Five Islands Vacation Rentals from $180: Search Short-Term Rentals

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Our top choices for Five Islands vacation rentals

Desk, iron/ironing board, WiFi (free), bed sheets

1. Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

Georgetown

Palmer M.

$429 nightly

Sep 16 - Sep 17

Total with taxes and fees

2. Pond Cabin: Private Sauna+Near Beach+FirePit+Pond

Georgetown

$535 nightly

Sep 8 - Sep 9

Total with taxes and fees

3. Harold Room 8 | 2 Queens + Gable Windows

Boothbay Harbor

$440 nightly

Aug 30 - Aug 31

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

4. Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor

East Boothbay

Andy H.

$563 nightly

Aug 20 - Aug 21

Total with taxes and fees

5. Modern Cape -3 Bedroom- Boothbay Harbor - Near Ocean -Golf-Botanical Gardens

Boothbay Harbor

Sharon H.

$582 nightly

Sep 1 - Sep 2

Total with taxes and fees

6. Boothbay Harbor, The Francis Greene House, downtown

Boothbay Harbor

Terry F.

$662 nightly

Sep 5 - Sep 6

Total with taxes and fees

7. Large suite/private bath/private entrance on quiet street near Thomas Bay

Brunswick

"Susan and Jeff were amazing hosts! There were so kind, thoughtful and welcoming. The suite was extremely spacious, well decorated and very comfortable. We were very close to the Air Show which was the reason for our trip. They gave us great instructions for a short cut to the airfield and amazing dinner recommendations. We could not have chosen a better place to stay. We highly recommend this place!"

Asha

$152 nightly

Aug 24 - Aug 25

Total with taxes and fees

8. Boothbay Harbor, 2-Story Cottage, downtown

Boothbay Harbor

Erik P.

$388 nightly

Aug 17 - Aug 18

Total with taxes and fees

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Top Five Islands Hotel Reviews

Best Western Plus Brunswick Bath

10/10 Excellent

"Very comfortable bed . Quiet even though they were fully booked . Exceptional Customer Service both at Check in and check out."

Travelers Inn

10/10 Excellent

"This place is a hidden gem!! Reminiscent of the motor courts of old, the charm starts as soon as you pull in. And then the rooms... WOW! Much more spacious than you would think from the outside and absolutely spotless. There is a walk-in closet with iron and ironing board perfect for stowing luggage and hanging clothes. My son and I had doors facing each other on the first floor. There's a little 4x8 ft patio/porch type area in between. Great for sitting out and enjoying the weather if you bring a camp chair. Breakfast was great with a large selection of options: 3 kinds of dry cereal, fruit, bagels, bread for toast or sandwiches (peanut butter & jelly available too), and my favorite, English muffins. The toaster was easy to use and turned everything out with the perfect toastiness. The staff is very personable and accommodating. We ended up leaving sooner than expected and there was no problem with a credit being issued almost immediately. Overall, the perfect Maine getaway!! We are already starting to discuss our next trip and this is definitely where we plan to stay."

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 $180 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?

Spacious Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: Visitors like this Five Islands vacation home rental. It is located on the beach and has a patio, a garden, 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. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Five Islands?

With 5 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 Maritime Museum, 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.

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Check prices for these dates

Our top choices for Five Islands vacation rentals

1. Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

2. Pond Cabin: Private Sauna+Near Beach+FirePit+Pond

3. Harold Room 8 | 2 Queens + Gable Windows

4. Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor

5. Modern Cape -3 Bedroom- Boothbay Harbor - Near Ocean -Golf-Botanical Gardens

6. Boothbay Harbor, The Francis Greene House, downtown

7. Large suite/private bath/private entrance on quiet street near Thomas Bay

8. Boothbay Harbor, 2-Story Cottage, downtown

9. Award Winning Luxury Carriage House a short stroll from town!

10. Top floor loft apartment in downtown Bath

11. Pelican Cottage | 2 BR + Waterfront Porch

12. Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor

13. Captain's 2BR Suite. Best value, near everything, big yard, treehouse. No fees.

14. Classic Maine Waterfront Home on the Back River – Trevett

15. Little Spruce Cottage | Wood Stove + Porch

16. Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

17. Cozy and charming coastal retreat

18. Fully Renovated "Saltbox" Home in Boothbay

19. Walk-to-Town Boothbay Harbor Retreat | Harbor Views | A/C | Parking| Pet Friendly

20. Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.

Find vacation rentals that suit your style

Top Five Islands Hotel Reviews

Best Western Plus Brunswick Bath

Relax Inn

Travelers Inn

Residence Inn Bath Brunswick Area

Fishermans Wharf Inn

Smuggler's Cove Inn

Topside Inn

Cod Cove Inn, BW Signature Collection

Ocean Gate Inn

Find out more about Five Islands

Frequently asked questions

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