Vacation Rentals in Monument Square, ME: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals
  3.  USA

  4.  Maine
  5.  Portland
  6.  Monument Square

Refine your search

Price per night

Amenity Filter

Rating

410 Best Vacation Rentals in Monument Square (Starting from $88)

The Downtown Downeast Room
The Downtown Downeast Room
Apartment
Portland, ME, USA
0.3k from Monument Square center

Security/Safety, Internet, Air Conditioner

1 Bedroom2 Guests
5.5

Review score

4 reviews

$163
Average price / night
Check Availability
Walkable near downtown 1 Bedroom
Walkable near downtown 1 Bedroom
Apartment
Portland, ME, 04101, United States
0.3k from Monument Square center

AC, Heater, Internet, Living Area, Microwave, No Smoking, TV

1 Bedroom2 Guests
5.2

Review score

5 reviews

$145
Average price / night
Check Availability
2-room downtown home
2-room downtown home
Apartment
Portland, ME, 04101, United States
0.3k from Monument Square center

Internet, Kitchen, No Smoking

2 Bedrooms6 Guests
New to Booking
$496
Average price / night
Check Availability
Trendy Remodeled 2BR Loft in Portlands Old Port
Trendy Remodeled 2BR Loft in Portlands Old Port
Apartment
Portland, ME, USA
0.4k from Monument Square center

Apartments, Cheap, Accommodations, Lodgings, Vacation rentals, Places to stay, Self-catering

2 Bedrooms4 Guests
7.9

Good

10 reviews

$346
Average price / night
Check Availability
Private Rooftop Deck!/Artsy Apt/Old Port Arts Dist
Private Rooftop Deck!/Artsy Apt/Old Port Arts Dist
Apartment
Portland, ME, 04101, United States
0.3k from Monument Square center

AC, Balcony, Dryer, Extra Bed, Heater, Internet, Kitchen, Laundry, No Smoking

1 Bedroom4 Guests
10.0

Exceptional

54 reviews

$498
Average price / night
Check Availability
Simple & Convenient Downtown Living
Simple & Convenient Downtown Living
Apartment
Portland, ME, USA
0.4k from Monument Square center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

1 Bedroom2 Guests
8.5

Very Good

6 reviews

$130
Average price / night
Check Availability
Charming Brownstone Downtown Free St|Perfect Getaway for 2
Charming Brownstone Downtown Free St|Perfect Getaway for 2
Apartment
Portland, ME, 04101, United States
0.4k from Monument Square center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, TV

1 Bedroom2 Guests
10.0

Exceptional

35 reviews

$359
Average price / night
Check Availability
3rd Floor Furnished Apt Downtown Portland
3rd Floor Furnished Apt Downtown Portland
Apartment
Portland, ME, USA
0.4k from Monument Square center

Apartments, Accommodations, Parking, Lodgings, Places to stay, Self-catering

1 Bedroom2 Guests
6.7

Good

3 reviews

$88
Average price / night
Check Availability
Studio Apartment near downtown Walkable!
Studio Apartment near downtown Walkable!
Apartment
Portland, ME, 04101, United States
0.4k from Monument Square center

AC, Free Parking, Heater, Internet, Microwave, No Smoking

1 Bedroom2 Guests
8.4

Very Good

7 reviews

$150
Average price / night
Check Availability
Luxury Penthouse in Downtown Portland
Luxury Penthouse in Downtown Portland
Apartment
Portland, ME, USA
0.4k from Monument Square center

Apartments, Luxury, Accommodations, Parking, Lodgings, Places to stay

1 Bedroom5 Guests
New to Booking
$2011
Average price / night
Check Availability
Luxurious Penthouse with Modern Design in Downtown
Luxurious Penthouse with Modern Design in Downtown
House
Portland, ME, 04101, United States
0.4k from Monument Square center

AC, Dryer, Elevator, Heater, Internet, Kitchen, Microwave, No Smoking, TV

2 Bedrooms5 Guests
New to Booking
$394
Average price / night
Check Availability
Luxury Penthouse Steps from Downtown Portland
Luxury Penthouse Steps from Downtown Portland
House
Portland, ME, USA
0.4k from Monument Square center

Luxury, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom5 Guests
New to Booking
$730
Average price / night
Check Availability
Incredible Location! Heart of Old Port/Spacious Apartment
Incredible Location! Heart of Old Port/Spacious Apartment
Apartment
Portland, ME, 04101, United States
0.4k from Monument Square center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms8 Guests
10.0

Exceptional

40 reviews

$1149
Average price / night
Check Availability
1 Bedroom Downtown Portland
1 Bedroom Downtown Portland
Apartment
Portland, ME, USA
0.4k from Monument Square center

