Home Vacation Rentals By Owner In Key West, FL

Showing 120 Of 2059 Vacation Rentals
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Exceptional(2)

$514.5

/ Nightly
House Boat

Modern 46' Yacht Grand Admiral 2BR + Salon Bed and 2Bath ~ Key West

Key West, Florida, United States

You and your guests will have exclusive use of this 45 foot yacht all to yourselves! brbrThe yacht stays docked at The Stock Island Yacht Club, and your guests can come and go on the yacht anytime, day or night.brbrThe weather in this area is ideal throughout the year for activities such as snorkeling, fishing, lobster catching (seasonal), kayaking, paddleboarding, learning to sail, scuba diving, or simply enjoying a relaxing sunset cruise. brbrYou have the option to cook your own meals in the fully furnished kitchen, arrange for food catering, or even hire a professional chef for an extra cost. If needed, provisioning service can be arranged upon request for an additional fee. brbrThe yacht features two staterooms, each with its own private bathroom and shower. The aft cabin bed is converted from a couch. She can accommodate up to six adults for an overnight charter and up to eight people for a day charter. brThe large cockpit and spacious interior make many of its European counterparts seem small in comparison. She is built on a deep-V hull with prop pockets and a relatively wide 14-foot beam. brbrThe luxurious two-stateroom, two-head floorplan is an impressive combination of high-gloss cherry joinery, Ultraleather seating, and designer fabrics.brbr Privacy doors, instead of curtains, separate both staterooms from the salon. Her full-service galley includes an under-counter refrigerator/freezer, Corian counters, and hardwood flooring.brbr At the helm, a flip-up bolster seat is standard, and the entire cockpit sole can be raised at the push of a button for engine access. Additionally, there is an extended swim platform, a split forward head, and an underwater exhaust system. As a good performer with Cummins 450hp V-drive diesels, brbrThe yacht can cruise in the mid 20s and reach a top speed of around 30 knots. Fully furnished, she can provide an amazing charter experience!brbrDue to the housing rules it is required that you choose at least one of the following options during your reservation: brbr- 4-hour excursion: $1000, Fuel $200 plus taxbr Captain Fee $400 & gratuity paid at time of charter in cash to Captain br- 6-hour excursion: $1200 Fuel 250 plus taxbr Captain Fee $500 & gratuity paid at time of charter in cash to Captain br- 8-hour excursion: $1400. Fuel $300 plus taxbr Captain Fee $600 & gratuity paid at time of charter in cash to Captain br- 24-hour excursion: $2050. Fuel 350plus taxbr Captain Fee $1000 & gratuity paid at time of charter in cash to Captain brbrPlease note that the cost of the excursions must be paid directly to our company at the time of booking. The price listed above do not include tax or gratuity. The Captain Fee must be paid directly to the Captain by you on the day of the charter To add a guest who is not staying on the boat to the excursion there would be a $100 additional charge per person.brbrThese excursions are highly recommended by our previous guests and are sure to provide you with a memorable experience. During these outings, you'll have the opportunity to learn how to navigate the yacht, snorkel around the coral reef, fish from the yacht, spot dolphins and sea turtles, and much more. Our 24-hour charter is particularly popular as it combines the activities of a day excursion with the unique experience of spending a night anchored on the ocean. You can even enjoy multiple excursions during your reservation period. brbrJust imagine sleeping under the stars on our overnight charters with no neighbors next to, above, or below you like in a hotel room. You can spend your days and nights fishing from the boat, relax on the deck while listening to the sounds of tropical fish jumping in the water, and experience the thrill of being away from the marina, cruising the ocean. If you're seeking an adventurous and extraordinary vacation surrounded by breathtaking ocean views, wildlife, and fish, this is the perfect choice for you. You might never want to return to land again! brbrA romantic charter to the Dry Tortugas would require a minimum of 3 nights and you would have to purchase 3-24 hour excursions in addition to what you pay VRBO, giving you one night at the Dry Tortugas. You would stay at the Marquesas islands halfway on your way there and on your way back. This is truly a bucket list charter that will provide memories that will last a lifetime. The Dry Tortugas is too far to go and come back in one day. brbrThe excursions/charters offered are discounted from the regular price and must be paid directly to our company outside of VRBO at the time of booking. brbrWe do not provide snorkel gear although some of the Captains may have some to rent, or it is recommended you rent a full set at a nearby dive shop to assure your gear will fit you properly. You can rent fishing gear here as well as this is not provided. Paddle board and kayak rentals are also available nearby and some companies will even deliver them to the marina. brbrThe advertised price on this listing covers the cost of insurance that covers you and the crew during your reservation period as well as the cost to survey the boat after you leave. You will be required to undergo a bareboat contract and will take full responsibility of the operation and safety of the yacht, crew, and all passengers. brbrGuests must be able to walk up & down stairs inside the boat and be able to make a longer than usual step at times to get on and off the boat.
Bed 2

