Vacation Rentals with Pool in Montauk

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Filtering by: Swimming pool

90 vacation rentals

(7) Excellent 

25

Ocean Front Cottage Montauk for rent

Hamptons / Montauk

Montauk cottage

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$299

Responds fast!
avg. 2 hours 43 minutes

Price per night from

$299

30

Montauk Oceanfront Estate

Hamptons / Montauk

Montauk manor house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$7,497

Responds fast!
avg. 2 hours 43 minutes

Price per night from

$7,497

25

6BR Montauk House w/Pool & Ocean Views!

Hamptons / Montauk

Montauk house

6 13 min stay varies

  • 6 bedrooms
  • sleeps 13
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,800

Responds fast!
avg. 1 hour 17 minutes

Price per night from

$1,800

18

MAGNIFICENT MODERN BEACH HOUSE, 5 MINUTE WALK TO OCEAN

Hamptons / Montauk

Montauk house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$1,992

Responds fast!
avg. 1 hour 51 minutes

Price per night from

$1,992

8

Montauk Royal Atlantic Beach Resort

Hamptons / Montauk

Montauk condo

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$349

Price per night from

$349

30

Fully Renovated Beautiful Montauk Waterfront Condo

Hamptons / Montauk

Montauk condo

2 5 4 nights min

  • 2 bedrooms
  • sleeps 5
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$450

Price per night from

$450

Great rentals within 20 miles that match your search

Distance approx 11.92 km from Montauk

11

Newly Renovated in East Hampton

Hamptons / East Hampton

East Hampton house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Private garden

Price per night from

$747

Price per night from

$747

Distance approx 18.4 km from Montauk

(5) Excellent 

15

Beech Tree Cottage

Hamptons / Sag Harbor

Sag Harbor cottage

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
“Loved this place” This is the perfect little getaway for those who wish to avoid the pretentiousness of East Hampton and Southampton and still enjoy everything that the Hamptons has to offer. Best things - very cute little cottage. Good enough spa
…see more

Price per night from

$500

Price per night from

$500

Distance approx 12.95 km from Montauk

(1) Excellent 

19

Village Fringe glassy Modern with Pool and Tennis

Hamptons / East Hampton

East Hampton house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$256

Price per night from

$256

Distance approx 19.83 km from Montauk

(2) Excellent 

14

Sag Harbor designer home, Chef's kitchen & one block from the water

Hamptons / Sag Harbor

Sag Harbor house

5 10 1 night min

  • 5 bedrooms
  • sleeps 10
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,643

Responds fast!
avg. 2 hours 40 minutes

Price per night from

$1,643

Distance approx 15.77 km from Montauk

(1) Excellent 

26

East Hampton/Sag Harbor Village Fringe

Hamptons / Sag Harbor

Sag Harbor house

6 12 6 nights min

  • 6 bedrooms
  • sleeps 12
  • 6 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Child Friendly

Price per night from

$2,987

Responds fast!
avg. 3 hours 39 minutes

Price per night from

$2,987

Distance approx 13.37 km from Montauk

(14) Excellent 

24

Hip & Stylish East Hampton Getaway

Hamptons / East Hampton

East Hampton house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
“Wonderful stay” Me, my husband and our daughter rented this nice house for a week. It was really great, Patricia was so nice and helpful from the start when we wanted to rent it until we left. The house is light, nicely furnished, comfortable beds wi
…see more

Price per night from

$356

Responds fast!
avg. 2 hours 53 minutes

Price per night from

$356

Distance approx 11.43 km from Montauk

(1) Excellent 

19

Serene & Private East Hampton Summer Rental w/pool

Hamptons / East Hampton

East Hampton house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$498

Price per night from

$498

Distance approx 10.73 km from Montauk

15

chic, comfortable home with pool

Hamptons / East Hampton

East Hampton house

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$513

Price per night from

$513

Distance approx 13.58 km from Montauk

(4) Excellent 

123

The Graybarn Cottage in the Heart of East Hampton

Hamptons / East Hampton

East Hampton house

4 12 3 nights min

  • 4 bedrooms
  • sleeps 12
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
“Amazing birthday celebration!” 5 out of 5. Our weekend at Graybarn was the celebration of a lifetime. It was my husband's 50th birthday, and we were celebrating his remission from lymphoma. We invited three other couples as our guest and had the most
…see more

Price per night from

$5,173

Price per night from

$5,173

Distance approx 9.44 km from Montauk

23

Amagansett Estate 3 BR 60ft Pool

Hamptons / Amagansett

Amagansett house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Nearest beach 8 mi
  • Swimming pool
  • Child Friendly

Price per night from

$896

Price per night from

$896

Distance approx 13.15 km from Montauk

(5) Excellent 

13

Quiet and Private in Heart of East Hampton Village

Hamptons / East Hampton

East Hampton house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
“Wonderful Home in Great Location” The Kaufman family takes great pride in their rental homes and it shows - it is close to being in your own home as possible. The Kaufmans are also a delight to deal with, they always deliver as promised. This home was
…see more

Price per night from

$1,450

Price per night from

$1,450

Distance approx 9.19 km from Montauk

26

CHIC RETREAT!! Walk to Desirable Bay BEACH!!

