Holiday Rentals in Portland
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5 km
335 rentals in Portland.
Portland Apartment With AMAZING View of Harbor!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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“Henry” Penthouse Suite: Amazing Views, Waterfront, in the heart of the Old Port
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Glorious getaway on Portland's Eastern Promenade.
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Cozy Portland Apartment - central to everything!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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“Cornelia” Waterfront Penthouse Suite, Prime Old Port Location, Amazing Views!
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Morrill Mansion Inn | 8 | Self Check In | Parking
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Morrill Mansion | 2 | Self Check In | Parking
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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“Percival” Penthouse Suite: Breathtaking Views, Cupola, Walk to Restaurants
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Inn at Parkspring 1 | Self Check In | Parking
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Walk to Old Port ♦ West End Condo ♦ Parking
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Sunny Modern Oasis in Portland’s Trendy East End
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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City Amenities, Casco Bay Sunrises and Natural Beauty
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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5 Star Back Cove Hide-Away1 bedroom Back Cove apartment with water views!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Remodeled Historic Apartment 5 mins from Downtown w/Life Changing Shower!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Adorable Portland getaway on the Eastern Promenade
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Luxury Old Port Penthouse Suite w/Stunning Harbor Views. Parking. Safe + Secure.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Historic West End Neighborhood
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Morrill Mansion Inn | 6 | Self Check In | Parking
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy, Elegant and Bright 2 bed in the East End
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming 2-bedroom steps from the Eastern Promenade
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Chic One Bedroom Apartment In Portland's Arts District
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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2 Bedroom Apartment on Top Floor in Portland's West End
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Skolfield Inn | Parking | Self-check-in | Garden 2
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming Peaks Island Cottage
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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The perfect refinement of vintage seduction
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Inn at Parkspring 4 | Self Check In | Parking
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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NEW LISTING ☼ Unique Oceanfront Home. Separate boat rental available.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Brand New 2 Bedroom Apartment in Heart of West End
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Elegant condo - walk to Portland's best restaurants & Old Port
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Rent a room in the gorgeous Holt House
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Classic Island Cottage
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Modern loft - Downtown, steps from all the action!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Bright and Fresh Back Cove4 Bedroom, Sleeps 8, Perfect for Reunions and Family
Condo/Apartment
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Sleek & newly-renovated third-floor condo w/ amazing water views - walk to bay
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Incredible Location!! Heart of the Old Port/Spacious Townhouse Condo!
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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As seen on
Morrill Mansion | 3 | Self Check In | Parking
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Charming, Secluded, Island Getaway!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Ocean view Victorian
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Rent a room in the gorgeous Holt House
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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As seen on
Morrill Mansion Inn | 4 | Self Check In | Parking
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Historic Condo w/ Casco Bay Views, Fireplace, WiFi & 2 Bikes - Walk Everywhere!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Downtown Portand-762 Congress St. Apartment
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Back Cove Charmer Close to Everything
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Vintage Maine & Modern Convenience in Portlands Exclusive East End
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Brand New 1 Bedroom Apartment in Portland
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Enjoy Portland With Family or Friends
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Showing results 1-50 of 335
Frequently Asked Questions about Portland
- Yes, here are some popular holiday rentals in Portland that have a pool:
- Portland Apartment With AMAZING View of Harbor!
- “Henry” Penthouse Suite: Amazing Views, Waterfront, in the heart of the Old Port
- Glorious getaway on Portland's Eastern Promenade.
- Yes, here are some popular holiday rentals in Portland that have internet access:
- Portland Apartment With AMAZING View of Harbor!
- “Henry” Penthouse Suite: Amazing Views, Waterfront, in the heart of the Old Port
- Glorious getaway on Portland's Eastern Promenade.
- Some of the most popular kid friendly rentals in Portland are:
- Portland Apartment With AMAZING View of Harbor!
- “Henry” Penthouse Suite: Amazing Views, Waterfront, in the heart of the Old Port
- Glorious getaway on Portland's Eastern Promenade.