50 Best Southampton Estates on Holiday Lettings - Apartments

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104 Vacation rentals

20

Vacation home in Southampton

Hamptons / Southampton

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Pet friendly
Located in Southampton, this 6 bedroom home is 8 km from Agawam Park. Southampton 6 Bed with Pool features a grand entrance, kitchen area with marble counters, stainless steel appliances and French doors with an outside seating area. The living room offers an archway w …see more

from $1500 / night

$10000 - $12000 / week

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from $1500 / night

37

Vacation home in Southampton

Hamptons / Southampton

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
A family place with wrap-around windows and skylights gives you the best of the Hamptons. Big beautify yard and gardens, magical garden-set pool, hot-tub and plenty of room for privacy, makes it a family dream. Backyard. 3 decks. Pool set amongst Maples and hibiscus. …see more

from $675 / night

$6000 - $8100 / week

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Responds fast!
avg. 2 hours 31 minutes

from $675 / night

8

Vacation cottage in Southampton

Hamptons / Southampton

2 4 14 nights min

  • 2 bedrooms
  • Sleeps 4
  • 14 nights min
  • Child friendly
Classic light-filled Southampton summer house nestled on private acre -- a perfect summer getaway. French doors open onto rolling lawns, summer flowers and trees. Walk or bike to Coopers Beach (rated No. l in the nation), secluded bay beaches, historic golf course and …see more

from $326 / night

$2282 - $2738 / week

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from $326 / night

14

Southampton Vacation home rental

Hamptons / Southampton

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Ask about children
  • Ask about pets
The Space Located in Southampton less then a half a mile from the quite beaches of Peconic Bay, this house is also just a 10 minute drive to Sag Harbor or Southampton Villages. Close to ArtHampton (5 mi), Art Market (5 mi) and Hampton Classic Showgrounds (6.5 mi)! Th …see more

from $434 / night

$3034 / week

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from $434 / night

11

Vacation cottage rental

Hamptons / Southampton

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
Enjoy the best of both worlds! Wake up and take your kayak or stand up paddle board across the street and out in the beautiful N. Sea Harbor & then head into nearby Southampton village for a nice relaxing lunch. Finish the day by soaking in the hot tub with a glass of w …see more

from $400 / night

$2800 / week

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from $400 / night

22

Home rental in Southampton with swimming pool

Hamptons / Southampton

3 8 6 nights min

  • 3 bedrooms
  • Sleeps 8
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Step inside this stylish, recently renovated 3 bedroom, 3 bath Southampton home, and the stage is set for a perfect Hamptons summer vacation. Gorgeously appointed and sun-lit, the open floor plan encompasses a great room with fireplace, a screened three-season dining ar …see more

from $1500 / night

$10000 / week

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from $1500 / night

14

Vacation private room with shared pool in Southampton

Hamptons / Southampton

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 12 mi
  • Swimming pool
  • Air conditioning
Newly renovated house with nice spacious rooms with comfortable new double beds. Double occupancy room /private bathroom/entrance, queen size bed newly renovated 4 bedroom-3 bathroom home in prime Southampton location. Close to bay, beach and town. Directly across the s …see more

from $250 / night

$1750 / week

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Responds fast!
avg. 2 hours 48 minutes

from $250 / night

23

Southampton Vacation home rental

Hamptons / Southampton

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Located east of the canal on the beautiful Peconic Bay, over 100 feet of sandy beach, walk down the shore to for food, drinks and entertainment! Beautiful, crystal clear water, 5000 sq ft custom Waterfront “GREEN” House, 5 bedrooms, 5 baths , CAC, hardwood floors, in-gr …see more

from $2800 / night

$17000 - $22000 / week

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Responds fast!
avg. 53 minutes

from $2800 / night

28

Vacation home in Southampton

Hamptons / Southampton

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Welcome to your private Hamptons escape! This immaculate Southampton vacation rental house is sure to provide the perfect vacation spot for your next family getaway. Featuring 4 bedrooms, 5 bathrooms, and enough space to comfortably sleep up to 7 guests, this gorgeous …see more

from $749 / night

$5243 - $8750 / week

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from $749 / night

30

Vacation home in Southampton

Hamptons / Southampton

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
Enjoy the summer at 147 Warfield Way, part of the Southampton Shores community offering a private community bay beach, marina, 3 tennis courts and playing fields. Convenience couldn't be easier with the Country Deli close by as well. Built by Farrell Building in 2014 th …see more

