
Guest house holiday rentals in Fire Island
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Top-rated guest house rentals in Fire Island
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.
Get Back to Nature at a Modern Wood Clad Getaway
HAPPY SPRING… PEEPERS are singing. The spring birds are arriving and the crocuses are up. Hawks, cardinals, blue jays, bluebirds, gold finches and more are here. Beautiful hiking trails in the woods and along the beachfront. Great places to shop and eat or catch a show at one of New Haven’s renowned museums or broadway theatres or relax. Great restaurants along the shore. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

WELCOME TO THE LOVE SHACK BY THE SEA
Escape the city, work in nature! Totally private cottage with garden views , central air and heated floors. 1 mile from pristine beaches and center of town, LIRR, Hampton Jitney, 3 large grocery stores, Starbucks, organic market, shopping & restaurants. King bed, cable TV, refrigerator w/ice, microwave, outdoor grill, private yard, Perfect for couples, solo, 1-2 small kids. We welcome small dogs for a $100 fee. Please message us with the size and type. Working couple/owners in main house.

1BR full cottage, 1 min walk to private beach
Enjoy time at this lovely studio located in the heart of Rowayton, a charming New England seaside village bounded on one side by Long Island sound and the other by a tidal inlet. Based in the southwest corner of CT, we are just a 1 minute walk to 2 separate and secluded beaches as well as 2 private, well manicured parks. Great amenities in town including tennis, sailing, outdoor yoga, sunbathing, plus nice restaurants. Pedestrian and dog friendly town; you don't even need a car while here.

The Quail’s Nest
A beautifully landscaped tranquil oasis. Newly constructed private two bedroom, one bathroom guest extension to owner occupied house. Guests share large yard and pool with owner, and have private deck and seating area. Private entry and parking. Guest's may enjoy outdoor shower and BBQ. Please note there is no kitchen, however a small fridge, Keurig coffeemaker and microwave, plates/utensils are provided. Conveniently located to beaches, shopping and local restaurants in East Hampton.

The Sunshine House
Enjoy your stay and visit the Bayard Cutting Arboretum, SUSA Orlin & Cohen Sports Complex, Robert Moses Beach; centrally located between The Hamptons Vineyard Wine Tours & Manhattan. This unique home was originally built in 1921 and has since undergone renovations with additions added to the original structure, including the three bedroom / bath guest wing with a private entrance from the main house. We provide beverages and continental breakfast. Please email us for more details!

North Country Cottage
Located near Long Island's beautiful beaches, vineyards, and wedding venues, this cozy cottage in the woods provides a quiet and comfortable place to stay while visiting! A spacious patio extends the living area, adding space to enjoy the outdoors in front of the fire pit or outdoor dining table. This property is located behind the owners' home and uses a shared driveway. While the owner is close by to address any issues during your stay, your space allows for total privacy.

A Lovely Cottage in the Woods
Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

French Guest House in Waccabuc
A private, European-style retreat just 60 minutes from NYC. Set on an eight-acre gated French estate with its own lake, this guest house feels like a mini Versailles with 18th-century statuary, fountains and manicured gardens. Designed by David Easton, it features heated stone floors, a heated towel rack, luxury linens, gold fixtures, fast WiFi, and a private entrance. Minutes from Waccabuc Country Club and the Katonah train station.

Gorgeous Waterfront Getaway
Perfect getaway from the city for couples wanting peace and tranquility and stunning views. A beautiful waterfront one bedroom guesthouse, one and one-half miles from downtown Mystic CT. Beautifully decorated with art and antiques. Kitchenette, full bath and loft bedroom. Queen bed. Air conditioning and heated. Belgian linen bedding! Private patio. Dock. Kayak/Canoe rentals close by. Internet.

