Vacation rentals in Pleasure Beach

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Top-rated vacation rentals in Pleasure Beach

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Guest suite in Fairfield

4.92 out of 5 average rating, 109 reviews

Suite; 1 Bedroom & Living Area/Xtra Bedrm; Kitchen

Fully accessorized, large (1,255 sq ft) beautiful suburban space consisting of bedroom (queen), an exclusive-use living room/extra bedroom with twin pull-out bed, private full bath; in-unit washer/dryer; for stays of 1 week or less: exclusive use of main kitchen; private entrance to space. Includes continental breakfast, 2 large-screen TVs. Unit on the ground floor of a 3 story home. Owners on property. Train station about a mile away (NYC: 70 minutes). Easy walk to Fairfield University.

Oct 25 – Nov 1

$99 per night
Guest favorite

Guest suite in Fairfield

4.93 out of 5 average rating, 107 reviews

Adorable private apt w/ W/D in lovely neighborhood

Enjoy a lovely experience at this centrally-located studio in-law apartment. It boasts a newly renovated kitchen and bath, king bed with brand new mattress, pull out full size sofa, ample closet space and more. The eat-in kitchen has all you need to feel right at home. The apartment is located adjacent to a nice residential house, but is fully private with your own front and back entrances. There are also no stairs, making it easily accessible. It’s located in a wonderful neighbor in Fairfield.

Aug 18 – 25

$107 per night
Guest favorite

Apartment in Milford

4.97 out of 5 average rating, 505 reviews

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

Aug 27 – Sep 3

$175 per night

Popular amenities for Pleasure Beach vacation rentals

Other great vacation rentals in Pleasure Beach

Guest favorite

Apartment in Bridgeport

5.0 out of 5 average rating, 11 reviews

Polita’s Place # 2

Apr 21 – 28

$81 per night
Guest favorite

Apartment in Fairfield

4.95 out of 5 average rating, 58 reviews

Sunny Fairfield Studio Apartment

Apr 21 – 28

$100 per night
Superhost

Home in Fairfield

4.9 out of 5 average rating, 31 reviews

Fairfield 2nd FL Suite w Private Entry & Parking

Aug 15 – 22

$93 per night
Guest favorite

Home in Fairfield

4.91 out of 5 average rating, 65 reviews

Fairfield 2nd FL Suite w Private Entry & Parking

May 7 – 14

$96 per night
Guest favorite

Apartment in Stratford

4.99 out of 5 average rating, 91 reviews

2-Bedroom 1st floor unit 7 minutes from beach

May 10 – 17

$144 per night
Guest favorite

Guest suite in Wilton

5.0 out of 5 average rating, 24 reviews

Guest suite with private enter

Apr 30 – May 7

$82 per night
Guest favorite

Apartment in Bridgeport

4.89 out of 5 average rating, 64 reviews

Seaside Studio in Historic Bridgeport Brownstone

Sep 7 – 14

$132 per night
Guest favorite

Tiny home in Milford

4.96 out of 5 average rating, 49 reviews

Beach Cabana

Sep 22 – 29

$150 per night
Guest favorite

Apartment in Fairfield

5.0 out of 5 average rating, 50 reviews

Bright, private 1,000 sq. ft. 1-Bedroom Apartment

Sep 30 – Oct 7

$120 per night
Guest favorite

Loft in Milford

4.93 out of 5 average rating, 92 reviews

Lovely water front lower-level loft, free parking

Sep 16 – 23

$109 per night
Guest favorite

Guesthouse in Milford

5.0 out of 5 average rating, 30 reviews

The studio downtown

Jul 31 – Aug 7

$114 per night
Guest favorite

Home in Stratford

5.0 out of 5 average rating, 10 reviews

Lordship Beach House - Pool & Beach (seasonal)

Sep 27 – Oct 4

$595 per night

Destinations to explore