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Five Islands Vacation Rentals

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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Five Islands vacation rentals

Terrace/patio

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Boothbay
8.0 out of 10, Very Good, (8 reviews)
"This was perfect for our one night stay to visit the botanical gardens, it was only minutes away. Also very close to quite a few dinner and shopping options. "
United States
Nichole W.
The price is ￥20,922
￥32,067 total
includes taxes & fees
Jun 25 - Jun 26
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Beach nearby

Across the road from Pemaquid Beach — wooded king-bed cabin for couples

Across the road from Pemaquid Beach — wooded king-bed cabin for couples
Pemaquid Beach
10.0 out of 10, Exceptional, (21 reviews)
"I wish we had more time to spend here! The cabin was well stocked and the location was out of the way, but close enough to sites and eateries "
United States
Sarah D.
The price is ￥28,216
￥51,201 total
includes taxes & fees
Jun 25 - Jun 26
Across the road from Pemaquid Beach — wooded king-bed cabin for couples
Beach nearby

Across the road from Pemaquid Beach — 2-bedroom seasonal family cottage

Across the road from Pemaquid Beach — 2-bedroom seasonal family cottage
Pemaquid Beach
9.8 out of 10, Exceptional, (6 reviews)
"Great beach cottage !"
United States
Gwen M.
The price is ￥23,821
￥49,570 total
includes taxes & fees
Jul 1 - Jul 2
Across the road from Pemaquid Beach — 2-bedroom seasonal family cottage
Exterior

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Brunswick
10.0 out of 10, Exceptional, (152 reviews)
"Such a fabulous stay. The space was bright, clean, and comfortable, and the special touches made it feel even more welcoming. It was larger than expected, and we loved having a mini fridge and coffee machine, perfect for slow mornings or a little wine and cheese at the end of the day. We’d return in a heartbeat."
Canada
Coral
The price is ￥18,134
￥23,262 total
includes taxes & fees
Jun 24 - Jun 25
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Interior

3 Bedroom Happy Cottage 15

3 Bedroom Happy Cottage 15
Edgecomb
10.0 out of 10, Exceptional, (6 reviews)
"Great property with central location in mid coast Maine. Beautifully decorated with very comfortable beds! Jeff was great with communication throughout to ensure we had everything we needed! Would stay again! "
United States
Decourcey D.
The price is ￥45,717
￥80,444 total
includes taxes & fees
Jun 22 - Jun 23
3 Bedroom Happy Cottage 15
Hair dryer, towels

Across the road from Pemaquid Beach — quiet wooded king-bed cabin

Across the road from Pemaquid Beach — quiet wooded king-bed cabin
Pemaquid Beach
9.2 out of 10, Wonderful, (5 reviews)
"Loved our stay"
United States
Jeanne
The price is ￥28,216
￥51,201 total
includes taxes & fees
Jun 23 - Jun 24
Across the road from Pemaquid Beach — quiet wooded king-bed cabin
Smart TV

Across the road from Pemaquid Beach — 4-bedroom 19th-century Maine home

Across the road from Pemaquid Beach — 4-bedroom 19th-century Maine home
Pemaquid Beach
10.0 out of 10, Exceptional, (8 reviews)
"Comfortable, clean and beautiful "
United States
Corina
The price is ￥48,524
￥110,417 total
includes taxes & fees
Jun 21 - Jun 22
Across the road from Pemaquid Beach — 4-bedroom 19th-century Maine home
Beach nearby

•Tranquil 2BR Summer Home•Steps to Private Beach•

•Tranquil 2BR Summer Home•Steps to Private Beach•
Harpswell
The price is ￥35,186
￥92,205 total
includes taxes & fees
Jul 14 - Jul 15
•Tranquil 2BR Summer Home•Steps to Private Beach•
Interior

Spacious 1 Bedroom Close to Everything 4

Spacious 1 Bedroom Close to Everything 4
Edgecomb
9.8 out of 10, Exceptional, (23 reviews)
"We will return next year! Love these little cottages. There is no better location for day tripping. Cottages are well equipped and very comfortable."
United States
Lee R.
The price is ￥21,335
￥44,264 total
includes taxes & fees
Jun 18 - Jun 19
Spacious 1 Bedroom Close to Everything 4
Interior

