We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals with Pools in Montauk, NY

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    $0
    $1,109 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travellers to Montauk are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    Clear All
    1 / 24
    5 of 5 bubbles (6) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    1 / 5
    3 of 5 bubbles (1) Average
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    1 / 14
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    1 / 18
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Housekeeping...
    • Ocean Views
    • Wi-Fi
    • Washer
    • Hot Tub
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The professionally styled, newly renovated/furnished upside down house is on a private wooded acre with ocean views from the living areas and is one block to ocean beach and Gurney’s. The open living/dining/kitchen and master bedroom suite are on the top floor. An additional bedroom suite, 2... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 30
    5 Bedrooms, 8 Bathrooms, Sleeps 10 | Quick View
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Private Outdoor...
    • Waterfront
    • DVD Player
    • Ocean Views
    • Wi-Fi
    • Satellite TV
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    ​This magnificent oceanfront estate in Montauk on Long Island's eastern tip is truly one-of-a -kind. This 5 bedroom, 7 bath home has been cleverly designed to maximize the spectacular ocean views from every possible vantage point. The open floor plan includes a living room with cathedral... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Washer
    • Grill
    • Private Outdoor...
    • Patio
    • DVD Player
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Contemporary Chalet with pool, beautifully furnished, is now available for Montauk's most beautiful season of all … Indian Summer. Accepting reservations for Sept & Oct. 3 Bedrooms / 2 full baths + Outdoor shower Room. Huge wrap around cedar deck. AC in every room (never needed). Perfect central... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 25
    6 Bedrooms, 4 Bathrooms, Sleeps 13 | Quick View
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Hot Tub
    • Patio
    • Washer
    • DVD Player
    • Shared Outdoor Pool...
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Spend your New York retreat in style by staying at this exquisite 6-bedroom, 4-bath vacation rental home. With room for 13 guests, outstanding at-home amenities and a prime location just a short walk from the beach, this home has everything you need! This phenomenal abode is outfitted with... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 44
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Hot Tub
    • Private Outdoor...
    • Washer
    • Air Conditioning
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy a view of Lake Montauk at our gorgeous Arty Montauk Villa. A wrap-around porch, dormers - without sacrificing any modern amenity - central air, stainless steel appliances, marble counters - that you are accustomed too. Close to the best surf beach, stroll to one of the best restaurants in... View all property information
    Location Information
    Montauk, Hamptons 11954
    We couldn't find properties that match all your filter selections. View all properties below, or reset your filters
    1 / 11
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other traveller has booked this property
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Housekeeping...
    • Ocean Views
    • Hot Tub
    • Sauna
    • Balcony
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Situated on Montauk's most pristine stretch of oceanfront real estate, Gurney's Montauk Resort & Seawater Spa is a Hampton's icon and the only four-season resort in Montauk. With five unique dining and cocktail venues, guests can enjoy a wide range of dining options, from elegant seasonal cuisine... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 18
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    other travellers have booked this property
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Patio
    • Waterfront
    • Hot Tub
    • Grill
    • Housekeeping...
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    WE OFFER ONLY MONTHLY RENTALS IN JULY AND AUGUST. Our Montauk Home is a 2 bedroom, 2 bathroom beautiful remodeled and refurbished villa. There is a queen size bed and closet in each room, the master bedroom has its on bath-toilet and shower. The living room and dining room is spacious with a fire... View all property information
    Location Information
    Montauk, Hamptons 11954
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 41
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Shared Garden
    • Grill
    • Wi-Fi
    • DVD Player
    • Washer
    • Outdoor Dining Area
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    One large fishing cabin from the 20's has been redesigned and renovated with upcycled materials for contemporary loft style living with a Mediterranean touch. 3 bedrooms, 2 bathrooms (claw foot bathtubs), and a loft style common room with cathedral ceiling. Concrete floors and antique tiles keep... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 5
    3.5 of 5 bubbles (6) Average
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Satellite TV
    • Parking
    • Balcony
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This newly renovated cottage in the heart of Montauk is 1000 feet from the ocean beach. It is a free standing cottage with a large back yard for entertaining. It has been in our family for over 70 years. It has central heat and air, with hard wood floors and modern. It is located between the... View all property information
    Location Information
    Montauk, Hamptons 11954
    5 of 5 bubbles Reviewed 30 August 2016
    Great location! Cottage was also very clean and well kept, perfect for our family beach vacation. Will definitely go back
    4 of 5 bubbles Reviewed 31 July 2016
    The cottage was very clean, well equipped and inviting. The location was terrific, only a block from the beach and town. We enjoyed the open floor plan and the lovely yard. We...
    See all reviews
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other traveller has booked this property
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Internet Access
    • Washer
    • Satellite TV
    • Parking
    • Patio
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    4BR House Minutes From Ocean & Across From Montauk Downs (golf, Tennis, Pool) This newly listed and furnished 4 bedroom, 2 bathroom beach house in Montauk is ready for August through Labor Day weekend. Also available in September. The property is across from Montauk Downs - public tennis, golf,... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Grill
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Two bedroom cottage with vaulted ceilings set on a double lot, last house on a dead end quiet road with a pond and a nature preserve across the road. Lots of outdoor living/dining space. Outdoor shower, gas grill, herb/flower gardens, washer/dryer. 5 minute walk to private neighborhood sound beach... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 12
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Washer
    • Patio
    • Satellite TV
    • Housekeeping...
