Holiday rentals with a pool in Milford

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

Meeker Hill House - Country Escape w/ Heated Pool

Meeker Hill House is a spacious and chic escape nestled in the heart of Fairfield County, located 90 minutes from NYC and minutes from the hamlet of Redding. Set on a quiet road, this 3 bedrooms and 3.5 baths house is riddled with old world charm. Amenities include a heated pool, fireplaces, fire pit, outdoor dining, screened in porch and a luxury chef's kitchen. Kick back and relax in this calm, stylish space as if in the English Countryside, all under two hours from NYC & under 3 hours fro

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

Looking for privacy, seclusion, and direct access to Sleeping Giant State Park right from your back yard? Then look no further! Entire Mid Century home centrally located to many great attractions and colleges. Featuring an open floor plan characterized by large glass windows and open space featuring simplicity and an integration with nature. Access to I-91 or Rt15 are both about 1 mile away, with Yale University and Downtown New Haven about a 20 minute drive. Farmington Canal bike trail-.5 miles

King 1BR W/ Parking, Pool & Gym

This gorgeous apt, located in a brand-new luxury building at the center of New Haven’s historic downtown, offers unparalleled comfort, service, and amenities. You can watch a movie on a 65" HDTV, work in one of 5 co-working spaces, or relax at the pool w/ grills and cabanas. Highlights: • Walkable access to Yale • Deep-clean prior to every guest • Coffee, fresh linens, and bathroom essentials provided • 24/7 fitness center • Sun terrace + pool and grills • Entertainment lounge w/ bowling alley

Garden Level Suite with Beautiful Pool

Enjoy complete privacy and 900+ square feet of living space in the ground floor suite/apartment of our home. Complete with its own private entrance and personal garage - our ground floor suite is your own private domain. There is one king bed, one queen bed, and a comfy sectional couch. Enjoy a small kitchenette for simple cooking inside, and an alfresco BBQ for bigger cooking. There is plenty of living space inside and out! A new washer/dryer unit will take care of all the pool towels used!

Spacious Cottage Loft

Welcome to the Spacious Cottage Loft! Please enjoy a nice quiet relaxed atmosphere in this unique space. Its a little bit rustic with its shiplap pine and exposed beams. Its a little bit rock and roll with its little music space along with some favorite framed albums hanging on the walls. Very comfy queen size bed. 2 smart TVs (65" up & 55" down) for your entertainment pleasure. Roomy kitchen with brand new appliances. Bath-walk in shower. THIS SPACE IS DESIGNED TO ACCOMMODATE 1-2 GUESTS.

The Pond Mill Retreat w/ 2 Bdrms & Pool

Catch up on a little work or simply unwind. Everything is waiting for you in this cozy, yet functional space surrounded by a beautiful wooded area with pond. Your private entrance accommodations include a finished, walk-out lower-level apartment (~730 sq ft) containing thoughtfully appointed bedrooms, living room, kitchen, and full bathroom. Experience solitude while enjoying the convenience to Rt 15, I-95, & Boston Post Rd destinations. And if you require assistance, we live right upstairs.

Artist Retreat in Beautiful Country Setting

Stay at this unique property, owned and designed by a Eu artist, and enjoy the quiet countryside and natural beauty that rural CT has to offer. A large one bedroom studio with an modern fireplace, is equipped with a comfortable king size bed, full bathroom, sauna, indoor resistance pool- available at an extra charge, kitchenette, a workspace, and high-speed internet for seamless remote work. Relax in the evening at your own private outdoor seating area surrounded by the property's charm.

1BR Guest Apt. Suite /full bath, kitchen -Pool/Spa

Private Apartment on 3-Acre Retreat | Heated Gunite Pool, Spa & Terrace. -Near Westport & NYC. Experience peace & privacy at this comfortable, 624sqft. apartment, tucked into a beautifully landscaped 3-acre retreat. With a private entrance, furnished terrace, and access to a shared heated 50-foot gunite pool & spa, this serene getaway is ideal for rest and recharge. It features a California king bed, sleeper couch, a kitchen and a bathroom. Washer & dryer are available in the pool house.

Renovated, Private, 4BR Cape w/Pool nr FFU/Town

Charming 4BR Cape on one acre of land, conveniently-located within a mile from Fairfield beaches, downtown shops & restaurants, train station, I95 and the Merritt. At end of cul-de-sac, set back from the street for maximum privacy. 4BR, 3 full bathrooms, newly-renovated kitchen/bathrooms/pool, enclosed back yard, beautiful gardens, and semi-finished basement with pull-out couch. Cozy enough for couples, but spacious enough for larger groups. Walking distance to Fairfield University.

Dream Home w/ Pool & Basketball Court on 3 Acres

Escape to a private 3-acre retreat with a pool, basketball court, fire pit, and high-end African-inspired interiors. A long, winding driveway offers privacy and space for strolls with strollers or furry friends. Inside, enjoy a double-height living room, chef’s kitchen, cozy den, and a primary suite with pool access. Close to Devil’s Den, Westport beaches & more. Please no parties. Maximum guests is 8. Please note bedroom configuration - the house is set up for families or 4 couples.

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.