Search and Rent Five Islands Condos

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Condo Rentals in Five Islands

Walking Distance To Shops, Restaurants And Footbridge
Enjoy cooking in this well-lit kitchen with an oven, stainless steel refrigerator, and wooden countertop.

Walking Distance To Shops, Restaurants And Footbridge

10.0 out of 10, Exceptional, (39)
"This is a great place right downtown which makes for easy walking access. Would definitely stay again!"
Walking Distance To Shops, Restaurants And Footbridge
Oceanfront, dog-friendly condo with Boothbay Harbor views & prime location
Enjoy a serene view of the marina from this balcony, featuring a table and two chairs.

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

9.4 out of 10, Exceptional, (16)
"Loved the location, lots of activity but also very private and relaxing. Great place, everyone was really nice and friendly"
Oceanfront, dog-friendly condo with Boothbay Harbor views & prime location
East Boothbay Waterfront One room Condo.Waterview from in side this room
Relax on the pier, surrounded by serene views and lush greenery, with benches and a covered seating area to unwind.

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

9.8 out of 10, Exceptional, (131)
"Our stay was great!!"
East Boothbay Waterfront One room Condo.Waterview from in side this room
Riverfront condo w/ deck overlooking the water - steps to dining & shopping
Enjoy a warm and inviting kitchen and dining area with a wooden island, stainless steel refrigerator, and cozy dining table.

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

9.0 out of 10, Wonderful, (45)
"Overall it was great for the money!"
Riverfront condo w/ deck overlooking the water - steps to dining & shopping
New Condo w/Water-View Deck in Edgecomb's Sheepscot Harbour Resort
Kitchen features a double sink, refrigerator, stove, and microwave, with a tiled backsplash and window above the sink.

New Condo w/Water-View Deck in Edgecomb's Sheepscot Harbour Resort

8.8 out of 10, Excellent, (29)
"Nice view, convenient location. Bedroom was way too small."
New Condo w/Water-View Deck in Edgecomb's Sheepscot Harbour Resort
Waterfront Condo in Boothbay Harbor
Property grounds

Waterfront Condo in Boothbay Harbor

10.0 out of 10, Exceptional, (1)
"This home was fully stocked and organized. Beautiful view and a great location. Easy walk to restaurants and shops. Would stay again!!"
Waterfront Condo in Boothbay Harbor
Mabel's Maine Studio on the River
Exterior

Mabel's Maine Studio on the River

10.0 out of 10, Exceptional, (1)
"Loved it. (Felt price was a bit high, but appreciated that we could have our small dog with us) . Bed is comfortable and loved the location. Thank you "
Mabel's Maine Studio on the River
Elegant Oceanfront Condo with Stunning Harbor Views & Spectacular Sunsets
Enjoy cooking in this kitchen with a central island, stainless steel appliances, and a unique art piece.

Elegant Oceanfront Condo with Stunning Harbor Views & Spectacular Sunsets

2.0 star property
9.6 out of 10, Exceptional, (5)
"This was a great condo. We really enjoyed watching the action on the harbor from the covered deck. The furnishings and appliances were brand new. There was plenty of room for a group with the layout of the bedrooms. It was very convenient to have the restaurant in the same building and it was a short drive to downtown. Our only suggestions would be to add a coffeemaker and directions for the dishwasher and garbage removal.Also it would be helpful to explain the parking situation and that the...
Elegant Oceanfront Condo with Stunning Harbor Views & Spectacular Sunsets
Seabed @ The Offshore House
Outdoor dining

Seabed @ The Offshore House

10.0 out of 10, Exceptional, (12)
"This was a great place to stay that let me explore the area I wanted to."
Seabed @ The Offshore House
Stylish Condo at Sheepscot Harbor Resort w/Free WiFi, River Views, & Balcony
Fully equipped kitchen with refrigerator, microwave, oven, and coffee maker.

Stylish Condo at Sheepscot Harbor Resort w/Free WiFi, River Views, & Balcony

9.4 out of 10, Exceptional, (60)
"Great place to stay"
Stylish Condo at Sheepscot Harbor Resort w/Free WiFi, River Views, & Balcony
The perfect seaside retreat overlooking scenic Mackerel Cove on Bailey Island
Enjoy a meal or social gathering on this balcony with a view of the harbor.

The perfect seaside retreat overlooking scenic Mackerel Cove on Bailey Island

9.8 out of 10, Exceptional, (21)
"We thoroughly enjoyed a long weekend on Bailey Island. The condo was clean and new, very nicely furnished. It was a quiet easy to access property, very good experience."
The perfect seaside retreat overlooking scenic Mackerel Cove on Bailey Island
Two room condo with ocean view! First floor with a Handicap Bathroom!
Relax in a serene outdoor seating area with two comfortable chairs, surrounded by a wooden fence and a paved walkway.

