Home Vacation Condo Rentals By Owner In Siesta Key, FL

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$386.65

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Siesta Key Direct Bay view 2-bedroom condo

Siesta Key, Florida, United States

Discover the beauty of Siesta Key from this 2-bedroom Bayfront condo in Peppertree Bay, a Gulf to Bay complex. Complex includes two pools, fitness center, and tennis / pickleball courts. Look for dolphins while enjoying your coffee from the enclosed lanai. Spend your afternoon casting from the fishing pier steps away from your unit or relaxing at one of the two pools in the complex. Keep up with your fitness routine in the on-site workout space. Or stroll across the street to the gulf and enjoy private beach access. The unit comfortably accommodates up to 4 guests, with a king bed in the primary bedroom and premium sofa bed in the second bedroom. The second bedroom includes a desk and can also be used as a den / office. Each of the bedrooms has a smart tv and wifi hi speed internet.br The kitchen is fully outfitted with everything you need for a homemade meal and a has a pass through to the living area. The dining area is open to the living area, with a table that seats 4. The living area has ample seating, with a couch and love seat and panoramic views of the intracoastal. It also includes as well as a TV and Bose Wave radio. The enclosed lanai has floor to ceiling windows and a cafe table where you can enjoy your morning coffee. Unit includes washer and dryer and dedicated parking spot at the base of the entry stairs.This is a second floor unit and requires a flight of exterior stairs to access.brbrWhether you’re unwinding indoors or exploring nearby, this enchanting condo offers everything you need to enjoy your stay in paradise. We look forward to hosting you at the Waterfront.br* Property Amenitiesbr* 2nd floorbr* 2 BD Garden Villasbr* Air Conditioningbr* Bay Sidebr* Coffee Makerbr* Cooking Basics - Pots & Pans, Salt & Pepperbr* Dining Tablebr* Dishes/ Utensilsbr* Essential Starter Suppliesbr* Exercise Facilitybr* Fire Extinguisherbr* Full Kitchenbr* Hair Dryerbr* Heatingbr* Internet Accessbr* Iron/Ironing Boardbr* Non-Smoking Unitbr* Refrigerator/Freezerbr* Smoke Detectorbr* Stove/Ovenbr* Toasterbr* Towels and Bed Sheetsbr* TV Cable/Satellitebr* Washer/Dryer
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Exceptional(96)

$465.72

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Prime Beachfront with Views, Views, Views!

