luxury seaside houses for rent Fairfield, United States

Welcome to 14 Island View Ave-a masterfully redesigned coastal retreat nestled in the heart of highly desirable Pine Orchard. Spanning 2,100 square feet, this thoughtfully renovated home seamlessly blends modern luxury with relaxed shoreline living. Boasting 5 spacious bedrooms and 2.5 beautifully appointed baths, the residence features a bright, open floor plan optimized to capture gorgeous, unobstructed water views. Every detail has been meticulously curated during its full remodel, offering an unparalleled turn-key experience in one of the area's most coveted neighborhoods.

The views from this charming Sachems Head waterfront home are exceptional. Located next to the Sachems Head Yacht Club this fully furnished academic rental is a dream come true. Four bedrooms and two full baths, with an additional bedroom and full bath on the ground level in the warmer months. Additional rooms offer an excellent option for home offices. The main level features a wood-burning fireplace and an open floor plan with views from nearly every window. Available September 1, 2026 through June 1, 2027. Flexibility in early June extension. Pets are considered with owner approval. Excellent credit required. Showings by appointment only.

Where New England architecture meets timeless elegance! Experience the pinnacle of shoreline living in this spectacular waterfront estate, perfectly positioned on a private, peninsula-like setting in Sachem's Head community. Boasting breathtaking, panoramic views of Long Island Sound, this 1930s residence is a masterwork of historic character and unique architectural artistry. The home's rich heritage is reflected in its exquisite details, from the enduring beauty of Stony Creek Granite and warm Pecky Cypress woodwork, to the original "porthole" windows in the grand family room. In the formal dining room, a distinctive ribbed ceiling, designed to evoke the overhead of a classic ship's cabin, creates an unforgettable atmosphere for entertaining. The heart of the home features a generous galley kitchen that balances functionality with style, offering abundant cabinetry, expansive counter space, and dining area with plenty of windows making sure no view is missed. Retreat to the second floor to find six spacious bedrooms, each offering its own unique perspective of the water, while the finished third-floor "flex" space serves as an ideal game room or private sanctuary. Spread across two manicured acres, enjoy relaxed seaside living with multiple sun porches and expansive patio for gatherings. Take advantage of the Vineyard Place Association amenities, all while being just a short drive from charming downtown Guilford!

SEPT '26 - MAY '27 ACADEMIC WATERFRONT RENT Plan ahead. With amazing views out over Long Island Sound & beyond this light & bright Beach Colonial was built in 2006 plus has a recent 3 BR addition! Featuring an open floor plan, all in excellent condition with lots of glass & a wrap around deck to take full advantage of it's setting. Located at the very end of a private street this special home is in a nice quiet setting especially in the off season. Hardwood floors both up & down, central vac, a first floor den with sleeper couch that is perfect for that unexpected guests with a full bath right around the corner, newer propane heat and fully air conditioned. Set up high on piers, you'll feel like you are on a boat! Enjoy awesome sunrises AND sunsets from a single location! August might be available too. Exact dates to be determined. Unique opportunity.

ACADEMIC RENTAL! The iconic, water-front 118 Middle Beach Road is available for rent for the academic year beginning October 1, 2026. This sensational property offers comfortable occupancy for up to fourteen people with 7 bedrooms, 5 full baths, and 2 half baths. The main level is an entertainer's dream featuring an oversized, eat-in kitchen, formal dining area, living room with water views from every angle, and generously-sized screened-in porch! In addition to six of the seven bedrooms, the second floor features a family room perfect for cozy afternoons soaking in the expansive views and stunning sunsets! The third floor is a private retreat with the seventh bedroom and spectacular recreation space. Outside, your very own, private beach awaits you! Schedule your viewing today and make "Red Top" your home for the academic year! Short-term rental also available; please inquire.