Two room condo with ocean view! First floor with a Handicap Bathroom!

8.6 out of 10, Excellent, (17)
"The unit was perfect for our stay. It was well appointed and nicely decorated. The location is great as you are close to Boothbay Harbor but not in it. Ocean Point is a fantastic place to walk to really experience the Maine coast. The screen porch was a hit with the seating area and table where you could see Linekin Bay. Bed was comfortable and kitchen had everything we needed with a gas grill outside. Would definitely stay here again. "
Two room condo with ocean view! First floor with a Handicap Bathroom!
Shipwright @ The Offshore House
Smart TV

Shipwright @ The Offshore House

9.4 out of 10, Exceptional, (11)
"Luv the area and the room location was great A few steps from Bets fish and chips short drive into town "
$342 nightly
The price is $365
Aug 12 - Aug 13
Total includes taxes and fees
Shipwright @ The Offshore House
Water-view condo at Sheepscot Harbour Resort with deck, full kitchen, and WiFi
Enjoy cooking in this well-equipped kitchen with a microwave, oven, refrigerator, coffee maker, and toaster.

Water-view condo at Sheepscot Harbour Resort with deck, full kitchen, and WiFi

8.2 out of 10, Very Good, (20)
"Great place to relax and jump out to surrounding areas from! "
Water-view condo at Sheepscot Harbour Resort with deck, full kitchen, and WiFi
New Riverfront Condo in Sheepscot Harbour - Walk to Famed Seafood Eatery
Prepare meals in a well-equipped kitchen with a refrigerator, microwave, gas stove, and kettle.

New Riverfront Condo in Sheepscot Harbour - Walk to Famed Seafood Eatery

9.2 out of 10, Wonderful, (68)
"Reds Lobster roll is definitely worth the hype!!"
New Riverfront Condo in Sheepscot Harbour - Walk to Famed Seafood Eatery
Solitude @ The Offshore House
1 bedroom, iron/ironing board, free WiFi

Solitude @ The Offshore House

9.6 out of 10, Exceptional, (4)
"Awesome place will stay again… Owners were a pleasure to deal with."
$340 nightly
The price is $362
Sep 1 - Sep 2
Total includes taxes and fees
Solitude @ The Offshore House
1890 Captain's House N.E. Charm w/Water Views over Mill Cove 5mins walk to town.
Relax on the porch with a view of the serene lake, surrounded by lush greenery and comfortable seating.

1890 Captain's House N.E. Charm w/Water Views over Mill Cove 5mins walk to town.

10.0 out of 10, Exceptional, (48)
"This is a great place to stay. Very close to downtown, Karen is extremely helpful, and the deck is a wonderful spot to enjoy the water and nature. I’m coming back!!"
1890 Captain's House N.E. Charm w/Water Views over Mill Cove 5mins walk to town.
Waterfront Condo: Walk to Downtown Boothbay Harbor
Cozy living room with a fireplace, comfortable seating, and a view of the water through large glass doors.

Waterfront Condo: Walk to Downtown Boothbay Harbor

9.6 out of 10, Exceptional, (4)
"Everything about this lovely condo is absolutely wonderful! Condo was immaculate upon arrival, location is within walking distance to downtown and the owners thought of every detail you could imagine. Beds were extremely comfortable and the condo is stunningly decorated- highly recommend!"
Waterfront Condo: Walk to Downtown Boothbay Harbor
Simple living in Midcoast Maine
Fridge, microwave, oven, stovetop

Simple living in Midcoast Maine

10.0 out of 10, Exceptional, (1)
"Great location, close to everything I wanted to do. Grocery store and restaurants near by.. state parks and preserves to walk. Condo was clean and comfortable,with easy access. Nice balcony looking out over the green space in the back. Great place to have coffee in the morning - I even saw a deer one morning!"
Simple living in Midcoast Maine
Boothbay Cottg | Oceanfront+Deck | No Hidden Fees
Enjoy a refreshing swim in the pool surrounded by lounge chairs and umbrellas, with a dock extending into the water and a scenic shoreline.

Boothbay Cottg | Oceanfront+Deck | No Hidden Fees

Boothbay Cottg | Oceanfront+Deck | No Hidden Fees
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Five Islands Hotel Reviews

Ocean Gate Resort

Ocean Gate Resort

10/10 Excellent
"Beautiful location with beautiful views and so much to do! We paddleboarded and kayaked every day. Breakfast was excellent."
Alyson 1-night trip
Posted 2 days ago
Ocean Gate Resort