Vacation rentals with a hot tub in Wainscott

The image captures a spacious outdoor area featuring a large heated pool with a fountain and surrounding stone patio. Nearby, lounge chairs are arranged for relaxation, while a generous lawn stretches in the background, accompanied by a well-designed home nestled among trees.

4.78 out of 5 average rating, 146 reviews

Sprawling Hamptons Estate with Hot Tub & Amenities

Spacious & private Hamptons Oasis. High speed WiFi. Family friendly. Massive home on 1.4 acres hosts 15 guests across 6 bedrooms, 8 beds, 4 full baths plus crib & pack 'n play. Gorgeously decorated by Judy Posey Large heated gunite pool (42 x 20 feet) hot tub and sundeck. Fireplace, over-sized kitchen w/ 3 fridges, electric wood-fired grill, huge yard, firepit, bar/lounge, Golden Tee arcade™, bikes & kayaks. Just 2 miles from towns of East Hampton and Amagansett and several white sand beaches

Guesthouse in East Hampton

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.

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

4.83 out of 5 average rating, 355 reviews

5.0 out of 5 average rating, 26 reviews

Cottage in Bridgehampton

Cozy Bridgehampton Cottage w/Hot Tub & Fire Pit

This exclusive modern cottage blends attractive architectural design with warm, inviting interiors, offering a private park like retreat just moments from the village's finest vineyards, restaurants, shops, & beaches. Family-friendly, work-ready and equipped with high speed internet. Ideal for small groups, families, or remote workers. Bridgehampton/Sag Harbor Attractions: Wolfer Estate Vineyard, Children’s Museum, Hampton Classic Horse Show, Bay Theatre, Long Wharf & Golf Clubs. Come and relax!

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.

4.91 out of 5 average rating, 92 reviews

Bright & Modern E Hampton Getaway w/ Pool & Spa

✨ New Pool & Peaceful Outdoor Oasis ✨ Your ideal Hamptons escape! Just 7 mins to East Hampton Village, 5 mins to Amagansett, & close to beautiful beaches, this updated saltbox home is perfect year-round. Enjoy: • A new pool, sunny patio, & hot tub • Fire pit, outdoor shower, & changing area • Open layout with bright kitchen, dining, & living areas • Cozy fireplace & private workspace Whether you’re poolside, beach-bound, or fireside, this home blends comfort & style for a relaxing getaway.

5.0 out of 5 average rating, 262 reviews

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.

Condo in Montauk

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 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, 148 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 contemporary house exterior features a combination of wood and metal finishes, set against a backdrop of lush greenery. Large glass windows provide ample natural light, and a pathway of stepping stones leads through a manicured lawn, enhancing the inviting atmosphere.

4.97 out of 5 average rating, 164 reviews

East Hampton (walking distance to village)

Relax by the hot tub and fire pit with local wines or walk to the village for shopping and dining. House is just a few blocks from Serafina and the famous Nick and Toni’s. Complimentary cruiser bikes included to get around town. IGA supermarket is around the corner and gas grill is on site and ready to use. The house is also walking distance to the train station if your coming from Manhattan. The second bedroom features a Murphy Bed that folds out of the wall and over the couch pictured.

4.96 out of 5 average rating, 189 reviews

Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊‍♂️ Heated Pool & Relaxing Hot Tub 4-person Sauna 🏀 Half Basketball Court & 🏐 Volleyball Area 🏌️‍♂️ Private Golf Putting Green 🔥 Cozy Firepit & Outdoor Lounge Area 🛝 Swing Set & Kid-Friendly Yard 🍽 Fully Stocked Kitchen & Spacious Dining 🌐 High-Speed Wi-Fi & Smart TVs 10 min to Smith Point Beach & Boardwalk 15–20 min to Long Island Wine Country Nearby hiking at Wertheim Wildlife Refuge Short drive to Tanger Outlets & restaurants

4.95 out of 5 average rating, 101 reviews

A well-designed outdoor area features a pristine pool with colorful floats, bordered by a spacious deck. Lounge chairs, adorned in striped blue and white, provide comfortable seating under large umbrellas. The house is illuminated, showcasing a welcoming atmosphere amidst lush greenery.

Villa in East Hampton

Insta: @staywithhamptonsmama PINKWOOD PLAYHOUSE is the perfect spot for your Hamptons stay, offering elevated design and relaxed luxury with laid back beach vibes. Perfect for families, friends or couples. This stylish and serene home features 4 bedrooms, 2.5 bathrooms, a fully equipped kitchen, soaring ceilings, games room and movie room. Bring the outdoors in with oversized windows and over 1000 square feet of deck space overlooking the gorgeous pool (can be heated for a fee).

A wooden structure with multiple windows is set among lush greenery. The deck surrounds a newly built pool, offering a serene outdoor space. The pool's clear water reflects the surrounding trees and the vibrant blue sky.

4.9 out of 5 average rating, 30 reviews

4 BR/3BA Quiet Pool Home

We welcome you to our family home, up to 5 guests, pets are welcome with additional pet fee. Nice new pool and surrounding deck with outdoor sitting area, chairs, umbrella, and charcoal grill. 1 gbps internet for movies streaming on disney plus, prime video, or for your work. 5-8 minutes to town and the beaches. Plenty of nice restaurants and great local shopping. We don't allow other guests on property that is not mentioned in advance. No gatherings and no parties. Thank You.

