Holiday rentals with outdoor seating in Springs

A serene sunset is captured over the bay, with warm hues reflecting on the water's surface. Silhouettes of wooden posts emerge from the calm waves, creating a tranquil atmosphere. The horizon showcases a mix of colors as the day transitions to evening.

4.95 out of 5 average rating, 251 reviews

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.

A bright living area features a light grey sofa paired with two black chairs, positioned around a glass coffee table. Large windows allow natural light to fill the space, while a minimalist fireplace offers visual interest. A small desk is visible against the wall.

4.95 out of 5 average rating, 487 reviews

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

A serene pool area is surrounded by lush greenery and colorful hydrangea flowers. Lounge chairs offer relaxation under large umbrellas, while the inviting pool reflects the clear blue sky. A charming home stands in the background, adding to the peaceful setting.

4.92 out of 5 average rating, 122 reviews

Southampton Charmer, 5 bedrooms w pool - Location

This 5-bedroom home boasts en-suite baths and elegant furnishings. The gourmet kitchen features marble countertops and stainless steel appliances, leading to a dining area. The lower level includes a spacious seating area and a game room with toys. The second floor houses a master suite with stunning views and three additional en-suite bedrooms. Located minutes from the village center, with restaurants, shops, and beaches nearby. A heated pool invites you to relax and enjoy the comfort of home.

A tranquil saltwater pool area is surrounded by lush greenery, featuring four sun loungers with colorful cushions. A large blue umbrella provides shade on the paved deck, enhancing the outdoor relaxation space.

4.87 out of 5 average rating, 223 reviews

CozyFallRetreat,Walk2Beach,FencedYard4Pup,Spotless

Meticulously cleaned home.Tranquil family neighborhood in historic artist's beach community.Heated saltwater pool.Wood burning fireplace.Private fenced-in backyard.Half mile to private bay beach. Bike great trails & savor delicious meals prepared in fully equipped kitchen.Enjoy Clearwater Beach's renowned sunset. Easy living home.We welcome all respectful guests.East Hampton's best restaurants are nearby.Smoke free.Small dogs permitted.Cell reception booster! Ask about EVcharger.RentalR-25-705

4.84 out of 5 average rating, 160 reviews

A light-filled living area features a cozy neutral sofa, accompanied by a matching armchair. A decorative coffee table sits in the center, and a Smart TV is mounted on the wall. Sliders lead to a private waterfront deck with seating, enhancing the space's openness.

Condo in North Fork

2 BR Waterfront Autumn Escape in Wine Country

Overlooking the Long Island Sound, this oceanfront condo is the ultimate escape. Bask in the sun on a private beach or unwind on the waterfront deck with breathtaking views Minutes from the town center, you’ll find local farms, award-winning wineries, gourmet restaurants & charming shops ⚓️ Explore Greenport: A historic seaport with coastal charm & rich culture 🏖 Premium Amenities – Waterfront deck, private balcony, grills, pool, private beach & parking ⛴ Ferry Access to Shelter Island & CT

4.9 out of 5 average rating, 114 reviews

Private oasis~1 block to water, 5 mins to Main St.

Escape to your chic, serene, Hamptons oasis! Perched back on a large piece of private property, located just steps to the water. During Summer, swim in your large pool, BBQ + spark up the firepit under the starry sky. Stroll just 1 block to waterfront dining for dinner, cocktails + the most magnificent sunsets in the area. Curl up at the wood burning fireplace, 80' TV + cook in the Chef's kitchen. You'll be 1 block to the water, 5-8 minutes to many beaches, Main Street, shopping + much more!

A modern home is set on a spacious green lawn, featuring a combination of wood and metal siding. Large windows allow natural light to fill the interior. A stone pathway leads to the entrance, framed by lush landscaping and trees, enhancing the outdoor tranquility.

4.89 out of 5 average rating, 116 reviews

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

A crystal-clear swimming pool is surrounded by a landscaped garden featuring lush greenery and blooming flowers. Natural stone patio borders the pool, offering space for lounging and relaxation in a private setting nestled among trees.

4.98 out of 5 average rating, 137 reviews

Explore the Water & Woods at a Relaxing Retreat

Flick through records under soaring ceilings and hang out in the year-round hot tub at this East Hampton open-plan retreat. Unwind in the wooded backyard, take a dip in the pool or spa, detox in the sauna, grill on BBQ, relax in the movie-theatre seats to watch a film, then snuggle up to fireplace or firepit before drifting to sleep in super comfy beds. Minutes to village, beaches and hiking trails. Terrific for families & friends looking for a relaxing getaway. (No AI used in these photos!)

A spacious backyard is highlighted by a blue in-ground pool surrounded by lounge chairs. Red umbrellas provide shade, while a tall wooden fence adds privacy. Lush green grass complements the natural setting, and a rustic home is visible in the background among the trees.

