Montauk Holiday Rentals
New
House
3 Bedrooms
2 Baths
7 Guests
Oceanfront
Fireplace/Heating
Ocean View
Balcony/Terrace
CA $2,050/Night
7 Nights - CA $14,353
House
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
8 Guests
2002.09 ft²
Hot Tub- Balcony/Terrace
Breakfast
Kitchen
CA $830/Night
7 Nights - CA $5,812
Condo
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
Spa- Fireplace/Heating
Pool
CA $1,096/Night
7 Nights - CA $7,670
House
3 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
Air Conditioner
Internet
Child Friendly
CA $1,689/Night
7 Nights - CA $11,825
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
6 Guests
355.21 ft²
Pet Friendly
Parking- Air Conditioner
- Internet
CA $982/Night
7 Nights - CA $6,877
House
- Montauk
- ·
- Culloden Shores
- 0.12 mi to center
4 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
CA $1,576/Night
7 Nights - CA $11,034
New
Condo
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
CA $1,326/Night
7 Nights - CA $9,279
Cottage
10.0Exceptional
(177 Reviews)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
View
CA $1,502/Night
7 Nights - CA $10,514
House
10.0Exceptional
(152 Reviews)
2 Bedrooms
1 Bath
6 Guests
1800 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
CA $1,233/Night
7 Nights - CA $8,632
Luxury Holiday Rentals in Montauk
Over 858+ Luxury Holiday Rentals in or Near Montauk
House
10.0Exceptional
(2 Reviews)
5 Bedrooms
6 Baths
10 Guests
Private Pool- Oceanfront
- Hot Tub
- Fireplace/Heating
Unlock the Best Price
Apartment
9 Bedrooms
9 Baths
38 Guests
411.71 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $13,836/Night
7 Nights - CA $96,851
New
House
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Oceanfront
- Spa
- Fireplace/Heating
CA $9,131/Night
7 Nights - CA $63,918
House
10.0Exceptional
(1 Review)
5 Bedrooms
3 Baths
11 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
CA $8,057/Night
7 Nights - CA $56,402
Resort
8.2Excellent
(79 Reviews)
10 Baths
30 Guests
272.68 ft²
- Oceanfront
- Spa
- Fireplace/Heating
- Pool
CA $6,521/Night
7 Nights - CA $45,650
House
7 Bedrooms
8 Baths
14 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Child Friendly
CA $6,120/Night
7 Nights - CA $42,837
House
4 Bedrooms
3 Baths
8 Guests
- Private Pool
- Oceanfront
- Spa
- Fireplace/Heating
CA $6,038/Night
7 Nights - CA $42,266
House
5 Bedrooms
4 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
CA $5,800/Night
7 Nights - CA $40,598
Top-Rated Holiday Rentals with a Pool in Montauk
Over 355+ The Best Private Villas and Holiday Rentals in Montauk with a Pool
Condo
10.0Exceptional
(79 Reviews)
1 Bedroom
1 Bath
4 Guests
500 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $646/Night
7 Nights - CA $4,522
Apartment
10.0Exceptional
(74 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $911/Night
7 Nights - CA $6,378
House
10.0Exceptional
(66 Reviews)
2 Bedrooms
1 Bath
4 Guests
500 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $949/Night
7 Nights - CA $6,640
House
10.0Exceptional
(63 Reviews)
5 Bedrooms
5 Baths
10 Guests
3500 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
CA $1,917/Night
7 Nights - CA $13,418
House
10.0Exceptional
(62 Reviews)
3 Bedrooms
2 Baths
8 Guests
1800 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $1,486/Night
7 Nights - CA $10,403
Condo
10.0Exceptional
(55 Reviews)
1 Bedroom
1 Bath
4 Guests
650 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
CA $870/Night
7 Nights - CA $6,087
House
- Montauk
- ·
- Culloden Shores
- 0.18 mi to center
10.0Exceptional
(54 Reviews)
5 Bedrooms
4 Baths
10 Guests
3001 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
CA $3,156/Night
7 Nights - CA $22,094
House
10.0Exceptional
(53 Reviews)
5 Bedrooms
2 Baths
10 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
CA $1,988/Night
7 Nights - CA $13,915
House
10.0Exceptional
(49 Reviews)
4 Bedrooms
3 Baths
12 Guests
2100 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
CA $3,367/Night
7 Nights - CA $23,572
Pet-Friendly Holiday Rentals in Montauk
Over 272+ Pet-Friendly Holiday Rentals in or Near Montauk
Cottage
10.0Exceptional
(82 Reviews)
2 Bedrooms
1 Bath
5 Guests
1200 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $1,501/Night
7 Nights - CA $10,504
Resort
8.7Fabulous
(171 Reviews)
8 Baths
53 Guests
367.51 ft²
- Private Pool
Private Beach- Oceanfront
- Spa
CA $1,597/Night
7 Nights - CA $11,178
House
10.0Exceptional
(28 Reviews)
1 Bedroom
1 Bath
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
CA $679/Night
7 Nights - CA $4,750
Apartment
10.0Exceptional
(52 Reviews)
1 Bedroom
1 Bath
2 Guests
450 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $678/Night
7 Nights - CA $4,749