Siesta Key, Florida, United States

You can't get much closer to the water than this! STEPS to the sand with stunning Siesta Beach views from every room. The Gulf seems to surround you from this gorgeous, completely remodeled 4th floor 2BD 2BA unit. Just a short ride down the elevator from the 4th floor and you're on the sand!brbrThe unit also overlooks the heated Beachfront Pool! brbrCoastal Chic can be used to describe the completely remodeled Beachfront unit. Attention to detail is apparent as you enter to find an open concept Living/Dining/Kitchen area with Gulf views all around! The Living area opens to a private, oversized L shaped balcony/patio perfect for enjoying the sunsets, and fabulous Siesta Beach views. brbrThe Master bedroom has two Queen beds, a large closet, and also opens to the private balcony with Siesta Beach views. The Guest bedroom has two Full size beds and a walk-in closet. Both baths are completely remodeled. Convenient washer and dryer IN unit. The unit has two Flat Screen TV's - a 58 in the living area and a 43 in the master bedroom. brbrBeach towels, and a medium size cooler is provided. The complex provides beach chairs and lounges at the beach. The unit features high speed, fiber-optic Wi-Fi with a dedicated router providing a secure connection. High speed Wi-Fi is also available throughout the property, with full coverage on the beach and down to the water! brbrThe dedicated parking spot is located directly beside the building providing very easy access to the unit. The oversized parking spot easily accommodates vehicles such as large SUV's or Minivans.brbrThe condo has satellite TV with over 200 channels. Enjoy easy access to the beachside grilling pavilion directly beside the building.brbrIf they gave awards for sand - well, they do.....brStephen Leatherman, known as Dr. Beach, says I use 50 criteria to rate every beach, and in terms of sand alone Siesta Key is definitely the best in the world.brbr#1 Best Beach in the US - Trip Advisor 2025br#4 Best Beach in the World - Trip Advisor 2025br#1 Best Beach in FL - US New & World Report 2025br#1 Best US Beach - US News & World Report 2024br#1 Best Beach in FL - U.S. News & World Report 2024br#1 Best Beach in FL - Trip Advisor 2024brOne of the Worlds Most Beautiful Beaches - U.S. News & World Report 2024br#2 Best Beach in the US & #14 in the World - Trip Advisor 2022br#1 Best Beach in the US & #11 in the World - Trip Advisor 2020br#1 Best Beach in the US - Dr. Beach 2017 and 2011br#2 Best Beach in the US - Forbes 2019br#1 Place to Live in Florida - US News & World RPT 2019br#3 Place to Retire in US - US News & World RPT 2019br#1 Best Beach in the US - TripAdvisor 2017 br#1 Best Coastal Place to Live in FL - Coastal Living Magazine 2017br#2 Best Beach in the US - Dr. Beach 2016br#1 Beach in the World - AARP 2015 br#1 Beach in the US - Trip Advisor 2015, 2014, 2013brFamily Beach Award' - Family Vacation Critic 2013 brTop Ten Beaches in the World - National Geographic 2011brBest Beach in the State of Florida- Florida Trend Magazine 2010brBest Sand Beach on the Planet - Travel Channel 2004 br brJamaica Royale provides 3 heated, freshwater pools, two beach Tiki Huts, chairs and lounges for the beach, as well as lovely tropical, manicured lawns and grounds. There is friendly and helpful on site property management, full time housekeeping, grounds maintenance, and security staff. The condo has an e-lock system so no need to keep up with keys. A unique code is generated to unlock the door for each guests stay. Enjoy easy check-in from the on-site office located in front of the complex.brbrIt's just one mile from the condo to popular Siesta Key Village where you'll find a wide variety of restaurants, shops, and nightlife. Everything from Zagat rated restaurants to very casual dining options exist on the Key. Free shuttles run throughout the day and night to Siesta Key Village. It's also just a short drive (15 mins) to mainland Sarasota where you can enjoy world class museums and cultural opportunities, as well as additional dining and shopping areas. brbrBe our guest and enjoy a stay in this beautiful beachfront unit on Siesta Key!
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Exceptional(10)

$186.93

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A spacious condo in beautiful Siesta Key, Heated Pool, Tennis, Waterfront Picnic

Siesta Key, Florida, United States

Recently fully renovated and tastefully decorated 2-bedroom 2 bathroom 3rd floor condo in the very desirable island community of Bay Oaks. Bay Oaks offers a heated pool, barbecue grill area, tennis courts, fishing area on the intra-coastal and pool table in the club house. Vacation on beautiful Siesta Key less than a ten-minute walk to the public beach access with provided beach chairs, towels, and cooler... everything you need to enjoy the pristine beach across the street. Located 1/2 mile from Siesta Key South-end Village with shopping, restaurants, and bars. If you are looking for even more selection, Siesta Key Village is also just 2 miles north. brbrStep inside and you will enter the main living area furnished with dining table with seating for 6 and the living room area furnished with comfortable lounge seating with queen sleeper sofa and flat screen TV. The kitchen is fully equipped with 4 piece appliance set among other small kitchen appliance, cookware, and dish-ware. Washer & dryer is located just off the kitchen. Around the corner you will find the guest bedroom and bathroom. The guest bedroom is furnished with queen-size bedroom set and access to walk-in closet and guest bathroom. The guest bathroom is equipped with tub/shower combo. Moving down the hall you find the master suite. The master bedroom is furnished with a king-size bedroom set and access to walk-in closet as well as the en-suite bathroom which is equipped with stall shower and double sink vanity. brbrThere is a handy free island trolley that runs the length of the island when you don't want to drive. You can also give a call to one of the free rides.brbrWhether it be a family vacation or just a romantic couple getting away on holiday or a much-needed vacation, you can't go wrong.brbr​​​​​​​No pets allowed, sorry. No smoking permitted in the condo. One carport is provided with additional guest parking if needed.
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$233.62

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Siesta Key Condo, Private Beach Access & Water Views - Midnight Cove II 122F