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Bath 2

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Sleep 5

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$624.38

/ Nightly
Condo

Key West Beachside Spacious Two Bedroom Condo in the Top Location on the Key

Key West, Florida, United States

Welcome to our Key West Condo, the Key West Cabana. This spacious well appointed 2 bedroom, 2 full bath condo that’s right next to the best beach on Key West, sleeps 6. This condo is the perfect alternative to staying in a hotel or a villa. It gives you the true island experience. It’s a part of one of the most popular, and most luxurious condo complexes on the Island, 1800 Atlantic.brbrRelax on the beachfront at our Luxury Key West Resort Condo Rental with it's perfect location and beautiful tropical landscaping. Enjoy the ambiance created by the sound of the ocean waves as you experience the famous Florida Key's sunsetbrbrOur resort accommodation features a huge world class heated pool and a beautiful sundeck area that is situated right on the Atlantic Ocean, you will be hard pressed to find another condo rental in Key West with the luxury and spaciousness that our vacation rental has to offer at almost 1400 square feet. We are among the finest beach rentals you will find.brbrCheck out the images of our luxurious, condo and book a week or two at this beautiful piece of paradise. However, unlike living on Island Time, you better book soon if you have a particular date in mind since rentals tend to go fast.brbrOur rental home features a modern fully equipped kitchen, two bedrooms, two full size bathrooms and a full size washer and dryer. Our house rental even features granite counters in the kitchen and wet bar.brbrOur Key West vacation rental also features 3 sliding glass doors to our patio, one in each bedroom and living room area. From there you will have access to the fantastic views of the tropical garden area from our private 40 foot veranda a great place to enjoy your morning coffee.brbrOur accommodation has a beautiful and spacious master bath with two sink areas. Both bedrooms come with king sized beds and in addition we have a queen size pullout sleeper sofa in the living area. brbrWith our recently remodeled home rental you will even receive free high speed wireless internet access unlike the small villas or hotels who will usually charge you for their internet service. brbrWe also feature nightly (Minimum 3 Nights), weekly, or even monthly vacation rentals. We offer discounts on our weekly and monthly vacation rentals. brbrVery few Key West condo rentals that can compare with the amenities our beautiful resort property has to offer. The resort is highlighted by our world class Olympic sized heated pool which sits right on the beach. The ocean front pool offers unbelievable ocean views!brbrYou also won't find a Jacuzzi at any of the inns or hotels with a twenty plus capacity like our resort has to offer. brbrOur luxury resort property also includes racquet ball, saunas for both him or her and 3 lighted tennis courts, including one constructed