Five Islands Holiday Rentals

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Our top choices for Five Islands holiday rentals

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, (145)
"Lovely space, comfortable bed, very convenient to downtown Brunswick."
United States
Kimberly G.
The price is AU$182
includes taxes & fees
18 Jan - 19 Jan 2026
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Queen non smoking efficiency, free parking in beautiful Boothbay,Maine.

Queen non smoking efficiency, free parking in beautiful Boothbay,Maine.
Boothbay
10.0 out of 10, Exceptional, (1)
"This efficiency apartment was nicely furnished with everything needed and conveniently located on the main road into Boothbay Harbor. The host was generous and accommodating. The region is fun to visit!"
United States
Mary D.
The price is AU$420
includes taxes & fees
31 Dec - 1 Jan 2026
Queen non smoking efficiency, free parking in beautiful Boothbay,Maine.

Escape to Positive Outlook

Escape to Positive Outlook
West Point
10.0 out of 10, Exceptional, (3)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
The price is AU$285
includes taxes & fees
4 Jan - 5 Jan 2026
Escape to Positive Outlook

Brunswick Downtown Sugar Cube next to Bowdoin

Brunswick Downtown Sugar Cube next to Bowdoin
Brunswick
8.4 out of 10, Very good, (7)
"Stayed for one night. Very convenient to campus"
United States
Lin-Lin R.
The price is AU$397
includes taxes & fees
1 Jan - 2 Jan 2026
Brunswick Downtown Sugar Cube next to Bowdoin

Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
10.0 out of 10, Exceptional, (8)
"Such a great location! We could easily walk all over the cute downtown."
United States
Keisha C.
The price is AU$333
includes taxes & fees
4 Jan - 5 Jan 2026
Modern style in historic building in downtown Bath

Little Lincoln beautiful home

Little Lincoln beautiful home
Brunswick
9.2 out of 10, Wonderful, (15)
"Simon was very easy to communicate with, the place was clean, the bed was quite comfortable, and we were right by Main Street in Brunswick which made for easy access to food and things to do. Wonderful place to stay!"
United States
Jessica B.
The price is AU$387
includes taxes & fees
25 Jan - 26 Jan 2026
Little Lincoln beautiful home

Historic Bath's, Home Away from Home

Historic Bath's, Home Away from Home
Bath
The price is AU$440
includes taxes & fees
1 Jan - 2 Jan 2026
Historic Bath's, Home Away from Home

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Brunswick
9.8 out of 10, Exceptional, (28)
"This property is newly renovated and is in a great location--right across from the Brunswick Hotel and next to campus. Parking is easy (in the driveway) and the apartment is really spacious!"
United States
Jill C.
The price is AU$532
includes taxes & fees
11 Jan - 12 Jan 2026
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Firstmate by Rocky Coast Rentals

Firstmate by Rocky Coast Rentals
Boothbay Harbor
10.0 out of 10, Exceptional, (4)
"The house was perfect and the floor fans were great for sleepers that need white noise. "
United States
Josh L.
The price is AU$770
includes taxes & fees
3 Jan - 4 Jan 2026
Firstmate by Rocky Coast Rentals

2King Bed BR Private Apt Downtown Brunswick

2King Bed BR Private Apt Downtown Brunswick
Brunswick
8.4 out of 10, Very good, (10)
"Small place in a great location. Easily walk to several shops and restaurants. "
United States
Jillian B.
The price is AU$369
includes taxes & fees
4 Jan - 5 Jan 2026
2King Bed BR Private Apt Downtown Brunswick

Fred Cottage - Spacious retreat on Popham Beach!

Fred Cottage - Spacious retreat on Popham Beach!
Phippsburg
9.0 out of 10, Wonderful, (2)
"Off the beaten path, easy access to beach and Spinneys"
United States
Sean B.
The price is AU$330
includes taxes & fees
1 Jan - 2 Jan 2026
Fred Cottage - Spacious retreat on Popham Beach!

Award Winning Luxury Carriage House a short stroll from town!

Award Winning Luxury Carriage House a short stroll from town!
2.0 star property
Bath
10.0 out of 10, Exceptional, (9)
"An exceptional property and guest. Would love to stay again next time Thank you Jared and Heather!"
United States
Ronald H.
The price is AU$975
includes taxes & fees
31 Dec - 1 Jan 2026
Award Winning Luxury Carriage House a short stroll from town!

Solitude @ The Offshore House

Solitude @ The Offshore House
Boothbay
9.8 out of 10, Exceptional, (7)
"Managers were very responsive and helpful. Condo was very clean and comfortable and close to the town of Boothbay Harbor and Ocean Point and the Botanic Gardens. "
United States
Linda O.
The price is AU$453
includes taxes & fees
31 Dec - 1 Jan 2026
Solitude @ The Offshore House

Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining
2.0 star property
Newcastle
The price is AU$251
includes taxes & fees
7 Jan - 8 Jan 2026
Peaceful Intown Studio ~ Walk to Shops & Dining

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 AU$658
includes taxes & fees
6 Jan - 7 Jan 2026
Maine Coast House with Spectacular Ocean Views and Beach for Swimming

Bird Watching Paradise @ Waterfront Harpswell with Private Deck

Bird Watching Paradise @ Waterfront Harpswell with Private Deck
Harpswell
10.0 out of 10, Exceptional, (2)
"Super location, very private, responsive host, lovely, clean. Very lucky to have been able to stay here!"
United States
Kate K.
The price is AU$453
includes taxes & fees
10 Jan - 11 Jan 2026
Bird Watching Paradise @ Waterfront Harpswell with Private Deck

Tiny A-Frame Romantic Getaway

Tiny A-Frame Romantic Getaway
Wiscasset
10.0 out of 10, Exceptional, (3)
"Very nice and very quiet "
United States
justin s.
The price is AU$497
includes taxes & fees
21 Jan - 22 Jan 2026
Tiny A-Frame Romantic Getaway

Laughton House @ Pemaquid Beach

Laughton House @ Pemaquid Beach
Pemaquid Beach
10.0 out of 10, Exceptional, (8)
"This house is in a great location. We could walk to the beach, or to Fort Henry to let my grandsons run around. The house is lovely and had everything we needed. We have come to this area of Maine since 2017, and this had been our favorite place to stay! "
United States
Dawn W.
The price is AU$918
includes taxes & fees
1 Jan - 2 Jan 2026
Laughton House @ Pemaquid Beach

Lovely 2-bedroom apartment with AC in charming Topsham. Close to everything!

Lovely 2-bedroom apartment with AC in charming Topsham. Close to everything!
Topsham
10.0 out of 10, Exceptional, (1)
"Pet friendly place and good spot! Would stay again "
United States
Shiloh F.
The price is AU$396
includes taxes & fees
3 Jan - 4 Jan 2026
Lovely 2-bedroom apartment with AC in charming Topsham. Close to everything!

Private Sauna+Near Beach+FirePit+Forest View+Pond

Private Sauna+Near Beach+FirePit+Forest View+Pond
2.0 star property
Georgetown
The price is AU$536
includes taxes & fees
19 Jan - 20 Jan 2026
Private Sauna+Near Beach+FirePit+Forest View+Pond
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, 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 favourite 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 depend 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 AU$333 per night. Entering your travel dates in the search wizard might find you 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?

8mn to Gardens Aglow! Peaceful Lake! Automatic Generator! Full Kitchen! Heat! : This holiday home rental outside of Five Islands is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Boothbay Harbor Marina.

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.