Sweet comfy cottage on Small Point Road

Sweet comfy cottage on Small Point Road
Small Point
9.4 out of 10, Exceptional, (3 reviews)
"Lovely home with plenty of space and seating. Not the most comfortable of beds but we enjoyed the space. Perfect location and would love to stay again. "
United States
Liz J.
Sweet comfy cottage on Small Point Road
Iron/ironing board, travel crib, WiFi, bed sheets

Fully Renovated "Saltbox" Home in Boothbay

Fully Renovated "Saltbox" Home in Boothbay
Boothbay
Fully Renovated "Saltbox" Home in Boothbay
Property grounds

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Georgetown
The price is ￥54,571
￥88,770 total
includes taxes & fees
Jun 21 - Jun 22
Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Hair dryer, towels, soap, shampoo

Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy

Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
Boothbay
6.0 out of 10, (5 reviews)
"It had a very homey feel, was nice to stay at for the night and wasn’t far from town."
United States
Audreyana P.
The price is ￥26,613
￥39,144 total
includes taxes & fees
Jun 25 - Jun 26
Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
Outdoor dining

Tiny Cottage Near Everything 10

Tiny Cottage Near Everything 10
Edgecomb
9.0 out of 10, Wonderful, (2 reviews)
"We recently stayed at the Tiny Cottage in Edgecomb, Maine, and truly enjoyed our visit. Except for a small initial issue, which was promptly and professionally addressed, everything was wonderful. The location is perfect for exploring the area, and the cottage itself was spotless, comfortable, and well-maintained. A lovely and relaxing getaway spot!"
United States
Elaine
The price is ￥17,324
￥37,634 total
includes taxes & fees
Jun 21 - Jun 22
Tiny Cottage Near Everything 10
House (2 Bedrooms) | Interior

1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
The price is ￥22,939
￥55,483 total
includes taxes & fees
Jul 16 - Jul 17
1 Mi to Maine Street! Mcm-style Home in Brunswick
Exterior

Spacious 1 Bedroom Cottage Close to Everything 3

Spacious 1 Bedroom Cottage Close to Everything 3
Edgecomb
9.6 out of 10, Exceptional, (15 reviews)
"Great central location"
United States
Bruce O.
The price is ￥20,212
￥42,865 total
includes taxes & fees
Jun 18 - Jun 19
Spacious 1 Bedroom Cottage Close to Everything 3
Beach

Pemaquid Escape | Curated Comfort + Hot Tub

Pemaquid Escape | Curated Comfort + Hot Tub
Walpole
10.0 out of 10, Exceptional, (3 reviews)
"The place was beautiful, with charming and had perfect design choices. Check in was so convenient, and the hosts were quite responsive to any needs. We all felt so comfortable there. It felt private, yet was conveniently located to Damariscotta. I would absolutely rent here again."
United States
Tera P.
The price is ￥55,611
￥119,181 total
includes taxes & fees
Jun 18 - Jun 19
Pemaquid Escape | Curated Comfort + Hot Tub
Terrace/patio

Tide Haven Cottage on Bay Point

Tide Haven Cottage on Bay Point
Georgetown
The price is ￥36,387
￥94,739 total
includes taxes & fees
Jul 1 - Jul 2
Tide Haven Cottage on Bay Point
Terrace/patio

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is ￥33,686
￥57,874 total
includes taxes & fees
Jun 18 - Jun 19
Camp Forever cottage
Property grounds

Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.

Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
Bath
7.6 out of 10, Good, (14 reviews)
"We stayed for two nights. Good location."
United States
Maryanne E.
The price is ￥21,335
￥26,752 total
includes taxes & fees
Jun 18 - Jun 19
Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
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

Topside Inn

Topside Inn

10/10 Excellent
"Very relaxing vibe with a most accommodating staff. Well maintained and a gorgeous view with a fabulous homecooked breakfast."
Dennis 2-night trip
Posted 3 hours ago
Topside Inn

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:

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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?

Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE: Visitors like this Five Islands vacation home rental. It is located on a river and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Five Islands?

With 5 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 Maine Maritime Museum, 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.