Five Islands vacation rentals

We found 736 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.

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Find out more about Five Islands

Why visit Five Islands

  • Scenic beaches: Enjoy the stunning, tranquil beaches of Georgetown Island, perfect for relaxation and sunbathing.
  • Outdoor adventures: Engage in various activities such as hiking, kayaking, and exploring the picturesque islands.
  • Charming local vibes: Experience the friendly atmosphere of the coastal community, ideal for families and solo travelers.
  • Vacation rentals: Choose from a variety of accommodations, including cozy cottages and stylish apartments with harbor views.
  • Botanical garden: Visit the local botanical garden to immerse yourself in beautiful flora and peaceful surroundings.

Popular types of accommodation in Five Islands

Planning your getaway to Five Islands? Discover the charm of this coastal paradise with a variety of vacation rentals, including private homes, cozy cottages, and stylish apartments. Enjoy outdoor seating with stunning harbor views, perfect for relaxing after a day of exploration. Whether you seek tranquility or adventure, Five Islands vacation rentals offer the ideal home base for your travels. Start your journey by finding the perfect spot to unwind.

  • Houses: The top choice for travelers in Five Islands, offering spacious and comfortable accommodations for families and groups.
  • Cottages: A charming and cozy option, perfect for those seeking a quaint and picturesque stay by the water.
  • Apartments: Convenient and flexible, apartments provide a home-like atmosphere for solo travelers or couples.
  • Cabins: Ideal for nature enthusiasts, cabins offer a rustic experience amidst the beautiful landscape.
  • Condos: A popular choice for those looking for modern amenities and shared facilities in a vibrant community.**

Top attractions near Five Islands

Five Islands, Maine, offers a perfect blend of outdoor adventures and scenic beauty, making it an ideal beach vacation destination. Visitors can explore local attractions such as beautiful beaches, a botanical garden, and the charming islands nearby. Whether you're seeking cultural experiences or outdoor activities, Five Islands has something for everyone, making it a great spot for families, solo travelers, or groups looking to enjoy nature and relaxation.

  • Coastal Maine Botanical Gardens: Experience stunning outdoor landscapes filled with vibrant flora. This serene setting is perfect for romance and family outings, showcasing the beauty of Maine's native plants and themed gardens.
  • Popham Beach: Enjoy miles of pristine sand and gentle surf at this beautiful beach. Ideal for sunbathing and beachcombing, Popham Beach offers a relaxing atmosphere to soak up the sun and sea.
  • Boothbay Harbor Marina: Dive into adventure with boating, kayaking, and fishing at this bustling marina. Surrounded by breathtaking coastal views, it’s a perfect spot for outdoor enthusiasts looking to explore the waters of Boothbay Harbor.

Things to do recommended for couples

For a romantic getaway in Five Islands, Maine, enjoy a sunset picnic by the shore or take a scenic boat ride to explore the nearby islands. Savor fresh lobster at a cozy seaside restaurant and stroll hand-in-hand along the picturesque coastal trails.

Things to do recommended for families

Families visiting Five Islands can explore the stunning coastline on a scenic boat tour, enjoy a fun-filled day at the local beaches, and indulge in delicious seafood at charming waterfront restaurants. Kids will love the tide-pooling adventures and spotting unique marine life along the shore.

Things to do recommended for groups

Explore the stunning coastline on a group kayak tour, or enjoy a seafood feast at a local clam shack. Don't miss a sunset sail to witness the breathtaking views of the surrounding islands, perfect for creating unforgettable memories 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 Five Islands

If you're traveling with a group, your family, or even bringing along your pets, or if you're considering longer stays, it's important to set your filters according to your top priorities. Here are some helpful tips for booking on Vrbo.

  • Traveling to Five Islands with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Five Islands with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety while also looking for 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 Five Islands: For many families, a trip isn't truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of your 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 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 features like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in Five Islands

Five Islands, Maine, offers a charming coastal escape perfect for outdoor enthusiasts and beach lovers. Explore the stunning natural beauty of Georgetown Island, where scenic views and relaxing beaches await. Enjoy friendly local vibes while embarking on excursions around the picturesque islands. With ample beach access and breathtaking landscapes, this village is an ideal destination for those seeking a tranquil getaway filled with recreation and scenic adventures.

