Squirrel Island Holiday Rentals
Apartment
- Boothbay Harbor
- ·
- East Boothbay
- 1.39 mi to center
10.0Exceptional
(108 Reviews)
1 Bedroom
1 Bath
2 Guests
750 ft²
Oceanfront
Parking
Ocean View
Balcony/Terrace
US $347/Night
7 Nights - US $2,432
House
- Maine
- ·
- Boothbay Harbor
- 0.68 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
688.89 ft²
- Parking
View
Internet
Security/Safety
US $155/Night
7 Nights - US $1,082
Bed & Breakfast
- Maine
- ·
- Boothbay Harbor
- 0.10 mi to center
9.4Exceptional
(130 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
- Balcony/Terrace
- Internet
US $287/Night
7 Nights - US $2,009
Apartment
- Maine
- ·
- Boothbay Harbor
- 0.27 mi to center
10.0Exceptional
(62 Reviews)
2 Bedrooms
1 Bath
4 Guests
574 ft²
- Parking
- Balcony/Terrace
Kitchen
Air Conditioner
US $340/Night
7 Nights - US $2,377
House
- Maine
- ·
- Boothbay Harbor
- 0.40 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
1001.04 ft²
- Parking
Skiing- Balcony/Terrace
- View
US $278/Night
7 Nights - US $1,946
Apartment
- Maine
- ·
- Boothbay Harbor
- 0.35 mi to center
10.0Exceptional
(57 Reviews)
1 Bedroom
1 Bath
2 Guests
750 ft²
- Oceanfront
- Parking
- Ocean View
- View
US $329/Night
7 Nights - US $2,300
Apartment
- Maine
- ·
- Boothbay Harbor
- 0.09 mi to center
10.0Exceptional
(51 Reviews)
1 Bedroom
1 Bath
2 Guests
592 ft²
- Oceanfront
Hot Tub- Parking
- Ocean View
US $263/Night
7 Nights - US $1,839
Apartment
- Maine
- ·
- Boothbay Harbor
- 0.24 mi to center
10.0Exceptional
(44 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $235/Night
7 Nights - US $1,646
Cabin
- Maine
- ·
- Boothbay Harbor
- 0.86 mi to center
10.0Exceptional
(38 Reviews)
2 Bedrooms
1 Bath
4 Guests
700 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $486/Night
7 Nights - US $3,400
Luxury Holiday Rentals in Squirrel Island
Over 638+ Luxury Holiday Rentals in or Near Squirrel Island
House
- Boothbay Harbor
- ·
- West Southport
- 0.26 mi to center
4 Bedrooms
2 Baths
10 Guests
3000 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $4,588/Night
7 Nights - US $32,118
House
- Boothbay Harbor
- ·
- West Boothbay Harbor
- 0.69 mi to center
8 Bedrooms
6 Baths
24 Guests
- Air Conditioner
- Internet
Pet Friendly
Child Friendly
US $4,181/Night
7 Nights - US $29,269
House
- Boothbay Harbor
- ·
- East Boothbay
- 0.46 mi to center
2 Bedrooms
2 Baths
6 Guests
- Breakfast
- Parking
- View
- Internet
US $3,069/Night
7 Nights - US $21,485
New
House
- Maine
- ·
- Boothbay Harbor
- 0.24 mi to center
4 Bedrooms
2 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $2,695/Night
7 Nights - US $18,863
House
- Boothbay Harbor
- ·
- Southport
- 0.89 mi to center
10.0Exceptional
(3 Reviews)
6 Bedrooms
3 Baths
14 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $2,219/Night
7 Nights - US $15,531
House
- Maine
- ·
- Boothbay Harbor
- 1.48 mi to center
5 Bedrooms
4 Baths
10 Guests
- Child Friendly
- Security/Safety
US $2,205/Night
7 Nights - US $15,436
House
- Boothbay Harbor
- ·
- East Boothbay
- 0.14 mi to center
10.0Exceptional
(1 Review)
8 Bedrooms
3 Baths
16 Guests
13728 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $2,177/Night
7 Nights - US $15,242
House
- Boothbay Harbor
- ·
- East Boothbay
- 1.66 mi to center
5 Bedrooms
4 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,993/Night
7 Nights - US $13,948
New
House
- Boothbay Harbor
- ·
- Southport
- 1.25 mi to center
