Browse Bailey Island Condos for Rent

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Condo Rentals in Bailey Island

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

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

Portland ME
The price is AU$751 per night from 30 May to 31 May
AU$751
30 May - 31 May
includes taxes & fees
With a stay at this condo, you'll be centrally located in Portland, within a 5-minute drive of Thompson's Point and Maine Jewish Museum.
Opens in a new windowElegant condo - walk to Portland's best restaurants & Old Port
Walk to Old Port ♦ West End Condo ♦ Parking

Walk to Old Port ♦ West End Condo ♦ Parking

Portland ME
The price is AU$535 per night from 27 May to 28 May
AU$535
27 May - 28 May
includes taxes & fees
With a stay at this condo in Portland (West End), you'll be within a 5-minute drive of Thompson's Point and Casco Bay.
Opens in a new windowWalk to Old Port ♦ West End Condo ♦ Parking
Casco Bay Vista

Casco Bay Vista

Portland ME
With a stay at this condo in Portland (East Deering), you'll be within a 10-minute drive of Thompson's Point and University of Southern Maine.
Opens in a new windowCasco Bay Vista
Save an average of 15% on thousands of hotels when you're signed in
Eastbayside/Munjoy - Charming Downtown Escape

Eastbayside/Munjoy - Charming Downtown Escape

Portland ME
With a stay at this condo, you'll be centrally located in Portland, within a 5-minute drive of Thompson's Point and Maine Jewish Museum.
Opens in a new windowEastbayside/Munjoy - Charming Downtown Escape
Centrally located off Back Cove, 2nd floor 4 bedroom, 2 Bath condo w/ deck

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

Portland ME
With a stay at this condo in Portland (Back Cove), you'll be within a 5-minute drive of Thompson's Point and Southworth Planetarium.
Opens in a new windowCentrally located off Back Cove, 2nd floor 4 bedroom, 2 Bath condo w/ deck
Gorgeously renovated, 2-condo property in the West End - walk everywhere

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

Portland ME
With a stay at this condo, you'll be centrally located in Portland, within a 5-minute drive of Thompson's Point and Casco Bay.
Opens in a new windowGorgeously renovated, 2-condo property in the West End - walk everywhere
Waterfront Two Master Suite Penthouse with Rooftop

Waterfront Two Master Suite Penthouse with Rooftop

Portland ME
With a stay at this condo in Portland (Downtown Portland), you'll be within a 10-minute drive of Thompson's Point and Fore Street Gallery.
Opens in a new windowWaterfront Two Master Suite Penthouse with Rooftop
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

Portland ME
With a stay at this condo, you'll be centrally located in Portland, within a 5-minute drive of Thompson's Point and Casco Bay.
Opens in a new windowHistorical & dog-friendly West End condo with parking - walk to all of Portland
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

Portland ME
With a stay at this condo, you'll be centrally located in Portland, within a 5-minute drive of Thompson's Point and Neal S. Dow House.
Opens in a new windowRenovated condo with prime West End location, 2 en suite bathrooms, & HGTV style
Don't see what you're looking for?
See all available properties in Bailey Island
View all properties
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.

Bailey Island Condo Rentals essential information

Accommodation
53 Condo Rentals
Lowest Price
AU$191
Highest Price
AU$751
Popular accommodation
Elegant condo - walk to Portland's best restaurants & Old Port, Walk to Old Port ♦ West End Condo ♦ Parking, Casco Bay Vista, Eastbayside/Munjoy - Charming Downtown Escape, Centrally located off Back Cove, 2nd floor 4 bedroom, 2 Bath condo w/ deck, Gorgeously renovated, 2-condo property in the West End - walk everywhere, Waterfront Two Master Suite Penthouse with Rooftop, Historical & dog-friendly West End condo with parking - walk to all of Portland, Renovated condo with prime West End location, 2 en suite bathrooms, & HGTV style

Top trending hotels in Bailey Island

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$340 per night from 25 May to 26 May
AU$340
25 May - 26 May
includes taxes & fees
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, within a 5-minute drive of Thompson's Point and Fore Street Gallery.
Opens in a new windowPortland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$249 per night from 26 May to 27 May
AU$249
26 May - 27 May
includes taxes & fees
With a stay at Portland Regency Hotel & Spa, you'll be centrally located in Portland, within a 10-minute drive of Thompson's Point and Fore Street Gallery.
Opens in a new windowPortland Regency Hotel & Spa
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundable
The price is AU$296 per night from 25 May to 26 May
AU$296
25 May - 26 May
includes taxes & fees
With a stay at Cambria Hotel Portland Downtown-Old Port in Portland (Downtown Portland), you'll be within a 10-minute drive of Thompson's Point and Maine Jewish ...
Opens in a new windowCambria Hotel Portland Downtown-Old Port
Save an average of 15% on thousands of hotels when you're signed in
HomeAwhile

HomeAwhile

2 out of 5
205 Southborough Drive Scarborough ME
Fully refundableReserve now, pay when you stay
The price is AU$191 per night from 26 May to 27 May
AU$191
26 May - 27 May
includes taxes & fees
With a stay at HomeAwhile in Scarborough, you'll be near the airport, within a 10-minute drive of Thompson's Point and Maine Mall.
Opens in a new windowHomeAwhile
Don't see what you're looking for?
See all available properties in Bailey Island
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.