Holiday Rentals in Five Islands

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Our top choices for Five Islands holiday rentals

Last minute deal Ocean Point OCEANFRONT with private BEACH

Last minute deal Ocean Point OCEANFRONT with private BEACH
Boothbay
10.0 out of 10, Exceptional, (101)
"Had a great stay! Such a beautiful secluded spot, but also close to boothbay harbor and a lot of other Maine coast activities. The apartment itself was clean and nice and everything was smooth and easy. Would definitely stay here again!"
United States
Richard L.
Last minute deal Ocean Point OCEANFRONT with private BEACH

Oceanfront Cabin-Castle in Maine Woods

Oceanfront Cabin-Castle in Maine Woods
Georgetown
9.8 out of 10, Exceptional, (45)
"Amazing views and good location "
United States
Adriana R.
Oceanfront Cabin-Castle in Maine Woods

8mn to Gardens Aglow! Peaceful Lake! Automatic Generator! Full Kitchen! Heat!

8mn to Gardens Aglow! Peaceful Lake! Automatic Generator! Full Kitchen! Heat!
Boothbay Harbor
10.0 out of 10, Exceptional, (105)
"Lovely home and perfect location"
United States
Sara A.
8mn to Gardens Aglow! Peaceful Lake! Automatic Generator! Full Kitchen! Heat!

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Bailey Island
10.0 out of 10, Exceptional, (234)
"Great property with amazing views."
United States
katie b.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Newly Renovated Haven w/ Deck, Walk to Shops, Dining & Marina, Pet friendly

Newly Renovated Haven w/ Deck, Walk to Shops, Dining & Marina, Pet friendly
Boothbay Harbor
9.2 out of 10, Wonderful, (62)
"We totally enjoyed our stay -walking distance to shops and restaurants."
United States
Pam K.
Newly Renovated Haven w/ Deck, Walk to Shops, Dining & Marina, Pet friendly

Captain's Guest Room w/private bath. Walk to everything.

Captain's Guest Room w/private bath. Walk to everything.
Bath
8.2 out of 10, Very good, (21)
"Great location and a beautiful property. Great walking/driving distance from town and the waterfront, we had a great stay and would do it again! "
United States
Nina P.
Captain's Guest Room w/private bath. Walk to everything.

1 room luxury ocean front studio cottage

1 room luxury ocean front studio cottage
Harpswell
9.6 out of 10, Exceptional, (171)
"Very clean beautiful view we definitely enjoyed ourselves "
United States
Ilona F.
1 room luxury ocean front studio cottage

Popham Beach Direct Oceanfront Cottage Steps to the sand

Popham Beach Direct Oceanfront Cottage Steps to the sand
Phippsburg
9.8 out of 10, Exceptional, (69)
"It was everything we hoped for!"
United States
Kate L.
Popham Beach Direct Oceanfront Cottage Steps to the sand

Beautiful Oceanfront House- Stunning Water Views

Beautiful Oceanfront House- Stunning Water Views
Harpswell
9.4 out of 10, Exceptional, (23)
"We loved our stay! Gorgeous view, lots of thoughtful little amenities. The home was extremely clean and the host was just lovely. "
United States
Catherine O.
Beautiful Oceanfront House- Stunning Water Views

Olde Post Office Cottage at Pemaquid Point

Olde Post Office Cottage at Pemaquid Point
Pemaquid Point
9.6 out of 10, Exceptional, (148)
"So so sweet and cozy. Loved the location and all the beautiful flowers and decor. It was even better than it looked in the photos. "
United States
Tanya K.
Olde Post Office Cottage at Pemaquid Point

Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor

Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor
East Boothbay
10.0 out of 10, Exceptional, (46)
"Quiet and peaceful. Location was close to everything we had on our agenda. We highly recommend this as great place to stay!"
United States
Malinda E.
The price is €437
includes taxes & fees
18 Dec - 19 Dec
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor

Peaceful home with forest views & great yard - minutes to town

Peaceful home with forest views & great yard - minutes to town
Wiscasset
7.8 out of 10, Good, (9)
"Fit our needs perfectly!"
United States
Aimee K.
Peaceful home with forest views & great yard - minutes to town

Make Shimmering River Retreat your Maine Coastal getaway!