6 Bedrooms
6 Baths
15 Guests
10000 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $1,790/Night
7 Nights - US $12,528
Top-Rated Holiday Rentals with a Pool in Squirrel Island
Over 146+ The Best Private Villas and Holiday Rentals in Squirrel Island with a Pool
House
- Maine
- ·
- Boothbay Harbor
- 0.29 mi to center
10.0Exceptional
(121 Reviews)
3 Bedrooms
2 Baths
10 Guests
2550 ft²
- Parking
Pool- Balcony/Terrace
- Kitchen
US $922/Night
7 Nights - US $6,456
Condo
- Maine
- ·
- Boothbay Harbor
- 0.08 mi to center
10.0Exceptional
(72 Reviews)
3 Bedrooms
2 Baths
6 Guests
1478 ft²
- Parking
- Pool
Spa- Ocean View
US $524/Night
7 Nights - US $3,665
Cabin
- Maine
- ·
- Boothbay Harbor
- 0.89 mi to center
10.0Exceptional
(38 Reviews)
3 Bedrooms
1 Bath
6 Guests
1500 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $513/Night
7 Nights - US $3,590
House
- Maine
- ·
- Boothbay Harbor
- 1.65 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $1,126/Night
7 Nights - US $7,879
Hotel
- Boothbay Harbor
- ·
- Ocean Point
- 0.41 mi to center
10.0Exceptional
(1 Review)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $351/Night
7 Nights - US $2,460
Hotel
- Boothbay Harbor
- ·
- Ocean Point
- 0.41 mi to center
10.0Exceptional
(1 Review)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $321/Night
7 Nights - US $2,246
Hotel
- Boothbay Harbor
- ·
- Ocean Point
- 0.41 mi to center
10.0Exceptional
(1 Review)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $290/Night
7 Nights - US $2,032
Hotel
- Boothbay Harbor
- ·
- Newagen
- 0.35 mi to center
9.4Exceptional
(361 Reviews)
1 Bath
- Parking
- Pool
- Balcony/Terrace
- View
US $417/Night
7 Nights - US $2,918
Hotel
- Boothbay Harbor
- ·
- Newagen
- 0.35 mi to center
9.4Exceptional
(138 Reviews)
10 Baths
446.1 ft²
- Oceanfront
- Breakfast
- Parking
- Pool
US $258/Night
7 Nights - US $1,806
Pet-Friendly Holiday Rentals in Squirrel Island
Over 168+ Pet-Friendly Holiday Rentals in or Near Squirrel Island
Cottage
- Boothbay Harbor
- ·
- West Boothbay Harbor
- 0.92 mi to center
10.0Exceptional
(33 Reviews)
2 Bedrooms
2 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $573/Night
7 Nights - US $4,013
House
- Maine
- ·
- Boothbay Harbor
- 0.92 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
1 Bath
6 Guests
828.82 ft²
- Parking
- Skiing
- Balcony/Terrace
- View
US $192/Night
7 Nights - US $1,344
Hotel
- Boothbay Harbor
- ·
- Ocean Point
- 0.41 mi to center
8.8Fabulous
(598 Reviews)
1 Bath
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $252/Night
7 Nights - US $1,761
Cottage
- Maine
- ·
- Isle of Springs
- 1.34 mi to center
10.0Exceptional
(32 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $293/Night
7 Nights - US $2,049
House
- Boothbay Harbor
- ·
- Ocean Point
- 0.27 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
9 Guests
602.78 ft²
- Parking
- Skiing
- Balcony/Terrace
- View
US $503/Night
7 Nights - US $3,521
Cabin
- Maine
- ·
- Boothbay Harbor
- 1.12 mi to center
10.0Exceptional
(29 Reviews)
3 Bedrooms
2 Baths
6 Guests
800 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $265/Night
7 Nights - US $1,857
Apartment
- Maine
- ·
- Boothbay Harbor
- 0.06 mi to center
10.0Exceptional
(8 Reviews)
1 Bedroom
1 Bath
3 Guests
592 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $359/Night
7 Nights - US $2,515
Apartment
- Maine
- ·
- Boothbay Harbor
- 0.00 mi to center
9.8Exceptional
