Five Islands vacation rentals

We found 745 vacation rentals — enter your dates for availability

Discover a selection of 5 homes and other vacation rentals in Five Islands that are perfect for your trip. Vacation rentals provide the amenities you need and want for your stay with friends, family, or just your pet, such as WiFi and a pool. You'll be able to choose a rental that has what everyone needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Five Islands

Showing deals for:Mar 27 - Apr 3

Image gallery for Waterfront. Private. Perfect.

Wake up to this!
10 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)

Waterfront. Private. Perfect.

Boothbay

6% off
Price is $931
$6,518 for 7 nights
All fees included
Waterfront. Private. Perfect.

Find spaces that suit your style

  • 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 Five Islands

Why visit Five Islands

  • Scenic beaches: Enjoy the beautiful sandy shores and stunning coastal views that Five Islands has to offer.
  • Historic lighthouses: Explore the charming lighthouses that dot the coastline, rich in history and picturesque settings.
  • Outdoor adventures: Engage in various outdoor activities such as hiking, fishing, and kayaking in a tranquil environment.
  • Local culture: Immerse yourself in the friendly atmosphere and authentic Maine life found in this quaint fishing village.
  • Delicious treats: Savor local delights, including fresh seafood and homemade ice cream while enjoying the coastal vibes.

Popular types of accommodation in Five Islands

If you're exploring vacation rentals in Five Islands, you're in the right place. Our most popular options include Houses, cozy Cottages, and well-equipped Apartments. Whether you're looking for hotels like PWM Hotels or the Freeport Inn, or considering charming stays at Aug Motels and the Coastline Inn, we provide transparent information to help you make the best choice for your getaway.

  • Houses: The top choice for travelers in Five Islands, these homes offer spacious and comfortable accommodations for families or groups.
  • Cottages: A beloved option for a quaint and charming stay, perfect for those seeking a cozy retreat.
  • Apartments: These contemporary spaces provide convenience and a home-like atmosphere for solo travelers or couples.
  • Cabins: Ideal for nature enthusiasts, these rustic lodgings offer a serene escape amidst beautiful surroundings.
  • Condos: A popular choice for those wanting modern amenities in a communal living environment, perfect for vacations.**

Top attractions near Five Islands

Five Islands, Maine, is perfect for outdoor enthusiasts and those seeking scenic beauty and adventure. Visitors can explore stunning beaches, historic lighthouses, and charming islands, making it an ideal destination for beach lovers, culture seekers, and outdoor adventurers alike. Whether you’re relaxing by the shore or immersing yourself in local history, Five Islands offers a variety of attractions that cater to all types of travelers.

  • Coastal Maine Botanical Gardens: Located 4 miles from Five Islands, this stunning botanical garden offers a serene escape with beautifully curated landscapes. Perfect for romance or family outings, you'll find vibrant flowers and peaceful walking paths amidst the natural beauty of coastal Maine.
  • Boothbay Harbor Marina: About 5 miles away, this bustling marina is ideal for adventure seekers and beach lovers. Enjoy boating, fishing, or simply soaking up the sun while taking in gorgeous harbor views.
  • Reid State Park: Just 3 miles from Five Islands, this national park features breathtaking scenery and outdoor activities. Explore sandy beaches, rugged coastlines, and scenic trails, making it an ideal spot for nature enthusiasts.

Things to do recommended for couples

For a romantic getaway in Five Islands, consider a fun round at Dolphin Mini Golf, just 7 miles away, perfect for some friendly competition. Also, enjoy the thrill of water sports at Paddleworks, located 14 miles away, where you can share an adventurous day on the water.

Things to do recommended for families

During your family vacation in Five Islands, explore the relaxing Pemaquid Point Lighthouse Park and Pemaquid Beach Park, both 10 miles away. Enjoy a day at Fort Point, just 8 miles away, offering fun outdoor activities and beautiful scenery, perfect for creating lasting memories together.

Things to do recommended for groups

Experience culture and entertainment at the Carousel Music Theater, just 5 miles from Five Islands. Enjoy outdoor sports at Boothbay Golf Course, also 5 miles away, or explore local goods at the Boothbay Farmers' Market, a lively spot 5 miles from your base.

*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 Five Islands

If you're traveling with a group, with family, bringing your pets, or seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Five Islands with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Five Islands with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with amenities that are suitable for their age, like a private pool. Additionally, considering how close you are to family-friendly activities is a wise choice.
  • Taking your pets with you to Five Islands: For many families, a vacation isn't truly fulfilled without their furry companion by their side. If this resonates with you, consider exploring Vrbo listings that welcome pets. Most pet-friendly accommodations offer amenities like food bowls and cozy beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Five Islands: If you're in search of vacation rentals that offer savings 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 rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Five Islands

Exploring Five Islands, Maine, offers a delightful experience of coastal charm and outdoor adventures. This picturesque fishing village invites travelers to enjoy stunning scenery, friendly locals, and memorable excursions. Don't miss the chance to savor delicious ice cream while soaking in the mid-coast vibes. With its relaxing atmosphere and various recreational opportunities, Five Islands is the perfect destination for those seeking a tranquil escape and a taste of authentic Maine life.