Resort
7.3Very Good
(144 Reviews)
13 Baths
98 Guests
500.26 ft²
- Private Pool
- Private Beach
- Oceanfront
- Hot Tub
CA $726/Night
7 Nights - CA $5,085
Apartment
10.0Exceptional
(19 Reviews)
1 Bedroom
1 Bath
2 Guests
200 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $497/Night
7 Nights - CA $3,480
Cottage
10.0Exceptional
(18 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $675/Night
7 Nights - CA $4,724
House
10.0Exceptional
(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
740 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $1,056/Night
7 Nights - CA $7,393
House
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $1,298/Night
7 Nights - CA $9,088
Large Holiday Rentals and Private Villas in Montauk
Over 186+ Large Holiday Rentals and Private Villas in or Near Montauk
House
10.0Exceptional
(76 Reviews)
3 Bedrooms
1 Bath
10 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $3,521/Night
7 Nights - CA $24,650
House
- Montauk
- ·
- Culloden Shores
- 0.59 mi to center
8.6Fabulous
(59 Reviews)
7 Bedrooms
1 Bath
4 Guests
1194.79 ft²
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Parking
CA $899/Night
7 Nights - CA $6,296
House
10.0Exceptional
(68 Reviews)
6 Bedrooms
3 Baths
12 Guests
3000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $2,793/Night
7 Nights - CA $19,553
Villa
4 Bedrooms
3 Baths
8 Guests
2798.62 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $1,512/Night
7 Nights - CA $10,583
House
10.0Exceptional
(46 Reviews)
5 Bedrooms
3 Baths
12 Guests
2600 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
CA $500/Night
7 Nights - CA $3,501
House
10.0Exceptional
(45 Reviews)
5 Bedrooms
3 Baths
12 Guests
2800 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
CA $3,320/Night
7 Nights - CA $23,240
House
10.0Exceptional
(39 Reviews)
5 Bedrooms
3 Baths
12 Guests
2200 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
CA $1,496/Night
7 Nights - CA $10,473
House
- Montauk
- ·
- Culloden Shores
- 0.10 mi to center
10.0Exceptional
(38 Reviews)
4 Bedrooms
4 Baths
10 Guests
1500 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
CA $1,507/Night
7 Nights - CA $10,547
House
10.0Exceptional
(35 Reviews)
4 Bedrooms
3 Baths
12 Guests
3500 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $2,401/Night
7 Nights - CA $16,805
Wheelchair Accessible Holiday Homes in Montauk
Over 34+ Wheelchair Accessible Holiday Homes in or Near Montauk
House
10.0Exceptional
(106 Reviews)
1 Bedroom
1 Bath
2 Guests
380 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $571/Night
7 Nights - CA $3,995
Resort
8.9Fabulous
(167 Reviews)
5 Baths
10 Guests
340.14 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $713/Night
7 Nights - CA $4,988
Apartment
9.2Exceptional
(1351 Reviews)
1 Bedroom
1 Bath
- Oceanfront
- Hot Tub
- Spa
- Pool
CA $265/Night
7 Nights - CA $1,857
House
10.0Exceptional
(81 Reviews)
1 Bedroom
1 Bath
2 Guests
380 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $498/Night
7 Nights - CA $3,486
Resort
8.4Excellent
(67 Reviews)
4 Baths
28 Guests
409.03 ft²
- Private Pool
- Private Beach
- Oceanfront
- Fireplace/Heating
CA $684/Night
7 Nights - CA $4,785
Condo
9.8Exceptional
(102 Reviews)
1 Bedroom
1 Bath
4 Guests
500 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
CA $680/Night
7 Nights - CA $4,759
Apartment
9.8Exceptional
(78 Reviews)
1 Bedroom
1 Bath
4 Guests
480 ft²
- Oceanfront
- Spa
- Fireplace/Heating
- Pool
CA $677/Night
7 Nights - CA $4,741
Condo
9.6Exceptional
(106 Reviews)
2 Bedrooms
2 Baths
6 Guests
860 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
CA $854/Night
7 Nights - CA $5,976
Condo
9.6Exceptional
(43 Reviews)
1 Bedroom
2 Baths
4 Guests
925 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Spa
CA $611/Night
7 Nights - CA $4,277
Montauk Private Villas and Holiday Homes Under $200
Over 11+ Montauk Private Villas and Holiday Homes Under $200
Cottage
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
475 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $269/Night
7 Nights - CA $1,886
Hotel
7.6Very Good
(45 Reviews)
14 Baths
388.33 ft²
- Private Beach
- Oceanfront
- Fireplace/Heating
- Pool
CA $210/Night
7 Nights - CA $1,472
Hotel
9.6Exceptional
(497 Reviews)
1 Bath
- Pool
- Ocean View
- Balcony/Terrace
- View
CA $198/Night
7 Nights - CA $1,384
Condo
- Montauk
- ·
- Villas at Montauk Downs
- 0.02 mi to center
3 Bedrooms
3 Baths
6 Guests
1550 ft²
- Child Friendly
CA $249/Night
7 Nights - CA $1,743
Hotel
9.6Exceptional
(492 Reviews)
1 Bath
- Pool
- Ocean View
- Balcony/Terrace
- View
CA $213/Night
7 Nights - CA $1,494
Apartment
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $175/Night
7 Nights - CA $1,229