4.92 out of 5 average rating, 127 reviews

Private & Pristine with Pool and Kid’s Playard

INSTANT BOOK/ dates are current. Private and Pristine 3 bed / 2 bath home in the heart of East Hampton set on 1.3 acres. Home features a chef's kitchen, in-ground gated pool, and pure privacy and relaxation. Close proximity to East Hampton Village (5 mins) and East Hampton, Amangansett and Bay Beaches (7mins), Montauk (20 mins), Sag Harbor (15 mins). Kids adore the huge playground! Entire property fenced-in to ensure the safety of kids! Heated Pool open: Memorial Day - Sept 30.

A cozy bedroom is shown, featuring a spacious bed adorned with a floral quilt. Light streams through multiple windows, illuminating the room. A white dresser and closet are visible, while a green yard can be seen through the windows.

4.82 out of 5 average rating, 138 reviews

Sunny & Serene Private Cottage near Downtown EH

Our lovely one-bedroom cottage sits on a quiet lane 3/4 of a mile from downtown East Hampton. The cottage is light and bright, with whitewashed walls, vaulted ceilings and skylights, lots of windows and beautiful minimalist décor. It's an incredibly peaceful place to wake up in the morning, with a gorgeous green yard right outside the many bedroom windows. Every bay and ocean beach around East Hampton is 5-10 minutes away and Nick and Toni's is less than a 10 minute walk.

4.94 out of 5 average rating, 381 reviews

A bright living room features a comfortable gray sofa against a neutral wall, complemented by a light-colored rug with geometric patterns. A wooden coffee table sits in front, with a lounge chair nearby. Natural light enters through multiple windows, creating a spacious feel.

Home in North Fork

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).

The exterior of the house is depicted, showcasing a light-colored siding with brick accents. The entrance features a covered porch supported by white columns. Two windows are visible on the front, framed with white shutters, and a well-maintained yard adds to the setting.

4.92 out of 5 average rating, 180 reviews

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

Popular amenities for Springs outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

A grassy backyard area features a circular arrangement of four wooden Adirondack chairs surrounding a fire pit. In the background, a saltwater heated pool is visible, framed by lush trees and shrubs, creating a serene outdoor space.

4.95 out of 5 average rating, 38 reviews

Designer Home w/ Heated, Salt-Water Pool

The living area features a cozy fireplace with modern seating options positioned around a stylish coffee table. A large overhead light fixture adds a unique touch, while greenery and decorative elements enhance the space's tranquility. Large windows allow natural light to fill the room.

5 out of 5 average rating, 22 reviews

Walkable Designer Home in East Hampton Village!

A bright living area features a spacious sectional sofa and an armchair, arranged around a rustic coffee table. Sunlight streams through multiple skylights and large windows, providing views of the lush greenery outside. A flat-screen TV is mounted above a brick fireplace.

5 out of 5 average rating, 27 reviews

Enchanted Story Book Home

A spacious deck surrounds a heated pool, featuring a light blue surface reflective of the sky. Four sun lounge chairs are positioned for relaxation, and an outdoor dining area with a retractable awning is available. Lush trees provide a natural backdrop to the serene setting.

5 out of 5 average rating, 74 reviews

East Hampton Rental w/ Pool, Moments to Amenities

The exterior of the home features a modern facade with natural wood siding and a green lawn surrounding a heated pool. Two umbrellas provide shade for patio seating, while large windows allow for ample natural light. Trees frame the backdrop for a serene atmosphere.

4.98 out of 5 average rating, 40 reviews

Chic East Hampton 7 Bedroom, 7 Bath, heated Pool

An in-ground salt-water pool is surrounded by natural stone, set amidst lush greenery. Sun loungers are positioned alongside the pool, and a shaded seating area is visible to the right. A wooden structure stands in the background, blending with the tranquil landscape.

4.88 out of 5 average rating, 49 reviews

East Hampton Secluded Escape with Gunite Pool

An open living area features a large, neutral-toned sectional sofa and two black accent chairs, arranged invitingly on a light-colored rug. A skylight provides natural light, and vertical blinds partially cover the windows. A neutral coffee table sits in the center, complemented by a modest side lamp.

4.94 out of 5 average rating, 47 reviews

Sparkling East Hampton Oasis 3/2, heated pool

A bright living room features large windows that showcase water views. Comfortable white sofas are arranged around a wooden coffee table, while a dining area is visible in the background. A ceiling fan and a wall-mounted TV add to the room's functionality.

4.91 out of 5 average rating, 46 reviews

Wake up to Stunning Views at a Serene Waterfront Haven

Apartment rentals with outdoor seating

A charming two-story house is nestled among lush greenery, with large windows reflecting sunlight. The wooden exterior features shingle siding, and a gentle slope of grass leads up to the entrance. Surrounding trees create a serene, private atmosphere.