Siesta Key, Florida, United States

Midnight Cove II – 122F by Tropical Sands Accommodations brCondo in Sarasota, Florida brbrDiscover your perfect retreat at Midnight Cove II – 122F, a stylish two-bedroom, one and a half bath condo just a short 10-minute walk from the pristine sands of Crescent Beach. Featuring private beach access and stunning views of the intercoastal waterway, this condo is designed for relaxation and fun. br brHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrMidnight Cove II is a spectacular bayside condominium complex with private beach access to Crescent Beach on Siesta Key and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details). brbrInside, you’ll find an open living space filled with natural light, a fully equipped kitchen with granite countertops, and cozy bedrooms featuring a King bed and twin beds. Additional conveniences include a washer and dryer, plus an extra half bath for guests. brbrBook your stay at Midnight Cove II – 122 today and immerse yourself in the beauty and vibrancy of Siesta Key! Experience private beach access, breathtaking views, and a comfortable home base for your unforgettable escape.
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$233.62

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Family-Friendly Condo with Private Beach Access & Views! - Midnight Cove II 127F

Siesta Key, Florida, United States

Midnight Cove II – 127F by Tropical Sands Accommodations Condo in Sarasota, Florida brbrWelcome to Midnight Cove II – 127F! This two-bedroom, one-and-a-half-bath condo is the perfect beach escape for families. Enjoy private access to stunning Gulf beaches and explore the charming shops, delicious dining, and vibrant entertainment of Siesta Key.brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrMidnight Cove II offers a fantastic bayside experience with access to Siesta Key Beach’s world-famous white sands and breathtaking sunsets. Families will love the heated pool and the variety of sports courts. Enjoy biking, BBQs, and a fitness center, or relax on the observation deck. For extra fun, consider renting a private dock (contact the office for details). brbrYour second-floor retreat features a welcoming living area with cozy seating, a TV, and a dining table. The fully equipped kitchen includes granite countertops, utensils, and island seating for two. Relax in the unique screened-in balcony, perfect for enjoying drinks while taking in intercoastal waterway views. brbrBoth bedrooms are thoughtfully designed for comfort, with a king bed in the primary suite and two twin beds in the second bedroom, ideal for kids. The main bath features an updated walk-in shower, and additional conveniences include a washer and dryer as well as a half bath. brbrBook your stay at Midnight Cove II – 127 and enjoy the perfect blend of relaxation and family fun in Siesta Key! Don't miss out on your dream beach getaway—reserve today!
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$628.31

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Beachside Elegance • 2 Pools + Gulf View

Siesta Key, Florida, United States

Summary:brbrExperience 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 to Siesta Key’s white sands. Includes Wi-Fi, fitness room, in-unit laundry, and space for up to six guests. Perfection! 2 week minimum January thru April. 1 week min May thru DecemberbrbrbrbrThe Space:brbrEnjoy a seamless arrival at Crescent, a keyless entry resort. Your access codes will be emailed to you before you arrive.brbrbrbrGuest Access:brbrYour stay includes access to the gated community and its grounds, which can be accessed using a code provided. The apartment is situated on the third floor, with elevator access for convenience. Covered parking is available within the building.brbrbrbrThe Neighborhood:brbrOur condo offers an ideal location directly on the stunning white sands of Siesta Key Beach. Across the street, you'll discover a wonderful selection of shops and restaurants. Enjoy a sweet treat with ice cream, get your caffeine fix with coffee, savor refreshing cocktails, or indulge in delicious donuts. For outdoor adventures, you can conveniently rent bikes, kites, kayaks, paddleboards (SUPs), scooters, and a variety of beach games. Everything you need for an unforgettable family vacation is easily accessible, ensuring a fun and relaxing experience for everyone!brbrbrbrGetting Around:brbrSiesta Key presents effortless accessibility. A curated selection of fine dining establishments, sophisticated bars, and exclusive boutiques are situated within easy reach. For those inclined to explore further, bicycle or scooter rentals offer a delightful alternative. A complimentary public trolley service, operating at thirty-minute intervals, gracefully traverses the island, connecting the northern and southern locales, including the charming village and the serene Turtle Beach. Complimentary parking is also provided for those who prefer the convenience of driving.brbrbrbrOther Things to Note:brbrFor your convenience, a House Manual is provided. This manual contains detailed instructions on using the television, accessing the internet, and other essential passwords. You will also find helpful maps, directories, and information about local restaurants and attractions to enhance your stay and make your visit more enjoyable. The manual may also include details about local transportation options, emergency contact information, and any specific house rules or guidelines to ensure a comfortable and safe experience for you and your family.brbrbrbrInteraction with Guests:brbrWe are readily available throughout your stay to assist with any needs or questions you may have. Our office is located just across the street from Crescent Beach at 6555 Midnight Pass Road on Siesta Key. You can reach us easily through the platform messaging system, where we aim to respond promptly. For urgent matters outside of regular business hours, please feel free to contact us at 941-400-1226.
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Exceptional(3)

