Vacation rentals with a pool in Springs

4.9 out of 5 average rating, 111 reviews

Cozy, serene and private Hamptons home near it all

Escape to your private, serene and peaceful Hamptons home! Set on .5 acre of nature and beauty, near all of the best attractions. Cozy up at the wood-burning fireplace, cook in the large Chef's kitchen + stream on your 80' TV. Spark up the BBQ + firepit under the starry sky! Choose from the large book collection. Walk 1 block to the marina for water views. During Summer swim all day in the pool, enjoy beaches within 3-5 minutes, seaside dining within 5-10 minutes, Main Street and so much more!

4.96 out of 5 average rating, 101 reviews

The image showcases a spacious outdoor area featuring a heated gunite pool surrounded by manicured grass. Four loungers with umbrellas are positioned near the pool, while a cozy seating arrangement is visible on the patio. A charming cottage is seen in the background.

Cottage in The Hamptons

Modern Southampton Cottage | Heated Pool & Peloton

Modern Hamptons cottage with mid-century modern interior, our 3 bedroom/ 2 bathroom cottage is set on manicured grounds and perfectly equipped for your stay. Heated gunite pool (summer months only) with retractable cover, Peloton bike and Central Air throughout. Newly renovated kitchen with high end appliances, large outdoor deck perfect for entertaining with new Weber grill. Private driveway accommodates 4 cars. 4 adult bicycles. 8 min ride to Southampton village. 15 min to Coopers Beach.

Guesthouse in The Hamptons

A cozy bedroom features a queen bed with a light blue quilt and a green loveseat nearby. Natural light enters through sliding glass doors, revealing a serene outdoor space. A decorative plant and framed artwork add a touch of interest to the room.

4.82 out of 5 average rating, 339 reviews

Detached bungalow w/ private bath

Cozy, simple living, in separate guest house w/ use of amenities (shared with our family of 4) including sauna & hot tub. The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for 2 guests. 2 Adult guests ONLY, no children due to size of guesthouse and proximity to the pool. Please NO pets allowed since owners have pets

A bright living area features large windows that offer views of the nearby pond. Comfortable seating includes a white sofa, patterned chairs, and a coffee table, all arranged on a natural fiber rug. Light from the windows enhances the serene atmosphere.

4.87 out of 5 average rating, 117 reviews

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)

Relax with friends / family at this home in a magical setting overlooking Lily pond Completely private but 5 mins to Sag Harbor downtown / restaurants / Havens beach, and 10 mins to Bridgehampton. Location, location! And Views! - 3 Beds and 2.5 baths + pool house - Pool house with twin sofa bed + full bath - 50ft heated Gunite pool (125/d extra to heat) - Outdoor deck overlooking pond - Amazing views! - Fire pit with Adirondack chairs Unique house to unwind while being close to the action

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

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, 245 reviews

Montauk Waterfront Condo w/ Sunset Views

Modern 1 Bedroom Condo in gated community (Rough Riders) with sunset views from beautiful deck. The community has multiple tennis courts, pool, jacuzzi, and sauna (pool / sauna / jacuzzi only open Late May - early October). The property is great for walks along the boardwalk and many guests enjoy swimming off the pier. The unit is less than a 5 minute car / Uber ride to town and a short 5-10 minute walk to Navy Beach and Duryea's. Strong wifi in unit, Smart TV ( Netflix, etc, - no cable)

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.

An outdoor area features a rectangular pool surrounded by a wooden deck. Lounge chairs are positioned along the pool's edge, and a shaded seating area is located nearby under an umbrella. Lush trees provide privacy and a natural backdrop.

4.83 out of 5 average rating, 126 reviews

East Hampton Oasis - Pool and Hot Tub

Nestled at the end of a private road in the Springs section of East Hampton, this classic Hamptons home will keep you and your friends/family entertained. Living room with sonos sound system, kitchen, 3 bedrooms, 2 bathrooms, outdoor living area with lounge chairs, a bbq, bar, pool and hot tub. All 3 bedrooms have AC. Towels and linens provided. Washer/dryer available. CLOSE TO BEACH AND EH VILLAGE. The pool is open May 5 through October 5. The hot tub remains open year round.

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.

Guest suite in The Hamptons

4.97 out of 5 average rating, 173 reviews

Private central cozy king suite 2 baths fireplace

Beautiful, bright, spacious King suite w fireplace, two en-suite bathrooms & private separate poolside entrance. We are just minutes to beaches, boating, golf, hiking, biking, yoga and wineries. Play games, grill or cozy up fireside w a good book or movie. The space is creatively designed with a nod to natural elements and luxe comfort. Sleep your very best on our super deluxe king sized bed w/your choice of pillows. Complimentary coffee/tea/treats

A spacious and heated swimming pool is surrounded by a brick patio and lush green landscaping. Two lounge chairs are positioned nearby, offering a tranquil spot to relax. The serene setting is enhanced by mature trees bordering the pool area.

