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Siesta Key Vacation Rentals with Private Pool

(89 rentals)
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Come relax in this quiet bayside complex that is surrounded by whispering oaks. 2nd floor unit is a 2 bedroom/2 bath remodeled unit. Complex offers tennis courts, community pool and pier for fishing. Unit has tile in main traffic areas with carpet in bedrooms. Leather sofa, open kitchen wit granite countertops....

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$298
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Wake up to breathtaking views of the award-winning Siesta Key Beach from every room in this stunning, updated two-bedroom, two-bath condo. Designed for relaxation, this bright and airy retreat features an open floor plan, neutral tile, and an abundance of natural light. Step onto the screened-in lanai...

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$258
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

4th floor Bayside 2 bedroom, 2 bath condo located in the Capri Building at Excelsior. Complex has two pools (one beachside/one bayside) with hot tub, 3 lighted tennis/pickleball courts, outdoor BBQ/picnic area. Unit has washer/dryer, WIFI, 2 TVs and DVD. No pets. No trucks/trailers or motorcycles allowed...

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Featured review

"2 hurricanes"

We were due to stay for 2 weeks from 26th sep unfortunately due to hurricane helene we weren't able to stay .siesta rentals returned all our sad but we will come ahain

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$326
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Come stay and relax in this beautiful 2 bedroom, 2 bath condo located in the tower at Palm Bay Club overlooking the world famous white sands of Siesta Key beach. Complex offers two pools (one bayside and one beachside), beach chairs and covered parking for 1 car. Tile flooring with granite countertops...

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$563
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Completely remodeled beachfront 11th Floor unit at Crystal Sands. Gulf views from each bedroom and living room south on Crescent beach. (The view in picture #3) is the view from your screened lanai. Elevator down to pool located on the white sands of Crescent Beach. Beach chairs provided by Crystal Sands....

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$551
avg per night

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Siesta Key Villa
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Come stay and relax on Siesta Key! Home of the #1 Beach in USA. Award winning white sand beaches await. Completely remodeled, 1 bedroom/1 bath, 1st floor condo with private screened lanai with new pergo floors and new kitchen. Washer/dryer in unit located just one block from the shops and restaurants...

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$363
avg per night
Siesta Key Apartment
Sleeps 3, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to paradise at this peaceful studio on Siesta Key! This ground-floor unit in the Casa Mar complex offers a prime location near the beach and pools. Featuring a queen Murphy bed, a twin bed, a covered parking space and WIFI. Guests have access to the complex's pools, tennis courts, shuffleboard...

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$213
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Breathtaking gulf front 2 bedroom/2 bath unit in beautiful Crystal Sands complex. Granite countertops, tile floors in living room, kitchen and bath. Wood flooring in the bedrooms. Leather furniture, 3 TVs, washer/dryer in unit, WIFI. No pets. No smoking. Sleeps 6 (1 king, 2 queens). 2-week minimum. Check...

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$578
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Discover your dream vacation in this beautiful 3rd floor walk-up Siesta Key condo! This 2-bedroom, 1.5-bath condo is located near the beach and offers a range of amenities, including pools, tennis courts, and a workout facility. Enjoy the convenience of a fully equipped kitchen and a comfortable living...

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$247
avg per night
Siesta Key Apartment
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

EXPERIENCE LUXURY AT IT'S FINEST IN THIS STUNNING 2ND FLOOR CONDO WITH PARTIAL GULF VIEW FROM SIDE BALCONY. BACK PATIO OPENS UP TO ONE OF THE TWO POOLS AND FEATURES A GORGEOUS OUTDOOR KITCHEN. KITCHEN HAS GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, AND NEW WOOD FLOORING IN ALL BEDROOMS. LARGE...

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$777
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Tucked away in a quiet neighborhood in the heart of world-famous Siesta Key with a private pool. Discover your own slice of paradise in this beautifully updated 3-bedroom + den, 2-bath canal-front home. This stunning retreat offers modern elegance, luxurious furnishings and the ultimate blend of indoor...

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$525
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Experience refined coastal living in this newly refurnished 2BR/2.5BA condo, where luxury meets relaxed island charm. Enjoy elegant décor, 800-thread-count linens, and a gourmet kitchen with granite and stainless steel. Sip coffee on the balcony with a Gulf breeze, unwind by two pools, or stroll...

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$581
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Second and third floor Bayfront townhome. Living area on second floor and interior stairs lead to bedrooms on third floor. Top of the line unit, offering travertine floors, new kitchen & baths, leather furnishings, 1/2 bath on the 2nd floor and 2 baths on the 3rd floor. Unit offers highspeed internet...

