Five Islands vacation rentals

We found 789 vacation rentals — enter your dates for availability

Escape to the serene shores of Georgetown Island, where stunning beaches meet breathtaking coastal landscapes. This charming destination invites travelers to unwind with outdoor adventures like kayaking and hiking, all while soaking in the warm, friendly atmosphere of the local community. With an array of vacation rentals—from cozy cottages to stylish apartments with harbor views—your group will find the perfect home base to create unforgettable memories, enjoying the comforts and amenities of a true getaway.

Holiday rentals with weekly discounts - Five Islands

Showing deals for:Dec 11 - Dec 18

Living area
Living area
Exterior
Celebrate Christmas here with your family.
Exceptional
(54 reviews)

Driftwood Beachfront Luxury Home Magnificent Ocean Views

Phippsburg

8% off
$793
$5,554 for 7 nights
All fees included
Driftwood Beachfront Luxury Home Magnificent Ocean Views
Interior
Property grounds
Dining
Private kitchen
Exceptional
(61 reviews)

Waterfront Cottage on Cove with Private Dock, Kayaks & Fire Pit

Trevett

8% off
$271
$1,894 for 7 nights
All fees included
Waterfront Cottage on Cove with Private Dock, Kayaks & Fire Pit
Property grounds
Exterior
Interior
Living area
Exceptional
(116 reviews)

Maine waterfront home, with hot tub and dock access, 1 mile from downtown Bath.

Woolwich

17% off
$388
$2,717 for 7 nights
All fees included
Maine waterfront home, with hot tub and dock access, 1 mile from downtown Bath.
Interior
Roof deck overlooking amazing Boothbay Harbor...
Interior
Private kitchen
Exceptional
(28 reviews)

Boothbay Harbor, ME 3 Bed Luxury Apartment With Roof Deck, Hot Tub, Shower Sauna

Boothbay Harbor

5% off
$1,165
$8,155 for 7 nights
All fees included
Boothbay Harbor, ME 3 Bed Luxury Apartment With Roof Deck, Hot Tub, Shower Sauna
Living area
Exterior
Exterior detail
Room
Exceptional
(10 reviews)

Quiet waterfront serenity awaits!

Georgetown

9% off
$482
$3,376 for 7 nights
All fees included
Quiet waterfront serenity awaits!
Kitchen
Outdoor dining
Upstairs master bedroom view
Front yard
Exceptional
(36 reviews)

Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.

Boothbay Harbor

8% off
$355
$2,487 for 7 nights
All fees included
Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.
Room
Private kitchen
Interior
Living area
Exceptional
(24 reviews)

New home in Boothbay, downtown Boothbay harbor is located about a mile away.

Boothbay

9% off
$204
$1,429 for 7 nights
All fees included
New home in Boothbay, downtown Boothbay harbor is located about a mile away.
Kitchen with granite counter top and high top seating.
Aerial view of condo on the left side.
Outdoor dining
Living room.
Exceptional
(9 reviews)

Beautiful Condo on Ocean Cove - Easy walk to harbor-side town

Boothbay Harbor

9% off
$413
$2,890 for 7 nights
All fees included
Beautiful Condo on Ocean Cove - Easy walk to harbor-side town
Back deck and screen porch
Exterior
Screen porch
Living area
Exceptional
(9 reviews)

Welcome to Owl House - Your Coastal Retreat in East Boothbay!

East Boothbay

9% off
$365
$2,554 for 7 nights
All fees included
Welcome to Owl House - Your Coastal Retreat in East Boothbay!
  • 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 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.

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:

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

What is the most popular type of vacation rental accommodation in Five Islands?
Based on our research, chalets are the most sought-after type of vacation property in Five Islands. But that goes without saying, everyone's idea of the perfect stay isn't the same. Vrbo has vacation homes of all shapes and sizes, so you're bound to find the perfect fit for you.
How much does it cost to rent a vacation rental in Five Islands?
Several things can influence how much you pay for a vacation rental in Five Islands, including the length of stay, season and type of property. However, all our vacation homes have one thing in common — amazing value. Just enter your travel dates to find your ideal match.
How much does it cost to rent a beach house in Five Islands?
When you travel and the size and style of the property will determine the cost of your beachside escape. Click on your Five Islands travel dates to view your options on Vrbo. Can't live without a hot tub, or maybe a private pool? Use the filters to choose the amenities and features you need.
Are there pet-friendly vacation rentals in Five Islands?
With five vacation rentals that allow pets, your little buddy can join you on your Five Islands vacation. Use our filter tool to search our pet-friendly vacation rentals and find a stay that'll set tails wagging on Vrbo.
What are popular rental amenities in Five Islands?
When it comes to rental amenities that guests are searching for in Five Islands, a nearby waterfront, a barbecue grill and an ocean view are at the top of the list. With Vrbo vacation rentals, you'll enjoy choices to match your taste and style, whether you're on a trip with friends, relatives or even pets.
Are there large group vacation rentals in Five Islands?
Yes, you can pick from one of five properties in Five Islands that can host a group of five or more guests. From family reunions to special occasions like birthday parties, these stays have ample space to spend time with the people that matter the most.
Are there vacation rentals in Five Islands that welcome kids?
Bring the whole family together for an adventure in Five Islands at one of our five family-friendly vacation properties. A lot of these stays come with conveniences that are ideal for trips with children, including kitchens, bunk beds and private pools. Just check the "Properties good for families" filter box and pick out your favorite.
Are there vacation rentals with WiFi in Five Islands?
You'll have a choice of four vacation rentals with WiFi in Five Islands. If you want to disconnect from daily life on your break, but still want to be connected to the web, these properties have just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How old do you have to be to rent a vacation rental in Five Islands?
You'll need to check with the Five Islands vacation rental you want on Vrbo as age restrictions vary. However, it's normally 16, 18 or 21.
How long can I rent a vacation rental in Five Islands for?
The amount of time you can stay in a Five Islands vacation home for is down to each property. Simply put in your dates of travel to browse available options offering extended stays. They include all the things you need to make your extended trip more enjoyable such as laundries and air conditioning. Some vacation homes might also offer weekly or monthly discounts, so you can stay longer for less money.
Does Vrbo offer discounts for vacation homes in Five Islands?
Whether you're interested in one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you're sure to score some fabulous deals and discounts on Vrbo. From short stays to extended vacations, we've got the ideal place for your next Five Islands escape.

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