable accommodation ideal for families or groups.
  • Cottages: A delightful option, these quaint lodgings provide a picturesque and homely atmosphere for a relaxing getaway.
  • Apartments: Perfect for those seeking convenience, apartments offer modern amenities and easy access to local attractions.
  • Cabins: For a rustic experience, cabins immerse you in nature, perfect for a peaceful retreat.
  • Condos: These stylish properties combine comfort and luxury, ideal for a pampered stay.**

Top attractions near Five Islands

Five Islands, Maine, is a picturesque destination ideal for outdoor and adventure holidays. Visitors can explore stunning islands, a charming marina, and a delightful botanical garden. The area offers a blend of beach activities, cultural experiences, and ample opportunities for outdoor pursuits. Don't miss the attractions around Georgetown as you indulge in the natural beauty and local charm that Five Islands has to offer.

  • Coastal Maine Botanical Gardens: Nestled 2.5km from Five Islands, these stunning gardens offer a romantic and family-friendly atmosphere, featuring beautifully curated landscapes and vibrant floral displays, ideal for leisurely strolls amidst nature.
  • Boothbay Harbor Marina: Located 3.1km away, this lively marina provides adventurous opportunities, including boating and seaside activities, while showcasing the charm of Maine's coastal lifestyle with picturesque views.
  • Reid State Park: Just 1.9km from Five Islands, this national park boasts breathtaking scenery, with sandy beaches and rugged coastline, perfect for outdoor enthusiasts seeking adventure and stunning natural landscapes.

Things to do recommended for couples

For a delightful couple's getaway in Five Islands, Maine, enjoy a round at Dolphin Mini Golf, just 4.3km away, for some light-hearted competition. For an adventurous twist, head to Paddleworks, 8.7km away, where you can partake in exhilarating water sports amidst stunning outdoor scenery.

Things to do recommended for families

Your family will delight in the scenic beauty of Pemaquid Point Lighthouse Park and Pemaquid Beach Park, both providing relaxing atmospheres just 6.2km from Five Islands. Fort Point, located 5.0km away, offers further opportunities for enjoyment and exploration amid nature's charm.

Things to do recommended for groups

Groups visiting Five Islands can enjoy a delightful evening at the Carousel Music Theater for a taste of local culture, hit the Boothbay Golf Course for some outdoor sports, and explore the Boothbay Farmers' Market for a vibrant local shopping experience.

What do I need to keep in mind when booking a vacation in 'Five Islands

If you're travelling with a group, family, or pets, or if you're seeking longer stays, it's essential to use the appropriate filters to prioritise your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Five Islands with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Five Islands with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, while also seeking out suitable 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 Five Islands: For many, a family holiday wouldn’t feel complete without their furry companion by their side. If you can relate to this, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortably at home.
  • Planning for a long term stay visiting Five Islands: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. You might also want to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Five Islands

Five Islands, nestled in the heart of Midcoast Maine, offers an idyllic escape for those seeking outdoor adventure and stunning scenery. With its charming coastal vibes, visitors can enjoy relaxing excursions and friendly locals. Explore the picturesque towns nearby, where recreation and natural beauty abound. Whether you're wandering the Southern Maine coastline or indulging in local delights, your vacation here promises a delightful blend of relaxation and adventure.

  • Boothbay Harbor: Nestled a mere 3.1km from Five Islands, Boothbay Harbor is a charming coastal city renowned for its stunning outdoor adventures and breathtaking scenery. Visitors flock here for activities such as hiking along picturesque trails and enjoying the local recreational areas. The vicinity is adorned with beautiful beaches and national parks, making it an ideal spot for nature enthusiasts. Golf aficionados can also indulge in a round at the nearby golf courses, ensuring a delightful experience amidst the stunning backdrop of coastal Maine.
  • Georgetown: Just 1.9km from Five Islands, Georgetown is a delightful city that captivates visitors with its enchanting beaches and serene lakes. Perfect for those seeking outdoor activities, Georgetown offers plenty of recreational areas and educational opportunities. Families will appreciate the inviting family beaches, providing a great environment for relaxation and fun in the sun. The natural beauty and tranquil atmosphere make Georgetown a must-visit for those looking to immerse themselves in Maine's scenic coastal landscape.
  • Phippsburg: Located 3.1km from Five Islands, Phippsburg is a picturesque city that combines outdoor adventures with stunning beach vistas. This gem is ideal for those who revel in outdoor pursuits, including golf and recreational activities. The beautiful local beaches and serene lakes provide a perfect setting for a day of relaxation or family fun. With its captivating scenery and welcoming community, Phippsburg is a fantastic destination for tourists eager to explore the natural wonders of Maine.