ACADEMIC RENTAL SEPTEMBER-JUNE . . . Charming Four Bedroom New England Contemporary Colonial with Beach Rights. Discover the perfect balance of relaxation and accessibility in this vibrant academic rental. Nestled in a picturesque New England setting, this home is designed for those who love to get out and explore. Start your morning with a stroll to Julie's Cup of Joe for coffee or enjoy your weekends utilizing your private beach rights. The home features 4 spacious bedrooms, 2.5 bathrooms and a layout that is perfect for entertaining indoors or outdoors. Whether you are hosting friends or settling in for a quiet evening, this property offers the ultimate convenience. Don't miss your chance to live in one of the town's most desirable locations!

Summer 2027 -- Available: June, July, August, September. This beautiful property is a direct waterfront, 4 bedroom, one-level home situated on a sandy beach in a private association. Wake up every morning to ocean waves, and enjoy the panoramic sunrises/sunsets which are magical here. Upon pulling into the driveway, you'll be greeted by breathtaking water views. The expansive patio right on the beach is perfect for entertaining or relaxing, and is just a few steps to the water. Enjoy spending days lounging on the beach, taking long walks, running, seashell collecting, swimming, entertaining, and making priceless memories. Inside, this beach home offers: stunning ocean views, high ceilings with fans, a wall of windows with sliding door, central air, recessed lighting, New England style light and bright design, open concept one-level living, ample closet space, laundry, 4 bedrooms (king bed in master), and 2 full baths. The kitchen is complete with granite, stainless steel appliances, and a large island with breakfast bar. Recent home upgrades include new furniture, new mattresses, and custom window treatments. Outside, there is a full bath, driveway parking for 4 cars, and grassy front yard. Saybrook marina, Fenwick golf course, The Kate theater, restaurants, and shopping are all close by. Only 2 hours from NYC and Boston.

Meet your coastal cozy ground level 1 bedroom, 1 bath apartment on this quiet block in East Atlantic Beach. Seconds away from private beach access, restaurants and shops. The kitchen includes a refrigerator and a stove. Private Entrance. Street Parking. ALL Utilities included. Pet friendly upon owner approval. Available immediately.

Spend the summer on one of the most iconic private streets in Southampton Village. The classic Beach House was completely renovated and brought up to todays high standards. The elegant, sunny house offers eight wonderful bedrooms, some with ocean views, and six baths spread out over three floors. The ground floor features a formal dinning room, eat in kitchen with living space, grand entrance hall, and a living room with French doors that go to a covered outdoor living space. The beautifully manicured yard is the perfect place to spend your summer. The in ground heated pool is already fenced in with a rose covered picket fence. The true highlight of this property is the private beach access. Rental Terms: June: $70,000

This perfect modern beach house with large heated pool on coveted Flying Point Road is available for August through Labor Day 2026. With 360 degree water views, it's light makes this house one of a kind as well as large front yard and location. The sun rises on Mecox Bay and sets on Channel Pond, and the house sited on 2 acres overlooks both as well as the Atlantic Ocean right across the street. There are a total of 6 bedrooms with both first floor and second floor primary bedrooms in addition to a sitting room, TV room, living room and open kitchen/dining room. There is also a walk-out lower level bedroom. There are 3 different outdoor decks on various levels and they face different locations for view/sun optimization. There is even an outdoor fireplace, spa and outdoor shower. Very bright and furnished in easy haute beach style makes 1030 Flying Point, the ideal summer rental. [[Rental Registration # RP240380]] EH RR #: RP240380 Rental Terms: August - Labor Day: $250,000

360-degress water views from every room at this delightful beach house perched on Flying Point with direct "put-in" access to Mecox Bay. This house offers an ideal open floor plan with powder room on the first floor and on the second floor, the primary en suite, two guest bedrooms and the second full bathroom. Easy, breezy, beachy living in a prime location. Amenities include a fully-modern kitchen with stainless appliances, water-facing decks on two levels with views to Channel Pond and the ocean, an outdoor shower, and its own private walkway to Mecox Bay. Only one property separates this house from ocean beach access at Flying Point, and the private walkway makes kayaking and paddle boarding easy. Very bright and beautifully furnished. Available for August and/or September as well as many other months in extended season. [[Rental Registration # RP260252]] EH RR #: RP260252 Rental Terms: September: $35,000 November: $12,000 Other / Short Term - Year Round: $220,000 August: $72,500 August - Labor Day: $75,000 October: $18,000