Hotel
- Montauk
- ·
- Culloden Shores
- 0.35 mi to center
9.0Exceptional
(269 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Kitchen
- Parking
CA $204/Night
7 Nights - CA $1,427
House
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
CA $192/Night
7 Nights - CA $1,345
Hotel
8.6Fabulous
(189 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Kitchen
- Parking
CA $213/Night
7 Nights - CA $1,492
Instantly Bookable Holiday Homes in Montauk
Over 246+ Instantly Bookable Holiday Homes in or Near Montauk
Condo
10.0Exceptional
(27 Reviews)
2 Bedrooms
1 Bath
8 Guests
1000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $2,331/Night
7 Nights - CA $16,318
Condo
10.0Exceptional
(10 Reviews)
1 Bedroom
1 Bath
6 Guests
650 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
CA $998/Night
7 Nights - CA $6,988
House
- Montauk
- ·
- Culloden Shores
- 0.40 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $1,555/Night
7 Nights - CA $10,882
Condo
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
CA $575/Night
7 Nights - CA $4,022
Apartment
9.8Exceptional
(87 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $867/Night
7 Nights - CA $6,069
Condo
9.8Exceptional
(72 Reviews)
2 Bedrooms
2 Baths
5 Guests
1000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $751/Night
7 Nights - CA $5,257
Apartment
9.8Exceptional
(59 Reviews)
1 Bedroom
1 Bath
2 Guests
500 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $633/Night
7 Nights - CA $4,429
House
9.8Exceptional
(46 Reviews)
1 Bedroom
1 Bath
4 Guests
500 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $777/Night
7 Nights - CA $5,441
House
9.8Exceptional
(10 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
CA $1,945/Night
7 Nights - CA $13,617
Book a Last Minute Place to Stay in Montauk
About Casai's Private Villas and Holiday Rentals in Montauk
Discover more than 867 vacation rentals available in Montauk. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Montauk.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Montauk, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Montauk. On average, places to stay near Montauk offer 925.56 ft², with nightly prices averaging CA $1,983.
With Casai, finding and comparing holiday rentals in Montauk is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Montauk
| Type | Count |
|---|---|
| Vacation Homes | 628 |
| Holiday Apartments | 41 |
| Cottages | 29 |
| Villas | 8 |
Use these Quick Filters to Find a Holiday Rental in Montauk
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Montauk.
Weather in Montauk, NY
View the weather forecast for Montauk before booking your Montauk Vacation Rentals to confirm your best time to go.
December - February
High 46°F Low 21°F
March - May
High 66°F Low 25°F
June - August
High 81°F Low 55°F
September - November
High 76°F Low 33°F
Top Attractions Around Montauk, NY
Casai offers a large selection of top attractions around Montauk . Research things to do on your vacation before you visit Montauk.
Other Places to Stay in Montauk, NY
Frequently Asked Questions About Montauk?
What are the top holiday rentals in Montauk?
With numerous options available in Montauk, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Montauk:
- Waterfront Cottage Perfection
- Beach House W/Short Walk to Ditch Plains Beach
- Montauk House with Lake View
- Relaxing Lake Retreat
- Ocean View Modern Cottage —Walk to Town, Beach Pass Included.
- Relaxing Lake Retreat
- Gorgeous 1 Bedroom, 1 Bathroom Condo Across from the Beach
- Oceanfront Home In Downtown Montauk! Private Ocean Beach Path!
- Fantastic Ocean View! Minutes' Walk to Beach! Brand New Split Unit for AC/Heat!
- MONTAUK Perfect Family and Friends Getaway
How many holiday rentals have private pools in Montauk?
Discover a selection of holiday rentals with private pools near Montauk with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- MONTAUK Condo ~ Stunning Sunsets & the Sea at your Doorstep
- Montauk Manor
- East Lake Dr. Lakefront home with a pool.
- Montauk Blue Hotel
Which holiday homes in Montauk are best for families?
If you're searching for a family-friendly holiday home in Montauk, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Montauk:
How many Casai.ca holiday rentals are available in Montauk?
As of 2026, Casai boasts over 867 properties listed in the Montauk area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Montauk.
Nearby Neighborhood (2)
| Neighborhood | Property Count |
|---|---|
| Culloden Shores Vacation Rentals in Montauk, New York | 40 |
| Villas at Montauk Downs Vacation Rentals in Montauk, New York | 780 |
People Also Ask
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