$282.15

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Peaceful Siesta Key condo - short stroll to the beach - GBB 1219

Siesta Key, Florida, United States

Discover the charm and convenience of this delightful 2-bedroom, 2-bathroom condo, ideally located just a short stroll from the beach. Professionally managed by Gulf Coast Vacation Rentals. This inviting Key West-style condo boasts a very rare 2-car garage, providing ample parking and storage space. Set within a beautifully landscaped property, the condo offers a serene and picturesque setting, surrounded by lush greenery and palm trees.brbrOne of the unique features of this ground-floor unit is that it does not have a unit above it, ensuring a peaceful and quiet living environment. The condo is impeccably clean and comfortable, with every detail thoughtfully attended to. The fully stocked kitchen allows you to prepare and enjoy meals with ease, while the provided linens and beach equipment ensure that your vacation is both easy and carefree.brbrThe community offers a wealth of amenities to enhance your stay. Take a refreshing dip in one of the two swimming pools, or engage in a friendly game on the tennis court or pickleball court. For those looking to stay active, there is a well-equipped workout room available. Additionally, a fishing dock is available for residents who enjoy spending time by the water.brbrCome and experience the perfect blend of relaxation and recreation in this charming condo. Whether you're lounging by the pool, enjoying a game of tennis, or exploring the nearby beach, this property offers everything you need for a memorable vacation.brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.
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Exceptional(5)

$308.59

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Gorgeous bay views from this ground floor Siesta Key Condo - GBB 1360

Siesta Key, Florida, United States

Welcome to the epitome of waterfront living on Siesta Key. Professionally managed by Gulf Coast Vacation Rentals and located within the prestigious Gulf & Bay Club Bayside, this first-floor condominium offers tranquil bay views and an exceptional blend of comfort, style, and relaxed coastal elegance.brbrAs you step through the front door, you're greeted by an airy and inviting open-concept living space adorned with tasteful coastal decor. The living area seamlessly flows into the dining space, creating the perfect setting for entertaining guests or enjoying quiet evenings with loved ones. Large windows allow natural light to flood the interior, while offering breathtaking views of the shimmering waters just beyond.brbrThe fully equipped kitchen boasts modern appliances, sleek cabinetry, and ample counter space, making meal preparation a delight. Whether you're whipping up a quick breakfast or preparing a gourmet dinner, this kitchen has everything you need to satisfy your culinary cravings.brbrThe primary bedroom is a sanctuary of comfort and relaxation, featuring a plush king-sized bed, ample closet space, and an en-suite bathroom complete with a luxurious walk-in shower. The second bedroom offers flexibility and convenience, with a day twin sized day bed and extra trundle bed that can easily accommodate family and loved ones. brbrStep outside onto your private patio and prepare to be captivated by the stunning waterfront vistas that stretch as far as the eye can see. Whether you're enjoying al fresco dining, lounging with a good book, or simply soaking in the serene surroundings, this outdoor oasis is sure to be your favorite spot to unwind.brbrResidents of Gulf and Bay Club Bayside enjoy access to an array of resort-style amenities, including a clubhouse, fitness center, tennis courts, and multiple swimming pools. With access to the pristine beaches of Siesta Key just a short walk away, every day feels like a vacation in paradise.brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.
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Exceptional(4)

$313.61

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Lakefront condo on Siesta Key with beach access, 2 pools, tennis and pickleball courts - GBB 1230

