Five Islands Holiday Rentals

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Holiday Rentals in Five Islands

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

9.4 out of 10, Exceptional, (11)
"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

4.8 out of 10, (5)
"The house was busted. Water went out the first night. We couldn’t go out on the decks where one of the pictures is taken. Floors were uneven and there were beads and remnants of things that were stuck between the floor boards. The lockbox they use for the front door is wonky so every time we tried to get into the house it took us 20 minutes. Payed way too much money for it. I would have rather stayed at a hotel. The house has potential to be great if they fixed it up just a little bit. The handy...
Charming Oceanfront House with Deck, Cozy Loft, and Direct Beach Access

Full sized home

9.8 out of 10, Exceptional, (42)
"The house was lovely. Very comfortable place. Within 15- 20 mins to a store or restaurants."
The price is AU$559
includes taxes & fees
21 Oct - 22 Oct
Full sized home

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

10.0 out of 10, Exceptional, (228)
"Beautiful views, very clean and enjoyed the oceanside vibe both inside and out! Easy walk to general store and walkable to Giant Stairs trail and Cedar Beach."
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Enjoyable 1-bedroom rustic cottage in Southport.

10.0 out of 10, Exceptional, (16)
"Lovely location, quiet, serene, and the cottage is totally cute and comfortable. "
Enjoyable 1-bedroom rustic cottage in Southport.

Captain's Guest Room w/private bath & house entrance. Walk to everything.

8.2 out of 10, Very good, (17)
"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 AU$228
includes taxes & fees
1 Oct - 2 Oct
Captain's Guest Room w/private bath & house entrance. Walk to everything.

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

Make Shimmering River Retreat your Maine Coastal getaway!

9.6 out of 10, Exceptional, (38)
"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!

Oceanfront Cabin-Castle in Maine Woods

9.8 out of 10, Exceptional, (34)
"Place was amazing with an incredible view and fun layout. "
Oceanfront Cabin-Castle in Maine Woods

Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room

10.0 out of 10, Exceptional, (52)
"This cozy cottage is in the beautiful town of Phippsburg, next to the break-taking beach of Popham State Park. With its site on the ocean shore, the sound of waves soothes your soul, and the beach lends all kinds of opportunities for exploring both at low tide and high tide. Our host and hostess were very responsive to our needs, and my daughter and I greatly enjoyed out stay."
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room

Newly Renovated Haven w/ Deck, Walk to Shops, Dining & Marina, Pet friendly

9.2 out of 10, Wonderful, (60)
"The house was the perfect size for my family of 7 adults. We enjoyed the short walk to downtown Boothbay too."
Newly Renovated Haven w/ Deck, Walk to Shops, Dining & Marina, Pet friendly

Camp Forever cottage

9.6 out of 10, Exceptional, (53)
"Connie and Mike are great hosts. The camp was clean and air conditioned! The view from camp was beautiful. The dock was amazing. "
The price is AU$411
includes taxes & fees
14 Oct - 15 Oct
Camp Forever cottage

Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers

9.6 out of 10, Exceptional, (78)
"Great stay, wonderful location"
Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers

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

10.0 out of 10, Exceptional, (107)
"Beautiful location, house is stunning - wish we had time to stay longer!"
Waterfront Cottage in South Bristol w/ private dock and lobster boat views

Large beautiful ocean front studio with private dock

9.8 out of 10, Exceptional, (43)
"Amazing spot, as someone who used live down the street, I felt like I was back at home! So happy to have the spot. Will for sure be coming back!"
Large beautiful ocean front studio with private dock

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 AU$399
includes taxes & fees
8 Oct - 9 Oct
Captain's Quarters 2BR Apartment. Walk to Everything!

1 room luxury ocean front studio cottage

9.6 out of 10, Exceptional, (160)
"Quaint with a great view."
1 room luxury ocean front studio cottage

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

9.2 out of 10, Wonderful, (93)
"Fantastic coastal cottage feel! Beautiful view of the the bay. Updated bathrooms and kitchen. Perfect location to walk to center of Boothbay harbor shops and restaurants. My only suggestion...replace any bad window shades with working ones..andCheck all ac unit filters.maybe consider updating the upstairs ac units.We had an amazing time."
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

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.

Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.

10.0 out of 10, Exceptional, (96)
"Beautiful home and scenery, hosts were communicative. "
Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.
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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Top Five Islands Hotel Reviews

Find out more about Five Islands

Find out more about Five Islands

Everything you need to know about Five Islands holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Five Islands holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Five Islands holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Five Islands holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Five Islands. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Five Islands holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Five Islands holiday rentals we have selected for you start as low as AU$228 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Five Islands rentals

At Expedia, we put the best Five Islands holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Five Islands rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Five Islands holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Five Islands. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.

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 Boothbay Railway Village, 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.