from $1000 / night

$7000 / week

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from $1000 / night

16

Home rental in Southampton

Hamptons / Southampton

5 10 14 nights min

  • 5 bedrooms
  • Sleeps 10
  • 14 nights min
  • Child friendly
Spacious, relaxing and beautiful Southampton rental with two nice and comfortable living rooms, brand-new kitchen, 5 bedrooms and 3 bathrooms. Heated pool, fire pit and a great pool area for every one to enjoy. Close to Lobster Grill and Maschutt Beach whenever you feel …see more

from $652 / night

$4564 - $5477 / week

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from $652 / night

12

Vacation cottage in Southampton

Hamptons / Southampton

4 7 30 nights min

  • 4 bedrooms
  • Sleeps 7
  • 30 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Charming century-old wood-frame and shingled cottage located in a former artists' colony in Southampton, NY, close to beaches, shopping and sight-seeing. Has been well-maintained and steadily upgraded to respond to modern expectations. Tenants may bring a dog. I am loo …see more

from $330 / night

$2310 / week

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from $330 / night

28

Southampton Vacation home rental

Hamptons / Southampton

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Newly build home, no expense spared. Beautiful pool and outdoor dining and cooking/BBQ area. The prefect home for entertaining and relaxing. Fully equipped kitchen for cooking and dining, plenty of space for entertaining. Master bedroom is fit for royalty, 4 more beauti …see more

from $1500 / night

$10500 / week

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Responds fast!
avg. 2 hours 12 minutes

from $1500 / night

11

Vacation villa in Southampton

Hamptons / Southampton

6 12 14 nights min

  • 6 bedrooms
  • Sleeps 12
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Fabulous Bay Front Villa on a private acre in Southampton close to village & Beaches. Beautiful fountain to greet you and your guests to the water front retreat with high end finishes. Vaulted ceilings, Professionally decorated and 6 Bedrooms with 4 1/2 baths with Jette …see more

from $5500 / night

$12000 / week

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from $5500 / night

18

Vacation home in Southampton

Hamptons / Southampton

4 8 14 nights min

  • 4 bedrooms
  • Sleeps 8
  • 14 nights min
  • Beach/lakeside relaxation
  • Air conditioning
  • Private garden
THIS SOUTHAMPTON HOME OFFERS PRIVACY, LUXURY ,SERENITY AND IS EXQUISITELY DECORATED ,THIS RENTAL HAS EVERYTHING ONE WOULD ASK FOR AS THE OWNER.I LIVE THERE PART TIME AS WELL AND HAVE GIVEN THE UTMOST ATTENTION TO EVERY DETAIL IN THE HOUSE FOR ONES COMFORTS THIS HOUSE …see more

from $1786 / night

$12500 / week

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from $1786 / night

10

Vacation bungalow in Southampton

Hamptons / Southampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Enjoy this charming 3 Bedroom 2 Bath Cottage with screened in back porch overlooking quiet yard. Close to village and beach! …see more

from $339 / night

$2373 - $2848 / week

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from $339 / night

17

Vacation home in Southampton

Hamptons / Southampton

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Newly Listed, one level home has been completely redone with style, two master suites and two guest rooms, living room with fireplace, great gourmet eat in kitchen with granite island and counter with French Doors leading to heated pool surround by deck- plenty of room …see more

from $620 / night

$4340 - $5425 / week

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from $620 / night

24

Home rental in Southampton with shared pool

Hamptons / Southampton

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
In the front is a beautiful woodland garden with rare woodland flowers and ferns, moss-covered boulders and miniature ponds. In the rear is a Japanese garden, complete with a moon bridge over a babbling brook, a waterfall you can swim behind, a pond house with a deck yo …see more

from $300 / night

$2100 / week

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from $300 / night

24

Vacation cottage in Southampton

Hamptons / Southampton

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This 3 bedroom waterfront cottage is a perfect family getaway. Located in a small beach community between Southampton and Sag Harbor, it is surrounded by water - from the dining room you look right out onto a serene lake, from the first floor you can see both lake and t …see more

from $921 / night

$6450 / week

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from $921 / night

16

Home rental in Southampton

Hamptons / Southampton

5 12 14 nights min

  • 5 bedrooms
  • Sleeps 12
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Newly Renovated Private Contemporary on 2 Acres of Privacy offers 5 Bedrooms 4 Bathrooms, Heated Pool, Hot Tub and All Weather Tennis Court. Bright and Airy lots of Glass & skylights with Glass doors to beautiful Bluestone patio perfect for Entertaining! Lush gardens …see more