Best time to go to Five Islands

If you're planning a trip to Five Islands, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from July to September, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.5°F (-3.6°C)Light RainMostly SunnyLowSlightly Low
February26.2°F (-3.2°C)Light RainMostly CloudyAverageSlightly Low
March32.9°F (0.5°C)Light RainMostly SunnyAverageSlightly Low
April43.0°F (6.1°C)Light RainMostly CloudyAverageAverage
May52.9°F (11.6°C)Light RainMostly SunnyAverageAverage
June60.8°F (16.0°C)Light RainMostly SunnyAverageSlightly High
July67.8°F (19.9°C)Light RainMostly SunnyHighSlightly High
August67.5°F (19.7°C)Light RainMostly SunnyHighSlightly High
September61.3°F (16.3°C)Light RainMostly SunnyHighAverage
October51.4°F (10.8°C)Light RainMostly SunnyAverageAverage
November40.5°F (4.7°C)Light RainMostly SunnyLowAverage
December32.2°F (0.1°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is simple

Are you aiming to save on your upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you could enjoy substantial savings by opting for a longer stay. 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 clever Trip Board offers you a dedicated space to plan new adventures, pick up from where you last paused, or manage your existing arrangements. You can easily find properties you have previously saved or booked under the sections for Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Choose a holiday rental for your Five Islands getaway

Learn about the unique charm of Five Islands with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Five Islands

Do you want to discover things to do in the area? Venture out of your holiday home and check out everything that Five Islands has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Boothbay Golf Course (5.5 mi / 8.8 km)
  • Paddleworks (14 mi / 22.6 km)
  • Maine State Aquarium (3.7 mi / 6 km)
  • Pemaquid Craft Co-op (11.1 mi / 17.8 km)
  • Brunswick Golf Course (15.4 mi / 24.9 km)
  • Ash Cove Pottery (15.8 mi / 25.5 km)

Exploring the natural features in Five Islands

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Five Islands is a great spot to appreciate mother nature. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Juniper Point (3.3 mi / 5.2 km)
  • Coastal Maine Botanical Gardens (4.2 mi / 6.7 km)
  • Barrett Park (4.9 mi / 8 km)
  • Cabbage Island (5.4 mi / 8.7 km)
  • Grimes Cove Beach (5.8 mi / 9.3 km)
  • Popham Beach (6.1 mi / 9.9 km)

How to get to and around Five Islands

Fly into Wiscasset, ME (ISS), the closest airport, located 9.7 mi (15.5 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Augusta, ME (AUG-Augusta State), which is 34.4 mi (55.3 km) away.

Frequently asked questions

What is the best area to stay in Five Islands when booking a holiday rental?
When looking for the best area to stay in Five Islands, Maine, you might consider the charming neighbourhood of Southport Island. This picturesque area is known for its stunning coastal views and laid-back atmosphere, making it an ideal spot for a relaxing holiday. Southport Island offers a range of holiday rentals, from quaint cottages to spacious homes, providing a delightful experience for visitors.

One of the top attractions in Southport is the iconic Southport Island Lighthouse, which offers breathtaking views of the surrounding waters and is a great spot for photography enthusiasts. Additionally, the nearby Boothbay Harbor is just a short drive away, where you can explore its bustling waterfront, indulge in fresh seafood, or take a scenic boat tour to admire the natural beauty of the coastline.
How much does it cost to rent a holiday home in Five Islands?
Prices for holiday rentals in Five Islands 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 Five Islands 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 Five Islands holiday house rentals?
You can find great discounts on house rentals in Five Islands 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 holiday rentals in Five Islands?
A long-stay holiday rental in Five Islands 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 Five Islands holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Five Islands 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.
When is the best time to visit Five Islands for a holiday rental?
September is the most popular time to visit Five Islands, Maine, as it perfectly captures the essence of late summer and early autumn. This month offers a wonderful blend of warm days and cooler evenings, making it ideal for outdoor activities such as kayaking, hiking, and exploring the picturesque coastline. Visitors can enjoy the stunning views of the Atlantic Ocean, with temperatures typically ranging from 10 to 20 degrees Celsius, ensuring a comfortable experience for those keen on sightseeing or simply relaxing by the shore.

The peak travel season in Five Islands runs from July to September, attracting travellers who flock to the area for its charming villages, fresh seafood, and beautiful landscapes. September, in particular, provides a slightly quieter atmosphere compared to the bustling summer months while still offering plenty of activities and opportunities to bond with fellow travellers.

For those seeking more economical options, November presents a fantastic opportunity to visit. The crisp autumn air and serene environment make it a wonderful time for peaceful walks and enjoying the natural beauty of the region. While some attractions may be closed for the season, the tranquillity of Five Islands during this time can be quite refreshing.

Ultimately, your choice of when to visit Five Islands will depend on whether you wish to revel in the lively summer scene or embrace the calm and beauty of autumn.
How early should I book a Five Islands holiday rental?
Book your Five Islands holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Five Islands?
In Five Islands, Maine, visitors can enjoy a range of picturesque attractions that showcase the area's coastal charm. The Five Islands Lobster Co. offers a quintessential Maine experience with fresh seafood and stunning views of the Damariscotta River, making it a popular spot for both locals and tourists.

Nearby, the scenic Five Islands Beach provides a lovely setting for beachgoers to relax and take in the beautiful surroundings. The area is also known for its charming fishing wharves and quaint shops, where visitors can find unique local crafts and souvenirs. For those interested in outdoor activities, the nearby conservation areas and trails offer opportunities for hiking and exploring the stunning coastal landscapes.
Can I change or cancel my Five Islands home rental booking on Vrbo?
To find Five Islands holiday 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 Five Islands holiday 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, 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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