Peekskill Carriage House Downtown Studio
Located close to the center of town, this is the perfect launchpad to experience local restaurants, coffee houses, the Paramount Theater, shopping, etc. and a short drive to stunning hikes, the Hudson Valley and beyond. The apartment is ideal for one or two and features a kitchenette, bathroom, dining island, comfortable queen bed, and couch. peekskillcarriagehouse.com

The Unhampton
This Brookhaven Hamlet detached space (totally separate) is for people who love nature and preserved quiet spaces. Fire Island is a ferry ride away, Manhattan is one hour by train and the Hamptons are a 25 minute ride.15 minutes from the restaurants and coffee shops in Patchogue and just a couple of minutes from Bellport Village. Centrally located and truly peaceful!

The Dacha at the Mystic Farmhouse
A Historic Artist’s Retreat Near Downtown Mystic Lovingly known as The Dacha for nearly 80 years, this one-of-a-kind gem was built in 1945 as a studio for the artist who once called the property home. Fully insulated for cozy winter stays, the unique structure is tucked away on a peaceful piece of land, just five minutes from downtown Mystic.
Popular amenities for guest house rentals in Fire Island
Family-friendly guest house rentals

Hidden Haven

Carriage house flat near beach

Home away from home

Super Adorable Cottage + Fire pit + King Bed!

Cozy Place

Guest Suite at Wisteria Gardens

Enchanting Guest Cottage

The cottage at Oasis Cove
Guest house rentals with a patio

The Cottage in Greenwich

2 BR Private Suite w/Private Living Room & Kitchen

Cozy 2 BR guest suite very close to JFK, UBS Arena

The Creekside Cottage

Apartment in New York near to Manhattan.

Waterfront Getaway - Norwalk, CT

The Bungalow at Sandy Hook House

Bayfront 1BR/2BR detached guesthouse with pool
Guest house rentals with a washing machine and dryer

Fully Renovated, Ocean Views, Fireplace & Beach

White Cedar Cottage

Beautiful guesthouse - Larchmont

Modern fully updated 2nd Floor apartment

Southold- Adorable 1 Bedroom Cottage

Bow’s Stays

The Perch: Saltwater Pool Woodland Cottage Retreat

New Haven Pizza Cozy Guest House 1 mile to yale
Quick stats about guest house rentals in Fire Island

Total holiday rentals
Explore 30 holiday rentals in Fire Island

Nightly prices starting at
Fire Island holiday rentals start at £68 per night before taxes and fees

Verified guest reviews
Over 1,260 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Fire Island holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Fire Island rentals

4.9 Average rating
Fire Island stays are highly rated by guests – averaging 4.9 out of 5!

Nearby attractions
Fire Island’s top spots include Fire Island National Seashore, Islip Cinemas and Plaza Cinema & Media Arts Center
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Rentals with pools Fire Island
- Rentals with a kayak Fire Island
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- Cottage rentals Fire Island
- Rentals with a firepit Fire Island
- Beachfront rentals Fire Island
- Apartment rentals Fire Island
- Pet-friendly rentals Fire Island
- House rentals Fire Island
- Private suite rentals Fire Island
- Rentals with breakfast Fire Island
- Beach house rentals Fire Island
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- Waterfront rentals Fire Island
- Rentals with a washing machine and dryer Fire Island
- Hotel rooms Fire Island
- Rentals with a fireplace Fire Island
- Bungalow rentals Fire Island
- Flat rentals Fire Island
- Rentals with outdoor seating Fire Island
- Rentals with a patio Fire Island
- Rentals with a hot tub Fire Island
- Rentals with beach access Fire Island
- Family-friendly rentals Fire Island
- Guest house rentals Suffolk County
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- Guest house rentals United States
- Times Square
- Madison Square Garden
- New York City Center
- Columbia University
- Central Park Zoo
- MetLife Stadium
- Yale University
- Bronx Zoo
- Brooklyn Bridge
- Yankee Stadium
- Rockefeller Center
- United Nations Headquarters
- Jones Beach
- Empire State Building
- Citi Field
- Grand Central Terminal
- Bryant Park
- Radio City Music Hall
- Statue of Liberty
- USTA Billie Jean King National Tennis Center
- Cooper's Beach, Southampton
- The Metropolitan Museum of Art
- Fairfield Beach
- Ohel Chabad-Lubavitch




