
Guesthouse holiday rentals in Fire Island
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Top-rated Guesthouses in Fire Island
Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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.

Little Blue Heron-Idyllic log cabin w/hot tub!
Amazing log cabin cottage, nestled across a picturesque bridge and waterfall on the serene Blue Heron Hollow estate! Featuring, outdoor natural stone fire pit, propane BBQ and brand new Life Smart hot tub! With wifi, parking and firewood, provided free of charge! Biking, hiking, hunting, horseback riding, wine tasting, pickleball and seasonal apple & pumpkin picking, all nearby! I’m a long time Super Host who took a break and now so excited to reopen Little Blue Heron to you all!

French Guest House in Waccabuc
A mini Versailles just outside of NYC - located on a private and gated eight acre estate with its own lake in Waccabuc, NY. Surrounded by 18C statuary, manicured gardens and fountains, it’s equivalent to staying in a 5-Star European luxury hotel suite (house designed by David Easton) with its heated stone floors and heated towel rack, luxury linens, gold taps and serene private entrance. (.7mi from Waccabuc Country Club, 60 min from NYC by car or train - Katonah train St)

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.

Square 6ix
Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. Stylishly decorated with mid-century modern furniture and adorned with pieces from local artists, this quiet home has a separate entrance, separate porch, high ceilings, and a fully equipped kitchen. The guest house is located a walking-block away from the charms of Westville Village and Edgewood Park.

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.

The Cottage in Greenwich
Brand new, light-filled private cottage guesthouse overlooking the woods in the heart of Greenwich, CT. Floor to ceiling windows, radiant heat bathroom floors, queen Casper mattress, a dedicated parking spot, Wi-Fi, TV, kitchenette with full fridge, Keurig coffee maker, microwave, toaster and induction stovetop and all utensils. Perfect for a weekend getaway or a quiet place to work.

Great South Bay Cottage
Fantastic private cottage on Long Island's South Shore. Great access to the best beaches in the world (walk to bay, ferries to ocean). Short train ride to/from NYC, Wineries & The Hampton's. Experience the Island’s charm and culture. Enjoy Long Island summers. We employ a professional cleaning regiment.

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt
A unique private and quiet 2 bedroom (1 double bed, two single full beds) totally self contained apt,with sitting room, bathroom ,mud room and full eat in kitchen, in Shaker Hollow, a classic 1795 colonial.Stone patio overlooking 3 1/2 acres of garden and a meadow along with a large fire pit.

Southport, CT across from BEACH
Located at Southport beach on Westport Line, this renovated 1 bedroom apartment totally private located above the garage and includes a full kitchen with new appliance and d/w and central air. Bdrm with queen, fine cotton sheets and towels, marble bath open living room w views.

Petite Cottage
Petite Cottage is quiet yet convenient to beautiful Long Island Beaches, North Fork Vineyards, South Fork, The Hampton's and fine eateries. Close to the excitement of Manhattan's Broadway Shows, Fine Dining, Central Park, Museums and Galleries.
Popular amenities for Fire Island guesthouses
Family-Friendly guesthouses

A Little House by the sea

The Hide-A-Way

Cottage by the Sea

Private guesthouse

Super Adorable Cottage + Fire pit + King Bed!

Adorable 1 bedroom beachside cottage

Beautiful Cottage in Greenwich CT

True Artist Loft, 5 minutes to downtown Mystic
Guesthouses with a patio

Private Luxe Cottage at Gates of Wine Country

White Cedar Cottage

Home away from home

The Estate Private Guest House -Lake Ronkonkoma!

Waterfront Getaway - Norwalk, CT

Quiet Family Guest Suite

The Perch, a luxe cottage in the woods 1h from NYC

North Country Cottage
Guest house rentals with a washing machine and dryer

Fully Renovated, Ocean Views, Fireplace & Beach

Chic Coastal Retreat: Modern Apt Steps from Beach

Your Modern Guest Wing Near NYC

Entire Guest House at Fox Pond Farm.

The Creekside Cottage

Modern fully updated 2nd Floor apartment

Guilford Lakes Cottage, with hot tub and fire pit.

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

Total holiday rentals
Explore 30 holiday rentals in Fire Island

Nightly prices starting at
Fire Island holiday rentals start at $160 NZD per night before taxes and fees

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

Pet-friendly accommodation
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

Wi-Fi availability
30 of Fire Island holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
- 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
- Mount Pocono Holiday rentals
- The Hamptons Holiday rentals
- Family-friendly rentals Fire Island
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- Times Square
- Rockefeller Center
- Bryant Park
- Madison Square Garden
- Empire State Building
- Columbia University
- Yale University
- MetLife Stadium
- Central Park Zoo
- Jones Beach
- Yankee Stadium
- Fairfield Beach
- Citi Field
- United Nations Headquarters
- Southampton Beach
- Grand Central Terminal
- Rye Beach
- Statue of Liberty
- Cooper's Beach, Southampton
- USTA Billie Jean King National Tennis Center
- Radio City Music Hall
- Canarsie Beach
- Gilgo Beach
- The Metropolitan Museum of Art