
Places to stay near Flaggy Hole Beach
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Top-rated holiday rentals near Flaggy Hole Beach
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Chic + serene Hamptons home. Near all attractions
Come escape to your serene, chic Hamptons home, any time of year! Just 1 block to the marina + moments to all of the best Hampton's attractions. Curl up @ the wood burning fireplace, cook in the large Chef's kitchen, stream on the 80' TV. Enjoy a BBQ + firepit under the starry sky! You will be surrounded by nature + tranquility. During summer swim all day + enjoy the Hamptons greenery + privacy, poolside. You’ll be 5-10 minutes to beaches, restaurants, shopping, Main St, cafes + so much more!

Private beach, fully updated house, on 2 acres.
Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

Silver House: 3BR Home with Private Beach Access
Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and late check-out are NOT available in season

Modern East Hampton Home w/ Heated Saltwater Pool
Peace and serenity in East Hampton and minutes from the Village. This exquisite modern home features high-end finishes such as Sub-Zero and Wolf appliances, quartzite waterfall kitchen island and counters, marble tiled bathrooms, designer mid-century decor and separately zoned air conditioning. The heated saltwater pool is surrounded by a bluestone patio, Ipe deck and huge yard. The house also features two wood-burning fireplaces in the living room and den and an outdoor fire-pit. RR# 24-656

East Hampton Village Fringe, Renovated with Pool
This remarkable East Hampton home, nestled along a quiet cul-de-sac, is just moments from shopping, restaurants, and ocean beaches. The residence features an abundance of natural light, crisp neutral color tones, and tall, pitched ceilings that enhance the sense of space. The calming, heated pool provides a perfect retreat for relaxation. Please review our disclosures and house manual to ensure this home meets your needs and expectations. We want to make sure it’s the perfect fit for you.

Modern farmhouse w/ pool, beach, horses and winery
A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

The Sandpiper
Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Spacious East Hampton Getaway with Pool
This bright and comfortable 3 bedroom, 2 bath Scandinavian home awaits! Located just a 5 minute drive Sag Harbor and 10 minutes to the heart of East Hampton to enjoy beaches, shopping, restaurants and bars. The light hardwood floors create a crisp feel that you have to witness. The first floor's two guest beds open out to a lovely eat-in kitchen with dining and living rooms featuring a wood-burning fireplace and pool to check every box for year-round fun.

Carriage House - Cottage in East Hampton Village
Darling cottage in East Hampton Village. Situated in a historic picturesque tree-canopied neighborhood. Easy stroll to Newtown Lane and Main Street shops. (1/2 mile). Classic atmosphere. Very comfortable, bright, and clean. A perfect place from which to enjoy East Hampton and the surrounding area. Fully renovated (2019).

Designer East Hampton Farmhouse - Winter Warmth
Tucked away on a private lot, just minutes from East Hampton Village, Amagansett Village, and Ocean Beaches this 3-bedroom, 2.5-bath cottage features a heated saltwater pool & Mahogany outdoor shower, outdoor lounge area, and charming children’s playhouse - creating the perfect setting for relaxing days spent at home.

Charming Quiet Cottage
Escape to a quiet area of East Hampton. Access to a private Bay beach, nearby Farmer's market and art galleries. Only 5 miles from unique shops, movie theater, trendy restaurants and performance center Guild Hall. House is equipped with Smart TV and wi-fi. *Minimum Stay in July and August is (5) Five Nights

4 BD w/ Heated Pool in E Hampton, Fully Furnished
Rent a beautiful and spacious 4 bedroom/3 bathroom property in East Hampton with a heated swimming pool in the backyard. This three level house with large kitchen, central A/C, BBQ in the backyard, and a garage is the perfect place to entertain guests or to relax and escape in East Hampton.
Popular amenities for holiday rentals near Flaggy Hole Beach
Other top sights near Flaggy Hole Beach
Condo rentals with Wi-Fi

1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!

Beautiful condo on Long Islands Northfork

Montauk Waterfront Condo w/ Sunset Views

Endless Summer Studio Condo w Balcony Bayview

Beautiful Waterview Condo on the North Fork of LI

Condo on the Sound - Navy Beach

Waterfront Autumn Escape in Wine Country: 2BR

Beachside Waterview 2Br Condo w/ Pool in Greenport
Family-friendly house rentals

Private & Pristine with Pool and Kid’s Playard

Historic East Hampton Home - Private Beach Access

Chic East Hampton 7 Bedroom, 7 Bath, heated Pool

Southampton Charmer, 5 bedrooms w pool - Location

Sag Harbor Cottage, Walk to the Beach!

Secluded Luxury: New Gunite Pool, Walk to Bay

Large heated pool, games room, near private beach

DITCH PLAINS SURF HOUSE
Apartment rentals with air conditioning

Hamptons Hills Escape

Duffy's on Lake Montauk

Sunny Southampton Studio

Ocean View Studio with King Bed

Whaling Captain Pierson's Cottage

Ridgeview Suite at Stony Creek Depot

Renovated Guest Cottage close to E.Hampton Village

Modern Montauk retreat with wood stove by Harbor
Other great holiday rentals near Flaggy Hole Beach

2 BR apartment near ocean in Hither Hills

Secluded Oasis Heated salt Pool 5 min ride beach

The Hideaway | Clearwater Beach

Sunny, walk to beach, large pool

Greenport Condo with Stunning Views & Beach Access

Blue Jay Villa by Rove Travel | 7BR Home with Pool

Captains Quarters | Off Season avail. ask for deal

Hamptons Oceanfront Oasis
Destinations to explore
- Yale University
- Foxwoods Resort Casino
- Charlestown Beach
- Southampton Beach
- Cooper's Beach, Southampton
- Point Judith Country Club
- Ocean Beach Park
- Walnut Public Beach
- Shinnecock Hills Golf Club
- Blue Shutters Beach
- Groton Long Point Main Beach
- Cedar Beach
- TPC River Highlands
- Napeague Beach
- Brownstone Adventure Sports Park
- Woodmont Beach
- Silver Sands Beach
- Amagansett Beach
- Wildemere Beach
- Sandy Beach
- Ninigret Beach
- Outer Beach at Smith Point County Park
- Groton Long Point South Beach
- Clinton Beach




