Vacation rentals with a hot tub in Sagaponack

Secluded Luxury: New Gunite Pool, Walk to Bay

Welcome to the beautiful 5-bed, 3-bath Harbor House, located just a short walk from Gardiners Bay beaches. Enjoy open-concept living, fully equipped kitchen, comfy beds, gunite pool, private patio with gas grill & outdoor dining, hot tub, & fully fenced backyard. Walk/bike to harbor, rent kayaks, use our paddleboards, or explore nearby restaurants and shops. Whether you’re looking for a romantic getaway for 2 or a family vacation, our home is the perfect retreat for your next Hamptons adventure!

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)

Beautiful Sag Harbor BEACH House

My neighbor is building a house, I’ve lowered the price to reflect any construction noise. Walk to the most magical beach in the Hamptons! House is beautifully designer decorated. Mint Condition, everything you could want in a great Hamptons, Sag Harbor Home! Finished, super comfortable Basement Heated Salt Water Pool and Spa, w/ auto pool cover. Outdoor Shower, Fire Pit, Ping Pong Super Clean Fully stocked Washer/Dryer on Main level and upstairs Fully enclosed fenced in Backyard

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.

Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)

Ranked #1 AirBNB. 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).

Detached bungalow w/ private bath

Cozy, simple living, in separate guest house with use of amenities (shared with our family of 4). The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, micrwave, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for 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.

Chic East Hampton 7 Bedroom, 7 Bath, heated Pool

Elegantly designed 7 Bedroom / 7 Bath home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches and the vibrant Easthampton Village. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Kindly familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property are smoke-free.

Luxury Beach House | Pool & Hot Tub | Sag Harbor

Home is professionally managed by Montauk Rental Management Group. Welcome to Island View House, your ultimate summer getaway! This newly renovated Hamptons retreat is just 8 mins away from the charming Village of Sag Harbor and a short stroll to the breathtaking Long Beach. Get ready to relax in our secluded oasis, complete with a 40 ft heated salt-water pool and a rejuvenating hot tub, surrounded by a lush, terraced garden and majestic oak trees.

Cedar Hot Tub, Suana, Heated Pool walk to water

Heated pool through April 25-November 1st. Sauna & hot tub open year round. Kayak, swim, fish 3 mile harbor, 5 min walk to water, 1 mile to Sammy's Beach, 9min to EH village and 13min to Sag Harbor. organic bedding, best cookware, decorated with ligne roset, Roche Bobois etc. 3 bikes , 2-single sea kayaks. New HUUM Sauna, 1200 sq ft ipe deck w/ cedar hot tub. *POOL HOUSE with additional queen bed, full bath and steam shower available May 1st.

Private Oasis W/Stunning Vinyard and Pool Views

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

Chic Southampton Retreat – Near Beaches & Village

Chic & cozy Hamptons retreat just minutes from Southampton Village and beaches! Enjoy a private backyard with sundeck, hot tub, fire pit, outdoor shower, and indoor fireplace. Next door to world-famous Shinnecock Hills Golf Club and 15 mins to Poxabogue public course. Close to Wölffer Estate, Duck Walk, and Channing Daughters wineries. Walk the nearby Scallop Pond Preserve or Elizabeth Morton Wildlife Refuge. Perfect year-round getaway!

Gated Amagansett Ranch Pool, Hot Tub & Fire Pit

Modern 4BR 3BA ranch in Amagansett with gated entry pool, hot tub, fire pit, and patio. Just a 5 minute drive to the ocean and a short stroll to the Village. Perfect for families or friends with a private gym and studio, central air, WiFi , and generator. Sleeps 8. Pool and hot tub open May to Oct. Guests rave about their stays, check out the amazing reviews and see why this Hamptons getaway is a guest favorite year after year.