Five Islands Vacation Rentals

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Dec 21 - Dec 22
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Dec 22 - Dec 23
Next weekend
Dec 26 - Dec 28
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Jan 2 - Jan 4

Our top choices for Five Islands vacation rentals

Microwave, oven, stovetop
Modern style in historic building in downtown Bath

Apartment in Bath

Modern style in historic building in downtown Bath
10.0 out of 10, Exceptional, (8)
"Clean comfortable and right downtown"
United States
stephen e.
The price is ￥15,775
￥34,905 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Modern style in historic building in downtown Bath
Dining
Escape to Positive Outlook

Vacation Home in West Point

Escape to Positive Outlook
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 ￥13,251
￥29,886 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Escape to Positive Outlook
Exterior
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Apartment in Brunswick

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
10.0 out of 10, Exceptional, (144)
"Lovely space, comfortable bed, very convenient to downtown Brunswick."
United States
Kimberly G.
The price is ￥14,198
￥18,915 total
includes taxes & fees
Dec 22 - Dec 23
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Property grounds
Captain's Quarters 2BR Suite. Near everything. No fees. Pets welcome.

Vacation Home in Bath

Captain's Quarters 2BR Suite. Near everything. No fees. Pets welcome.
8.6 out of 10, Excellent, (10)
"Nice, clean, cosy, conveniently located and easy enough to find. Great communication with host, comfortable beds and plenty of hot water. very responsive and would definitely consider using again. "
United States
A M.
The price is ￥22,085
￥27,512 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Captain's Quarters 2BR Suite. Near everything. No fees. Pets welcome.
Property grounds
Queen non smoking efficiency, free parking in beautiful Boothbay,Maine.

Apartment in Boothbay

Queen non smoking efficiency, free parking in beautiful Boothbay,Maine.
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 ￥15,617
￥44,018 total
includes taxes & fees
Dec 23 - Dec 24
Queen non smoking efficiency, free parking in beautiful Boothbay,Maine.
Terrace/patio
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

Cabin in Boothbay

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
7.8 out of 10, Good, (7)
"Affordable and quiet location that felt safe and is conveniently close to Boothbay Harbor & surrounding attractions. "
United States
Melanie L.
The price is ￥20,586
￥31,553 total
includes taxes & fees
Dec 22 - Dec 23
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
TV
Tiny A-Frame Romantic Getaway

Mobile Home in Wiscasset

Tiny A-Frame Romantic Getaway
10.0 out of 10, Exceptional, (3)
"Very nice and very quiet "
United States
justin s.
The price is ￥25,335
￥55,470 total
includes taxes & fees
Jan 21 - Jan 22, 2026
Tiny A-Frame Romantic Getaway
TV
Mere Point Sunrise Views at Eastern Shore!

Vacation Home in Brunswick

Mere Point Sunrise Views at Eastern Shore!
9.8 out of 10, Exceptional, (7)
"Such a beautiful home and peaceful location. We loved our stay and the host was responsive and helpful with any questions we had!"
United States
Diana H.
Mere Point Sunrise Views at Eastern Shore!
Private kitchen
Classic New England 1st Floor 3 BR Downtown Brunswick

Apartment in Brunswick

Classic New England 1st Floor 3 BR Downtown Brunswick
9.6 out of 10, Exceptional, (9)
"We had a good time in Brunswick.... great location and jumping off point to explore."
United States
Karin S.
The price is ￥19,719
￥53,304 total
includes taxes & fees
Dec 22 - Dec 23
Classic New England 1st Floor 3 BR Downtown Brunswick
Terrace/patio
Laughton House @ Pemaquid Beach

Vacation Home in Pemaquid Beach

Laughton House @ 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 ￥50,259
￥101,723 total
includes taxes & fees
Dec 30 - Dec 31
Laughton House @ Pemaquid Beach
Living area
Fred Cottage - Spacious retreat on Popham Beach!