    • Air Conditioning
    • Secure Parking
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This Is a smartly furnished, relaxing house close to everything that beautiful Montauk has to offer. We just purchased the house In April 2015 and did an extensive renovation... new bathrooms, new floors, new A/C, painted, and new appliances. The house Is warm and relaxing and is drenched in... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 10
    3 Bedrooms, 5 Bathrooms, Sleeps 6 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • DVD Player
    • Patio
    • Air Conditioning
    • Washer
    • Porch
    • Parking
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Try finding another rental so fully-stocked with all of the comforts you're used to in your own home! <BR><BR>This is a beautiful and cozy Montauk beach home, newly-renovated with clean, hardwood floors, spacious living area and kitchen. This house includes an awesome deck, complete with full... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Washer
    • Patio
    • Balcony
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Stay in Montauk, but hide from the club scene at our clean and roomy beachhouse Our spacious and modern condo townhouse on the golf course is perfect for one or two families to share. There are two master suites, and a kids room with 5 beds. 2 full bathrooms and one half, ensure there is never a... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 12
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Patio
    • Internet Access
    • Satellite TV
    • Secure Parking
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    Wonderfully relaxing home with view of the Atlantic Ocean and morning sunrise.Our home is walking distance to town and the beach.Gentle afternoon breezes surround you as you relax with a glass of wine, barbecuing your dinner on the outside deck ,contemplating the day you just spent at the... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 5
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Terrace
    • DVD Player
    • Balcony
    • Ocean Views
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    A beautiful home in Montauk is available for the hottest month of the summer! Enjoy ocean views, private beach access, an outdoor patio with a gas grill, wifi, washer and drier and many more benefits that will make your summer amazing. Montauk is the place to be this summer, The Surf Lodge and many... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 17
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    No Match
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This spectacular 4-bedroom 2-bathroom house is just a short walk (2 blocks) from one of the most beautiful ocean beaches in the Hampton’s. The house is modern and spacious with cool ocean breezes and plenty of natural light. The house is set with spacious cathedral ceilings, many skylights and two... View all property information
    Location Information
    Montauk, Hamptons 11954
    Get the List
    1 / 19
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Washer
    • Internet Access
    • Balcony
    • Ocean Views
    • Air Conditioning
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Sunrise House is an ocean view home with 5 lovely bedrooms, within walking distance to the town of Montauk. We are literally steps from a beautiful beach that is all but secluded. We have three 300 sq. ft. master suites with breathtaking ocean views, fireplaces and all have ensuite bathrooms flat... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 8
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Private Garden
    • Parking
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    PLEASE READ: This house is only available for one 2 week period (14 consecutive days) between Memorial Day and Labor Day of 2016. Unfortunately, the rental cannot be longer than 14 days and cannot be broken up into different time periods. If the listing is active, then the house is still available.... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 11
    4 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • DVD Player
    • Central Heating
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Luxury rental overlooking Lake Montauk. Close to all that Montauk has to offer. Golf ,Beaches, a short walk. New beds, appliances, washer dryer and full kitchen for your cooking pleasure. Full wrap around deck for the sun bathers and a private deck for the Yoga people. Lovely Waterview of Lake... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 17
    5 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Porch
    • Grill
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This cozy Tudor will make you feel at home as soon as you drive through the hedges, as if entering in to a fairy tale. Just far enough(1 mile) from the hustle as bustle of town but close enough to ride your bike to the beach. It offers 3 large bedrooms(two have queen sized beds, one has two twin... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 7
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • DVD Player
    • Balcony
    • Secure Parking
    • Grill
    • Satellite TV
    • Patio
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    DIAMOND BEACH HOUSE ,IS LOCATED IN THE CULLEN SHORES AREA.ONE BLOCK, TO PRIVATE BEACH . HOME HAS TWO DECKS, NEW APPLIANCES ,CEILING FANS THREW OUT. .AND AC IN BACK ROOM SLEEPS 9 .OUTDOOR SHOWER. PRIVATE BACKYARD .THERE IS THE CROWS NEST LOOKOUT, OF THE SOUND .AMAZING SUNSETS TO ENJOY. CIRCULAR... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 14
    4 Bedrooms, 3 Bathrooms, Sleeps 2 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Private Garden
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Plus Utilities, Oceanview, 4 Bedrooms, 3 Baths, Full Bsmt, Description: This 2200 sq ft home features 4 bedrooms, 3 baths, and spacious living areas great for entertaining. With a beautiful ocean view this home is your perfect Hamptons escape. Located in the heart of Montauk. Close to all. Perfect... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Balcony
    • Washer
    • DVD Player
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This post and beam house is only a walk away from Montauk’s famous Ditch Plains Beach, home to surf casters, surfers, and sun bathers. With the backyard secluded by thickly forested wetlands, and sound of the surf as background you will find relaxation and activity blended perfectly to provide an... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 7
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    No Match
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Grill
    • Patio
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Well furnished 2 bedroom 1 bath cedar shingled cabin that was originally erected by a French-Canadian fishermen in 1930's and then recently renovated. The grounds are shared with another cottage and a house, the cabin itself is totally private. The décor is a mix of bought and handmade objects... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 4
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    No Match
    Show Prices
    Amenities & Details
    • Porch
    • DVD Player
    • Washer
    • Patio
    • Internet Access
    • Air Conditioning
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Brand New Renovation 2 blocks from Ditch Plains Beach! 2,600 Square Feet, 4 Bedrooms, 3 full bathrooms, outdoor shower, back patio with gas grill, awning, storage shed for bikes/boards. Brand new finishes throughout! $6750 per week July, 1wk min. Beds: 1 King Bed, 2 Double Beds, 3 Twin Beds View all property information
    Location Information
    Montauk, Hamptons
    Also consider these instantly bookable condos
    4 of 5 bubbles (477) Very good
    Montauk Manor
    Apartment / Speciality Lodging
    Show Prices
    4 of 5 bubbles (22) Very good
    Stone Lion Inn
    Apartment / Speciality Lodging
    Show Prices