Pet Friendly, Security/Safety, Air Conditioner, Internet, Child Friendly

1 Bedroom3 Guests
5.0

Review score

1 reviews

$258
Average price / night
Check Availability
Superb Location!! Heart of Old Port/Spacious Condo
Superb Location!! Heart of Old Port/Spacious Condo
Apartment
Portland, ME, 04101, United States
0.4k from Monument Square center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, TV

3 Bedrooms9 Guests
9.8

Exceptional

26 reviews

$1143
Average price / night
Check Availability
Top of the Old Port/East Bayside1 BR Free Parking
Top of the Old Port/East Bayside1 BR Free Parking
Apartment
Monument Square, Portland, Maine, USA
0.4k from Monument Square center

Laundry, Smoking, Parking, Air Conditioner, Pet Friendly, Breakfast, Internet

1 Bedroom3 Guests
New to Booking
$185
Average price / night
Check Availability
Free St Apt D · New Luxury Apt/Arts Dist/Sleeps8
Free St Apt D · New Luxury Apt/Arts Dist/Sleeps8
Apartment
Portland, ME, 04101, United States
0.4k from Monument Square center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms8 Guests
10.0

Exceptional

19 reviews

$1282
Average price / night
Check Availability
The Weldon Hotel
The Weldon Hotel
Apartment
Portland, ME, USA
0.5k from Monument Square center

Apartments, Cheap, Accommodations, Parking, Serviced apartments, Pet-friendly, Lodgings, Places to stay, Self-catering

13 Bedrooms16 Guests
9.7

Exceptional

20 reviews

$535
Average price / night
Check Availability
Stylish Old Port 2BR Loft, Walk to Everything
Stylish Old Port 2BR Loft, Walk to Everything
Apartment
Portland, ME, 04101, United States
0.4k from Monument Square center

AC, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
9.8

Exceptional

22 reviews

$491
Average price / night
Check Availability
The Docent's Collection
The Docent's Collection
Apartment
Portland, ME, USA
0.5k from Monument Square center

Apartments, Accommodations, Parking, Serviced apartments, Lodgings, Vacation rentals, Places to stay, Self-catering, Accessible hotels

11 Bedrooms27 Guests
9.0

Fabulous

92 reviews

$690
Average price / night
Check Availability
Chef's Dream Kitchen in Downtown 2 Bedroom Loft
Chef's Dream Kitchen in Downtown 2 Bedroom Loft
Apartment
Portland, ME, 04101, United States
0.5k from Monument Square center

AC, Crib, Elevator, Free Parking, Heater, Hot Tub, Internet, Kitchen, Living Area

2 Bedrooms5 Guests
New to Booking
$784
Average price / night
Check Availability
Cumberland Casa - A
Cumberland Casa - A
Apartment
Portland, ME, USA
0.6k from Monument Square center

Apartments, Cheap, Accommodations, Lodgings, Vacation rentals, Places to stay

2 Bedrooms6 Guests
8.2

Very Good

7 reviews

$398
Average price / night
Check Availability
Cumberland Casa - B
Cumberland Casa - B
Apartment
Portland, ME, USA
0.6k from Monument Square center

Apartments, Accommodations, Lodgings, Vacation rentals, Places to stay

1 Bedroom2 Guests
6.6

Good

8 reviews

$263
Average price / night
Check Availability
Evalina Hotel
Evalina Hotel
Apartment
215 Commercial St, Portland, ME, 04101, United States
0.5k from Monument Square center

AC, Elevator, Internet, Kitchen, Living Area, Microwave, Parking Available, Soundproof Room, Washer And Dryer

New to Booking
$502
Average price / night
Check Availability
Luxury Condo Downtown Portland Old Port
Luxury Condo Downtown Portland Old Port
Apartment
Portland, ME, 04101, United States
0.5k from Monument Square center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Outdoor Space

9.4

Superb

19 reviews

$367
Average price / night
Check Availability
Historic Home in the West End. Private Parking.
Historic Home in the West End. Private Parking.
Apartment
Portland, ME, 04101, United States
0.6k from Monument Square center

AC, Crib, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

1 Bedroom3 Guests
10.0

Exceptional

54 reviews

$288
Average price / night
Check Availability
Charming West End Hideaway. Private Parking
Charming West End Hideaway. Private Parking
Apartment
Portland, ME, 04101, United States
0.6k from Monument Square center

AC, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Patio, TV

1 Bedroom2 Guests
10.0

Exceptional

49 reviews

$241
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Monument Square.

Where to stay in Monument Square? Best neighborhoods & areas

Monument Square Vacation Rentals on the Map

Frequently Asked Questions

You can explore 410 verified vacation rentals in Monument Square. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Monument Square vary depending on the season, property size, and location. Rates typically start from around $88 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Monument Square include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Monument Square welcome pets. Currently, 35 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Monument Square often include amenities such as Internet, Fireplace/Heating, and Kitchen. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.