from $1929 / night

$13500 / week

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from $1929 / night

9

Vacation home in Southampton

Hamptons / Southampton

5 10 14 nights min

  • 5 bedrooms
  • Sleeps 10
  • 14 nights min
  • Child friendly
This spacious 5 bedroom, 5.5 bath home provides an amazing living room with vaulted ceilings and 2 wood burning fireplaces. Expansive windows and French Doors overlook the landscaped grounds and heated gunite pool. Top-of-the-line appliances in the kitchen with granite …see more

from $1109 / night

$7763 / week

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from $1109 / night

(3) Excellent 

20

Vacation home rental

Hamptons / Southampton

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 12 mi
  • Swimming pool
  • Ask about children
This well-appointed and maintained 2,200 sq.ft., 4 bedroom, 3 bath Contemporary has a bright sunlit breakfast area directly off the gourmet kitchen, Situated on a sprawling manicured acre with a 20x40 sparkling swimming pool and directly across the street from the fasci …see more

from $643 / night

$4500 - $7000 / week

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Responds fast!
avg. 2 hours 48 minutes

from $643 / night

12

Home rental in Southampton

Hamptons / Southampton

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Child friendly
Price: $36,000 (June 15 to Labor Day) $17,000 (June) $18,000 (July) $29,000 (July through Labor Day) $20,000 (August through Labor Day) Neighborhood: Flanders Centrally Located West of Shinnecock Canal. Minimal traffic! Easy access to NYC and airports. Town of Southamp …see more

from $567 / night

$3967 / week

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from $567 / night

(2) Excellent 

32

Vacation home rental

Hamptons / Southampton

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Experience the exquisite relaxation of upper Long Island, New York by staying at this luxurious Southampton vacation rental home! With incredible upscale amenities, an alluring private pool, exclusive access to a pristine natural sand beach and close proximity to all th …see more

from $700 / night

$4900 - $17500 / week

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from $700 / night

15

Vacation cottage rental

Hamptons / Southampton

4 10 14 nights min

  • 4 bedrooms
  • Sleeps 10
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
Getaway to this charming Cottage on the water with spectacular views!! 3 Bedrooms & Baths in the main house with a separate guest cottage with Bedroom, Kitchen & Bathroom. Heated water front Gunite Pool, Hot Tub, Dock plus Kayaks & Bikes. Close to the village of Sout …see more

from $4500 / night

$10500 / week

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from $4500 / night

7

Home rental in Southampton

Hamptons / Southampton

5 16 7 nights min

  • 5 bedrooms
  • Sleeps 16
  • 7 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets
You can rent this weekly, bi-weekly or full summer season. Summer 2015 weekly rentals start at $7000/week for any weeks in June, $8750/week for any weeks in July and $9200/week for any weeks in August. You can rent for as little as a week in the summer season or monthly …see more

from $1286 / night

$9000 / week

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from $1286 / night

14

Vacation home in Southampton

Hamptons / Southampton

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Child friendly
This charming property located on North Sea Harbor is a true delight. Completely renovated in 2009 including all new appliances, this house features 3 bedrooms and 1.5 baths. Access to water for small boat. Watch beautiful sunsets from deck. The location is ideal betwee …see more

from $356 / night

$2492 - $2990 / week

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from $356 / night

24

Vacation townhouse in Southampton

Hamptons / Southampton

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Bishops Pond is a new high-end condo development in Southampton Village. The clubhouse offers a pool, fitness center, billiards, outdoor tennis court, and more. This beautiful and comfortable second floor level home located on the far south east corner of the developme …see more

from $184 / night

$1284 / week

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from $184 / night

22

Southampton Vacation home rental

Hamptons / Southampton

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Fully completed, this stunning home situation on a private acre in Southampton Village is close to village and beaches. With over 5300 sq. ft with an additional 2000 sq ft of lower level living space, this 7 bedroom, 7 bathroom home has everything you could possibly wan …see more

from $3848 / night

$26937 - $32323 / week

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from $3848 / night

17

Vacation home in Southampton

Hamptons / Southampton

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Mint-renovated and newly decorated Southampton Village home offers a sunny living room, eat-in chef's kitchen and four bedrooms with two baths. Subzero and Wolf appliances, Waterworks fixtures, Cararra marble throughout. Enjoy the summer in our fully-fenced backyard sit …see more