4.87 out of 5 average rating, 117 reviews

Cheerful East Hampton home with Pool

Situated off of a quiet lane on one and a half-acres of land, this amazing residence offers a peaceful and quiet Hamptons getaway. The home consists of 4 wonderful bedrooms, 3.5 modern bathrooms, a heated pool & mature landscaping. Additionally, please read my disclosures and "rules". Not a party house. No Events, parties & No smoking will be permitted. The house is beautiful, tranquil and very comfortable. THANK YOU!

Popular amenities for Springs rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 45 reviews

Home in North Fork

Corwin House

A tranquil outdoor space features a sparkling pool surrounded by greenery. A light-colored bench with patterned cushions is positioned beside the water, offering a comfortable spot to relax. Bright flowers add a splash of color to the scene, enhancing the inviting atmosphere.

4.79 out of 5 average rating, 38 reviews

The Hummingbird House: E Hampton Beach House

A spacious living area features large windows dressed with natural shades, allowing ample light to filter in. Comfortable seating includes a plush sofa with blue accents, woven chairs, and a wooden coffee table. A modern kitchen area with a wine fridge is visible in the background.

5 out of 5 average rating, 43 reviews

Stunning Central E. Hampton Home w/ gunite pool.

Luxe

5 out of 5 average rating, 4 reviews

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

A spacious outdoor area features a heated gunite pool surrounded by natural stone tiles. Poolside loungers are positioned on one side, while a shaded table with umbrellas and a grill are visible on the patio. Lush landscaping and flowering plants enhance the serene environment.

4.86 out of 5 average rating, 43 reviews

Private East Hampton Estate

The exterior of a two-story house is depicted, featuring natural wood siding and multiple windows. A welcoming front porch with white railings is visible, surrounded by well-maintained shrubs and landscaping. The expansive green lawn enhances the outdoor space, complemented by a smooth driveway.

4.82 out of 5 average rating, 56 reviews

East Hampton Home w/Heated Pool & pizza oven

A serene outdoor space features a newly installed heated pool surrounded by a patio. The area is complemented by comfortable lounge chairs and lush greenery, providing a tranquil setting for relaxation. A wooden fence offers privacy, while manicured shrubs frame the pool.

4.9 out of 5 average rating, 78 reviews

Bright & Modern E Hampton Getaway w/ Pool & Spa

A well-maintained outdoor space showcases a heated pool lined with lounge chairs and umbrellas. Lush greenery surrounds the property, providing privacy and a serene ambiance. The modern home is visible in the background, with a patio area leading to the pool for ease of access.

5 out of 5 average rating, 7 reviews

3BR/3.5BA: East Hampton, Heated Pool, Hot Tub

Condo rentals with a pool

An aerial view captures a sandy beach bordered by lush dunes and shrubs. In the distance, the resort's accommodations are visible, nestled among greenery. The sky is clear with scattered clouds, creating a serene coastal atmosphere.

4.92 out of 5 average rating, 26 reviews

Second Floor Corner Unit Overlooking the Ocean

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, 40 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

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

4.88 out of 5 average rating, 160 reviews

A living room features a light-colored sofa against a neutral wall, complemented by a striped area rug. A wall-mounted TV and decorative elements, including a mirror and wall hooks, enhance the space. Soft lighting is provided by two standing lamps, creating a welcoming environment.

Condo in North Fork

Waterfront Autumn Escape in Wine Country: 2BR

Home rentals with a private pool

An inviting heated pool is surrounded by lush greenery and flowering landscaping. Comfortable loungers are positioned along the wooden deck, accompanied by a shaded umbrella. Steps lead from the poolside to a charming surrounding garden, offering a serene environment for relaxation.

4.84 out of 5 average rating, 49 reviews

Enchanting Home with Large Decks and Heated Pool

4.92 out of 5 average rating, 111 reviews

Bungalow in The Hamptons

East Hampton Ranch with Access to Clearwater Private Beach

A spacious backyard is highlighted by a bright blue swimming pool, featuring a whimsical white swan float. Surrounding the pool are several lounge chairs and umbrellas, set against lush green hedges and trees that provide privacy.

4.96 out of 5 average rating, 24 reviews

Perfect Getaway at Sunny Modern Shampton LakeHouse

A spacious deck is shown surrounding a large pool, with wooden flooring and colorful umbrellas providing shade. Comfortable outdoor couches with striped throws are positioned to face the pool, creating an inviting space for relaxation amid lush greenery.