Experience world-class coastal living in this extraordinary modern estate, perfectly suited for US Open visitors seeking privacy, space, and proximity to the Hamptons' premier destinations. This stunning property offers 8 bedrooms and 9 full bathrooms on over an acre, featuring direct private beach access and breathtaking ocean views. Designed for both relaxation and entertaining, the home includes a chef's kitchen, expansive open-concept living areas, and floor-to-ceiling windows that flood the space with natural light. Each bedroom is a luxuriously appointed suite, ensuring comfort and privacy for guests. Additional amenities include elevator access, a spectacular oceanfront pool, and a rooftop entertaining area with panoramic views-perfect for hosting or unwinding after a day at the tournament. Located in a private and secure setting in the heart of the Hamptons, this home offers convenient access to golf courses, beaches, dining, and US Open event venues. Special Notice: This property is available for select short-term rental periods. Pricing and availability shown under June are for reference only and do not guarantee full-month availability. Portions of June may be unavailable at the listed rate. All dates, rates, and availability are subject to change. Please inquire for confirmed pricing and specific rental dates. [[Rental Registration # RP251520]] EH RR #: RP251520 Rental Terms: June: $350,000

Timeless East Hampton Estate has been recently renovated with old world charm, style, and a true Hampton flare. The 1st floor of the main house features an open living area with fireplace, media room, library/sitting area, formal dining room with fireplace, country kitchen with breakfast nook, fireplace and seating area. The second floor is highlighted by 6 stylish bedrooms and 4 baths. The 3rd floor offers an additional guest bedroom, private office, and an inviting primary suite with ocean views, a drawing room, and fabulous primary bath. The grounds are accented by wrap around porches, an out door grilling station with outdoor fireplace and dining pavilion. The hedged for privacy pool area offers a 2 bedroom guest house, heated gunite pool, another dining pavilion, and lawn areas perfect for the afternoon soccer match. Your vacation will be magical as ocean breezes relax you. Electric Car ready with a 220 voltage outlet, this home is understated perfection. EH RR #: village Rental Terms: Two Weeks: $125,000 Other / Short Term - Weekly: $62,500

Discover this modern gem of a beach house on 3 private acres with 355 feet of water frontage on Gardiner's Bay. The private path over a dune leads to an oasis of wide sandy beach perfectly situated for sensational direct evening sunsets. The open interior has walls of glass for continuous water views and to invite in warm coastal breezes throughout. There are 5 bedrooms, 6 baths, den and separate studio. The waterside heated pool and hot tub are surrounded by expansive decking. Architect designer Joe D'Urso worked on the design of the compound which consists of the main house, an art studio, guest house and pool. The house was designed "upside down" by having the bedrooms on the first floor and the living room, dining room and kitchen on the second floor. [[Rental Registration # 24-1298]] EH RR #: 24-1298 Rental Terms: August - Labor Day: $100,000 Two Weeks: $55,000

Rental registry #: 22-129, Expires 03/08/2024. A spectacular beach house in the heart of Napeague . Two blocks to the ocean beach. This home features a great room with sliders to your deck to enjoy the ocean breezes. Three bedrooms, 2 full bathrooms, large den area and laundry room. Private outdoor shower. Two decks, front and back of the home. This is an ideal location for playing at the ocean, walk to Napeague bay and bike to Lobster Roll .Easy to reach Jitney stop and minutes from both Amagansett and Montauk. A special opportunity to spend your summer in this seaside community. No need for a beach pass, oceanfront community!!! Also available October for $5K; Nov for $5K; Dec for $5K. EH RR #: 22-129 Rental Terms: July: $25,000 Other / Short Term - June: $12,000

OFF-SEASON RENTAL-As the summer crowds fade, there is no better place to escape & find your peaceful retreat in this charming 3 BR 2BA fully furnished home overlooking the Shrewsbury River. Whether you're between homes, renovating or just need a change of pace, this home with breath-taking river views invites you to slow down. If work takes you to NYC, commuting is made easy with the Highlands Seastreak Ferry right down the road. This year-round community offers tons of dining, shopping, cultural & holiday events. Come visit this special place where you can truly experience a balanced life in a picture perfect atmosphere. Utilities included. Excellent credit required. Pets considered. No smokers please.

