Five Islands Vacation Rentals

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Vacation Rentals in Five Islands

1 room luxury ocean front studio cottage

9.6 out of 10, Exceptional, (149)
"Very clean, amazinv views, perfect weekend!!!! "
1 room luxury ocean front studio cottage

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

10.0 out of 10, Exceptional, (99)
"This property is stunning, and the view is spectacular. If this were my house, I’d never leave! We had a fabulous time. "
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

East Boothbay Waterfront One room Condo.Waterview from in side this room

9.8 out of 10, Exceptional, (127)
"perfect love to be back next year"
East Boothbay Waterfront One room Condo.Waterview from in side this room

A Charming Waterfront Cottage with Touches of Elegance

10.0 out of 10, Exceptional, (98)
"Beckoning Bay cottage is a warm and welcoming place to relax and enjoy time with family. The cottage is clean and comfortable, and David, the host, is easy to communicate with and more than kind. The big porch is absolutely beautiful, and we spent a good deal of time watching the ducks and geese. There are many trails to choose from for walking nearby. We would not hesitate to book one of David’s properties again in the future. "
A Charming Waterfront Cottage with Touches of Elegance

Popham Beach Direct Oceanfront Cottage Steps to the sand

9.8 out of 10, Exceptional, (58)
"Well taken care of and maintained. Comfortable."
Popham Beach Direct Oceanfront Cottage Steps to the sand

Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces

8.4 out of 10, Very good, (41)
"GORGEOUS house and view! Very spacious and accommodating. Things you should know before booking is that it is about an hour away from anything and everything. House could use some more TV's if you're going with children, pinball machines did not work and neither did "workout equipment" which was an elliptical and treadmill. One of the showers did not work and some of the fans that were provided did not either. I think its a tad over priced for its distance to do things but the views from...
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces

Bayfront home with 270-degree views, large deck & porch - near Popham Beach

8.2 out of 10, Very good, (29)
"The house is beautiful, comfortable and was pristine when we checked in. Decks and screened porch are wonderful. The kids loved the 3rd floor bedroom space, and it was fabulous being so close to Popham Beach. Definitely recommend. Kitchen on 2nd floor ... so have some strong helpers to bring in groceries ;)"
Bayfront home with 270-degree views, large deck & porch - near Popham Beach

Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe

9.4 out of 10, Exceptional, (33)
"Very cozy house in an absolutely lovely spot. We really enjoyed the outdoor space and the peace and quiet. "
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe

Unique oceanfront home with a deck, tons of natural light, & amazing views

8.6 out of 10, Excellent, (53)
"Property was great. But we had no water for one of our three days of our stay. We had to call to get someone out to fix it, and they didn’t know how. It set the tone for our stay."
Unique oceanfront home with a deck, tons of natural light, & amazing views

Cozy Cottage with spectacular salt water view / 3 Kayaks available/

9.8 out of 10, Exceptional, (38)
"I had an excellent visit. The kitchen was well stocked with utensils and small appliances. Everything was super clean; magazines and books were available (as well as good WiFi). I never turned the tv on as the view was spectacular. I wasn’t able to have an outdoor fire due to weather but everything was great. I hope to return. I look forward to doing more exploring as the area is beautiful. Also, very responsive with owners live next door. Thanks for offering up this quant little cabin for...
Cozy Cottage with spectacular salt water view / 3 Kayaks available/

Gorgeous Waterfront Home on Westport Island with 2 Sunrooms

9.6 out of 10, Exceptional, (44)
"Absolutely beautiful views. Very well appointed and comfortable. "
Gorgeous Waterfront Home on Westport Island with 2 Sunrooms

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

8.8 out of 10, Excellent, (35)
"Our party of 8 enjoyed our stay. The house is well equipped and stocked to get you started. Conveniently located to town and the Botanical Gardens. Plenty of outside space for kids to run around and play. It has a beautiful view of the cove but is very rocky. This didn't stop us from hunting hermit crabs and catching fish. The house is old but that gives it the Maine charm. "
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK

Expansive Modern Home w/ Ocean View, Gorgeous Garden & Multiple Sitting Areas

8.4 out of 10, Very good, (23)
"Spacious house with nice views."
Expansive Modern Home w/ Ocean View, Gorgeous Garden & Multiple Sitting Areas

Riverfront condo w/ deck overlooking the water - steps to dining & shopping

9.0 out of 10, Wonderful, (41)
"Overall it was great for the money!"
Riverfront condo w/ deck overlooking the water - steps to dining & shopping

Full sized home

9.6 out of 10, Exceptional, (24)
"The house is very clean, and it's very well situated. There are plenty of room in and out. Will come again."
Full sized home

Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

9.2 out of 10, Wonderful, (83)
"This house is in perfect spot in Boothbay Harbor. Easy walk to town, right on the water. Everything about the house was perfect and exactly what we needed. "
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

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

9.4 out of 10, Exceptional, (13)
"Staying at the Carousel Marina is like no other VASCA experience for vacation. First, anyone renting should realize they will be staying at the actual marina and will be witness to all the activities that occur there – boats arriving, departing, people coming and going on the docks and the influx of people coming each night to enjoy cocktails, dinner and live music at the attached restaurant either inside or outside on the patio by the firepit. If you are fortunate enough to stay for an extended...
Oceanfront, dog-friendly condo with Boothbay Harbor views & prime location

Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina

9.4 out of 10, Exceptional, (51)
"There were four of us so we each had a bedroom. We have been friends since 1955!!! It was a wonderful getaway! "
Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina

Sunrise Catcher with a Panoramic View!

10.0 out of 10, Exceptional, (36)
"Very good location for day trips along the coast."
Sunrise Catcher with a Panoramic View!

Charming 3BR, 1.5BA beachfront cottage with multi-level decks

9.2 out of 10, Wonderful, (31)
"Wonderful "
Charming 3BR, 1.5BA beachfront cottage with multi-level decks
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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Other types of properties in Five Islands you may be interested in

The Brunswick Hotel

3.0 star property
9.2 out of 10, Wonderful, (754)
"I real hotel, not a chain. Very comfortable, peaceful, and welcoming. Breakfast was terrific. The service and the staff were friendly and helpful."
The price is CA $159
CA $174 total
includes taxes & fees
Jan 27 - Jan 28
The Brunswick Hotel

Tugboat Inn

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Needs updating. Paint. Bathroom needs a look of work"
Tugboat Inn

The Federal

2.5 star property
9.6 out of 10, Exceptional, (436)
"Staff friendly and at the restaurant. Love the bathroom products and quality of bed linens. I am usually there once a month on my own or with my husband. Perfect location for us."
The price is CA $171
CA $186 total
includes taxes & fees
Jan 20 - Jan 21
The Federal
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.

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?

Bayfront home with 270-degree views, large deck & porch - near Popham Beach: Visitors like this Five Islands vacation home rental. It is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 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.

How many vacation rentals will I find in Five Islands?

With 6 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 Maine State Aquarium, or get out into nature at a spot like Reid State Park. In the larger area, you’ll find Coastal Maine Botanical Gardens and Boothbay Harbor Marina.

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.