(61 Reviews)
1 Bedroom
1 Bath
2 Guests
375 ft²
- Oceanfront
- Ocean View
- View
- Kitchen
US $304/Night
7 Nights - US $2,130
House
- Boothbay Harbor
- ·
- West Southport
- 0.33 mi to center
9.6Exceptional
(19 Reviews)
2 Bedrooms
2 Baths
8 Guests
3587 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $667/Night
7 Nights - US $4,668
Large Holiday Rentals and Private Villas in Squirrel Island
Over 69+ Large Holiday Rentals and Private Villas in or Near Squirrel Island
Apartment
- Maine
- ·
- Boothbay Harbor
- 1.08 mi to center
10.0Exceptional
(37 Reviews)
5 Bedrooms
3 Baths
10 Guests
12917 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $560/Night
7 Nights - US $3,917
House
- Boothbay Harbor
- ·
- East Boothbay
- 0.71 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
10 Guests
1625.35 ft²
- Parking
- Skiing
- Balcony/Terrace
- View
US $495/Night
7 Nights - US $3,465
House
- Boothbay Harbor
- ·
- Southport
- 0.64 mi to center
10.0Exceptional
(16 Reviews)
4 Bedrooms
3 Baths
13 Guests
2200 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,096/Night
7 Nights - US $7,675
House
- Boothbay Harbor
- ·
- East Boothbay
- 1.63 mi to center
9.8Exceptional
(7 Reviews)
4 Bedrooms
3 Baths
10 Guests
1571.53 ft²
- Parking
- Skiing
- Balcony/Terrace
- View
US $148/Night
7 Nights - US $1,036
House
- Boothbay Harbor
- ·
- Ocean Point
- 0.43 mi to center
10.0Exceptional
(14 Reviews)
6 Bedrooms
2 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $759/Night
7 Nights - US $5,314
House
- Maine
- ·
- Boothbay Harbor
- 0.52 mi to center
10.0Exceptional
(12 Reviews)
4 Bedrooms
3 Baths
10 Guests
2650 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $1,141/Night
7 Nights - US $7,985
House
- Maine
- ·
- Boothbay Harbor
- 0.27 mi to center
10.0Exceptional
(7 Reviews)
5 Bedrooms
5 Baths
10 Guests
2000 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $778/Night
7 Nights - US $5,445
Cottage
- Maine
- ·
- Capitol Island
- 0.01 mi to center
10.0Exceptional
(6 Reviews)
5 Bedrooms
2 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $1,743/Night
7 Nights - US $12,200
House
- Maine
- ·
- Boothbay Harbor
- 1.19 mi to center
10.0Exceptional
(6 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $582/Night
7 Nights - US $4,075
Wheelchair Accessible Holiday Homes in Squirrel Island
Over 9+ Wheelchair Accessible Holiday Homes in or Near Squirrel Island
Cottage
- Boothbay Harbor
- ·
- Ocean Point
- 0.19 mi to center
4.6Average
(13 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
Wheelchair Accessible
US $136/Night
7 Nights - US $952
Resort
- Maine
- ·
- Boothbay Harbor
- 1.51 mi to center
8.5Fabulous
(112 Reviews)
2 Baths
53 Guests
604.73 ft²
- Oceanfront
- Hot Tub
- Breakfast
- Parking
US $523/Night
7 Nights - US $3,662
Hotel
- Maine
- ·
- Boothbay Harbor
- 0.05 mi to center
8.8Fabulous
(933 Reviews)
1 Bath
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $263/Night
7 Nights - US $1,839
Cottage
- Boothbay Harbor
- ·
- West Boothbay Harbor
- 0.31 mi to center
3 Bedrooms
1 Bath
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Child Friendly
US $208/Night
7 Nights - US $1,456
Resort
- Maine
- ·
- Boothbay Harbor
- 0.87 mi to center
8.4Excellent
(105 Reviews)
10 Baths
33 Guests
381.04 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $232/Night
7 Nights - US $1,624
Hotel
- Maine
- ·
- Boothbay Harbor
- 0.50 mi to center
9.1Exceptional
(778 Reviews)
4 Baths
