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 19 - Sep 21
In two months
Oct 31 - Nov 2
In three months
Nov 28 - Nov 30
In four months
Dec 26 - Dec 28

Vacation Rentals in Five Islands

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
Charming Oceanfront House with Deck, Cozy Loft, and Direct Beach Access
Fridge, microwave, oven, stovetop

Charming Oceanfront House with Deck, Cozy Loft, and Direct Beach Access

4.8 out of 10, (5)
Charming Oceanfront House with Deck, Cozy Loft, and Direct Beach Access
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
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)
The price is ￥25,169
￥37,439 total
includes taxes & fees
Sep 30 - Oct 1
Captain's Quarters 2BR Apartment. Walk to Everything!
Full sized home
Interior

Full sized home

9.8 out of 10, Exceptional, (37)
"The house was lovely. Very comfortable place. Within 15- 20 mins to a store or restaurants."
The price is ￥30,065
￥54,781 total
includes taxes & fees
Sep 15 - Sep 16
Full sized home
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 ￥10,364
￥24,207 total
includes taxes & fees
Sep 30 - Oct 1
Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!
Camp Forever cottage
Outdoor dining

Camp Forever cottage

9.6 out of 10, Exceptional, (52)
"Great stay. My husband and I were there for 4 days. Peaceful and quiet. Lovely views. Just perfect for the two of us. Short drive to area sites, businesses and restaurants."
The price is ￥21,528
￥41,591 total
includes taxes & fees
Oct 1 - Oct 2
Camp Forever cottage
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
Oceanfront Cabin-Castle in Maine Woods
Interior

Oceanfront Cabin-Castle in Maine Woods

9.8 out of 10, Exceptional, (32)
"Place was amazing with an incredible view and fun layout. "
Oceanfront Cabin-Castle in Maine Woods
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!
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
Interior

Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room

10.0 out of 10, Exceptional, (52)
"Cozy spot on a beautiful beach - hard to beat!"
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
1 room luxury ocean front studio cottage
Fridge, microwave, oven, stovetop

1 room luxury ocean front studio cottage

9.6 out of 10, Exceptional, (156)
"Quaint with a great view."
1 room luxury ocean front studio cottage
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)
"Adorable place, roomy, quiet, upscale yet felt just like home. Will definitely stay again! "
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C
Enjoyable 1-bedroom rustic cottage in Southport.
Terrace/patio

Enjoyable 1-bedroom rustic cottage in Southport.

10.0 out of 10, Exceptional, (14)
Enjoyable 1-bedroom rustic cottage in Southport.
Your own private island! Rustic and close to Nature.
Dining

Your own private island! Rustic and close to Nature.

9.4 out of 10, Exceptional, (33)
"wonderful place, glamping, wildlife all around, you can't but enjoy the beauty of Mid Coast Maine. Thanks for sharing your island with all of us !"
Your own private island! Rustic and close to Nature.
Shipwright @ The Offshore House
Smart TV

Shipwright @ The Offshore House

9.4 out of 10, Exceptional, (12)
"Luv the area and the room location was great A few steps from Bets fish and chips short drive into town "
The price is ￥30,935
￥53,661 total
includes taxes & fees
Sep 6 - Sep 7
Shipwright @ The Offshore House
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK
Outdoor dining

Century-old oceanfront home with wraparound porch - walk downtown, dogs OK

8.8 out of 10, Excellent, (38)
"This was our second stay here. We love the comfort of this home and the location is perfect."
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK
Large beautiful ocean front studio with private dock
Dining

Large beautiful ocean front studio with private dock

10.0 out of 10, Exceptional, (38)
"Great place to relax and watch the seagulls and heron. Quiet even though there is a building in back of the boathouse that is a rental. General store and small restaurant just down the road. The king size bed was very comfortable. The boathouse has everything you need. "
Large beautiful ocean front studio with private dock
Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace
TV, fireplace, DVD player, books

Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace

9.2 out of 10, Wonderful, (68)
"Wonderful views."
Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace
Kayakers’ Cabin- “Maine Cabin Masters” remodel.
Fridge, microwave, oven, stovetop

Kayakers’ Cabin- “Maine Cabin Masters” remodel.

10.0 out of 10, Exceptional, (48)
"Loved this place. Amazing quiet location with so many water toys and activities. Had zero need to leave the whole weekend because there was so much to do there. "
Kayakers’ Cabin- “Maine Cabin Masters” remodel.
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

Flagship Inn and Suites

Flagship Inn and Suites

10/10 Excellent
"It wasn’t a fancy place, but they had a heated pool, even though the Jacuzzi was empty, and a nice breakfast the next day"
Gail 1-night trip
Posted 5 days ago
Flagship Inn and Suites

Find out more about Five Islands

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 Quarters 2BR Apartment. Walk to Everything!: Visitors like this Five Islands vacation home rental. It offers a patio, a garden, and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware.

How many vacation rentals will I find in Five Islands?

With 8 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.