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, (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

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

10.0 out of 10, Exceptional, (225)
"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!

8.6 out of 10, Excellent, (7)
$239 nightly
The price is $261
Sep 23 - Sep 24
Total with taxes and fees
Captain's Quarters 2BR Apartment. Walk to Everything!

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."
$339 nightly
The price is $369
Sep 15 - Sep 16
Total with taxes and fees
Full sized home

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."
$150 nightly
The price is $164
Sep 30 - Oct 1
Total with taxes and fees
Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!

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."
$249 nightly
The price is $272
Sep 15 - Sep 16
Total with taxes and fees
Camp Forever cottage

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

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!

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

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

9.6 out of 10, Exceptional, (155)
"Quaint with a great view."
1 room luxury ocean front studio cottage

Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C

10.0 out of 10, Exceptional, (102)
"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.

10.0 out of 10, Exceptional, (13)
Enjoyable 1-bedroom rustic cottage in Southport.

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

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 "
$340 nightly
The price is $362
Sep 5 - Sep 6
Total with taxes and fees
Shipwright @ The Offshore House

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

10.0 out of 10, Exceptional, (37)
"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

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.

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.
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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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Five Islands vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Five Islands vacation 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 low season months. For more hustle and bustle, you may prefer to visit Five Islands in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $164 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Five Islands rentals

At Expedia, we put the best Five Islands vacation 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 vacation.

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 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.