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$338
avg per night
Siesta Key Apartment
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Updated 1 bedroom, 2nd Floor unit in Siesta Village offers great location just two buildings from the beach and 1 block into the village with restaurants and shopping. The unit offers tile floors, leather furniture, updated kitchen and TVs in living room and bedroom. Complex offers community pool and...

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Featured review

"Siesta Key paradise"

We had a great vacation here! Condo was very nice, clean and well supplied. Close to Siesta Village, Beach and within walking distance of almost everything. A definite hidden treasure!

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$300
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to the island and experience the #1 Beach in the USA! This updated end unit condo offers a spacious floor plan with a pool and is just two blocks from the award-winning white sand beaches. Enjoy convenient access to shopping and the shared laundry facilities. Assigned parking. No smoking. No pets....

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$232
avg per night
Siesta Key Apartment
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Beautiful ground floor 1 bedroom/1 bath unit with screened porch at White Sands located just a few blocks from Siesta Key public beach. Community coin-operated laundry right outside door. Covered parking with community pool and clubhouse. Unit has beach chairs, umbrella and beach wagon. 2 TVs with WIFI....

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$208
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Second floor, 2 bedroom/2.5 bath townhome located in the quiet complex of Bay Oaks. Unit nicely furnished and offers tile flooring kitchen, dining room and living room, 2 TVs, washer/dryer inside, 2 screened lanai's. Small balcony and full kitchen with wireless high-speed internet. Complex offers...

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$298
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our vacation oasis. We love the peaceful, friendly vibe of the Bay Oaks community and hope you do as well. Our two bedroom, two bathroom second floor condo unit has been recently upgraded with new living and dining room furniture and new bedding in relaxed but upscale style. The complex sits...

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$329
avg per night
Siesta Key Villa
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Contemporary 3 Bedroom 3 Bath Luxury townhome. Beach views from the 3rd bedroom on top floor with full bath and bonus room and murphy bed. Master suite with tub and walkin shower, Gourmet kichen, leather furniture, balcony with partial views of the Gulf from the 3rd floor balcony. Laundry in unit, 2 car...

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$720
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Discover the perfect balance of comfort, charm, and Florida sunshine in this beautiful home, ideally located just a short stroll from the world-famous Siesta Key Beach and the lively Siesta Village, filled with restaurants, cafés, and boutique shops. Bedrooms & Comfort Left side of the home: • One...

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Featured review

"great location to the Village and beach"

A wonderful location on Siesta Key--we loved being able to walk to the Village and easily walk to the beach. The house has an open feeling with a large living/eating/kitchen area. I cooked a good bit...

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$179
avg per night
Siesta Key House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to paradise! Your tropical oasis awaits you in this spacious two-story home. This stunning 4 bedroom, 4.5 bath luxury home with a private heated pool is just blocks from Siesta key beach! Five star amenities include; expansive gourmet kitchen with granite counter tops, handsome wood cabinetry,...

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$486
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

3rd floor unit in the clubhouses located on the beachside of Palm Bay Club, which is steps from the beach. Custom cabinets, granite counters, stainless steel kitchen appliances, screened lanai, 3 LCD TV's, stackable washer/ dryer in unit. WIFI. Complex offers elevators, 2 pools (1 beachside, 1 bayside),...

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$446
avg per night
Siesta Key House
Sleeps 10, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Escape to your Siesta Key haven! This fully renovated 3-bedroom, 2-bath home, a mile from the world-famous beach, offers a perfect blend of comfort and convenience. Enjoy a modern open floor plan, a fully equipped kitchen, and a private pool in a fenced backyard. With comfortable sleeping arrangements...

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$350
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

BEAUTIFUL BEACHFRONT CONDO WITH VIEWS FROM LIVING ROOM AND BOTH BEDROOMS. BEACH CHAIRS PROVIDED ON THE BEACH. LARGE LANAI RUNS ENTIRE WIDTH OF UNIT. LEATHER FURNITURE, ONE OF OUR MOST POPULAR UNITS. BIG SCREEN TV, VCR& DVD, TV IN EACH BEDROOM. WASHER & DRYER IN UNIT. HIGH SPEED INTERNET ACCESS....

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$691
avg per night
Siesta Key Apartment
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to paradise on Siesta Key! This charming 2 bedroom/2 bath condo is just steps from the award-winning white sands of Siesta Key beach. Enclosed patio. Enjoy the refreshing pool and amenities like tennis and grilling. WIFI. No pets. Sleeps 4 (1 King, 2 Twins). 2-week minimum. Check in: 15:00 - 23:59 Check...

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$268
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Come stay and relax on Siesta Key! Home of the #1 Beach in USA. Award winning white sand beaches await. Gorgeous Gulf front 2 bedroom/2 bath unit at Crystal Sands complex. Tile floors through kitchen, baths and living room. 3 TVs with washer/dryer in unit. Screened-in lanai off all rooms with direct access....

