Five Islands Holiday Rentals

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Holiday Rentals in Five Islands

Laughton House @ Pemaquid Beach

10.0 out of 10, Exceptional, (6)
"Wonderful, spacious home that has been beautifully decorated and maintained. Francine and Greg were great hosts. Will definitely be back."
The price is NZ$1,408
includes taxes & fees
14 July - 15 July
Laughton House @ Pemaquid Beach

New! Pemaquid Escape | Curated Comfort + Hot Tub

10.0 out of 10, Exceptional, (1)
"This was a last minute booking for our family as we had a basketball tournament, there were 8 of us including 3 children. This was the most kid friendly house we have stayed in! It was so well stocked for the entire family. The house was meticulously cleaned and the hosts were very responsive to any questions! "
The price is NZ$1,270
includes taxes & fees
8 July - 9 July
New! Pemaquid Escape | Curated Comfort + Hot Tub

Downtown Boothbay Harbor, The Francis Greene House

9.4 out of 10, Exceptional, (40)
"We had a blast, home was just the local place we needed for our weekend! Home was beautiful and nice and clean! Would love to stay again!"
The price is NZ$1,201
includes taxes & fees
20 July - 21 July
Downtown Boothbay Harbor, The Francis Greene House

Greenleaf Inn Alyson's Room Main House King, Ocean views, Large Bath

2.5 star property
10.0 out of 10, Exceptional, (1)
"This was one of our very favorite places we have visited. The Greenleaf Inn was perfect and we lacked for nothing. Make sure you relax on the roof top deck with a coffee or glass of wine!"
The price is NZ$513
includes taxes & fees
7 July - 8 July
Greenleaf Inn Alyson's Room Main House King, Ocean views, Large Bath

Greenleaf Inn Room 4 – King Room with Harbor & Island Views in Boothbay

2.5 star property
10.0 out of 10, Exceptional, (2)
"As soon as we got there we felt welcome. John was amazing, showing us around the whole property & explaining all that was offered. We got there late & had not had a chance to eat so we asked him if there was any suggestions. He immediately got on the phone & got us a reservation for the Thistle Inn. He was amazing & could not do enough for us, including bringing us pastries every morning & having campfires at night so that we could get to know the other guests staying at the inn.The room was...
The price is NZ$490
includes taxes & fees
7 July - 8 July
Greenleaf Inn Room 4 – King Room with Harbor & Island Views in Boothbay

Greenleaf Inn Penthouse King w/ Panoramic Ocean views off Rooftop Deck

10.0 out of 10, Exceptional, (2)
"Great room. Friendly staff. Ocean views. Had a fantastic weekend!"
The price is NZ$593
includes taxes & fees
8 July - 9 July
Greenleaf Inn Penthouse King w/ Panoramic Ocean views off Rooftop Deck

Greenleaf Inn #3 - Gorgeously Renovated King Suite, Large Bath, Balcony, Harbor Views!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Our host did a tremendous job making us feel welcome. "
The price is NZ$719
includes taxes & fees
14 July - 15 July
Greenleaf Inn #3 - Gorgeously Renovated King Suite, Large Bath, Balcony, Harbor Views!

Greenleaf Inn - Mary's Room! First Floor King Suite, w/ Balcony, Harbor Views!

8.0 out of 10, Very good, (2)
"The property was on a great location and the service was excellent! We will definitely stay here again!"
The price is NZ$571
includes taxes & fees
9 July - 10 July
Greenleaf Inn - Mary's Room! First Floor King Suite, w/ Balcony, Harbor Views!

Greenleaf Inn Room 6 | Private Entry, Balcony, and Harbor Views

10.0 out of 10, Exceptional, (3)
"Greenleaf Inn was a great place to stay. Staff was friendly and checked on needs of the people staying. We had room 6 which had a good view of the harbor. It overlooked Tugboat Restaurant and was a short walk to the stores downtown and the harbor. Food was delicious anywhere we went. Recommended.Thanks"
The price is NZ$626
includes taxes & fees
22 July - 23 July
Greenleaf Inn Room 6 | Private Entry, Balcony, and Harbor Views

Greenleaf Inn Room 2: Cozy King Room With Harbor Views

The price is NZ$496
includes taxes & fees
10 July - 11 July
Greenleaf Inn Room 2: Cozy King Room With Harbor Views

Boothbay Harbor King Suite – Room 11 at Admiral's Quarters Inn

10.0 out of 10, Exceptional, (3)
"We loved being in the heart of the bay. Jersey was a fabulous host who served me a delicious breakfast in the solarium overlooking the bay. The full kitchen with snacks on hand was nice. We enjoyed relaxing at the end of the day by the fire pit. We're so glad that we found this gem in Boothbay Harbor. "
The price is NZ$536
includes taxes & fees
7 July - 8 July
Boothbay Harbor King Suite – Room 11 at Admiral's Quarters Inn