A rare rental in Shrewsbury. An exquisite, spacious ranch in a quiet neighborhood set on a peaceful, landscaped acre. 4 bedrooms, 3 baths. Some features include: Hardwood floors throughout, updated Kitchen and baths, fireplace, basement and a 2 car garage. Enjoy the peaceful grounds, yard and a beautiful deck area. Owner prefers a multi-year rental. * SF approx. - per tax.

This exceptional new construction home is nestled in the heart of Newport’s Fifth Ward neighborhood. This one-of-a-kind rental property is located only a few blocks from Newport Harbor and a quick bike ride to the beach. This design-driven home is filled with original details that live in perfect harmony with luxury- grade appliances and fixtures throughout. The main level features a fully open-flow space with a chef’s eat-in kitchen, dining area and living room. The main floor also features a wonderful mudroom, full bath with glass-encased shower, plus a cozy yet bright den which effortlessly flows out to a bluestone patio from oversized French doors. The upstairs offers 3 bedrooms all with en suite bathrooms. The primary bedroom offers a vaulted, natural shiplap ceiling, a spacious closet and a gorgeous full bath with an oversized, walk-in, tiled shower. The second bedroom is adorned with a stunning custom wood lattice wall design, ruffled built-in corner shelving and a sleek full bath with glass encased shower. The final bedroom has hand-painted, nautical striped walls, and a tranquil blue and white color palette – complemented by a full bath, beautifully tiled. Also on the second floor is a sophisticated and stylish laundry room with honed black granite counters, and blush cabinetry. Outside, you will find an outdoor oasis set for relaxing and/or entertaining-- a blue stone patio is set for dining al fresco, adorned with a chic pergola, plus additional lounge furniture. Please note: there is a 2 month minimum for summer rentals at this property.

Exclusive oceanfront on Penzance Point - A Classic Cape Cod Summer Awaits. Nestled in the private enclave of Penzance Point, this nostalgic Cape offers a rare blend of seclusion, charm, and sweeping water views. This spacious oceanfront haven hosts 5 bedrooms and 3.5 baths, with stunning vistas from every room and an expansive deck that wraps the home, drawing you into the natural beauty of Buzzards Bay and Woods Hole Harbor. Watch the steady rhythm of boat traffic by day and toast unforgettable sunsets by night. The sun-drenched living room opens effortlessly onto the deck, creating the perfect flow for summer entertaining and relaxed coastal living. A well-equipped kitchen and pantry make dining easy, whether you're whipping up a simple lunch or a seafood feast. Let the sound of rolling waves lull you to sleep, and wake to sea breezes and salt air. Just minutes away, discover the charm of Woods Hole Village and downtown Falmouth with its laid-back eateries, boutique shopping, and maritime allure. Your Cape Cod summer starts here. Rental Terms: Summer Weekly: $7,000 Per Week

Chip Chop is the legendary 20-acre beach compound set on Vineyard Sound. The property has lived large in Martha's Vineyard lore since the 1940s when it was built for celebrated Broadway star Katharine Cornell. For many decades it has hosted a broad spectrum of well-known figures from the worlds of literature, theater, cinema, and politics. A mile of private shoreline surrounds the property, including 2000 feet of sandy beach on the exquisite swimming waters of Vineyard Sound, and a large swath of sandy beach on Lake Tashmoo. Features include a two bedroom main house, outside of which sit the Pond Pavilion and the Ocean Pavilion, two separate, detached bedroom suites. There are also two elegant beach houses built in 2007 which offer astonishing water views on Martha's Vineyard. The swimming pool overlooking Vineyard Sound with views of the mainland beyond is simply stunning. A Har-Tru tennis court is discretely nestled in a private corner of the property. Supremely stylish and yet consummately casual, this famed Martha's Vineyard compound is the perfect setting for your dream Martha's Vineyard getaway.

