A rocky shoreline with a boat, a house, and a forest in the background.

Search and Rent Bailey Island Condos

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Bailey Island condo rentals

A modern kitchen with a dining area, featuring a round table, chairs, and a hanging light fixture.

1. Elegant condo - walk to Portland's best restaurants & Old Port

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.4 out of 10, Exceptional, (83 reviews)
"It was nice if you like being right in town. There is no view and it's a bit noisy."
United States
Nancy S.
$471 nightly
The price is $513
Aug 26 - Aug 27
Total with taxes and fees
Elegant condo - walk to Portland's best restaurants & Old Port
A modern house with a wooden exterior, a small garden, and a visible window.

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

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (39 reviews)
"Overall a pleasing stay."
United States
Mallory D.
$434 nightly
The price is $473
Aug 31 - Sep 1
Total with taxes and fees
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
A kitchen with wooden cabinets, a stainless steel dishwasher, a coffee maker, and a potted plant.

3. Cozy Two Bedroom on Munjoy Hill

Cozy Two Bedroom on Munjoy Hill
Munjoy Hill
$299 nightly
The price is $325
Sep 1 - Sep 2
Total with taxes and fees
Cozy Two Bedroom on Munjoy Hill
A harbor with boats docked, a pier, and buildings in the background.

4. Casco Bay Vista

Casco Bay Vista
East Deering
10.0 out of 10, Exceptional, (4 reviews)
"Our stay was very comfortable; beautiful view from our deck. Mat was great with communication and the atmosphere was a perfect fit for us. We highly recommend for your stay in Portland."
United States
Susan R.
$406 nightly
The price is $443
Sep 14 - Sep 15
Total with taxes and fees
Casco Bay Vista
A living room with a television, a wooden chest, a glass coffee table, a sofa, and a chair.

5. Walk to Old Port ♦ West End Condo ♦ Parking

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.6 out of 10, Exceptional, (89 reviews)
"Host was very responsive, and helpful. Location is amazing for walking the city."
United States
Chris P.
$347 nightly
The price is $378
Sep 2 - Sep 3
Total with taxes and fees
Walk to Old Port ♦ West End Condo ♦ Parking
A beach with a wooden chair and a small building in the background.

6. Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (70 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
$533 nightly
The price is $580
Aug 26 - Aug 27
Total with taxes and fees
Arlie`s Digs! - One Block To Willard Beach!
A modern living room with a wooden dining table, a sofa, and a coffee table.

7. Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!

Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!
West End
9.6 out of 10, Exceptional, (8 reviews)
"Great place to stay - lovely building and really nicely kept, and it’s a perfect location if you want to walk down to Old Port, about 20 minutes. Would love to come back!"
United States
Cate
$431 nightly
The price is $470
Sep 9 - Sep 10
Total with taxes and fees
Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!
A modern living room with a large sectional sofa, a fireplace, and large windows offering a city view.

8. Waterfront Two Master Suite Penthouse with Rooftop

Waterfront Two Master Suite Penthouse with Rooftop
Downtown Portland
10.0 out of 10, Exceptional, (200 reviews)
"Great property. It was clean, comfortable, and the location was amazing"
United States
Jaylene G.
$1,477 nightly
The price is $1,609
Sep 7 - Sep 8
Total with taxes and fees
Waterfront Two Master Suite Penthouse with Rooftop
A circular pool with lounge chairs and umbrellas, surrounded by a rocky shoreline and a pier extending into the water.

9. Sunset A | Oceanfront King + Gas Fireplace

Sunset A | Oceanfront King + Gas Fireplace
Boothbay Harbor
$964 nightly
The price is $1,051
Sep 20 - Sep 21
Total with taxes and fees
Sunset A | Oceanfront King + Gas Fireplace
A circular pool with lounge chairs and umbrellas, surrounded by a rocky shoreline and a pier extending into the water.

10. Oriole Suite | Stone Fireplace + Woodland

Oriole Suite | Stone Fireplace + Woodland
Boothbay Harbor
$720 nightly
The price is $785
Aug 31 - Sep 1
Total with taxes and fees
Oriole Suite | Stone Fireplace + Woodland
A circular pool with lounge chairs and umbrellas, surrounded by a rocky shoreline and a pier extending into the water.

11. Little Spruce Cottage | Wood Stove + Porch

Little Spruce Cottage | Wood Stove + Porch
Boothbay Harbor
$729 nightly
The price is $794
Aug 31 - Sep 1
Total with taxes and fees
Little Spruce Cottage | Wood Stove + Porch
A circular pool with lounge chairs and umbrellas, surrounded by a rocky shoreline and a pier extending into the water.

12. Cardinal Cottage | 3BR + 3 Porches + Fireplace

Cardinal Cottage | 3BR + 3 Porches + Fireplace
Boothbay Harbor
$1,104 nightly
The price is $1,203
Sep 23 - Sep 24
Total with taxes and fees
Cardinal Cottage | 3BR + 3 Porches + Fireplace
A circular pool with lounge chairs and umbrellas, surrounded by a rocky shoreline and a pier extending into the water.

13. Tanager Cottage | 3BR + 2 Porches + Fireplace

Tanager Cottage | 3BR + 2 Porches + Fireplace
Boothbay Harbor
$1,084 nightly
The price is $1,181
Sep 20 - Sep 21
Total with taxes and fees
Tanager Cottage | 3BR + 2 Porches + Fireplace
A circular pool with lounge chairs and umbrellas, surrounded by a rocky shoreline and a pier extending into the water.

14. Osprey Cottage | Oceanfront + Full Kitchen

Osprey Cottage | Oceanfront + Full Kitchen
Boothbay Harbor
$1,342 nightly
The price is $1,463
Sep 20 - Sep 21
Total with taxes and fees
Osprey Cottage | Oceanfront + Full Kitchen
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 Bailey Island Hotel Reviews

Find out more about Bailey Island

Bailey Island Condo Rentals information

Number of reviews
493
Accommodation
49 Condo Rentals
Lowest Price
$325
Highest Price
$1,609

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