of clay.brbrOur 1800 Atlantic condo comes with all the comforts of home and is not only located on the beach it also includes some of the best resort amenities to be found in the Florida Keys. You won't find four hundred feet of private beach area at any of the Duval Street hotels or bed and breakfast cottages like we have at our 1800 Atlantic. brbrOur resort's beach area is also located adjacent to the most popular beach on the island, Smathers Beach. At Smathers you will find just about every watersport activity there is to offer. You can rent jetskis, sailboats, kayak rentals, paddleboards and many more. Smathers is also the most popular spot for Key West parasailing.brbrHigh speed internet is free with our vacation rental.brbrThe island is known for it's premium on finding parking spaces. Parking is not a problem with our vacation home rental. Our condo even comes with a reserved parking spot in our buildings indoor garage. brbrWith our condo you will have access to any of the resorts tropical landscaped barbeque huts where you can spend a peaceful evening cooking out doors and enjoying the warm tropical breeze. brbrAt the end of your stay our resort accommodation will leave you yearning for yet another trip back to our tropical paradise.brbr1800 Atlantic A213 Vacation Rental – Additional Condo Amenities Included.br-1374 Square Feet of Generous Living Space (one of the largest in Key West)br-24-Hour Security Guardbr-Air Conditioningbr-Alarm Clockbr-BBQ Area with Shelters br-Beach Towelsbr-Blenderbr-55″ Smart TV with Internet Wi-Fi.br-Cable TVbr-Ceiling Fansbr-Coffee Makerbr-Conference Rooms Availablebr-Elevator / Liftbr-Full Sized Kitchen (fully equipped – granite counters)br-Game Roombr-Gazebobr-Garden Area (tropical landscaping)br-Hair Dryerbr-Handicap Servicesbr-Heatingbr-Housekeeping Upon Requestbr-Internet Access – FREE High Speed Wirelessbr-Interior Corridorsbr-Ironing Board / Ironbr-Jacuzzi / Hot Tub (20+ capacity)br-King Sized Beds in Both Bedroomsbr-Linens Providedbr-Large Master Bath – 2 Shower Heads & 2 Separate Sink Areasbr-Luxurious Master Bedroombr-Microwavebr-Non-Smoking Roomsbr-Heated Outdoor Olympic-Sized Poolbr-Parking (assigned spot in gated garage area, Hight limit 6'3)br-Parking (additional parking areas for extra vehicles)br-Private Balcony (40′ overlooks tropical garden)br-Private Beach area for Resort Guestsbr-Security Guardbr-Saunas (both a his and a hers)br-Sleeper Sofa in Living Roombr-Sleeping for 6br-Steps Away from Smather's beachbr-Starter Supply for Kitchen, Laundrybr-Sun Deckbr-Tennis Courts (3 total – one is made of clay)br-Toasterbr-Towels Providedbr-Two Spacious Bedroomsbr-Wash Machine and Dryerbr-Water Sports (right next door at Smathers Beach)br-Wet bar (granite counter)br-Wheelchair Accessbr-Wireless Internet (free)brbrThe property is completed gated and security guards are on property 24/7brbrStart by checking the availability and be sure to email us to save your date today!brbr All rates are subject to 12.5% sales tax, a one time $65 condo registration fee and a $215 cleaning fee unless included in special offer
Bed 3

