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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 43 Condo Rentals in Bailey Island with updated reviews, rates, and availability.

Cozy, Elegant and Bright 2 bed in the East End
Living area

Cozy, Elegant and Bright 2 bed in the East End

9.8 out of 10, Exceptional, (36)
"Very clean. Nice walk along bikepath to downtown. Will look to stay here again. Loved the neighborhood and parking was easy. Kitchen had everything we needed to cook. "
The price is AED 735
AED 1,317 total
includes taxes & fees
21 Feb - 22 Feb
Cozy, Elegant and Bright 2 bed in the East End
Renovated condo with prime West End location, 2 en suite bathrooms, & HGTV style

Renovated condo with prime West End location, 2 en suite bathrooms, & HGTV style

9.8 out of 10, Exceptional, (35)
"The condo lived up to all of our expectations. Well situated near excellent bakeries and restaurants, yet on a quiet residential street. Condo was very clean and had good beds and linens. Nicely decorated. Washer /dryer a definite plus. Parking is indeed a bit tight; you just have to back in the driveway so you can get out. Thank you! "
Renovated condo with prime West End location, 2 en suite bathrooms, & HGTV style
Oceanfront, dog-friendly condo with Boothbay Harbor views & prime location

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

9.4 out of 10, Exceptional, (13)
"Staying at the Carousel Marina is like no other VASCA experience for vacation. First, anyone renting should realize they will be staying at the actual marina and will be witness to all the activities that occur there – boats arriving, departing, people coming and going on the docks and the influx of people coming each night to enjoy cocktails, dinner and live music at the attached restaurant either inside or outside on the patio by the firepit. If you are fortunate enough to stay for an extended...
Oceanfront, dog-friendly condo with Boothbay Harbor views & prime location
Historical & dog-friendly West End condo with parking - walk to all of Portland

Historical & dog-friendly West End condo with parking - walk to all of Portland

9.4 out of 10, Exceptional, (31)
"We enjoyed the apartment very much. there is only one parking place so that can be tricky if two groups are meeting up for a stay. There isn't a ton of parking in this residential area but you will find it if you wander a little. The apt. is well appointed and comfortable. We liked hanging out there and it was Quiet!"
Historical & dog-friendly West End condo with parking - walk to all of Portland
Shipwright @ The Offshore House

Shipwright @ The Offshore House

9.4 out of 10, Exceptional, (9)
"Clean, neat, short hop to Boothbay. Perfect for couple. Very safe as well. Neighborhood is not picturesque… not important to us. Only small, small picky note: heat was too high for us at night without ability to regulate. Highly recommend!"
The price is AED 382
AED 885 total
includes taxes & fees
20 Feb - 21 Feb
Shipwright @ The Offshore House
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

9.0 out of 10, Wonderful, (28)
"Great place, a little difficulty controlling temperature."
The price is AED 489
AED 1,391 total
includes taxes & fees
20 Feb - 21 Feb
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Walk to Old Port ♦ West End Condo ♦ Parking
Living area

Walk to Old Port ♦ West End Condo ♦ Parking

9.8 out of 10, Exceptional, (74)
"Everything was amazing!!"
The price is AED 420
AED 1,011 total
includes taxes & fees
20 Feb - 21 Feb
Walk to Old Port ♦ West End Condo ♦ Parking
Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo
Comfy living room with WiFi, 40" Roku TV and games for the kiddos

Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo

10.0 out of 10, Exceptional, (9)
"My friends and I had a great stay at Nick & Kayla’s place! It was an ideal location, easy check in process and even with some weather issues the hosts were very accommodating. The off street parking was a huge plus. Would recommend! "
The price is AED 424
AED 1,275 total
includes taxes & fees
23 Feb - 24 Feb
Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo
Gorgeously renovated, 2-condo property in the West End - walk everywhere

Gorgeously renovated, 2-condo property in the West End - walk everywhere

9.6 out of 10, Exceptional, (8)
"Simple nice places. Everything worked as designed. "
Gorgeously renovated, 2-condo property in the West End - walk everywhere
Centrally located off Back Cove, 2nd floor 4 bedroom, 2 Bath condo w/ deck
Private kitchen

Centrally located off Back Cove, 2nd floor 4 bedroom, 2 Bath condo w/ deck

2.0 star property
10.0 out of 10, Exceptional, (1)
"This place was perfect for our weekend getaway! The unit was huge with plenty of space for everyone. It was clean and nicely stocked, with easy access to downtown Portland. "
Centrally located off Back Cove, 2nd floor 4 bedroom, 2 Bath condo w/ deck
Spacious 4 bedroom luxury Condo
Living area

Spacious 4 bedroom luxury Condo

10.0 out of 10, Exceptional, (26)
"This place was perfect. The location was great. The neighborhood was quiet. The place was clean, provided plenty of space for all of us, and was well stocked. I definitely recommend and would stay again if in the area. "
Spacious 4 bedroom luxury Condo
Beautiful Falmouth Condo w/ Patio: Near Portland!
Falmouth Vacation Rental | 3BR | 2BA | 1,600 Sq Ft | Stairs Required

Beautiful Falmouth Condo w/ Patio: Near Portland!