309.46 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $196/Night
7 Nights - US $1,370
Hotel
- Maine
- ·
- Boothbay Harbor
- 0.16 mi to center
8.3Excellent
(788 Reviews)
14 Baths
247.57 ft²
- Hot Tub
EV Charge Station- Parking
- Balcony/Terrace
US $285/Night
7 Nights - US $1,995
Hotel
- Maine
- ·
- Boothbay Harbor
- 0.24 mi to center
8.3Excellent
(238 Reviews)
11 Baths
204.51 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $269/Night
7 Nights - US $1,883
Hotel
- Maine
- ·
- Boothbay Harbor
- 0.24 mi to center
8.2Excellent
(580 Reviews)
15 Baths
215.28 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $187/Night
7 Nights - US $1,307
Squirrel Island Private Villas and Holiday Homes Under $200
Over 30+ Squirrel Island Private Villas and Holiday Homes Under $200
Cottage
- Boothbay Harbor
- ·
- West Boothbay Harbor
- 0.80 mi to center
10.0Exceptional
(11 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $197/Night
7 Nights - US $1,377
House
- Boothbay Harbor
- ·
- Southport
- 0.67 mi to center
2 Bedrooms
2 Baths
6 Guests
1151.74 ft²
- Parking
- Skiing
- Balcony/Terrace
- Air Conditioner
US $160/Night
7 Nights - US $1,120
Cottage
- Boothbay Harbor
- ·
- West Boothbay Harbor
- 0.74 mi to center
9.6Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $199/Night
7 Nights - US $1,395
Hotel
- Boothbay Harbor
- ·
- Ocean Point
- 0.41 mi to center
8.6Fabulous
(254 Reviews)
23 Baths
226.04 ft²
Private Beach- Oceanfront
- Breakfast
- EV Charge Station
US $179/Night
7 Nights - US $1,253
House
- Boothbay Harbor
- ·
- West Boothbay Harbor
- 0.43 mi to center
9.2Exceptional
(80 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $140/Night
7 Nights - US $980
Cottage
- Maine
- ·
- Isle of Springs
- 1.68 mi to center
9.2Exceptional
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $197/Night
7 Nights - US $1,381
House
- Boothbay Harbor
- ·
- Ocean Point
- 0.15 mi to center
1 Bedroom
1 Bath
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $160/Night
7 Nights - US $1,123
Apartment
- Boothbay Harbor
- ·
- Southport
- 1.40 mi to center
1 Bedroom
1 Bath
2 Guests
8611 ft²
- Kitchen
- Internet
- Child Friendly
Laundry
US $152/Night
7 Nights - US $1,067
House
- Boothbay Harbor
- ·
- West Boothbay Harbor
- 0.50 mi to center
9.6Exceptional
(21 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $95/Night
7 Nights - US $668
Instantly Bookable Holiday Homes in Squirrel Island
Over 424+ Instantly Bookable Holiday Homes in or Near Squirrel Island
House
- Maine
- ·
- Boothbay Harbor
- 0.57 mi to center
10.0Exceptional
(31 Reviews)
2 Bedrooms
1 Bath
4 Guests
1440 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $590/Night
7 Nights - US $4,133
House
- Boothbay Harbor
- ·
- Ocean Point
- 0.41 mi to center
1 Bedroom
1 Bath
6 Guests
- Breakfast
- Parking
- Pool
- Kitchen
US $895/Night
7 Nights - US $6,262
House
- Maine
- ·
- Boothbay Harbor
- 0.30 mi to center
10.0Exceptional
(16 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $623/Night
7 Nights - US $4,360
Cabin
- Maine
- ·
- Boothbay Harbor
- 0.68 mi to center
10.0Exceptional
(11 Reviews)
2 Bedrooms
1 Bath
4 Guests
686 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $266/Night
7 Nights - US $1,862
Apartment
- Maine
- ·
- Boothbay Harbor
- 0.20 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $426/Night
7 Nights - US $2,979
House
- Boothbay Harbor
- ·
- Southport