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Bath 2

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Sleep 6

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Exceptional(2)

$1063.13

/ Nightly
House Boat

Stay Together, Somewhere - 4 Bed & 4 Bath - Catamaran in Key West

Key West, Florida, United States

You and your guests will have exclusive use of this 50 ft yacht all to yourselves. The yacht stays docked at The Stock Island Yacht Club,brbr 50’ sailing catamaran yacht Somewhere is very spacious and bright with windows surrounding it making views of the ocean amazing. Whether you’re inside her spacious salon or on her massive deck, she will be a memory maker forever! The living space on board, evocative of a home on the ocean, is simply breathtaking. brbrThis yacht is remarkable for the seamless circulation between inside and outside. In the passageway, the private spaces, all with a full view of the sea, combine intimacy and pleasure: an impressively sized four equally spaced staterooms, along with a bunk bed stateroom with each of the 4 staterooms having its own privately attached bathroom. This yacht is set to satisfy your wildest demands for the highest level of comfort.brbrYou have the option to cook your own meals in the fully furnished kitchen, arrange for food catering, or even hire a professional chef for an extra cost. In the charter industry on an over night charter, it is customary to share your food and beverages with the captain and mate. If needed, provisioning service can be arranged upon request for an additional fee.brbrDue to the housing rules it is required that you choose at least one of the following options during your reservation: brbr- 4-hour excursion: $1150, Fuel $50 plus taxbr Captain Fee $400 & gratuity paid at time of charter in cash to Captain br- 6-hour excursion: $1450 Fuel 75 plus taxbr Captain Fee $500 & gratuity paid at time of charter in cash to Captain br- 8-hour excursion: $1600. Fuel $75 plus taxbr Captain Fee $600 & gratuity paid at time of charter in cash to Captain br- 24-hour excursion: $2050. Fuel 100 plus taxbr Captain Fee $1000 & gratuity paid at time of charter in cash to Captain brbrPlease note that the cost of the excursions must be paid directly to our company at the time of booking. The price listed above do not include tax or gratuity. The Captain Fee must be paid directly to the Captain by you on the day of the charter To add a guest who is not staying on the boat to the excursion there would be a $100 additional charge per person.brbrThese excursions are highly recommended by our previous guests and are sure to provide you with a memorable experience. During these outings, you'll have the opportunity to learn how to navigate the yacht, snorkel around the coral reef, fish from the yacht, spot dolphins and sea turtles, and much more. Our 24-hour charter is particularly popular as it combines the activities of a day excursion with the unique experience of spending a night anchored on the ocean. If you are staying for more than two nights, you can even enjoy multiple excursions during your reservation period.brbrJust imagine sleeping under the stars on an overnight charter with no neighbors next to, above, or below you like in a hotel room. You can spend your days and nights fishing from the boat, relax on the deck while listening to the sounds of tropical fish jumping in the water, and experience the thrill of being away from the marina, anchored on the ocean. If you're seeking an adventurous and extraordinary vacation surrounded by breathtaking ocean views, wildlife, and fish, this is the perfect choice for you. You might never want to return to land again!brbrThe weather in this area is ideal throughout the year for activities such as snorkeling, fishing, lobster catching (seasonal), kayaking, paddleboarding, learning to sail, scuba diving, or simply enjoying a relaxing sunset cruise which can be incorporated into any excursion.brbrbrA bareboat charter to the Dry Tortugas would require a minimum of five nights and you would have to purchase three-24 hour excursions in addition to what you pay Airbnb, giving you one night at the Dry Tortugas. You would stay at the Marquesas islands halfway on your way there and on your way back. This is truly a bucket list charter that will provide memories that will last a lifetime. The Dry Tortugas is too far to go and come back in one day.brbrThe excursions/charters offered are discounted from the regular price and must be paid directly to our company outside of VRBO at the time of booking.brbrWe do not provide snorkel gear, & it is recommended you rent a full set at a nearby dive shop to assure your gear will fit you properly. You can rent fishing gear here as well as this is not provided. Paddle board and kayak rentals are also available nearby and some companies will even deliver them to the marina. brbrGuests must be able to walk up & down stairs inside the boat and be able to make a longer than usual step at times to get on and off the boat.brbrThere is one security camera located in the cockpit outside this boat, pointed towards the outside of the boat, used for security purposes only between reservations. There are no cameras located inside the boat.
Bed 4

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Bath 4

Bath

Sleep 8

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Exceptional(1)

$868.21

/ Nightly
Condo

Sweet's Spot at The Truman Annex in Key West

Key West, Florida, United States

This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breathtaking water and sunset views from the large and luxurious pool area and decks. This breathtaking penthouse enjoys open water views from most rooms. Sweeping and luxurious with three bedrooms, four and one half baths and plenty of room to spread out and relax.brThe master suite has stunning views of the Key West sunsets, features a large walk in closet and a charming bathroom. The handsome office/study enjoys a front row seat of the community pool complex below and the inner mole pier! brEach bedroom includes a bathroom.brThe living room opens up on two sides with decks; one featuring views of Truman's Little White house and the other of the Key West Harbour. This unique property is outfitted with washer/dryer, pots & pans, towels; linens, central air conditioning, and WIFI. There is a well equipped kitchen with an expansive dining area. The waterfront pool complex is the most beautiful pool compound on the island.brThere is covered off street parking for two vehicles.brEnjoy wonderful views of the Atlantic Ocean and Sunset Key along the length of the Outer Mole pier which is adjacent to the beautiful Truman Waterfront Park... The Truman Annex is an award-winning community located 2 blocks from Duval Street and all of the Old Town Key West attractions. brPlease note: This property has a 28 night minimum stay
Bed 3