A Cape Cod Quintessential summer retreat with spectacular views of the Ocean and saltmarsh. A wonderful home to create those Cape Cod Memories. This home is located in the Sippewissett area in desirable West Falmouth. The private association beach is steps away where you can swim, sun, kayak and paddle board. With west facing views you will be mesmerized by the amazing sunsets of West Falmouth. This home has a terrific floor plan for large families with numerous gathering areas, and private sitting areas There are views from nearly every room of the home. With close proximity to downtown Falmouth and Woods Hole, you will be able to enjoy the shopping, restaurants, and access the ferry boat to Martha’s Vineyard. No Availability left for 2021. Rental Terms: Summer Weekly: $3,900 Per Week

Experience the pinnacle of Vineyard living at this extraordinarily updated 9-acre estate, nestled within the exclusive Herring Creek Farm Association. Set along the tranquil shores of Edgartown Great Pond, this 10,000+ square foot residence offers unmatched privacy, refined elegance, and direct access to pristine beaches. The main level showcases timeless design with a grand foyer, sweeping staircase, sunlit formal dining room, gourmet chef’s kitchen, and multiple living areas designed for both relaxation and entertaining. A separate guest wing ensures comfort and privacy for visitors. French doors open to a resort-style outdoor oasis with a heated pool, expansive bluestone patio, and a covered porch with fireplace for elegant al fresco dining. Upstairs, five spacious bedrooms include an expansive primary suite featuring a private balcony with water views, a large walk-in closet, private office, and spa-like bath. Spend your days lounging poolside, enjoying sunset views over the Pond, or following a short private path to your own sandy beach. The Association’s exclusive Atlantic beach is a short golf cart ride away. Framed by beautifully landscaped grounds and open farm fields, this exceptional property offers total seclusion just minutes from downtown Edgartown.

Vacation in this Spectacular Oceanfront Estate in Falmouth with a private beach on Vineyard Sound. Walls of over-sized windows and sliders provide beautiful ocean views from nearly every room in the home. This custom built contemporary is impeccable, has over 6,000 sqft of living space, and offers 3 floors of living with 2 extraordinary Master Bedroom ensuites with private sitting areas. The home is equipped with an elevator to access second and third floor bedrooms. There are numerous gathering areas for relaxing and entertaining inside the home, and there are tiers of private exterior balconies and decks that wrap around the home to relax in the sun or shade and take in the beautiful vistas. Swim, paddle board, and kayak off of the sandy white beach at your back door. Both Master bedrooms have king size beds, bedrooms 3 and 4 have Queen sized beds, and the 5th bedroom has 2 twin beds. There is a terrific BBQ grill and large yard for cookouts. This home is located in close proximity to downtown Falmouth for shopping, restaurants, and ferry to Martha's Vineyard. Rental Terms: Other / Short Term - Two weeks: $40,000

SEPTEMBER RENTAL INCLUDING LABOR DAY WEEK! Step into timeless coastal charm with this exceptional summer rental in the historic St. Leonard’s Tract of Ventnor, just 7 houses from the beach and boardwalk in one of the island’s most coveted locations. Built in 1915, this beautifully preserved home has been meticulously updated and professionally decorated, seamlessly blending modern luxury with original character. Flooded with natural light from its many windows, the home feels bright, airy, and welcoming throughout. This is no cookie-cutter home. The spectacular design and details throughout, combined with the home's classic features is a true delight. The residence offers 4 bedrooms and 3 full baths, including a convenient main-floor bedroom with double bunk beds and a full bath, ideal for guests. The designer kitchen flows into a spacious dining area, perfect for entertaining. The main floor is complete with a large living room (don't miss the hidden bar) with the perfect reading area for quiet moments. Upstairs, the serene and spacious primary suite features an en suite bath and sitting area, while two additional charming bedrooms share a Jack-and-Jill bathroom. Outdoor living shines with a large front porch, a sprawling backyard with outdoor dining for warm summer evenings, an outdoor shower, and an original barn that adds historic appeal while providing ample storage for bikes and beach gear. A rare opportunity to enjoy classic Ventnor elegance with every modern comfort - your perfect end of summer escape awaits. Don't miss the best month of the year at the shore!