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, 144 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.

4.88 out of 5 average rating, 16 reviews

Home in Sag Harbor

Heated Pool and Spa in Sag Harbor w/ Tennis Access

Private Sag Harbor retreat just minutes from the Village, Beach & bay. This 4 bedroom, 2 bath home features a Brand New heated saltwater Gunite pool and built-in spa, spacious yard, outdoor dining. Inside are 2 living room areas, with a pullout couch and bright sunroom, 2 king bedrooms, 1 queen and 1 full, plus a fully equipped kitchen and dining for up to 10. Perfect for families and friends looking for a relaxing Hamptons getaway. Inquire below: IG @ Tal.Adla.Hamptons

Popular amenities for Wainscott hot tub rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a hot tub

Home in Shelter Island Heights

Surf Scoter Cottage Shelter Island

4.92 out of 5 average rating, 100 reviews

4.99 out of 5 average rating, 211 reviews

A screened-in patio features a wooden ceiling and overhead fans, providing a comfortable space for relaxation. A navy blue sofa pairs with a coffee table, while tall chairs surround a dining table. Views of a spacious yard and trees are visible through the screens.

Home in Greenport

Greenport Village walking distance to all

Home in Westhampton Beach

A contemporary ranch-style home is surrounded by lush greenery. The custom-shaped heated pool features a waterfall and is bordered by a stone patio with lounge chairs and umbrellas. A state-of-the-art hot tub is positioned nearby, enhancing the outdoor relaxation space.

Hampton's Haven

4.93 out of 5 average rating, 167 reviews

The exterior of a spacious home is illuminated by soft twilight, showcasing a private pool with a smooth, blue surface. A shaded dining area beneath a pergola sits next to the inviting outdoor seating area, featuring a fire table. The wooden deck surrounds the house.

5.0 out of 5 average rating, 41 reviews

Hamptons Pool & Spa Retreat | Gym + 3.5 Acres

A serene backyard features a heated salt-water pool with stone tile surrounding it. Lounge chairs are positioned beside a shaded cabana and an umbrella. Lush greenery offers a sense of privacy, enhancing the tranquil atmosphere of the outdoor space.

4.84 out of 5 average rating, 67 reviews

Salt Pool 4BR Sanctuary w ~Private Beach Access

5.0 out of 5 average rating, 20 reviews

Home in Water Mill

Luxury Southampton Home/outdoor Sauna/hottub

5.0 out of 5 average rating, 26 reviews

East Hampton Escape | Pool & Private Beach Access

5.0 out of 5 average rating, 45 reviews

A spacious backyard is featured, with a circular stone fire pit surrounded by several colorful Adirondack chairs. Lush green grass extends towards a charming white house in the background, bordered by trees under a clear blue sky.

Home in Southold

Private Waterfront Access + Hot Tub + Scenic Yard

Other vacation rentals with a hot tub

Guesthouse in Southampton

A serene outdoor space showcases a heated saltwater pool framed by neatly trimmed hedges. Comfortable lounge chairs are arranged beside the water, while a large umbrella provides shade. A two-story house is visible in the background, surrounded by greenery.

3 Bedroom Guest House in Southampton

4.96 out of 5 average rating, 23 reviews

5.0 out of 5 average rating, 17 reviews

Cottage in Hampton Bays

Swim into Fall & Hot Tub through Winter!

Guest suite in Sag Harbor

A refreshing outdoor pool is surrounded by a paved area, featuring several potted plants and lounge chairs. Shade is provided by an umbrella next to the pool, while a wooden fence offers privacy. Sunlight illuminates the vibrant blue water.

1 Bedroom Apartment Sag Harbor with Pool/Hot Tub

5.0 out of 5 average rating, 29 reviews

4.96 out of 5 average rating, 45 reviews

A spacious backyard is bordered by lush greenery and has a view of the tranquil water. Two surfboards are propped against the house, and a set of bright pink chairs surrounds a dining table. Pathways made of stones lead to the water's edge.

Home in Shelter Island

Waterfront shelter island gem

5.0 out of 5 average rating, 12 reviews

A bright living area features wood-paneled ceilings and large windows with natural light filtering in. Two black sofas are arranged around a coffee table on a light-colored rug. A television is positioned on a wooden stand, while plants add a touch of greenery.

Home in Hampton Bays

Relax & fun home

A modern round house stands prominently, featuring large windows that allow natural light to illuminate the interior. The exterior showcases a sleek design and is surrounded by a landscaped area, providing a serene and inviting entrance. Two chairs are positioned on the front porch.

4.77 out of 5 average rating, 35 reviews

Rare ROUND home in EH - salt water pool & hot tub

5.0 out of 5 average rating, 57 reviews

The exterior of a contemporary home is presented, featuring a well-maintained lawn with a fire pit surrounded by several outdoor chairs. A hot tub is visible on the side, set against a backdrop of lush greenery and a clear blue sky.

Home in Montauk

Stylish Montauk Village Escape for Any Season