Castle In Hawaii - Vacation Rentals in Portland

Waterfront, Luxury, Spacious home in Freeport! From US $2,164
         

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10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Huge Historic Downtown Townhome From US $390
         

9.8 (8 Reviews)
Villa
  • Air Conditioner
  • Parking
  • TV
Beautiful and Spacious Ocean Front Spanish Villa Mansion From US $856
         

Luxury Places to Stay in Portland

Over 4262+ Luxury Places to Stay in or Near Portland
Entire Privately Owned Island Estate From US $6,800
         

House Island Luxury Residence - BellMoor From US $4,467
         

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New
House
  • Air Conditioner
  • View
  • Ocean View
Ocean front estate. 15 min to Portland. From US $3,627
         

9.6 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
House Island Private Residence - WatchHouse From US $3,600
         

Top-Rated Vacation Rentals with a Pool in Portland

Over 617+ Top-Rated Vacation Rentals with a Pool in or Near Portland
Maine Dream Cottage From US $273
         

10.0 (114 Reviews)
Cottage
  • Parking
  • Pool
  • TV
Pristine 2 bdrm Condo near Goose Rocks Beach From US $285
         

10.0 (49 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Peaceful Waterfront Apt w/Deck, 22 Mi to Portland From US $280
         

10.0 (48 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • TV
Walk the Beautiful Beaches of Chebeague Island From US $448
         

Exceptional Oceanfront House With Private Beach & Backyard From US $1,886
         

10.0 (31 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Location! Location! Location! Oh Those River Views! From US $555
         

Pet-Friendly Vacation Rentals in Portland

Over 1197+ Pet-Friendly Vacation Rentals in or Near Portland
Thisgood Cove From US $1,422
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Luna Lodge - close to old Orchard beach From US $886
         

New
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Beach Odyssey From US $200
         

9.6 (36 Reviews)
Condo
  • Parking
  • Pet Friendly
  • TV
Falmouth Waterfront Carriage House Apt From US $268
         

9.8 (51 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Kennebunkport Summer Rental walk to Dock Square! PET Friendly! From US $682
         

Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers From US $700
         

10.0 (49 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Portland on PetFriendly.io

Large Vacation Homes & Villas in Portland

Over 791+ Large Vacation Homes & Villas in or Near Portland
Arbor Lane Delight From US $127
         

New
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Spectacular Oceanfront Beach House on Gooch's Beach From US $664
         

PORTLAND PENINSULA-SPACIOUS WALKABLE EAST END SPOT From US $1,859
         

Wheelchair Accessible Vacation Homes in Portland

Over 389+ Wheelchair Accessible Vacation Homes in or Near Portland
Panther Run River Retreat From US $417
         

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10.0 (2 Reviews)
House
  • Pet Friendly
  • Wheelchair Accessible
  • Balcony/Terrace
84 Main From US $184
         

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9.8 (56 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Penthouse Two Master Waterfront Suite with Rooftop From US $726
         

10.0 (259 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Old Port Penthouse Suite - Amazing Harbor Views From US $567
         

10.0 (246 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Downtown Penthouse Suite - Stunning Harbor Views From US $558
         

10.0 (226 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Modern, Luxury Lakefront Home on Crescent Lake, Maine From US $853
         

10.0 (110 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious Portland Home: Walk Downtown! From US $812
         

10.0 (27 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Portland Vacation Rentals and Airbnb Places to Stay Under $200

Over 657+ Portland Vacation Rentals and Airbnb Places to Stay Under $200
Sea Shell From US $198
         

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10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • View
The Inn at English Meadows From US $191
         

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10.0 (26 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Perfect Location & Best Prices! 5th house from the Beach From US $196
         

West End 2nd Floor Apartment 762 Congress Street From US $196
         

9.0 (39 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Goose Rocks Retreat - relax, refresh, recharge From US $186
         

10.0 (66 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Historic Home in the West End. Private Parking. From US $192
         

10.0 (51 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Portland

Over 2271+ Instantly Bookable Vacation Homes in or Near Portland
Pine Point Beach - Private, quaint, charming space From US $322
         

10.0 (17 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Fall In Love With Portland! From US $683
         

9.6 (134 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Downtown Kennebunk Home From US $267
         

10.0 (73 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
1/2 Mi to Beach: Lovely Guesthouse in Kennebunk! From US $298
         

About Portland Vacation Rentals

With more than 46 Portland vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Castleinhawaii and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Portland.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Castleinhawaii Portland, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Portland. Places to stay near Portland are 1106.14 ft² on average, with prices averaging $765 a night.

Castleinhawaii makes it easy and safe to find and compare vacation rentals in Portland with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Portland

Type Count
Others 15
Resorts 12
Villas 12
Vacation Homes 4
Hotels with Suites 3

Use these Quick Filters to Find a Vacation Rental in Portland

Pro Tip: Castleinhawaii makes it easy to compare the best listings on Castleinhawaii homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Castleinhawaii homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Portland.

Weather in Portland

View the weather forecast for Portland before booking your Portland Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Portland Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Portland?
How many vacation rentals are available in Portland?

Currently, the total number of properties listed in 2026 is over 46 in the Portland area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Portland.