from $1429 / night

$10000 / week

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from $1429 / night

22

Vacation villa in Southampton

Hamptons / Southampton

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
ONE-OF-A-KIND VILLA NESTLED ALONG THE SHORE OF THE GREAT PECONIC BAY, with 180 degree views. The newly renovated and newly furnished (indoor as well as out) with all white interior consists of an open kitchen, living and dining area which lead to french doors, opening o …see more

from $893 / night

$6250 / week

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from $893 / night

15

Vacation home in Southampton

Hamptons / Southampton

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
New to the rental market this sought after Southampton property, is nestled in magnificent gardens and countryside while facing north, across the street from Bullhead Bay. This sunny newly renovated modern split level house offers tasteful furnishings open floor plan, 3 …see more

from $652 / night

$4564 - $5477 / week

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from $652 / night

6

Southampton Vacation home rental

Hamptons / Southampton

4 4 14 nights min

  • 4 bedrooms
  • Sleeps 4
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This 4 bedroom, 3 bath unique home is located South of the highway, with water views! Enjoy your summer sitting by the heated pool or play basketball. The house was recently renovated with all new baths, master has steam shower and new kitchen.and appliances, HVAC, inte …see more

from $1200 / night

$8400 / week

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from $1200 / night

11

Vacation home in Southampton

Hamptons / Southampton

6 12 14 nights min

  • 6 bedrooms
  • Sleeps 12
  • 14 nights min
  • Child friendly
Wonderful house in Southampton with six bedrooms, five baths, formal living room and dining, heated swimming pool. Three fireplaces, great kitchen, beautiful grounds and pool. Just a couple of minutes to Main Street and then a couple more minutes to ocean beaches. …see more

from $1304 / night

$9128 - $10955 / week

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from $1304 / night

23

Southampton Vacation villa rental

Hamptons / Southampton

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This two-story Southampton Traditional sits on nearly 3+/- acres and enjoys several magnificent amenities and attributes, including seven bedrooms and six and one half baths. The living room has a cathedral ceiling, a fireplace, windows rising nearly to the rooms full h …see more

from $2600 / night

$18200 - $35000 / week

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from $2600 / night

6

Vacation cottage in Southampton

Hamptons / Southampton

2 2 2 nights min

  • 2 bedrooms
  • Sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden
This private and quiet waterfront cottage is the perfect Hamptons retreat for one or two people. A short drive to the ocean beach or Main Street in the village for strolling and dining. Located near Southampton Village, the cottage is convenient for wine tasting excurs …see more

from $550 / night

$3850 / week

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Responds fast!
avg. 3 hours 50 minutes

from $550 / night

12

Vacation home rental

Hamptons / Southampton

4 8 14 nights min

  • 4 bedrooms
  • Sleeps 8
  • 14 nights min
  • Child friendly
Just 1/2 mile to the Village's Main Street and minutes to Coopers Ocean Beach from this Traditional home. The interior has been recently remodeled and boasts 4 bedrooms, 5 1/2 baths, formal dining room, country kitchen with fireplace. The spacious living/family room wi …see more

from $1174 / night

$8218 - $9862 / week

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from $1174 / night

24

Southampton Vacation home rental

Hamptons / Southampton

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Pack your bags for an unforgettable East Coast escape at this 3-bedroom, 2.5-bathroom Southampton vacation rental house. Boasting 2,500 square-feet of luxurious living space, this home offers sleeping accommodations for up to 6 guests, a covered front porch and a spacio …see more

from $457 / night

$3200 - $4750 / week

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from $457 / night

7

Vacation home in Southampton

Hamptons / Southampton

2 4 14 nights min

  • 2 bedrooms
  • Sleeps 4
  • 14 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Unbelievable rental property in the heart of Southampton Village. This two bed, one and a half bath is a great summer rental property. Within minutes you are …see more

from $261 / night

$1827 - $2192 / week

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from $261 / night

10

Southampton Vacation cottage rental

Hamptons / Southampton

2 4 14 nights min

  • 2 bedrooms
  • Sleeps 4
  • 14 nights min
  • Child friendly
Brand new very stylish renovation - two bedroom cottage with one bathroom - with bayviews mome …see more

from $313 / night

$2191 - $2629 / week

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from $313 / night

1