Five Islands Vacation Rentals

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 26 - Sep 28
In two months
Nov 7 - Nov 9
In three months
Dec 5 - Dec 7
In four months
Jan 2 - Jan 4

Browse Select Five Islands Vacation Homes

2 bedroom 1 bath, large deck and dock, on the water in peaceful cove, Year
Exterior

2 bedroom 1 bath, large deck and dock, on the water in peaceful cove, Year

10.0 out of 10, Exceptional, (27)
"The location of tgis property is wonderful. Quiet, convenient to boothbay harbor. We enjoyed our stay very much."
2 bedroom 1 bath, large deck and dock, on the water in peaceful cove, Year
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor
Terrace/patio

Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor

9.6 out of 10, Exceptional, (40)
"Very clean and had everything we needed for a nice long weekend with our pup in Boothbay Harbor"
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor
Captain's Quarters 2BR Apartment. Walk to Everything!
Property grounds

Captain's Quarters 2BR Apartment. Walk to Everything!

8.6 out of 10, Excellent, (7)
"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. "
The price is CA $235
CA $357 total
includes taxes & fees
Sep 17 - Sep 18
Captain's Quarters 2BR Apartment. Walk to Everything!
Beautiful house on the Harpswell Peninsula over looking Casco Bay
Terrace/patio

Beautiful house on the Harpswell Peninsula over looking Casco Bay

9.6 out of 10, Exceptional, (71)
"I stayed here with my family and sisters, and one of my sisters brought her husband and two children. The house had enough space for all of us to be together and yet have space to ourselves. We had a lovely time. We came for my daughter’s graduation and would recommend this space to anyone."
Beautiful house on the Harpswell Peninsula over looking Casco Bay
Full sized home
Interior

Full sized home

9.8 out of 10, Exceptional, (38)
"The house was lovely. Very comfortable place. Within 15- 20 mins to a store or restaurants."
The price is CA $279
CA $506 total
includes taxes & fees
Sep 15 - Sep 16
Full sized home
Beautiful Oceanfront House- Stunning Water Views
Interior

Beautiful Oceanfront House- Stunning Water Views

9.6 out of 10, Exceptional, (15)
"The Host and his wife were so pleasant and accommodating. We enjoyed watching seals, fish and birds during our visit. Highly recommend."
Beautiful Oceanfront House- Stunning Water Views
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
On the beach

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

10.0 out of 10, Exceptional, (226)
"We had a wonderful stay at this cottage. Great location to explore the surrounding areas."
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Camp Forever cottage
Outdoor dining

Camp Forever cottage

9.6 out of 10, Exceptional, (52)
"Great little getaway. Would recommend this place to others for sure."
The price is CA $200
CA $387 total
includes taxes & fees
Oct 1 - Oct 2
Camp Forever cottage
Make Shimmering River Retreat your Maine Coastal getaway!
Fridge, microwave, oven, stovetop

Make Shimmering River Retreat your Maine Coastal getaway!

9.6 out of 10, Exceptional, (37)
"It was a very nice place for a family vacation. There was plenty of room for all of us (10).Yard and inside games provided along with kayaks for the river and a pool."
Make Shimmering River Retreat your Maine Coastal getaway!
Charming 2-bedroom house in small-town neighborhood
Microwave, oven, stovetop, dishwasher

Charming 2-bedroom house in small-town neighborhood

9.2 out of 10, Wonderful, (5)
Charming 2-bedroom house in small-town neighborhood
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Exterior

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

9.8 out of 10, Exceptional, (80)
"Great for exploring Bailey Island trails"
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Oceanfront Retreat with Dock, Boothbay Harbor
Terrace/patio

Oceanfront Retreat with Dock, Boothbay Harbor

2.0 star property
Oceanfront Retreat with Dock, Boothbay Harbor
Downtown Boothbay 3BR – Harbor Views, Private Deck, Walk Everywhere
Dining

Downtown Boothbay 3BR – Harbor Views, Private Deck, Walk Everywhere

Downtown Boothbay 3BR – Harbor Views, Private Deck, Walk Everywhere
Oceanfront Cabin-Castle in Maine Woods
Interior

Oceanfront Cabin-Castle in Maine Woods

9.8 out of 10, Exceptional, (33)
"Place was amazing with an incredible view and fun layout. "
Oceanfront Cabin-Castle in Maine Woods
Quaint Coastal Cottage w/ Deck & High-Speed WiFi - Walk to Town
Dining

Quaint Coastal Cottage w/ Deck & High-Speed WiFi - Walk to Town

8.0 out of 10, Very good, (24)
"Wonderful stay!"
Quaint Coastal Cottage w/ Deck & High-Speed WiFi - Walk to Town
Beautiful River-View Retreat | Home Office | Walk 5 MInutes to Main Street
TV, books

Beautiful River-View Retreat | Home Office | Walk 5 MInutes to Main Street

9.6 out of 10, Exceptional, (18)
"Nice house, close to great dining and only 5 min to a great grocery store"
Beautiful River-View Retreat | Home Office | Walk 5 MInutes to Main Street
Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!
Property grounds

Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!

8.0 out of 10, Very good, (15)
"Clean, well maintained, slighly funky in an historical way . Very convenient to great breakfast spots and downtown Bath. Would stay there again."
The price is CA $103
CA $232 total
includes taxes & fees
Sep 10 - Sep 11
Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C
Property grounds

Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C

10.0 out of 10, Exceptional, (103)
"A wonderful stay in every way! Beautiful view of lake, very clean, good communication, everything we needed in the kitchen…"
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C
Charming cottage near the beach with balcony, deck, grill, fireplace - dogs OK
Fridge, microwave, oven, stovetop

Charming cottage near the beach with balcony, deck, grill, fireplace - dogs OK

9.2 out of 10, Wonderful, (10)
"This was a wonderful place to stay!"
Charming cottage near the beach with balcony, deck, grill, fireplace - dogs OK
Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer
Fridge, microwave, oven, stovetop

Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer

2.0 star property
10.0 out of 10, Exceptional, (27)
"Beautiful location, comfortable beds and wonderful linens. This place was wonderful"
Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer
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
Sign in
Sign up, it's free

Top Five Islands Hotel Reviews

Find out more about Five Islands

Find out more about Five Islands

Five Islands Vacation Homes information

Number of reviews
Accommodation
527 Vacation Homes
Lowest Price
CA $103
Highest Price
CA $279

Explore a world of travel with Expedia

Explore a world of travel with Expedia