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$578
avg per night
Siesta Key Apartment
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Modern 1 bedroom, 2nd Floor unit in Siesta Key Village offers great location just two buildings from the beach and one block into the village with restaurants and shopping. The unit offers leather furniture, updated kitchen, 1 smart TV. Complex offers community pool and laundry facilities located just...

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Featured review

"Close to everything"

Kitchen was well stocked, condo had everything we need. Would stay again. Bed was comfortable. Close to everything

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$300
avg per night
Siesta Key Villa
Sleeps 10, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to paradise! Your oasis awaits you. 4 bedrooms, 2.5 bath luxury townhome with a private pool is just 1 block from Siesta Village and only 2 blocks from the beach! Five star amenities include; Fully stocked gourmet kitchen with granite counter tops, top of the line stainless steel appliances, laundry...

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$766
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Experience luxurious living in one of the largest units on Siesta at this stunning 2 bedroom, 2 bathroom condo. This immaculate condo features porcelain tile flooring in the living areas, brand new plush carpeting in both bedroom, and beautiful crown molding. The kitchen is a chef's dream, with custom...

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$452
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Breathtaking Direct Oceanfront Condo – Wake up to panoramic views stretching the entire length of Siesta Key Beach in this elegantly appointed 9th-floor oceanfront retreat, perfectly located near the Stickney Point Bridge Village shops and restaurants and a marina. This residence offers designer...

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Featured review

"Great condo"

Location and condition and furnishings of condo are the best, the only suggestion we have (and it's not a deal breaker ) is a recliner or two would be great.

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$578
avg per night
Siesta Key Apartment
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This 2nd floor luxury beachfront condo is updated with designer furniture and furnishings. Fully restocked kitchen with granite countertops and stainless steel appliances. 3 bedroom/3 bath direct beach and pool views from either of the two balconies. Access to small workout room. Washer/Dryer in unit...

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$819
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This two bedroom(master King bed), second bedroom double bed/ single bed (with pull out trundle) full kitchen, dining, living room and lanai open into living space. Out back you sit on the bay and across the street is number 1 beach in the U.S. Pool heated year round 80 degrees, grill areas and laundry...

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Featured review

"Very nice host and home. Home needs work."

The owner could not have been nicer. The home is beautiful but does need attention to details like, no ice from icemaker, hot water takes forever to get to kitchen and master bath. Carpet in bedroom needed...

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$185
avg per night
Siesta Key House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Very nice 4 Bedroom home on a canal just about 5 blocks to Siesta Village. offering: 1 car garage, Duet washer/dryer, Private pool, decorated with a Island flare. Tile throughout with granite and stainless steel kitchen appliances. Beautiful setting pool and patio overlooking canal with boat dock. (Boat...

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$571
avg per night
Siesta Key House
Sleeps 9, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Tucked away amid the tropical tranquility of Siesta Keys Grand Canal, this remodeled home delivers on design, location and lifestyle. Featuring four bedrooms, two-and-one-half baths and washer & dryer. Please note that the garage is not available but there is plenty of parking in the driveway. Beautiful...

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$638
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to paradise at this beautifully remodeled 2-bedroom, 2-bath condo in a tranquil bayside complex on Siesta Key! This third-floor unit boasts a stylish open kitchen with granite countertops and stainless steel appliances, perfect for preparing meals. Enjoy comfortable living with tile flooring in...

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$294
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Come stay and relax on Siesta Key! Home of the #1 Beach in USA. Award winning white sand beaches await. Completely remodeled ground floor unit at Jamaica Royale. Complex offers 3 swimming pools to enjoy along with 300 feet of private award winning white sand beach. WIFI. Washer/Dryer in unit. No pets....

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$425
avg per night
Siesta Key Apartment
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Indulge in a luxurious stay at this completely renovated home in the center of the island, offering a private pool and a tranquil atmosphere. , you can immerse yourself in the beauty of this home. This home is ideal for families with children and infants, providing a perfect blend of comfort and convenience....

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$465
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beautiful Crescent 2 bedroom penthouse with partial beach views, large balcony overlooking pool area in the center of the complex. Additional beach front pool also offered. Equipped with hardwood floors, large kitchen and laundry. 3 TVs, WIFI. Complex offers fitness center, 2 parking spaces and located...

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$649
avg per night
Siesta Key Apartment
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Second floor, 2 bedroom/2.5 bathroom townhome located in the quiet complex of Bay Oaks. Unit is nicely furnished with plenty of space. Tile flooring in kitchen, dining room and living room. 2 TVs with washer/dryer inside unit. 2 screened lanai's, small balcony and full kitchen. WIFI in unit. Complex...

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$313
avg per night
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