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Bath 4

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Sleep 6

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$771.7

/ Nightly
Hotel

2 Rooms for the whole family w/ Pool Access & Near Museums!

Key West, Florida, United States

This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 420 sq. ft, equipped with complimentary toiletries, standard quality TV, available with Standard cable.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 18 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Outdoor shared pool is available, opened from 7:00AM to 10:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $200 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $45.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Pets are welcome with an additional charge of USD 50.00 per night, with no restrictions on size or breed.
Bed 2

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Bath 2

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Sleep 8

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$679.46

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Hotel

2 Bedroom Suite w/ Outdoor Pool in Old Town Key West!

Key West, Florida, United States

This listing is for a room within a hotel.brbr✦ Your room is 800 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, standard quality TV, available with Standard cable, ensuring cleanliness and comfort throughout your stay.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 18 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Outdoor shared pool is available, opened from 7:00AM to 10:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $45.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Pets are welcome with an additional charge of USD 50.00 per night, with no restrictions on size or breed.
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Bath 1

Bath

Sleep 6

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$315.38

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Private Vacation Home

70 Sunset Key: Experience Idyllic Island Life, Shared Pool, Beach Access & Latitudes Restaurant!

Key West, Florida, United States

Homeowners' Association (HOA) mandates a minimum rental period of 30 nights, and no exceptions can be made. Please review additional policies below. brbr brbrWelcome to 70 Sunset Key, Your Personal Slice of Tropical Paradise Located on the Serene Sunset Key! brbr brbrJust a brief ferry ride away from the vibrant and exciting Key West, you'll immerse yourself in the true essence of island life, where relaxation and adventure seamlessly blend. Step into a world where the sun warms your skin as you bask by the inviting community pool, and the sound of gentle waves lapping the sandy beach soothes your senses. Sunset Key offers picturesque walking paths, perfect for leisurely evening strolls, and the renowned Latitudes restaurant awaits to indulge your culinary desires. Whether it's a morning cup of coffee or an evening cocktail, the multiple balconies provide the perfect backdrop for every moment. For those seeking a bit of excitement, a quick boat ride transports you to the heart of Key West, where you can explore its famous restaurants, bars, and unique shops. This harmonious blend of tranquility and adventure sets the stage for the perfect getaway. 70 Sunset Key invites you to experience the best of both worlds, offering serenity and excitement in equal measure. Book your stay today and savor the tranquility and adventure that Sunset Key and Key West have to offer. Your tropical getaway awaits! brbr brbrSLEEPS MAXIMUM OF 6 GUESTS: brbr brbrBedroom 1: King Bed, En-Suite Bathroom, Smart TV (no cable/satellite TV) brbr brbrBedroom 2: King Bed, En-Suite Bathroom, Smart TV (no cable/satellite TV) brbr brbrLiving Room: Sofa with Pull-Out Queen Bed, Smart TV (no cable/satellite TV) brbr brbrKitchen: Nicely Equipped (everything needed to prepare and serve meals) brbr brbrAMENITIES: brbr brbr- Shared Pool brbr brbr- Sandy Beach brbr brbr- Multiple Balconies brbr brbr- Keurig, Toaster, Blender brbr brbr- Linens and Towels Provided brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrAge & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing. brbr brbrPeak Season Monthly Bookings: All bookings from December through March must be for the entire month, starting at the beginning and ending at the end of the month. Consecutive months may be booked if they follow this requirement. Bookings that do not adhere to this policy are subject to cancellation. If you are interested in alternative dates, please contact us for approval before booking. brbr brbrSmoking Policy: Smoking is strictly prohibited to maintain a smoke-free environment. brbr brbrPet Policy: Pets are strictly prohibited by the HOA. To help maintain a pet-free environment for all, we require every guest to confirm they are not bringing a pet/animal. It's free, and does not require creating an account. After booking, you'll receive a link to complete the process. brbr brbrMid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay. brbr brbrLocal Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure. brbr brbrConstruction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by nearby construction. brbr brbrPhoto Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time.
Bed 2

