Five Islands Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Vacation Rentals in Five Islands

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
10.0 out of 10, Exceptional, (232)
"Tremendous stay, great property and host."
United States
Curtis G.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Captain's Guest Room w/private bath & house entrance. Walk to everything.
8.0 out of 10, Very Good, (19)
"Lots of character and a great location. Walking distance from everything in Bath. Really good price for the area!"
United States
Hall F.
The price is ¥11,617
¥24,326 total
includes taxes & fees
Oct 27 - Oct 28
Captain's Guest Room w/private bath & house entrance. Walk to everything.
1 room luxury ocean front studio cottage
9.6 out of 10, Exceptional, (163)
"Very clean beautiful view we definitely enjoyed ourselves "
United States
Ilona F.
1 room luxury ocean front studio cottage
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
10.0 out of 10, Exceptional, (53)
"The cottage location was beautiful, we had a wonderful time on the beach. The cottage could have been a little more clean than it was, but after letting the property owner know she addressed those issues. "
United States
Hannah K.
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
Beautiful house on the Harpswell Peninsula over looking Casco Bay
9.6 out of 10, Exceptional, (74)
"Great view, nice property, cool area in Harpswell. Great to stay at if you are in town for Live Well Farm. Lots of rooms, beds, and privacy. "
United States
Lauren B.
Beautiful house on the Harpswell Peninsula over looking Casco Bay
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C
10.0 out of 10, Exceptional, (104)
"We loved our stay! This place had everything you could ever need while on vacation; kayaks, lifejackets, games, movies, and more. Wendy was responsive and thoughtful! The space was beautiful and peaceful with easy access to many activities. Highly recommend!!!"
United States
Jill K.
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C
Oceanfront Cabin-Castle in Maine Woods
9.8 out of 10, Exceptional, (40)
"Place was amazing with an incredible view and fun layout. "
United States
Jeremy H.
Oceanfront Cabin-Castle in Maine Woods
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
9.2 out of 10, Wonderful, (99)
"Great views from backyard and living room. Others have described the place as rustic, which is fair as regards wood flooring, paneling and rugs. But beds, sofas and chairs are very comfortable. Heating wasn’t working on the second floor, but they sent someone to look at it almost immediately. Although they couldn’t fix it during our stay, they gave us a fair partial refund."
United States
Daniel
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
8.0 out of 10, Very Good, (6)
"Awful experience!!! Arrived at property and nobody was present to check in. Owner wanted us to go down the street to a different location to check in. He met us at property and said he never received payment which is a lie…… paid for property back in July. Left property and had to find another place last minute because they turned us away. The property is also not as it appears online . This place should not even be available to rent."
United States
Arline
The price is ¥45,812
¥62,764 total
includes taxes & fees
Oct 27 - Oct 28
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Fantastic Waterfront Views
9.8 out of 10, Exceptional, (10)
"Our favorite part about our stay at this location was being able to look out the many sliding door windows to see the ocean view. It was a very relaxing place to stay. "
United States
Heather S.
The price is ¥21,668
¥44,070 total
includes taxes & fees
Nov 17 - Nov 18
Fantastic Waterfront Views
Beautiful Oceanfront House- Stunning Water Views
9.6 out of 10, Exceptional, (21)
"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
Maine Coast House with Spectacular Ocean Views and Beach for Swimming
9.4 out of 10, Exceptional, (27)
"Perfect base for exploring the mid-coast region. "
United States
Rebecca M.
The price is ¥28,004
¥72,679 total
includes taxes & fees
Oct 27 - Oct 28
Maine Coast House with Spectacular Ocean Views and Beach for Swimming
Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers
9.6 out of 10, Exceptional, (81)
"Great stay, wonderful location"
United States
Dustin F.
Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers
Kayakers’ Cabin- “Maine Cabin Masters” remodel.
10.0 out of 10, Exceptional, (54)
"Waking up every morning to see this beautiful lake right outside the window was just wonderful. The cabin was clean, comfortable and cozy. It had everything we needed. Would stay again."
United States
Meg
Kayakers’ Cabin- “Maine Cabin Masters” remodel.
Chic Studio Cabin in Boothbay Harbor: Ocean Views, Sprucewold Beach Access
9.0 out of 10, Wonderful, (48)
"Overall our stay was very enjoyable, the cabin was as advertised and came stocked with toiletries needed for our stay. Just a heads up for those wanting to explore boothbay harbor, parking can be challenging to find so I would recommend if you own E-bikes bringing them for easier transportation around the area. "
United States
Allyson
Chic Studio Cabin in Boothbay Harbor: Ocean Views, Sprucewold Beach Access
Waterfront Cottage in South Bristol w/ private dock and lobster boat views
10.0 out of 10, Exceptional, (112)
"Our family loves this property and the location. We look forward to visiting every year!"
United States
Karen M.
Waterfront Cottage in South Bristol w/ private dock and lobster boat views
Camp Forever cottage
9.6 out of 10, Exceptional, (56)
"Most enjoyed vacation this year.Location was beautiful. "
United States
Debra S.
The price is ¥21,599
¥42,704 total
includes taxes & fees
Oct 31 - Nov 1
Camp Forever cottage
Make Shimmering River Retreat your Maine Coastal getaway!
9.6 out of 10, Exceptional, (40)
"This is our second stay at Shimmering River Retreat. Property is private with a pool and large dock. Jessica quickly responds to any questions. Well equipped home, with the bonus of additional common and sleeping space in the other building. Definitely would recommend for a large group!"
United States
Cynthia M.
Make Shimmering River Retreat your Maine Coastal getaway!
Newly Renovated Cozy Cove Cabin at White Anchor Inn
8.4 out of 10, Very Good, (6)
"As advertised, comfy bed cozy cabin. Would stay again "
United States
Joseph B.
The price is ¥50,902
¥68,979 total
includes taxes & fees
Nov 2 - Nov 3
Newly Renovated Cozy Cove Cabin at White Anchor Inn
Renovated home with water views, dock access, - dogs okay
6.6 out of 10, (8)
"The property was clean and nice, and the location is terrific."
United States
Mary E.
Renovated home with water views, dock access, - dogs okay
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Five Islands Hotel Reviews

Find out more about Five Islands

Search for holiday rentals in Five Islands on Expedia! You can easily find your home rentals, villas, holiday apartments in Five Islands using one of the methods below:

  • View our selection of featured holiday rentals in Five Islands
  • Use the map to find apartments and other holiday homes in the Five Islands neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Five Islands while they last

Look no further and take a look at our great range of rental properties in Five Islands!

Frequently asked questions

Can I find a vacation rental in Five Islands?

Yes, you can find vacation rentals near well known attractions in Five Islands, or you can go with a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Five Islands?

Captain's Guest Room w/private bath & house entrance. Walk to everything.: Visitors like this Five Islands vacation home rental. It comes with WiFi so you can feel at home during your trip. Kitchen amenities include an electric kettle to make your meal-planning easier.

How many vacation rentals will I find in Five Islands?

With 6 Expedia vacation rentals, you're sure 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 larger area, you’ll find Reid State Park and Burnt Island Living Lighthouse.

What’s a vacation rental in Five Islands like?

A vacation rental is a private property where you can stay for short or long periods in Five Islands. Vacation rentals feature extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a family trip.