7.0 out of 10, Good, (2)
"No comment "
Beautiful Falmouth Condo w/ Patio: Near Portland!
The perfect seaside retreat overlooking scenic Mackerel Cove on Bailey Island

The perfect seaside retreat overlooking scenic Mackerel Cove on Bailey Island

9.8 out of 10, Exceptional, (19)
"Highly recommend! We absolutely loved our stay at this condo! It was beautifully styled, with lots of charming touches that made it feel like a cozy home away from home. We were provided with plenty of towels, which was a nice bonus, and the deck and balcony offered stunning views at any time of day—truly a highlight of our stay. The location was ideal: there were multiple great places to eat nearby, offering a variety of dining options, but the area itself was peaceful and quiet, perfect for...
The perfect seaside retreat overlooking scenic Mackerel Cove on Bailey Island
Seabed @ The Offshore House

Seabed @ The Offshore House

10.0 out of 10, Exceptional, (11)
"Owner greeted us and was very friendly and helpful. Room was very nice clean and easily accessible. Wonderful time! Would highly recommend staying there. "
The price is AED 463
AED 977 total
includes taxes & fees
20 Feb - 21 Feb
Seabed @ The Offshore House
Historic Brick Corner Apartment, off street parking

Historic Brick Corner Apartment, off street parking

10.0 out of 10, Exceptional, (5)
"Visited my adult children and new baby granddaughter. Beautiful home, very convenient spot, and equipped with all the amenities needed- including a decorative Christmas tree. Thank you, Steve and Kristen!"
Historic Brick Corner Apartment, off street parking
Elegant Oceanfront Condo with Stunning Harbor Views & Spectacular Sunsets

Elegant Oceanfront Condo with Stunning Harbor Views & Spectacular Sunsets

2.0 star property
10.0 out of 10, Exceptional, (4)
Elegant Oceanfront Condo with Stunning Harbor Views & Spectacular Sunsets
Solitude @ The Offshore House

Solitude @ The Offshore House

9.6 out of 10, Exceptional, (4)
"I wasn't aware I would be charged an additional fee on my card the day I was supposed to check in. We stopped by their offices which were closed for the season and left a message with no reply. I also tried to the phone number provided on here and it was disconnected. Very disappointed my credit card information was released and there was a charge without my knowledge. Even for a hold the fee is way too much. I paid less than half of this for my one night stay. Still trying to reach them...
The price is AED 251
AED 722 total
includes taxes & fees
20 Feb - 21 Feb
Solitude @ The Offshore House
Eastbayside/Munjoy - Charming Downtown Escape
Living Room

Eastbayside/Munjoy - Charming Downtown Escape

10.0 out of 10, Exceptional, (21)
"We loved our stay! Great location, great property! They had anything you’d need for a short stay, even travel size soaps etc. we only had two small issues. 1. A group of young boys stayed above us and they were very loud. They were up until 2am/later making a lot of noise and kept a lot of the group up. 2. The floors were very dirty. The rest of the apartment seemed cleaned but the floors would turn your socks black. I even used their swiffer on them to try and make it better. I think both of...
Eastbayside/Munjoy - Charming Downtown Escape
Waterfront Condo: Walk to Downtown Boothbay Harbor
Boothbay Harbor | 2BR | 2BA | 1,300 Sq Ft | 2 Steps Required

Waterfront Condo: Walk to Downtown Boothbay Harbor

9.6 out of 10, Exceptional, (4)
"The condo unit was exactly as described and we found the property manager to be immediately responsive to our questions. The entire unit was beautifully decorated and the beds/furniture was quite comfortable. The kitchen was well appointed and there were plenty of towels/linens. The location is within walking distance of central Boothbay Harbor but in a secluded neighborhood that is very quiet. We enjoyed the “shoulder season” a few weeks before the tourists began to arrive, but found enough...
Waterfront Condo: Walk to Downtown Boothbay Harbor
Walking Distance To Shops, Restaurants And Footbridge
The apartment is above this store.

Walking Distance To Shops, Restaurants And Footbridge

10.0 out of 10, Exceptional, (39)
"My family of 5 had a lovely stay at this home in Boothbay Harbor. This home was roomy and had everything we needed. Location was great, walking to cute shops and restaurants. Only downside to location was noisy traffic at night and gas station lights outside. We had a great trip and would stay here again."
Walking Distance To Shops, Restaurants And Footbridge
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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Other property types in Bailey Island

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Taken from the point which faces east. There is a small rocky beach to the left.

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

10.0 out of 10, Exceptional, (212)
"We had a peaceful time at this home. It served as a home base for exploring. When my daughter left her most priced possession, her stuffed otter, the lovely hosts found it and shipped it back to us. We're so grateful for the thoughtfulness. "
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Dining Room Seating for ten, extra dining also available

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

9.8 out of 10, Exceptional, (68)
"Great house very comfortable and well appointed. Very roomy for our entire family. Nice to have en suite bathrooms with all the bedrooms. The host was very good with communication. Located on a busy road and the driveway is on a curve which made it a little challenging entering and exiting the property. "
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
THE GILLS GROUP has two additional cottages available for larger groups

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

10.0 out of 10, Exceptional, (99)
"This property is stunning, and the view is spectacular. If this were my house, I’d never leave! We had a fabulous time. "
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
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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