Vacation rentals with a hot tub in Southold

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Top-rated hot tub rentals in Southold

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Guest favorite

Cottage in Guilford

4.96 out of 5 average rating, 158 reviews

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

Feb 23 – Mar 2

G$70,039 GYD per night

Superhost

Villa in Greenport

4.84 out of 5 average rating, 32 reviews

Year-Round Heated Pool Villa - 3 blocks from town

Pool heated to hot tub temperatures & open year round! This brand new construction house is perfect for large groups. Gather with friends and family in the double height ceiling open concept living room/dining room/kitchen area. Soak up the sun lounging by the pool. Take a super short walk to town to enjoy the incredible local shops, restaurants, and bars. Then end with a nightcap relaxing in the heated hot tub seating section of the pool. There's no better place to stay in Greenport Village.

Mar 10 – 17

G$181,780 GYD per night

Superhost

Cottage in Cutchogue

4.69 out of 5 average rating, 187 reviews

Lovely 2 BR Beach House No. Shore

Our adorable 2 BR cottage in the heart of wine country in LI's North Shore is impeccably decorated with a separate breezy, sunny dinning room and screened in porch and a Jacuzzi in our bathroom. We are less than 1/2 mile walking distance to two beaches or less via our kayak! Wifi. Please note that local Southold town ordinance requires a 14 night minimum stay. Please contact us to discuss. Please contact us about our off season rates. Unfortunately, we can no longer accept pets of any kind.

Apr 19 – 26

G$41,276 GYD per night

Guest favorite

Home in East Hampton

4.97 out of 5 average rating, 120 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.

Oct 15 – 22

G$146,276 GYD per night

Guest favorite

Home in Southold

4.88 out of 5 average rating, 16 reviews

Luxury by the Sea!!

Your search 👀 is over! Brand New 🔨 Construction. Charming, luxurious, private, comfortable Beach 🏖 House. This home is beautifully designed with too many architectural details to list. Property is fully furnished 🛋 with no detail spared . Open floor plan, spacious great room with gas fire place and flat screen, and gourmet eat 🍝 in kitchen with large island is a wonderful place to entertain 🥂. Brand new washer/dryer, butlers pantry and mud room. Where the country meets the sea 🌊.

Mar 11 – 18

G$103,677 GYD per night

Guest favorite

Guesthouse in Southampton

4.98 out of 5 average rating, 45 reviews

Southampton Modern Barn, Private Hot Tub and Pool

This magical getaway delivers peace and relaxation. Wake up to coffee on your private deck with bucolic views. Play in your heated, saltwater pool, and relax under the stars in your hot tub (open year round). During your stay, these amenities and more will be for your personal use. Stroll to the owner’s dock on Big Fresh Pond, for paddle boarding, kayaking and sunsets. You can also drive 8 minutes to Southampton Village for shopping, restaurants, art galleries and Ocean Beaches.

Sep 9 – 16

G$137,269 GYD per night

Guest favorite

Home in Southold

4.92 out of 5 average rating, 12 reviews

Beach/Lake house Fireplace & Hot Tub, By Wineries

Welcome to The Dune Retreat, a Beach & Lake House in the charming North Fork, close to all wineries. Perfect for 8 to 10 guests, enjoy the indoor fireplace, outdoor fire table and fire pit, ensuring a memorable getaway for Friends & Family. Enjoy a Private access to Great Pond Lake directly from our backyard and a 5min walk to Kenney's Beach. Soak in the hot tub on the deck after a day exploring the North Fork, kayak on the lake, swim in the Sound, relax and stay a while.

Jun 11 – 18

G$137,795 GYD per night

Guest favorite

Home in East Hampton

4.97 out of 5 average rating, 116 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.

Nov 9 – 16

G$190,757 GYD per night

Guest favorite

Home in Peconic

5.0 out of 5 average rating, 50 reviews

Charming Victorian-style Mansion near Greenport

Timeless antique-style furnishings inspired by our rich history at the turn of the 20th century. Each room has been carefully selected to preserve the unique architecture and character of the house. Excellent location for small gatherings and families. Large dining table with adjoining kitchen. Plenty of kitchenware for communal meals. House comfortably sleeps 12. If you are a party of 14 please confirm with us and we will give you special accommodations.

Sep 15 – 22

G$193,469 GYD per night

Guest favorite

Home in Cutchogue

4.96 out of 5 average rating, 190 reviews

Stunning Vinyard Views - Spring Special $475/Nt!

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.

Mar 19 – 26

G$173,654 GYD per night

Guest favorite

Guesthouse in Shelter Island

5.0 out of 5 average rating, 50 reviews

Bayfront 1BR/2BR detached guesthouse with pool

Perfect relaxing getaway for a couple or family. Bayfront 1BR/2BR fully detached guest house with gorgeous morning views. Property has saltwater pool + hot tub (open May -October) and bay access via private dock. Central to both north & south forks (wineries + Hamptons or Montauk just short drive away). Down the road from famous Shelter Island Sunset Beach + golf course. Come explore the beauty of the Hamptons without the stress!

Sep 21 – 28

G$84,188 GYD per night

Guest favorite

Home in Mattituck

4.95 out of 5 average rating, 37 reviews

Mattituck Dream House - Summer Rental Opportunity

The Mattituck Dream House, is high on a hill overlooking the Mattituck Inlet on the North Side of town. Four bedrooms, with queen beds in 2rooms, a full in one room and a king bed in the master suite. Friends tell me it feels like they are away at a destination vacation! I would like to rent my house for the summer, but I could also do monthly. June, July & August. You could get beach passes from Southold Town if renting.

Oct 2 – 9

G$108,272 GYD per night