Five Islands Vacation Rentals

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Vacation Rentals in Five Islands

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

9.2 out of 10, Wonderful, (7)
"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

4.0 out of 10, (2)
"The amenities on Travelocity site does not match the amenities Vacasa sends to you after you book. No washer, no (working?) central heating (1 electric oil heater on wheels provided). Safety lists deadbolt lock but only 2 of 5 doors have a deadbolt, 2 doors have no locks or latches. Several windows also don't have locks. We didn't have anyone in our party willing to try the shower but the stains downstairs hinted it might leak. The house is acrossed the street from the water, not on the...
Charming Oceanfront House with Deck, Cozy Loft, and Direct Beach Access

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

2.0 star property
10.0 out of 10, Exceptional, (19)
"Beautiful location, comfortable beds and wonderful linens. This place was wonderful"
Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer

Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town

9.8 out of 10, Exceptional, (25)
"The cabin was very clean and a nice quiet location. Had everything we needed for a comfortable stay."
Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town

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

8.8 out of 10, Excellent, (3)
"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 $209
CA $330 total
includes taxes & fees
Jul 16 - Jul 17
Captain's House 2BR Apartment. Walk to Everything!

1BR Guest Suite w/Private Bath & Entrance. Best Value in Town!

7.0 out of 10, Good, (10)
"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 $111
CA $211 total
includes taxes & fees
Jul 16 - Jul 17
1BR Guest Suite w/Private Bath & Entrance. Best Value in Town!

NEW! Coveside! Designer decor, waterfront, AC, 2 Bedroom in Harpswell.

10.0 out of 10, Exceptional, (2)
" Absolutely SpectacularThis stunning Maine home exceeded every expectation. Waking up each morning to watch sunshine sparkle off the bay with coffee became our cherished daily ritual – there's simply no better way to start the day in this idyllic setting.The attention to detail throughout is extraordinary. Beautiful design, thoughtful decoration, and pristine cleanliness with no clutter anywhere. Super comfortable beds with the softest sheets we've experienced, luxurious towels, and perfect...
NEW! Coveside! Designer decor, waterfront, AC, 2 Bedroom in Harpswell.

Dog-friendly bay view home - water views, dock access

6.4 out of 10, (6)
"Nice and quiet. Beautiful view of the water"
Dog-friendly bay view home - water views, dock access

Well-located, dog-friendly home - walk to footbridge & Barrett Park

9.4 out of 10, Exceptional, (33)
"A nice, quiet location that is just a walk away from a pretty town, and not too far of a drive away from many great places to visit along the coastline."
Well-located, dog-friendly home - walk to footbridge & Barrett Park

Oceanfront, dog-friendly condo with Boothbay Harbor views & prime location

9.2 out of 10, Wonderful, (15)
"Loved the location, lots of activity but also very private and relaxing. Great place, everyone was really nice and friendly"
Oceanfront, dog-friendly condo with Boothbay Harbor views & prime location

Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor

3.0 star property
Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor

Beautiful Oceanfront House- Stunning Water Views

9.6 out of 10, Exceptional, (5)
"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

10.0 out of 10, Exceptional, (25)
"This place was amazing and so special- incredible views, great cabin, and amazing access to the water. "
Oceanfront Cabin-Castle in Maine Woods

Large beautiful ocean front studio with private dock

9.8 out of 10, Exceptional, (29)
"Great stay at a well-maintained property with a wonderful view and private dock! Fantastic communication with the owner, thank you!"
Large beautiful ocean front studio with private dock

Beachfront Delight with detached guesthouse, sunset views & private beach access

9.6 out of 10, Exceptional, (14)
"no place is a 10 BUT 8-9 is pretty good. Great Location to relax"
Beachfront Delight with detached guesthouse, sunset views & private beach access

Waterfront Cottage in South Bristol w/ private dock and lobster boat views

10.0 out of 10, Exceptional, (104)
"We stayed at the property for two nights for a family getaway after the holidays. The house was in a great location, beautiful views, spotlessly clean, and very well equipped. We loved waking up to the light hitting the water and being able to explore the beautiful peninsula. Great hikes a short drive away. We would gladly stay again! "
Waterfront Cottage in South Bristol w/ private dock and lobster boat views

Centerview cottage

9.8 out of 10, Exceptional, (51)
"Very good people, excellent stay and we highly recommend this place, good home feeling and beautiful view"
The price is CA $404
CA $654 total
includes taxes & fees
Aug 15 - Aug 16
Centerview cottage

Cozy Waterfront Cottage with Dock

10.0 out of 10, Exceptional, (1)
"Gem of a cottage with wonderful views of Townsend Gut and Deckers Cove. Morning coffee on the porch great way to start the day. Clean and comfortable cottage. Close to great restaurants. Would definitely stay here again."
Cozy Waterfront Cottage with Dock

Sunrise Catcher with a Panoramic View!

10.0 out of 10, Exceptional, (41)
"Great get away & girls weekend. Plenty to do & see. Home is very well equipped for guest needs."
Sunrise Catcher with a Panoramic View!

Make Shimmering River Retreat your Maine Coastal getaway!

9.6 out of 10, Exceptional, (33)
"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!
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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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?

Charming cottage near the beach with balcony, deck, grill, fireplace - dogs OK: Visitors like this Five Islands vacation home rental. It is located in a rural location and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. Another good choice for your trip to Five Islands is Charming Oceanfront House with Deck, Cozy Loft, and Direct Beach Access.

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.