Siesta Key, Florida, United States

Escape to paradise in this stunning one-bedroom condo at Gulf & Bay Club Bayside, Professionally managed by Gulf Coast Vacation Rentals, where luxury meets the tranquility of Siesta Key living. This beautifully updated unit features a separate sleeping den with a queen-size bed, closet, and door for privacy, comfortably accommodating up to four guests. The condo is turnkey furnished and equipped with a washer and dryer, ensuring convenience for your stay. A private garage is also included—a rare gem in vacation rentals.brbrStep into the spacious living area, perfect for relaxing after a day of beachcombing or exploring. The updated kitchen boasts a convection oven/microwave, granite countertops, and everything you need to whip up a delicious meal. When it's time to dine out, you're less than three miles from Siesta Key's vibrant restaurant scene, accessible via the island's convenient pedicabs or a quick drive.brbrThe screened lanai offers a serene retreat to sip your morning coffee or unwind with a glass of wine while enjoying the sights and sounds of native birds. Outside your door, Gulf & Bay Club Bayside offers a “Key West” style village experience with lush tropical landscaping, shell paths, and tranquil lakes adorned with fountains.brbrOn-site amenities include two heated pools, tennis and pickleball courts, an exercise room, and BBQ grills for al fresco dining. Stroll the scenic path to the fishing dock overlooking the Intracoastal Waterway, where you might spot dolphins, manatees, or even reel in your own catch.brbrThis condo is your gateway to the world-renowned Siesta Key Beach, with its powder-soft sand and breathtaking sunsets. Whether you're seeking adventure or relaxation, Gulf & Bay Club Bayside provides the perfect backdrop for an unforgettable vacation.brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.
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Exceptional(39)

$173.36

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Siesta Key Condo: Resort Amenities, Walk to Beach!

Siesta Key, Florida, United States

Experience the beauty of Siesta Key when you and your whole beach-loving crew stay at this fabulous 2-bedroom, 1.5-bathroom vacation rental at Midnight Cove II. Located just steps from the bay and the Gulf of Mexico, this 900-square-foot condo boasts views of the intracoastal waterway, private beach access, a community pool, and much more! Whether you spend your days sunbathing in the sand or luxuriating on your furnished balcony, you're sure to fall in love with this Sunshine State sanctuary.brbr-- THE PROPERTY --brbrFree WiFi | Community Grilling Area | Central A/C | 2.7 Miles to Siesta Village PlazabrbrLive like it's summertime every day at this beautiful beachside condo with its sunny location, stunning views, and inviting atmosphere.brbrBedroom 1: Queen Bed | Bedroom 2: 2 Twin Beds | Living Room: Sleeper Sofa brbrCOMMUNITY AMENITIES: Clubhouse, heated pool, tennis & basketball courts, fitness center, boat dockbrOUTDOOR LIVING: Furnished balcony, dining set, lounge furniture, bay viewsbrINDOOR LIVING: 2 flat-screen TVs w/ streaming services, DVD player, stereo, dining table brKITCHEN: Fully equipped, drip coffee maker, hot water pot, stainless steel appliances, pots & pans, cooking utensils, ice maker, microwave, toaster, toaster oven, dishware & flatware, breakfast barbrGENERAL: Central heat, complimentary starter toiletries, beach chairs & towels, in-unit washer/dryer & additional coin laundry facilities in buildingbrFAQ: Stairs required to access the 3rd-floor unit, no elevator access, single-story interior brPARKING: Carport (1 vehicle)brbr-- THE LOCATION --brbrBEACHES: Crescent Beach (0.3 miles), Siesta Key Beach (1.7 miles), Sarasota Beach (2.6 miles), Lido Key Beach (10.6 miles), Manasota Key Beach (22.2 miles)brTEE TIME: Village Green Golf Club (5.6 miles), The Palms Golf Club at Forest Lakes (6.5 miles), Rolling Green Golf Village (9.6 miles), The Highlands Golf Course (10.6 miles), The Groves Golf Course (10.6 miles)brTHINGS TO SEE + DO: Siesta Village Plaza - bars, restaurants, shopping (2.7 miles), Marie Selby Botanical Gardens (6.4 miles), Sarasota Jungle Gardens (10.0 miles), The John and Mable Ringling Museum of Art (11.0 miles), Ca’ d’Zan (11.5 miles), Riverwalk (19.7 miles)brFAMILY FUN: Bayfront Park (7.2 miles), Big Cat Habitat Gulf Coast Sanctuary (11.2 miles), Mote Marine Laboratory & Aquarium (11.2 miles)brAIRPORTS: Sarasota Bradenton International Airport (11.1 miles), Tampa International Airport (69.6 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This property is located on the 3rd floor and requires stairs to access. As there is no elevator available, this area may be difficult for guests with limited mobility
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