Cottage in Phippsburg

Fred Cottage - Spacious retreat on Popham Beach!
9.0 out of 10, Wonderful, (2)
"Off the beaten path, easy access to beach and Spinneys"
United States
Sean B.
The price is ￥23,505
￥34,562 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Fred Cottage - Spacious retreat on Popham Beach!
3 bedrooms, WiFi
Fantastic Waterfront Views

Vacation Home in West Point

Fantastic Waterfront Views
9.6 out of 10, Exceptional, (14)
"The views are amazing! A very relaxing place to be, and the house was clean and comfortable. "
United States
Monika G.
The price is ￥24,846
￥49,048 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Fantastic Waterfront Views
1 bedroom, iron/ironing board, free WiFi
Solitude @ The Offshore House

Condo in Boothbay

Solitude @ The Offshore House
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 ￥24,846
￥47,471 total
includes taxes & fees
Dec 22 - Dec 23
Solitude @ The Offshore House
Fridge, microwave, oven, stovetop
2King Bed BR Private Apt Downtown Brunswick

Apartment in Brunswick

2King Bed BR Private Apt Downtown 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 ￥15,775
￥38,688 total
includes taxes & fees
Jan 4 - Jan 5, 2026
2King Bed BR Private Apt Downtown Brunswick
Interior
Brunswick Downtown Sugar Cube next to Bowdoin

Apartment in Brunswick

Brunswick Downtown Sugar Cube next to Bowdoin
8.4 out of 10, Very Good, (7)
"Stayed for one night. Very convenient to campus"
United States
Lin-Lin R.
The price is ￥14,986
￥41,955 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Brunswick Downtown Sugar Cube next to Bowdoin
Outdoor dining
Vacation Creation Downtown Brunswick 2King Beds

Apartment in Brunswick

Vacation Creation Downtown Brunswick 2King Beds
9.6 out of 10, Exceptional, (18)
"Stayed here while visiting Bowdoin. Great place!"
United States
Deborah B.
The price is ￥23,663
￥51,585 total
includes taxes & fees
Dec 22 - Dec 23
Vacation Creation Downtown Brunswick 2King Beds
Outdoor dining
Seabed @ The Offshore House

Condo in Boothbay

Seabed @ The Offshore House
9.8 out of 10, Exceptional, (14)
"Our room was excellent!!! Everything was clean and organized and looked beautiful. Location was just far enough from all the attractions to make it very comfortable. Will definitely return next time we are in the area. "
United States
Steve G.
The price is ￥24,846
￥47,471 total
includes taxes & fees
Dec 22 - Dec 23
Seabed @ The Offshore House
Interior
Lovely 2-bedroom apartment with AC in charming Topsham. Close to everything!

Apartment in Topsham

Lovely 2-bedroom apartment with AC in charming Topsham. Close to everything!
10.0 out of 10, Exceptional, (1)
"Pet friendly place and good spot! Would stay again "
United States
Shiloh F.
The price is ￥25,272
￥41,457 total
includes taxes & fees
Dec 22 - Dec 23
Lovely 2-bedroom apartment with AC in charming Topsham. Close to everything!
1 bedroom, iron/ironing board, WiFi, bed sheets
Peaceful Intown Studio ~ Walk to Shops & Dining

Apartment in Newcastle

Peaceful Intown Studio ~ Walk to Shops & Dining
2.0 star property
The price is ￥20,949
￥26,273 total
includes taxes & fees
Dec 22 - Dec 23
Peaceful Intown Studio ~ Walk to Shops & Dining
Smart TV, books
Little Lincoln beautiful home

Apartment in Brunswick

Little Lincoln beautiful home
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 ￥14,040
￥40,580 total
includes taxes & fees
Dec 22 - Dec 23
Little Lincoln beautiful home
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

The Federal

The Federal

10/10 Excellent
"Room is clean and staffs are very nice. Will be back next year."
Zhi 2-night trip
Posted 2 days ago
The Federal

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?

Oceanfront Cabin-Castle in Maine Woods: Visitors like this Five Islands vacation home rental. It is located by the ocean and has a fireplace, a selection of games, and a barbecue grill 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 you can cook with friends or family.

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 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.