4.96 out of 5 average rating, 163 reviews

Hamptons Hills Escape

4.96 out of 5 average rating, 166 reviews

A bright and airy great room combines kitchen, dining, and living areas. Light wood cabinetry and stainless steel appliances complement the open layout. Soft white sofas with navy pillows are arranged around a wooden coffee table, and a round mirror enhances the natural light from multiple windows.

Apartment in North Fork

Upscale Newly Constructed Apartment

Apartment in Shelter Island Heights

A round wooden dining table is surrounded by four metal chairs. Natural light enters through two large windows, with framed black-and-white photographs arranged on the wall beside them. A decorative centerpiece is placed on the table, offering a rustic touch to the space.

4.9 out of 5 average rating, 259 reviews

Squire Chase House

A well-lit living area is highlighted by a cream-colored sofa with nautical-themed pillows. A wooden coffee table features shells and a vase of flowers. Display shelves in the background hold decorative items, with natural light streaming through large windows.

4.84 out of 5 average rating, 141 reviews

Vacation at the Beach: Entire Home

A bright living area is depicted, featuring a sleek sofa, a wooden coffee table, and a round dining table surrounded by red chairs. The space incorporates a large potted plant, and light streams through a nearby window, illuminating the whitewashed wood floors.

4.97 out of 5 average rating, 129 reviews

Renovated Guest Cottage close to E.Hampton Village

4.94 out of 5 average rating, 139 reviews

A serene beach scene captures a golden sunset reflecting on calm waters. The sandy shore leads to gentle ripples, while distant land silhouettes frame the horizon. A tranquil ambiance is created as the sun descends, providing a peaceful setting for evening strolls.

Apartment in South End

Bright, Southold Studio Apt near beach & town

4.92 out of 5 average rating, 121 reviews

A cozy living area features a comfortable gray sofa adorned with patterned pillows. A light-colored side table and an illuminated lamp create a soft glow. A decorative coffee table sits in front, accompanied by a potted plant in the corner, adding a touch of greenery.

Apartment in North Fork

Private 1st flr apt w/ patio 3 blocks from beach

A sandy path leads through beach grass, flanked by wooden fencing, toward a tranquil ocean beyond. Clear blue skies complement the scene, where gentle waves are visible on the horizon.

4.98 out of 5 average rating, 130 reviews

Walk to Bay and Ocean-Newly Renovated

Condo rentals with outdoor seating

An expansive hallway features arched doorways and rustic wooden beams overhead. Potted plants add greenery, while large windows dressed with floral curtains allow natural light to illuminate the stone floor. Comfy seating arrangements are positioned along the walls, creating inviting spaces for relaxation.

4.93 out of 5 average rating, 41 reviews

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

An aerial view displays the condo complex adjacent to the waterfront, featuring a central pool surrounded by a landscaped patio. The blue ocean extends beyond the property, with boats visible in the distance under a clear sky, enhancing the serene coastal environment.

4.94 out of 5 average rating, 34 reviews

Sun N Sound Resort, Montauk, NY

4.86 out of 5 average rating, 130 reviews

A living area features shiplap walls and ample natural light from large windows. A dark sectional sofa is positioned next to a glass coffee table with a small plant. An open kitchen area is visible, along with access to a screened porch through sliding doors.

Condo in North Fork

Beautiful condo on Long Islands Northfork

A view from the balcony overlooks the pool area, featuring a clear blue pool surrounded by lounge chairs. Colorful umbrellas provide shade for several tables, while the surrounding buildings reflect a simple, two-story design.

4.8 out of 5 average rating, 241 reviews

Montauk Royal Atlantic Beach Resort North

Two wooden Adirondack chairs are positioned on a spacious sun deck, overlooking expansive views of lush greenery and the waterfront. The bright blue sky complements the serene atmosphere, creating an inviting space for relaxation and enjoyment of the natural surroundings.

5 out of 5 average rating, 246 reviews

Montauk Waterfront Condo w/ Sunset Views

A spacious studio is shown, featuring a king-size bed with crisp white linens. Natural light floods the room through large sliding doors that open to a private balcony with views of the waterfront. A ceiling fan hangs above, and a sitting area with a green sofa is present.

4.9 out of 5 average rating, 10 reviews

Endless Summer Studio Condo w Balcony Bayview

4.9 out of 5 average rating, 176 reviews

The living area features a spacious dark gray couch, a light wooden coffee table, and a white dining table with woven chairs. Natural light filters through the window with plantation shutters, while decorative elements like a round mirror and wall art create a welcoming ambiance.

Condo in North Fork

Beautiful Waterview Condo on the North Fork of LI

A sunlit corner of the room features a tall plant stand made of natural materials, adorned with various plants. Sheer curtains are gracefully draped over a glass door, leading to a balcony overlooking a pool area, creating an open and airy feel.