Room 14 at Admiral's Quarters Penthouse | Stunning Views + King Bed + Trundle

10.0 out of 10, Exceptional, (2)
"Great location. Very nice room. Jersey (manager) was very helpful. "
The price is NZ$651
includes taxes & fees
7 July - 8 July
Room 14 at Admiral's Quarters Penthouse | Stunning Views + King Bed + Trundle

Admiral's Quarters Room 13 - PREMIER Ocean View 2 Room King Suite w/ Living Room, Fireplace, Patio

10.0 out of 10, Exceptional, (1)
"The location of the property was awesome, with beautiful Harbor views. The room we stayed in was very clean and a very comfortable size with once again great views. The amenities on the property were much better than we've experienced elsewhere. Kitchen/ eating area and the solarium were large and well stocked.As per most of the reviews you cant leave out "Jersey", who checks you in and runs the place basically. Super nice guy and very accommodating. Great sense of humor and makes everyone feel...
The price is NZ$618
includes taxes & fees
9 July - 10 July
Admiral's Quarters Room 13 - PREMIER Ocean View 2 Room King Suite w/ Living Room, Fireplace, Patio

Admiral's Quarters Jersey's Room - Garden Level w/ Gas Stove & Stunning Harbor Views

10.0 out of 10, Exceptional, (1)
"The greenleaf/admirals quarters was fantasic! John, was an unbelievable host. He made sure to give us a tour of the whole property, as well as made us feel welcome with an abundance of complementary items to include food and drink, as well as a bonfire at dusk with s’mores. All around fantastic experience. The room was extremely clean and comfortable and the whole place seems to have had brand new renovation. 100% recommend."
The price is NZ$575
includes taxes & fees
7 July - 8 July
Admiral's Quarters Jersey's Room - Garden Level w/ Gas Stove & Stunning Harbor Views

2-Story Harbor View Suite King and Queen w/ 3 Balconies | Admiral's Quarters Inn Room 12

9.2 out of 10, Wonderful, (7)
"We had a wonderful time at Admiral’s Quarters and wish we’d had one more night to spend in Boothbay Harbor. Our room was cozy and the two levels made it perfect for our family of four. The location was fantastic and John always had great recommendations for things to do or places to eat. "
The price is NZ$721
includes taxes & fees
20 July - 21 July
2-Story Harbor View Suite King and Queen w/ 3 Balconies | Admiral's Quarters Inn Room 12

Room 15 at Admiral's Quarters Penthouse | Stunning Views + King Bed + Trundle

10.0 out of 10, Exceptional, (2)
"We loved this property. The views from the premium suites were unbelievable. Property also has shared space that includes a well-stocked, full kitchen (with breakfast food and coffee/nespresso provided), sun room, and outdoor patio. We would definitely stay here again."
The price is NZ$618
includes taxes & fees
10 July - 11 July
Room 15 at Admiral's Quarters Penthouse | Stunning Views + King Bed + Trundle

Admiral's Quarter Room 10 - Accessible 2 Room King Suite w/ Bedroom and study

The price is NZ$562
includes taxes & fees
7 July - 8 July
Admiral's Quarter Room 10 - Accessible 2 Room King Suite w/ Bedroom and study

Premium Family Suite - 2 Double Beds, 1 King Bed

5.0 out of 10, (2)
"Location is close to what we wanted (botanical gardens and Boothbay Harbor shops). The plusses were free breakfast, nice trails connected to property, icecream across the street. The minuses were the pool/hot tub not open as expected,our room was not deep cleaned."
The price is NZ$999
includes taxes & fees
7 July - 8 July
Premium Family Suite - 2 Double Beds, 1 King Bed

More then a Motel With Garden , Renovated Rooms at heart of Boothbay

2.0 star property
8.0 out of 10, Very good, (2)
"clean, affordable accomadations. Manager helpful and responsive"
The price is NZ$746
includes taxes & fees
12 July - 13 July
More then a Motel With Garden , Renovated Rooms at heart of Boothbay

Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome

9.0 out of 10, Wonderful, (60)
"We stayed in October when the trees were gorgeous and the dome house is nestled in a wooded area. So pretty! Lots of room for everyone. Wish we could have stayed longer."
The price is NZ$730
includes taxes & fees
12 July - 13 July
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome
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 holiday rental in Five Islands?

Yes, there are holiday rentals close to the most popular sights in Five Islands, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Five Islands has to offer?

Charming cottage near the beach with balcony, deck, grill, fireplace - dogs OK: This highly rated holiday home rental in Five Islands is located in a rural location, and has a fireplace, a balcony and a BBQ 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 that 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 holiday rentals will I find in Five Islands?

With 8 Expedia holiday rentals, you're guaranteed 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 Coastal Maine Botanical Gardens. In the wider area, you’ll find Reid State Park and Burnt Island Living Lighthouse.

What’s a holiday rental in Five Islands like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Five Islands. Holiday rentals feature extras such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for families.