Middlesex County Vacation Rentals with Pools
House
10.0(12 Reviews)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
Fireplace/Heating
Pool
Balcony/Terrace
Kitchen
US $289/Night
7 Nights - US $2,020
Apartment
10.0(5 Reviews)
7 Bedrooms
1 Bath
4 Guests
592.02 ft²
Oceanfront- Fireplace/Heating
- Pool
Ocean View
US $341/Night
7 Nights - US $2,385
Hotel
9.8(1007 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
US $201/Night
7 Nights - US $1,407
Apartment
10.0(9 Reviews)
2 Bedrooms
1 Bath
5 Guests
1001 ft²
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
US $440/Night
7 Nights - US $3,080
Apartment
9.9(9 Reviews)
17 Bedrooms
2 Baths
5 Guests
1001.04 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $901/Night
7 Nights - US $6,304
Apartment
10.0(9 Reviews)
1 Bedroom
1 Bath
3 Guests
Hot Tub- Fireplace/Heating
- Pool
- Balcony/Terrace
US $211/Night
7 Nights - US $1,476
Apartment
9.6(11 Reviews)
8 Bedrooms
2 Baths
5 Guests
1001.04 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $433/Night
7 Nights - US $3,031
Apartment
10.0(6 Reviews)
6 Bedrooms
2 Baths
5 Guests
990 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $427/Night
7 Nights - US $2,989
Apartment
9.3(11 Reviews)
2 Bedrooms
2 Baths
7 Guests
1097.92 ft²
- Fireplace/Heating
- Pool
View
Pet Friendly
US $688/Night
7 Nights - US $4,818
Apartment
10.0(4 Reviews)
6 Bedrooms
2 Baths
5 Guests
1055 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $619/Night
7 Nights - US $4,333
Apartment
8.8(4 Reviews)
2 Bedrooms
2 Baths
5 Guests
947.22 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $492/Night
7 Nights - US $3,444
House
10.0(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $465/Night
7 Nights - US $3,258
Why Choose Rent By Owner for your Middlesex County Vacation Rentals with Pools?
What makes our Vacation Rentals with Pools special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Middlesex County
How to Book Your Middlesex County Vacation Rentals with Pools
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals with pools. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Middlesex County
Common Vacation Rentals with Pools Amenities
What amenities can you expect?
Our Vacation Rentals with Pools are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Middlesex County, MA
Cambridge
Somerville
Arefth
East Cambridge
Everett
Central Square
The Port
Medford
Waltham
Woburn
Winter Hill
Malden
Middlesex County Vacation Rentals with Pools Frequently Asked Questions
1. What are the top Rentals With Pools in Middlesex County?
There are a lot of options in Middlesex County. If you plan on staying in the Middlesex County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Rentals With Pools in Middlesex County:
- Sunny and immaculately clean 3 bed/2 bath - fast wifi - 5 min walk to Alewife T
- Beautiful Spacious 4BRM House!
- Majestic lakefront 3-bedroom with pool, hot tub, water sports and birdwatching
- Quiet, upscale Boston Suburb stay-fast access to Boston hub & hospitals STR25-22
- Home in Woburn - Family + Pet Friendly!
- Luxury Boston Ranch –Sleeps 8|Pet+|Private pool
- Well-Maintained Property; Quiet, Tree-Lined Neighborhood. Ideal Location. Pool.
- Contemporary Room | Free Breakfast, Parking & Gym Access
- Double Room at Fairfield Waltham | EV Charger, Pool & Fitness Center| 2 Units
- Serene Hotel w/Indoor Pool and ArtBar Dining Near Harvard
2. How many Rentals With Pools are available in Middlesex County?
Currently, the total number of properties listed by RBO in 2026 is over 385 in the Middlesex County area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Rentals With Pools in Middlesex County.
More Rentals You May Like Near Middlesex County
Apartment
8.2(7 Reviews)
1 Bedroom
1 Bath
5 Guests
753.47 ft²
- Fireplace/Heating
- Pool
- View
- Pet Friendly
US $680/Night
7 Nights - US $4,760
Apartment
10.0(3 Reviews)
5 Bedrooms
1 Bath
4 Guests
603 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $407/Night
7 Nights - US $2,849
Cottage
10.0(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
800 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $361/Night
7 Nights - US $2,524
Cottage
10.0(1 Review)
2 Bedrooms
1 Bath
6 Guests
873 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $599/Night
7 Nights - US $4,195
Apartment
10.0(1 Review)
6 Bedrooms
2 Baths
5 Guests
904 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $431/Night
7 Nights - US $3,017
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
5 Guests
1065 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $303/Night
7 Nights - US $2,120
Apartment
9.6(18 Reviews)
3 Bedrooms
2 Baths
5 Guests
1001 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $526/Night
7 Nights - US $3,684
Cottage
9.4(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
825 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $287/Night
7 Nights - US $2,006
Apartment
8.6(12 Reviews)
2 Bedrooms
2 Baths
5 Guests
1022 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $237/Night
7 Nights - US $1,658
Apartment
8.0(1 Review)
1 Bedroom
1 Bath
1100 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $439/Night
7 Nights - US $3,073
Apartment
2 Bedrooms
2 Baths
4 Guests
1108 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $378/Night
7 Nights - US $2,646
Apartment
2 Bedrooms
2 Baths
5 Guests
1190 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $372/Night
7 Nights - US $2,606