  • Boothbay Harbor: Located a mere 5 miles from Five Islands, Boothbay Harbor is a picturesque coastal city known for its stunning outdoor scenery and adventurous spirit. Visitors can immerse themselves in nature by exploring numerous hiking trails and recreational areas. The local golf courses offer a perfect blend of relaxation and sport. Notable landmarks include beautiful beaches, as well as nearby national and state parks that provide excellent opportunities for hiking, birdwatching, and enjoying the breathtaking views of the coastline.
  • Georgetown: As Five Islands is situated in Georgetown, this charming city offers a delightful mix of outdoor adventures and romantic experiences. Georgetown is renowned for its serene beaches and tranquil lakes, making it an ideal spot for family outings or a peaceful day by the water. The recreational areas provide opportunities for education and exploration, while the ski fields attract winter sports enthusiasts. The idyllic setting is perfect for couples wanting to enjoy a scenic getaway or families looking for a fun day outdoors.
  • Boothbay: Just 5 miles away from Five Islands, Boothbay is another beautiful city that captivates visitors with its outdoor activities and scenic views. This destination is perfect for adventure seekers, with access to hiking trails and recreational areas that encourage exploration and discovery. Educational opportunities abound, making it a great place for families. With nearby national parks, lakes, and beaches, Boothbay is an excellent spot to unwind and soak in the natural beauty of Maine’s coastline.

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 a breeze

Are you aiming to save on your next journey? Being flexible with your travel dates can help, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental.

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll earn OneKeyCash on the full booking amount. Being the organizer has its perks. Enroll in our One Key rewards program to unlock exclusive savings for members and accumulate OneKeyCash on eligible stays. Sign up today and start reaping the benefits.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient way to plan new adventures, pick up right where you left off, and keep your travel arrangements organized. You can easily access properties you've saved or booked by checking out your Potential, Upcoming, or Current Trips. To explore 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)
  • Barrett Park (4.9 mi / 8 km)
  • Cabbage Island (5.4 mi / 8.7 km)
  • Popham Beach (6.1 mi / 9.9 km)
  • Waterfront Park (8 mi / 12.9 km)
  • Bates-Morse Mountain Conservation Area (8.2 mi / 13.2 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

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 during September, when the summer crowds begin to dwindle, yet the charm of the coastal village remains vibrant. This month offers a unique blend of pleasant weather and fewer tourists, making it ideal for outdoor activities such as kayaking, hiking, and exploring the picturesque shoreline.

Peak season runs from July to September, with July being the height of tourist activity. Visitors flock to Five Islands for its stunning beaches, fresh seafood, and the delightful experience of local festivals. The warm summer temperatures, typically ranging from the mid-50s to low 80s Fahrenheit, create a great backdrop for enjoying the area's natural beauty and engaging in various water sports.

If you're looking for a more budget-friendly option, consider November. While this month is quieter, it offers a unique opportunity to experience the serene beauty of Five Islands in the offseason. The peaceful ambiance allows for leisurely walks along the coast and a chance to appreciate the local scenery without the hustle and bustle.
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, Maine, United States of America?
In Five Islands, Maine, visitors can enjoy a charming coastal experience with several attractions that highlight the area's natural beauty and maritime heritage. The picturesque Five Islands Lobster Company is a popular spot for fresh seafood, where guests can savor local dishes while taking in scenic views of the water. The surrounding area features stunning coastal landscapes, superb for walking and photography.

Nearby, the famous Popham Beach State Park offers a long stretch of sandy beach ideal for swimming, sunbathing, and beachcombing. The park's natural beauty is complemented by its historic sites, including the remnants of Fort Popham, which provide a glimpse into the region's history.

For those interested in boating, Five Islands serves as a gateway to the nearby islands, where visitors can explore scenic trails and enjoy the tranquility of the ocean.
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.

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