Holiday rentals with a hot tub in Sag Harbor

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

Outdoor spaces · Bathroom · Condition

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

Outdoor spaces · Hot tub · Layout

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!

Outdoor spaces · Hot tub · Comfort

Swimming pool wIth Fire Pit /Coffee Bar

Relax in this cozy loft filled with amenities that will create lasting memories. Recently renovated so fresh and clean. Located on a wooded lot. Large fenced in landscaped yard with hammocks and firepit. Heated pool seasonal. We are just minutes from the beach. Spend time in our 6 person jacuzzi. 10 min to Southampton village. 15 min to Sag Harbor. Centrally located. Fresh farm (home of Tate’s Cookies) around the corner with fresh meats and produce. A tasty restaurant near by and a deli too.

Hot tub · Outdoor spaces · Amenities

Calf Creek Cottage (Water Mill/Bridgehampton)

Enjoy the peaceful seclusion of this charming, updated 3 bedroom, 2 bath cottage located on a private, acre-sized flag-lot south of the highway right on the border of Water Mill and Bridgehampton. Each bedroom (1 king, 2 queen) features ample closet space and new smart TVs . The new, fully-stocked kitchen, propane BBQ, outdoor dining table for 8, outdoor shower and spa with lounge furniture, and wood burning fireplace make it the perfect getaway for either summer or the winter season. Pets OK.

Outdoor spaces · Hot tub · Condition

Southampton Village Newly Built Gem

Enjoy a stylish experience at this 3765+ sq ft., just built, SH Village gem! Beautiful and bright spacious home with 5 well appointed bedrooms, multiple custom closets and 5.5 baths (4 ensuite). Luxurious lighting fixtures throughout the home. Living room fireplace, vaulted wooden beam kitchen ceiling with formal dining for 10 plus. Gunite pool and spa, with multiple outdoor seating areas. Expansive media room with 75 inch TV and room length comfy cloud sofa. Two sets of washers and dryers.

Bathroom · Outdoor spaces · Access

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!)

Bathroom · Outdoor spaces · View

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.

Bathroom · Hot tub · Cleanliness

Luxe|Pool|Games|Movie|HotTub|Firepit|MegaChess

SERENITY AT SHOREWOOD Pool is Open April 1 - November 1. Must be 25+ to book. Luxurious Newly Renovated Mid Century Modern Home in East Hampton with Beach Car! Peaceful and stylish with three bedrooms, 3 1/2 baths, spectacular great room, huge deck, heated pool and more, less than four miles to the heart of East Hampton Village, world renowned for its restaurants, shopping and ocean beaches. A designer-curated architectural gem! Kick back and relax in this calm, stylish space.

Bathroom · Outdoor spaces · Layout

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.

Bathroom · Hot tub · Walkability

Stylish & Chic w hot tub/ Near Beaches & Village

Stylish Hamptons retreat just minutes from Southampton Village and the area's best beaches. Enjoy a private backyard with a brand-new oversized deck, new outdoor shower, hot tub, fire pit, and sun lounge - perfect after a day at the beach. Cozy up by the indoor fireplace on cooler evenings. Next to Shinnecock Hills Golf Club, 15 minutes from Poxabogue, and close to Wölffer Estate, Duck Walk, Channing Daughters, Scallop Pond Preserve, and Elizabeth A. Morton Wildlife Refuge.

Outdoor spaces · Bathroom · Indoor spaces

1 Bedroom Apartment Sag Harbor with Pool/Hot Tub

Enjoy a relaxing experience at this charming apartment in our private home in Sag Harbor with shared use of pool and hot tub. The apartment has a separate entrance. 10 minute walk into town and bay beach. Bathroom has a shower stall no tub. Kitchen has a full refrigerator, toaster oven and microwave. Shared use of washer/dryer. Bath towels, sheets and beach towels included. Minimum 3 night stay. Maximum 2 people per stay. No smoking, no overnight guests.

Hot tub · Outdoor spaces · Hospitality