  • Boothbay Harbor: Located 5 miles from Five Islands, Boothbay Harbor is a vibrant coastal city renowned for its stunning outdoor experiences and picturesque scenery. Visitors can immerse themselves in adventure through various activities, including hiking trails and recreational areas, or enjoy a round of golf at local courses. The area boasts beautiful beaches and is adjacent to both a national state park and a national park, providing ample opportunities for exploration and relaxation. The charming waterfront is dotted with shops and restaurants, making it a perfect spot for a leisurely stroll while soaking in the maritime atmosphere.
  • Georgetown: As the home of Five Islands, Georgetown offers a delightful blend of outdoor activities and scenic beauty. This charming city is known for its inviting beaches and tranquil lakes, making it an ideal destination for families and nature lovers. The recreational areas provide opportunities for education and exploration, while nearby ski fields add a unique twist for winter sports enthusiasts. Whether you’re enjoying a family beach day or taking in the stunning waterfront views, Georgetown embodies the quintessential Maine coastal experience.
  • Boothbay: Just 5 miles from Five Islands, Boothbay is another delightful city known for its outdoor allure and captivating scenery. Visitors can enjoy various adventures, including hiking trails and recreational areas, alongside opportunities for golf. The local landmarks feature a national state park, serene lakes, and additional national park areas, providing a perfect backdrop for outdoor exploration. Boothbay’s welcoming atmosphere, combined with its scenic views, makes it an attractive destination for tourists looking to experience the best of Maine's natural beauty.

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 hoping to cut costs on your upcoming journey? It can be beneficial to remain flexible with your travel dates, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to narrow down options by price, location, and type of vacation rental.

Save more with One Key

Plan your group getaway by booking an eligible Vrbo and earn OneKeyCash on your entire reservation. It's truly rewarding to be the organizer. When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and accumulate OneKeyCash on qualifying bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or easily view and manage your travel plans. You can now find your saved and booked properties organized under Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Choose a vacation rental for your Five Islands getaway

Experience the unique character of Five Islands with a stay in a vacation home rental. There's no shortage of things to see and do in the area.If you're looking for accommodations with space to entertain friends and family, Vrbo 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 attractions to visit in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Five Islands 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:

  • Maine State Aquarium (3.7 mi / 6 km)
  • Boothbay Golf Course (5.5 mi / 8.8 km)
  • Pemaquid Craft Co-op (11.1 mi / 17.8 km)
  • Paddleworks (14 mi / 22.6 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 looking for exciting outdoor activities or just want to spend some time taking in the scenery, Five Islands is a great place to spend some time outside. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Coastal Maine Botanical Gardens (4.2 mi / 6.7 km)
  • Cabbage Island (5.4 mi / 8.7 km)
  • Linekin Bay (5.4 mi / 8.7 km)
  • Grimes Cove Beach (5.8 mi / 9.3 km)
  • Popham Beach (6.1 mi / 9.9 km)
  • Thomas Point Beach (10.2 mi / 16.4 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 center. If you can't find a flight that works for your travel itinerary, 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 vacation rental?
When considering a vacation rental in Five Islands, Maine, the best area to stay is along the waterfront, particularly near the picturesque Five Islands Harbor. This charming locale offers an authentic coastal experience, with stunning views and easy access to the water. You'll find a variety of vacation properties, from cozy cottages to more spacious homes, making it a great choice for families or couples seeking a romantic getaway.

Being close to the harbor, you can enjoy top attractions such as the scenic Five Islands Lobster Company, where you can indulge in fresh seafood right by the water. The nearby islands, including the beautiful Chebeague Island, offer opportunities for exploration and adventure, whether you're kayaking, hiking, or simply soaking in the breathtaking views.

Another appealing aspect of this area is its proximity to local art galleries and charming shops that reflect the region's rich maritime heritage.
How much does it cost to rent a vacation home in Five Islands?
Prices for vacation 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 vacation 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 vacation rentals in Five Islands?
A long-stay vacation rental in Five Islands 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 Five Islands vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Five Islands 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.
When is the best time to visit Five Islands for a vacation rental?
The best time to visit Five Islands for a vacation rental is in September, when the summer crowds begin to dissipate, yet the weather remains pleasantly mild. This transitional month offers a wonderful opportunity for travelers seeking a blend of outdoor adventures and coastal charm, with temperatures typically ranging from the mid-50s to low 70s Fahrenheit.

During the peak season from July to September, Five Islands comes alive with activity, making it an ideal time for those interested in sailing, kayaking, and exploring the beautiful rocky coastlines. The vibrant local culture is on full display, and visitors can enjoy fresh seafood and local art exhibitions at nearby galleries.

For those looking for a more tranquil experience, consider planning your visit in November. While this month is part of the low season, it offers a unique perspective on the region, allowing you to savor the peacefulness of the area, great for reflection and cozy coastal walks.

Ultimately, your choice of when to visit Five Islands can open up various experiences, from busy summer festivities to serene autumn escapes.
How early should I book a Five Islands vacation rental?
Book your Five Islands 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 Five Islands?
In Five Islands, Maine, visitors can immerse themselves in the picturesque coastal scenery and charming small-town atmosphere. The Five Islands Lobster Company is a must-visit for fresh seafood and stunning views of the harbor, where travelers can enjoy a casual meal while watching the boats come and go. Nearby, the historic Popham Beach State Park offers beautiful sandy shores and opportunities for swimming and sunbathing, making it a great spot for families and beachgoers.

The area is also known for its scenic hiking trails, such as those found in the nearby Georgetown Island, which provide breathtaking views of the surrounding coastline and rich wildlife. For a taste of local culture, exploring the quaint shops and galleries in the nearby towns of Bath and Boothbay Harbor can offer insight into Maine's maritime heritage.
Can I change or cancel my Five Islands home rental booking on Vrbo?
To find Five Islands 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 Five Islands 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.

More Vacation Ideas