- 1.51 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $324/Night
7 Nights - US $2,271
House
- Maine
- ·
- Boothbay Harbor
- 0.94 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
1116 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $451/Night
7 Nights - US $3,160
House
- Boothbay Harbor
- ·
- East Boothbay
- 1.12 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
700 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $422/Night
7 Nights - US $2,952
Cottage
- Maine
- ·
- Boothbay Harbor
- 0.11 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $397/Night
7 Nights - US $2,781
Book a Last Minute Place to Stay in Squirrel Island
About Casai's Private Villas and Holiday Rentals in Squirrel Island
Discover more than 647 vacation rentals available in Squirrel Island. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Squirrel Island.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Squirrel Island, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Squirrel Island. On average, places to stay near Squirrel Island offer 938.33 ft², with nightly prices averaging US $568.
With Casai, finding and comparing holiday rentals in Squirrel Island is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Squirrel Island
| Type | Count |
|---|---|
| Vacation Homes | 301 |
| Cottages | 94 |
| Holiday Apartments | 61 |
Use these Quick Filters to Find a Holiday Rental in Squirrel Island
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Squirrel Island.
Weather in Squirrel Island, ME
View the weather forecast for Squirrel Island before booking your Squirrel Island 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
Top Attractions Around Squirrel Island, ME
Casai offers a large selection of top attractions around Squirrel Island . Research things to do on your vacation before you visit Squirrel Island.
Frequently Asked Questions About Squirrel Island?
What are the top holiday rentals in Squirrel Island?
With numerous options available in Squirrel Island, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Squirrel Island:
- Stunning Renovated Waterfront Home with Private Deepwater Dock; Windows Galore!
- Topside Inn
- LUXURY OCEAN FRONT BOOTHBAY HARBOR HOME- 3 BED, 2 BATH, SLEEPS 10- PETS OK
- AIR-CONDITIONED Ocean Point OCEANFRONT with Lawn & Beach
- Year Round Luxury Waterfront Condo, Heart of Boothbay Harbor
- Year Round Charming & Cozy Cottage at Ocean Point
- Convenient Downtown Location w/Harbor View
- Sail Loft: Oceanfront Apartment on a Pier.
- Downtown Boothbay Harbor, walk to the Opera House, shops, restaurants and piers
- 3 Bedroom Oceanfront Cottage with Private Dock, Windjammer days available!
How many holiday rentals have private pools in Squirrel Island?
Discover a selection of holiday rentals with private pools near Squirrel Island with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Squirrel Island are best for families?
If you're searching for a family-friendly holiday home in Squirrel Island, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Squirrel Island:
- Exceptional waterfront cottage in Boothbay Harbour
- Oceanfront Cottage w/Deck 2 Mi to Boothbay Harbor
- Greenleaf Inn
How many Casai.com holiday rentals are available in Squirrel Island?
As of 2026, Casai boasts over 647 properties listed in the Squirrel Island area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Squirrel Island.
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