Hamptons / East Hampton

East Hampton house

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$2,191

Responds fast!
avg. 34 minutes

Price per night from

$2,191

Distance approx 18.28 km from Montauk

15

ROMANTIC LUXURY RETREAT WITH POOL & WATER VIEWS, 1 MILE FROM SAG HARBOR VILLAGE

Hamptons / Sag Harbor

Sag Harbor house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$792

Price per night from

$792

Distance approx 13.28 km from Montauk

(4) Excellent 

23

Beautiful East Hampton Home / Heated Pool / Luxury Sheets and Towels

Hamptons / East Hampton

East Hampton house

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.16 mi
  • Swimming pool

Price per night from

$1,494

Responds fast!
avg. 1 hour 50 minutes

Price per night from

$1,494

Distance approx 19.17 km from Montauk

18

Ideal Bridgehamtpon Getway with Pool & Tennis

Hamptons / Bridgehampton

Bridgehampton house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$750

Responds fast!
avg. 1 hour 54 minutes

Price per night from

$750

Distance approx 15.41 km from Montauk

(1) Excellent 

16

East Hampton/ Sag Harbor, 8 Acres, Pool, Tennis Ct, Hot tub, Sauna

Hamptons / East Hampton

East Hampton house

5 8 7 nights min

  • 5 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 7 mi
  • Swimming pool
  • Child Friendly

Price per night from

$1,186

Responds fast!
avg. 3 hours 39 minutes

Price per night from

$1,186

Distance approx 11.96 km from Montauk

18

Waterview renovated 5 bedroom house with pool

Hamptons / East Hampton

East Hampton house

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$996

Price per night from

$996

Distance approx 11.31 km from Montauk

(1) Excellent 

36

East Hampton Luxury Home PERFECT FOR FAMILIES

Hamptons / East Hampton

East Hampton house

5 11 7 nights min

  • 5 bedrooms
  • sleeps 11
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$1,423

Price per night from

$1,423

Distance approx 10.32 km from Montauk

(5) Excellent 

41

East Hampton Family Retreat with Cottage

Hamptons / East Hampton

East Hampton house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool
“Great House, Great Host” My friends and I spent a great weekend at this house and were blown away by house nice the house was and how gracious Leanna was as a host. We made good use of the pool (played several house of pool volleyball) and the hot tu
…see more

Price per night from

$598

Responds fast!
avg. 3 hours 46 minutes

Price per night from

$598

Distance approx 12.97 km from Montauk

(3) Excellent 

13

Spectacular Water Views & Sunsets in East Hampton

Hamptons / East Hampton

East Hampton house

4 8 4 nights min

  • 4 bedrooms
  • sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“First time in the Hamptons” My first visit to the Hamptons could not have been better. After reviewing several rental homes I came across Hamptons Vacations. Their selection of rentals was good, but ultimately was drawn to the home Island View. Nor
…see more

Price per night from

$2,131

Price per night from

$2,131

Distance approx 9.69 km from Montauk

24

Amagansett Estate 4BR 60ft Pool

Hamptons / Amagansett

Amagansett manor house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$1,046

Price per night from

$1,046

Distance approx 12.64 km from Montauk

29

Contemporary Hampton Home w/Heated Pool + Fire Pit

Hamptons / East Hampton

East Hampton house

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

Price per night from

$447

Responds fast!
avg. 46 minutes

Price per night from

$447

Distance approx 16.07 km from Montauk

20

East Hampton/Wainscott.Exclusive/Pvt, 6BR, 3500'

Hamptons / East Hampton

East Hampton house

6 11 7 nights min

  • 6 bedrooms
  • sleeps 11
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

Price per night from

$1,138

Price per night from

$1,138

Distance approx 10.65 km from Montauk

26

Elegant East Hampton Home - Pool & Putting Green

Hamptons / East Hampton

East Hampton house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$470

Responds fast!
avg. 1 hour 39 minutes

Price per night from

$470

Distance approx 18.05 km from Montauk

7

Village traditional on a quiet cul de sac

Hamptons / Sag Harbor

Sag Harbor house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,114

Price per night from

$1,114

Distance approx 11.4 km from Montauk

14

Beautiful East Hampton Home in Private Beach Community with Pool

Hamptons / Springs

Springs house

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$996

Price per night from

$996

Distance approx 13.1 km from Montauk

25

East Hampton Home w/Pool & Fire Pit - Near Village

Hamptons / East Hampton

East Hampton house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$475

Responds fast!
avg. 2 hours 0 minutes

Price per night from

$475

Distance approx 11.77 km from Montauk

23

Brand New, 2016, Custom Boutique Home

Hamptons / East Hampton

East Hampton house

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$925

Price per night from

$925

Distance approx 10.89 km from Montauk

24

Vacation home in Artistic / Historic area of East Hampton, NY

Hamptons / Springs

Springs house

4 8 30 nights min

  • 4 bedrooms
  • sleeps 8
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,327

Price per night from

$1,327

Distance approx 11.79 km from Montauk

13

East Hampton Charming Cottage South Of the Highway Near Ocean/ Further Lane

Hamptons / East Hampton

East Hampton house

3 8 14 nights min

  • 3 bedrooms
  • sleeps 8
  • 14 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,237

Price per night from

$1,237

Distance approx 10.9 km from Montauk

13

Lushly Landscaped Contemporary With Pool East Hampton North

Hamptons / East Hampton

East Hampton house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child Friendly

Price per night from

$498

Price per night from

$498

Distance approx 12.43 km from Montauk

11

Spectacular East Hampton Mansion

Hamptons / East Hampton

East Hampton house

8 20 7 nights min

  • 8 bedrooms
  • sleeps 20
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$5,689

Responds fast!
avg. 17 minutes

Price per night from

$5,689