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Bath 2

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Sleep 6

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$253.65

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Private Vacation Home

Sunshine Escape- 3 bedroom 3 bath w/ parking for 2, private pool, balcony

Key West, Florida, United States

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrFEATURES:brBedrooms: 3 (1king, 1 queen and 1 double)brBathrooms: 3brLocation: Casa Marina NeighborhoodbrSquare Feet: 1672brParking: Two off street spaces in the drivewaybrAmenities: Private pool, in-unit laundry, balcony, Wifi, TVsbrbrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No Pets.brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.brbrPool heating is $100 per week and must be requested prior to check in
Bed 3

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Bath 3

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Sleep 6

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Exceptional(37)

$507.99

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Condo

Spectacular Ocean View Amazing quality- Massage Chair. Newly renovated

KEY WEST, Florida, United States

Blue HavenbrbrAn Exquisite Oceanfront Penthouse in Key WestbrWelcome to Blue Haven — Your Premier Oceanfront EscapebrbrNestled on the pristine shores of Key West, Blue Haven is the ultimate luxury penthouse condominium, offering breathtaking direct ocean views and an unmatched vacation experience.brAbout the Penthousebrbr Completely remodeled with over $750,000 in upgradesbr Floor-to-ceiling windows framing panoramic ocean vistasbr Spacious open-concept living with designer touches and modern elegancebr Gourmet kitchen with custom cabinetry and top-tier appliancesbrbr Relaxation & entertainment: zero-gravity massage chair, 80” smart TV, Sonos sound system, Nintendo Switch, and board gamesbrbr Master suite & guest rooms with private balconies and ocean viewsbr Business-ready with fast internet and dedicated work-spacesbrbrAmenities & Featuresbrbr Direct ocean views from every roombr Full kitchen, dining, living areasbr 2 bedrooms (king bed & twin beds), 2 bathrooms, queen sofa bed, plus powered blow-up mattressesbr Air-conditioned throughoutbr Washer/dryer, hair dryers, smart TVs in bedroomsbr Assigned covered parking (standard size vehicle)brbr Access to 1800 Atlantic Complex amenities: botanical gardens, Olympic-size pool, 20-person Jacuzzi, tennis courts (clay & hard), fitness center, ping pong, library, grilling stations, and morebrbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.
Bed 2

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Bath 2

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Exceptional(5)

$956.25

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Condo

Hyatt Sunset Harbor, overlooking the Gulf of Mexico; 2 bd villa!

