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

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Bailey Island condo rentals

A beach with a wooden chair and a small building in the background.

1. 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.
The price is NZ$865
includes taxes & fees
27 Oct - 28 Oct
Arlie`s Digs! - One Block To Willard Beach!
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, (40 reviews)
"Overall a pleasing stay."
United States
Mallory D.
The price is NZ$832
includes taxes & fees
4 Oct - 5 Oct
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
A modern kitchen with a dining area, featuring a round table, chairs, and a hanging light fixture.

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

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.2 out of 10, Wonderful, (85 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.
Elegant condo - walk to Portland's best restaurants & Old Port
A living room with a television, a wooden chest, a glass coffee table, a sofa, and a chair.

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

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.6 out of 10, Exceptional, (91 reviews)
"Was great for our few days in Portland! Having a designated parking space was great and the location was convenient for everything we wanted to do."
United States
Britney G.
The price is NZ$732
includes taxes & fees
25 Oct - 26 Oct
Walk to Old Port ♦ West End Condo ♦ Parking
A circular pool with lounge chairs and umbrellas, surrounded by a rocky shoreline and a pier extending into the water.

5. Little Spruce Cottage | Wood Stove + Porch

Little Spruce Cottage | Wood Stove + Porch
Boothbay Harbor
The price is NZ$1,081
includes taxes & fees
28 Sept - 29 Sept
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.

6. Oriole Suite | Stone Fireplace + Woodland

Oriole Suite | Stone Fireplace + Woodland
Boothbay Harbor
The price is NZ$1,068
includes taxes & fees
28 Sept - 29 Sept
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.

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

Cardinal Cottage | 3BR + 3 Porches + Fireplace
Boothbay Harbor
The price is NZ$1,698
includes taxes & fees
29 Sept - 30 Sept
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.

8. Sunset A | Oceanfront King + Gas Fireplace

Sunset A | Oceanfront King + Gas Fireplace
Boothbay Harbor
The price is NZ$1,436
includes taxes & fees
28 Sept - 29 Sept
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.

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

Tanager Cottage | 3BR + 2 Porches + Fireplace
Boothbay Harbor
The price is NZ$1,678
includes taxes & fees
28 Sept - 29 Sept
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.

10. Osprey Cottage | Oceanfront + Full Kitchen

Osprey Cottage | Oceanfront + Full Kitchen
Boothbay Harbor
The price is NZ$2,146
includes taxes & fees
1 Oct - 2 Oct
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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"Comfortable beds, convenient location, free coffee and water available. Very clean"
Teri 3-night trip
Posted 3 hours ago
Portland Regency Hotel & Spa

Find out more about Bailey Island

Bailey Island Condo Rentals information

Number of reviews
286
Accommodation
49 Condo Rentals
Lowest Price
NZ$732
Highest Price
NZ$2,146