Westport, CT Houses for Rent with Community Pool

Your Summer vacation, elevated. Walk to the train. Walk to dinner or coffee. Wake up to waterfront views. This isn't just a summer rental, it's the retreat you've been dreaming about. Sprawling across six bedrooms and nine baths, this gem was built for the art of summer living. Soaring 9ft+ ceilings, walls of natural light, and water views set the stage. The house was designed for entertaining

Debra Shaughnessy Coldwell Banker Realty

Family retreat with in ground pool and outdoor entertaining and cooking area is available for your summer getaway. Bike to the beach from this 4 bedroom 4 full bath cozy home with welcoming front porch, playroom and full bath on every level. Primary suite is private and features a full bath, and balcony for your morning coffee. Huge new deck off kitchen. Three family bedrooms with full bath, open

Lisa Neufeld William Raveis Real Estate

Nestled in the coveted Greens Farms neighborhood, this impeccably updated residence offers a refined rental experience with every detail considered. The chef's kitchen commands attention with a dramatic waterfall island and premium appliances, seamlessly transitioning from intimate dinners to sophisticated entertaining. Retreat to the generous primary suite, where a spa caliber bath, complete

Demetrios Dassouras Coldwell Banker Realty

It is the luxury rental you have been waiting for... Perfectly positioned at the edge of Mill Pond, this exceptional home offers breathtaking views and fabulous sunrises from every room. Whether you are looking for a summer vacation or considering making Westport your home, this is a rare opportunity to experience the very best of coastal living. Featuring a first floor bedroom and 4 additional

Meredith Cohen Serhant Connecticut, LLC

NEWLY RENOVATED! Gorgeous spacious fully furnished home situated at the end of a long private driveway in a fully fenced professionally exquisite landscaped park like property on 2.14 level acres. This beautiful colonial with a dramatic two story foyer, high ceilings, custom millwork & beautiful details is finished on 4 levels. New light natural hardwood floors. 2 Home Offices with extensive

Cindy Saul Coldwell Banker Realty

Is this Westport or Provence? Sited high above Greens Farms is this charming and spacious renovated cottage on a prime, flat and open estate property. A water lover and swimmer's dream, with stunning, large heated pool (with kick pads) and spa (seats 8+). All-new gourmet kitchen, newly finished pickled wood floors, fresh paint throughout. Decorated for stylish and comfortable living, it's the

Thomas Broadbent William Pitt Sotheby's Int'l

Furnished Short Term Rental with dramatic views of the Long Island Sound and pool at one of the areas premier addresses- Steps To Compo Beach and Longshore Country Club. Located on prestigious Bluewater Hill, this home is part of association with deeded Beach rights and Tennis courts. This home offers 4 bedrooms, 3 full baths, flexible floor plan with great entertaining areas, outdoor patios and

Doug Bross Coldwell Banker Realty

15 Timber Lane, Westport, CT | School Year Furnished Rental Experience luxury living in the coveted Roseville neighborhood of Westport. Situated on 1.45 private acres at the end of a quiet cul-de-sac, this beautifully furnished 4-bedroom, 5-bath home offers the perfect school year retreat. Designed for comfortable living and entertaining, the home features two spacious primary suites with vaulted

Cody Nizzardo Nizzardo Real Estate Services

Imagine being able to view one of the town's loveliest Formal Gardens, from huge windows, throughout this stunning Mid-Century Modern home....Nestled tranquilly on a park-like private cul de sac, in Westport's highly-sought Coleytown neighborhood. 8 Bayberry Ridge is minutes from the Merritt and multiple Train stations. Become a resident of the Westport, CT community! Enjoy its pristine Beaches,

Laurie Mortensen William Pitt Sotheby's Int'l

Yearly Unfurnished Rental Available mid August! Experience an exceptional coastal lifestyle in the private waterfront enclave of Bluewater Hill in Compo Beach. Set on one of the area's premier streets, residents enjoy access to private association tennis courts & are just steps from Compo Beach & the LI Sound. This sophisticated 6,200-square-foot contemporary residence with 5 bedrooms, 4 full & 2

Erica Acheychek Compass Connecticut, LLC

Fully Furnished Seasonal Rental in Westport - Fall 2026 through Spring 2027 Fully furnished contemporary home located on a quiet cul-de-sac, minutes from downtown Westport, beaches, and restaurants. Offering 4 bedrooms, 3 full bathrooms, and 4,711 sq ft of living space, this home features an open floor plan with high ceilings, oversized windows, and a double-sided brick fireplace. The property

Alexey Gavrilov William Pitt Sotheby's Int'l

Fully Furnished, WATERFRONT PARADISE! Tranquil location offers unrivaled access to Panoramic Ocean views of Long Island Sound. A short walk across the Wooden Footbridge w/ Sherwood Mill Pond on your left and LI Sound on your right leads to the gated private Island of Compo Mill Cove & a handful of unique waterfront homes. The property itself has been customized from top to bottom w/ exceptional

Robert Perriello Century 21 AllPoints Realty

Charming Cape house situated on one acre of beautifully landscaped and maintained grounds. Prime location across from the Hunt Club with unencumbered views of serene horse stables. Enter the home through an inviting sun porch and convenient mudroom nook before stepping into the newly renovated kitchen. The spacious living room has an easy flow that is ideal for entertaining friends and spending

Sean Sullivan Keller Williams Realty