Vacation rentals with a pool in Bridgeport

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

Family · Location · Hot tub

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Guest favorite

Shoreline Carriage House

Overlooking acres of salt marsh and distant views of Long Island Sound, this cozy one-bedroom carriage house is perfect for a weekend (or week!) away. The Carriage House boasts access to the pool, a quick 3-5 minute walk to gorgeous beaches, a short drive or bike to restaurants and breweries, and a charming historic downtown. If you are in the mood to stay in (we totally get it), the space includes a brand new queen-sized bed, comfy couch, smart TV and a deck to enjoy the view and sea breeze.

Family · Location · Quiet

Top guest favorite

Guest favorite

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!

Family · Location · Laundry

Midcentury Modern ZenHouse Sculptor Studio

Mid-century modern historic private estate surrounded by river @Zenhouse_satori and main house. Great for memorable romantic getaway, photoshoots and film locations! ZENHOUSE mission is rooted in the values of respect, creativity, and excellence. Inspired by the timeless principles of Zen, we offer a luxurious and exclusive experience where tranquility blends with art, spirituality, and nature. We provide a serene environment and personalized service to awaken your true nature and find Zen

Location · Family · Quiet

Top guest favorite

Guest favorite

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.

Value · Location · Kitchen

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Guest favorite

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.

Family · Location · Walkability

Breathtaking Panoramic Waterfront

Relax to sweeping views from every room in this unique, 4600 sq foot direct-waterfront home with large pool, hot-tub, bar, kayaks, and fire pit. 2 floors of wraparound patio/deck, plus 3rd floor loft and roof patio. Open floor plan, 5 bedrooms (bedroom 5 has separate entrance by pool and is summer only) plus loft, 3.5 bath plus half bath and outdoor shower by pool. (Note: pool not heated and open mid-may to mid-Oct only; hot tub closed after new year until March; parking for 6 cars max)

Family · Location · Amenities

Family Fun! Pool, Gameroom, Yard | 5 min to Train

Welcome to our family-friendly 2-story Cape Cod! Enjoy a private fenced-in pool, game room and: - Expansive fenced backyard w/ grill + pool - Game room: foosball table w/ Roku TV - 4 bedrms: 2 king, 1 queen, 2 Twin XL - Pack&Play cribs for kids - High-Speed 1 Gig Fiber-optic internet & 2 desks - Private parking for 2 cars with additional free street parking - 3 full baths, stocked kitchen, washer/dryer, - 8min to Downtown/UConn, 5min to Train Station (50m Express to Grand Central)

Location · Value · Indoor spaces

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

Family · Value · Layout

Top guest favorite

Guest favorite

Lovely Country Retreat:

This beautifully renovated country house is set on 2 acres with a pool in the summer, ( heated , additional charge) ,outdoor gas BBQ, playground & treehouse set back on a quiet, circular road. The house sleeps up to 8 people, has a playroom, movie theatre and is ideal for 2 families traveling with children. Surrounded by bucolic scenery it provides the best blend of country living and fun family activities. If you are looking for a special place, only 1 1/2 h. from NYC

Location · Family · Kitchen

Top guest favorite

Guest favorite

Peaceful Light-Filled Guesthouse salt pool/sauna

Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit, or unwind in the pool side sauna. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Location · Family · Check-in

Beautiful Bayfront Home • Heated Pool & Jacuzzi

Come and enjoy the peaceful nature at this unique and stunning house on the Bay, a perfect getaway with family and friends. Our house has a perfect relaxing backyard to lounge and relax at our infinity jacuzzi overlooking the bay. The house is conveniently located just a few minutes away from the beach. Also, we are located 7 minutes away from Downtown New Haven, where you can visit various restaurants, coffee shops, and bars.

Family · Value · Hospitality