Search and Rent Bailey Island Condos
Bundle & SaveGet more, spend less whenever you see Bundle & Save deals
OneKeyCashEarn OneKeyCash on all your eligible bookings
Upfront pricingWe are not like the others - we include taxes and fees
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Bailey Island condo rentals
1. Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Spacious and Contemporary Condo in the Heart of Portland - Close to BeachEast Bayside
8.8 out of 10, Excellent, (38 reviews)
"Overall a pleasing stay."
Mallory D.
$433 nightly
The price is $471
Aug 25 - Aug 26
Total with taxes and fees
2. Elegant condo - walk to Portland's best restaurants & Old Port
Elegant condo - walk to Portland's best restaurants & Old PortEast Bayside
9.4 out of 10, Exceptional, (81 reviews)
"I had a wonderful week at this perfect place. Met my expectations and way more. So walkable all over Portland. I will be back. Thank you so very much."
Margaret H.
$471 nightly
The price is $513
Aug 23 - Aug 24
Total with taxes and fees
$298 nightly
The price is $324
Aug 30 - Aug 31
Total with taxes and fees
4. Walk to Old Port ♦ West End Condo ♦ Parking
Walk to Old Port ♦ West End Condo ♦ ParkingWest End
9.6 out of 10, Exceptional, (88 reviews)
"It was what we were looking for- in Portland, with a parking spot. Some nice restaurants nearby- walking distance! Note the bathroom is on the first floor, bedrooms are on second. Modest but had everything we needed! What we were disappointed in was we had no idea how many museums and local attractions in a city are closed till the end of April or May! "
Susan R.
$388 nightly
The price is $423
Sep 1 - Sep 2
Total with taxes and fees
5. 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
9.4 out of 10, Exceptional, (6 reviews)
"All was great...clean and convenient."
Krista P.
$450 nightly
The price is $491
Aug 17 - Aug 18
Total with taxes and fees
6. Renovated Exchange St. Loft w/Free Parking
Renovated Exchange St. Loft w/Free ParkingDowntown Portland
$421 nightly
The price is $458
Aug 12 - Aug 13
Total with taxes and fees
7. Eastbayside/Munjoy - Charming Downtown Escape
Eastbayside/Munjoy - Charming Downtown EscapeEast Bayside
9.8 out of 10, Exceptional, (37 reviews)
"Very nice location, clean and comfortable!"
Ryan R.
$824 nightly
The price is $898
Aug 14 - Aug 15
Total with taxes and fees
8. Waterfront Two Master Suite Penthouse with Rooftop
Waterfront Two Master Suite Penthouse with RooftopDowntown Portland
10.0 out of 10, Exceptional, (200 reviews)
"We’ve stayed here several times and have had a wonderful experience each time. The property was clean and comfortable and the host was very responsive. Highly recommended!"
Arthur B.
$1,479 nightly
The price is $1,612
Aug 17 - Aug 18
Total with taxes and 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.
Find vacation rentals that suit your style
Cabins
Cottages
Save an average of 15% on thousands of hotels when you're signed in
Top Bailey Island Hotel Reviews
Best Western Merry Manor Inn
10/10 Excellent
Find out more about Bailey Island
Bailey Island Condo Rentals information
Number of reviews | |
|---|---|
Accommodation | Condo Rentals |
Lowest Price | |
Highest Price |
Frequently asked questions
Explore a world of travel with Expedia
- Falmouth Hotels
- Rv Parks in Bailey Island
- Motels in Bailey Island
- Pet-Friendly Hotels in Portland
- Freeport Hotels
- Cottages in Casco Bay Islands
- Wells Hotels
- Brunswick Hotels
- Cottages in Orrs Island
- B&B in Harpswell
- Cape Elizabeth Hotels
- Chalets in Orrs Island
- Oceanfront Hotels in Old Orchard Beach
- B&B in Bailey Island
- Motels in Portland
- Bailey Island Hotels
- Downtown Portland Hotels
- Cottages in Bailey Island
- Cabin Rentals in Bustins Island
- Portland Hotels
- Cottages in Chebeague Island
- Old Orchard Beach Hotels
- Cottages in Bustins Island
- Cheap Hotels in Portland
- Scarborough Hotels
- Cabin Rentals in Chebeague Island
- Rv Parks in Casco Bay Islands
- Condo Rentals in Orrs Island
- Old Port Hotels
- Castles in Bailey Island
- Boothbay Harbor Hotels
- B&B in Portland
- Vacation Homes in Orrs Island
- Condo Rentals in Casco Bay Islands
- Vacation Homes in Great Island
- Hotels with Free Airport Shuttle in Portland
- Condo Rentals in Chebeague Island
- Ogunquit Hotels
- Bath Hotels
- Hotels near Portland Intl. Jetport
- Cabin Rentals in Portland
- South Portland Hotels
- Villas in Cliff Island
- Cabin Rentals in Bailey Island
- B&B in Casco Bay Islands
- Oceanfront Hotels in Portland
- Cabin Rentals in Harpswell
- B&B in Freeport
- Inns in Bustins Island
- B&B in Chebeague Island
- Cabin Rentals in Casco Bay Islands
- Yarmouth Hotels
- Flights from Chicago (ORD) to Portland (PWM)
- Flights from Seattle (SEA) to Portland (PWM)
- Flights from Brunswick Executive
- Flights from Portland (PDX) to Portland (PWM)
- Flights from Washington (DCA) to Portland (PWM)
- Flights from Phoenix (PHX) to Portland (PWM)
- Flights from Cincinnati (CVG) to Portland (PWM)
- Flights from Columbus (CMH) to Portland (PWM)
- Flights from Boston (BOS) to Portland (PWM)
- Flights from Jacksonville (JAX) to Portland (PWM)
- Flights from Minneapolis (MSP) to Portland (PWM)
- Flights from Salt Lake City (SLC) to Portland (PWM)
- Flights from Portland Intl. Jetport
- Flights from Tampa (TPA) to Portland (PWM)
- Flights from Baltimore (BWI) to Portland (PWM)
- Flights from Newark Liberty Intl. Airport (EWR) to Portland (PWM)
- Flights to Portland
- Flights from Philadelphia (PHL) to Portland (PWM)
- Flights from Tucson (TUS) to Portland (PWM)
- Flights from Nashville (BNA) to Portland (PWM)
- Flights from Raleigh (RDU) to Portland (PWM)
- Flights from Orlando (MCO) to Portland (PWM)
- Flights from Austin (AUS) to Portland (PWM)
- Flights from Houston (IAH) to Portland (PWM)
- Flights from Los Angeles (LAX) to Portland (PWM)
- Flights from Charlotte (CLT) to Portland (PWM)
- Flights from Denver (DEN) to Portland (PWM)
- Flights from Pittsburgh (PIT) to Portland (PWM)
- Flights from Dallas (DFW) to Portland (PWM)
- Flights from Atlanta (ATL) to Portland (PWM)
- Flights from New York (LGA) to Portland (PWM)
- Flights to Bailey Island
- Flights from Detroit (DTW) to Portland (PWM)
- Flights from New York (NYC) to Portland (PWM)
- Flights from New York (JFK) to Portland (PWM)