Sanibel Island Villas - Vacation Rentals in Stroudwater

The Chadwick Bed and Breakfast From US $349
         

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9.2 (29 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Blind Tiger Portland - Danforth Street. From US $240
         

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9.6 (179 Reviews)
Bed & Breakfast
  • Air Conditioner
  • TV
  • Accessibility
West End 2nd Floor Apartment 762 Congress Street From US $234
         

9.0 (39 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Chic One Bedroom Apartment In Portland's Arts District From US $286
         

10.0 (226 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
5 Star Back Cove Apartment with water view! From US $319
         

10.0 (154 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Stroudwater

Over 463+ Luxury Places to Stay in or Near Stroudwater
Stunning Entire Three Units Apts (USM AREA) From US $2,135
         

10.0 (30 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Entire Home | Sleeps 16 | w/Roof Deck | 5 mins to Downtown From US $2,011
         

7 Bed Historic Home for Group Stays From US $1,698
         

10.0 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Stroudwater

Over 87+ Top-Rated Vacation Rentals with a Pool in or Near Stroudwater
Back yard paradise From US $506
         

9.8 (22 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Embassy Suites by Hilton Portland Maine From US $125
         

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9.4 (1146 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Homewood Suites by Hilton Portland From US $142
         

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9.4 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Homewood Suites by Hilton Portland From US $285
         

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9.1 (119 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Best Western Merry Manor Inn From US $105
         

9.0 (1014 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Courtyard by Marriott Portland Airport From US $96
         

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9.0 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
TownePlace Suites by Marriott Portland Airport ME From US $102
         

Pet-Friendly Vacation Rentals in Stroudwater

Over 162+ Pet-Friendly Vacation Rentals in or Near Stroudwater
2 Bedroom Apartment on Top Floor in Portland's West End From US $457
         

10.0 (74 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
The Heart of the West End #3 From US $810
         

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9.4 (5 Reviews)
Apartment
  • Pet Friendly
  • Security/Safety
  • Sports/Activities
HomeAwhile From US $125
         

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9.4 (22 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Brand New 1 Bedroom Apartment in Portland From US $391
         

10.0 (45 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
New England Charm, Portland - Parking included From US $472
         

10.0 (18 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy 3BR | Pet Friendly | Near Portland | Parking From US $469
         

10.0 (12 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Romantic apt:West End +parking From US $415
         

10.0 (9 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Stroudwater

Over 46+ Large Vacation Homes & Villas in or Near Stroudwater
Two Beautiful apartment From US $949
         

10.0 (25 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
West End Inn From US $459
         

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9.3 (117 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Breakfast
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11 From US $714
         

Huge Historic Downtown Townhome From US $593
         

9.8 (8 Reviews)
Villa
  • Air Conditioner
  • Parking
  • TV
Luxe Coastal Retreat with Hot Tub & Spring Fires From US $967
         

9.2 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious Portland Home + Parking From US $652
         

9.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Modern West End 2 Bedroom Apartment From US $567
         

7.8 (28 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV

Wheelchair Accessible Vacation Homes in Stroudwater

Over 118+ Wheelchair Accessible Vacation Homes in or Near Stroudwater
The Francis Hotel From US $388
         

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9.0 (233 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Longfellow Hotel From US $181
         

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9.6 (155 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV

Stroudwater Vacation Rentals and Airbnb Places to Stay Under $200

Over 126+ Stroudwater Vacation Rentals and Airbnb Places to Stay Under $200
Simple & Convenient Downtown Living From US $130
         

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8.5 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Blind Tiger Portland – Carleton Street From US $184
         

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9.6 (121 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Balcony/Terrace
  • Accessibility
A Cozy 1 Bedroom Gem You'll LOVE!nSleeps 4, Pet Friendly, With Parking, From US $182
         

Stunning - modern 2 bedroom Victorian mansion pad From US $177
         

10.0 (2 Reviews)
House
  • Security/Safety
  • Bedding/Linens
  • Child Friendly
Beautiful Back Cove Area/"Maine the Way Life Should Be" From US $171
         

Hidden private one bedroom gem From US $167
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Ultra cool new modern flat From US $164
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Security/Safety

Instantly Bookable Vacation Homes in Stroudwater

Over 222+ Instantly Bookable Vacation Homes in or Near Stroudwater
Private Rooftop Deck!/Artsy Apt/Old Port Arts Dist From US $533
         

10.0 (54 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Historic Home in the West End. Private Parking. From US $286
         

10.0 (54 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Near Portland Trails: Walkable Apartment w/Deck From US $330
         

10.0 (50 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Charming West End Hideaway. Private Parking From US $241
         

10.0 (49 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Bright & Sunny West End Apartment with Private Parking. From US $307
         

Charming Brownstone Downtown Free St|Perfect Getaway for 2 From US $396
         

Spectacular 3rd Floor Apt Near Downtown Portland From US $505
         

10.0 (31 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

About Stroudwater Vacation Rentals

With more than 472 Stroudwater vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Sanibelislandvillas 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 Stroudwater.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Sanibelislandvillas Stroudwater, 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 Stroudwater. Places to stay near Stroudwater are 1022.16 ft² on average, with prices averaging $443 a night.

Sanibelislandvillas makes it easy and safe to find and compare vacation rentals in Stroudwater 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 Stroudwater

Type Count
Holiday Apartments 179
Vacation Homes 131
Hotels with Suites 124
B&B 9
Villas 2
Cottages 1
Hostels 1
Others 1

Use these Quick Filters to Find a Vacation Rental in Stroudwater

Pro Tip: Sanibelislandvillas makes it easy to compare the best listings on Sanibelislandvillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Sanibelislandvillas 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 Stroudwater.

Weather in Stroudwater

View the weather forecast for Stroudwater before booking your Stroudwater 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

Other Places to Stay Near Stroudwater, ME


Complexes around Stroudwater, ME


Stroudwater Vacation Rental Frequently Asked Questions

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

Currently, the total number of properties listed in 2026 is over 472 in the Stroudwater area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Stroudwater.