Make Shimmering River Retreat your Maine Coastal getaway!
Westport Island
9.6 out of 10, Exceptional, (40)
"Very private and peaceful! We enjoyed the yard, the dock, and the campfire. There was lots of room to spread out and enjoy the property."
United States
Becky M.
Make Shimmering River Retreat your Maine Coastal getaway!

Maine Coast House with Spectacular Ocean Views and Beach for Swimming

Maine Coast House with Spectacular Ocean Views and Beach for Swimming
South Bristol
9.4 out of 10, Exceptional, (27)
"Perfect base for exploring the mid-coast region. "
United States
Rebecca M.
The price is €430
includes taxes & fees
18 Dec - 19 Dec
Maine Coast House with Spectacular Ocean Views and Beach for Swimming

Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.

Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.
Boothbay Harbor
10.0 out of 10, Exceptional, (92)
"Beautiful home, very clean and great locations. "
United States
Chris N.
Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.

Spacious 3 Bedroom, 2 bath, new home, ocean views, close to Maine seafood!

Spacious 3 Bedroom, 2 bath, new home, ocean views, close to Maine seafood!
Orr's Island
10.0 out of 10, Exceptional, (53)
"We loved this house, the view, and Orrs Island! Enjoyed lobster at nearby restaurants, the local candy/ice cream shop, hiking, and paddling kayaks on the bay. A great August vacation!"
United States
Holly W.
Spacious 3 Bedroom, 2 bath, new home, ocean views, close to Maine seafood!

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

Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.
Boothbay Harbor
10.0 out of 10, Exceptional, (21)
"We loved our stay in Boothbay. The cottage was clean and comfortable, location was ideal, easy walk into town and to the park. Everything was fantastic, would highly recommend. "
United States
Emma D.
Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.

Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces

Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
Westport
8.4 out of 10, Very good, (49)
"This home was absolutely stunning! Beautiful inside, amazing view of the water. I loved sitting out on the porch so much. I would highly recommend!"
United States
Brian Q.
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces

Downtown Boothbay Harbor Studio – Ocean Views, Dog-Friendly, Walk to Pier

Downtown Boothbay Harbor Studio – Ocean Views, Dog-Friendly, Walk to Pier
Boothbay Harbor
10.0 out of 10, Exceptional, (2)
"This location was very convenient for tour boat trips, restaurants and shopping. There are high end appliances and lighting, and the interior is furnished in a rustic dog-themed way. There is a dedicated parking space, which was wonderful as available street parking was limited over the holiday weekend."
United States
Steve K.
Downtown Boothbay Harbor Studio – Ocean Views, Dog-Friendly, Walk to Pier

Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views!

Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views!
Orr's Island
9.8 out of 10, Exceptional, (37)
"Great place! Very private and quiet. Really well done renovated cottage. Loved it"
United States
Tim T.
Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Five Islands Hotel Reviews

Find out more about Five Islands

Everything you need to know about Five Islands holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Five Islands holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Five Islands holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Five Islands holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Five Islands. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Five Islands holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Five Islands holiday rentals we have selected for you start as low as €430 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Five Islands rentals

At Expedia, we put the best Five Islands holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Five Islands rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Five Islands holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Five Islands. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Five Islands?

Yes, there are holiday rentals close to the most popular sights in Five Islands, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Five Islands has to offer?

Oceanfront Cabin-Castle in Maine Woods: This holiday home rental outside of Five Islands is located by the ocean, and has a fireplace, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals will I find in Five Islands?

With 5 Expedia holiday rentals, you're guaranteed to find just the right place for your Five Islands stay.

What’s there to see and do in Five Islands?

Explore the area and family-friendly sights such as Boothbay Railway Village, or get out into nature at a spot like Coastal Maine Botanical Gardens. In the wider area, you’ll find Reid State Park and Burnt Island Living Lighthouse.

What’s a holiday rental in Five Islands like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Five Islands. Holiday rentals feature extras such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for families.