Key West, Florida, United States

Concierge Realty is proud to present luxury villas at Hyatt Sunset Harbor!brbr**Reservations are available in weekly (7 night) increments with arrivals and departures on Fridays, Saturdays, and Sundays only.brbr**All bookings are time sensitive and availability can change at any time. Send us a message to confirm exact availability prior to making a booking request. brbrWhere Fun Meets Sun!brbrDiscover a relaxing oasis overlooking the Gulf of Mexico in the heart of Old Town, steps from the shops, galleries, and cafes of Duval Street, and close to the nightly sunset celebration at Mallory Square. brbrHyatt Sunset Harbor’s spectacular gulf coast setting is matched only by the gracious service, top-tier amenities and meticulous attention to detail.brbrTropical Key West welcomes you to this classic Florida two-bedroom villa, offering a master suite with plush king bed and connecting bath with available jetted spa tub. In addition, there is a guest suite with queen bed and full bath. This two-bedroom unit offers a fully-equipped kitchen, dining area, seating area with TV, stereo and DVD player and private balcony with pool or harbor views.brbrThe ultimate luxury amenity here is the incomparable location in the heart of Old Town. Tin-roofed conch houses, historic museums, quirky locals and art treasures. If you love Key West, you’ll love it even more when staying at our villa!br brbrThe Vrbo calendar helps provide availability and estimated price quote. Always inquire with the agent and do not reserve airfare until your confirmation has been received.brbrAny issues with resort service, accommodations, physical plant, amenities, etc. are the direct responsibility of the developer and must be handled through the resort, not Concierge Realty.  Photos are thought to be truly representative of the resort and accommodations.  Any variation from the photo and actual property are unintentional, so guests are encouraged to do their own due diligence prior to reserving. Any variance or disruption including but not limited to renovation, unavailable amenity, change in decor, etc. during the stay, whether announced prior to reservation, occurring during the stay or announced after confirmation, is a matter strictly between the guest and resort, are not deceptive advertising, breach of contract or the responsibility of Concierge Realty.brbrNote that the images are representative of this villa and that a specific view type is not implied nor promised by virtue of the images. A specific view category must be addressed with rental agent. Concierge Realty reserved the right to reserve any view category unless one has been agreed upon in writing.  The resort confirmation will show the view designation and the villa will be placed within that view category unless, in a rare instance the view will be noted as not guaranteed in which case the resort reserves the right to place the guest anywhere within the property.  Issues regarding view within the guaranteed view category are to be addressed with the resort management as Concierge Realty is not responsible for villa placement.brbrPlease be advised that if a non-domestic credit card is used to reserve a vacation rental, additional fees may be incurred.brbrAll details are accurate to the best of our knowledge.  Any questions with regard to view, amenities, bedding configuration, decor or other details should be addressed with Concierge Realty, Winter Garden, FL.brbrGuests are encouraged to do their own due diligence to assure that the resort and villa will meet their expectations.
Bed 2

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Bath 2

Bath

Sleep 6

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Exceptional(5)

$775.39

/ Nightly
Condo

**HARBORSIDE HARMONY @ TRUMAN ANNEX** Waterfront Condo + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrHARBORSIDE HARMONY is the epitome of luxurious waterfront living! With scenic views of the Gulf from the living area and private balcony, coupled with a spacious layout and island-style furnishings, this gorgeous condo is the ideal place to call home during your Key West vacation. Best of all, HARBORSIDE HARMONY is located in the exclusive gated community of Truman Annex, which is situated a few short blocks from world famous Duval Street and Fort Zachary Taylor State Park Beach. Combined with Last Key Realty’s unrivaled Guest Services & Complimentary Concierge, your stay at HARBORSIDE HARMONY is sure to be one you will cherish for a lifetime.brbrTHE LIVING AREA...brbrSpectacular views of the Gulf can be enjoyed from anywhere in the open living area, thanks to the large windows that allow plenty of natural light to enter. Sunsets are especially breathtaking to take in from this condo. The large flat screen TV can be enjoyed from the comfortable seating options, including the sofa that pulls out to a Queen sleeper to accommodate extra guests. The kitchen of HARBORSIDE HARMONY is fully equipped with every appliance and tool you’ll need to prepare meals from home. There's even a bar with seating for two. A convenient powder room is located in the hall.brbrTHE POOL & THE BEACH...brbrThe Community Pool is right downstairs, located directly on the waterfront. There are plenty of chaises for your comfort and a cabana with restrooms for your convenience. Best of all, you’ll have “orchestra seats” to watch the sunset on the Gulf of Mexico. Fort Zachary Taylor State Park is a half mile away, with the prettiest beach in Key West.brbrCompliance with Truman Annex Community Rules & Regulations is expected of all Last Key guests. This includes “Quiet Time” in all outdoor areas, public and private, after 10PM.brbrTHE ACCOMMODATIONS...brbr** Master Bedroom: King bed, a flat screen TV, direct access to the sundeck, large closet, and an en-suite bathroom with twin vanities, a tub, and a shower.brbr** Second Bedroom: Two Twins OR One King bed, a flat screen TV, large closets, and access to the hall bathroom with a shower and tub combination.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Private Sun Deckbr** Large Community Pool Accessbr** Two Covered Off-Street Parking SpacesbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** No Pets Allowedbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.
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$729.66

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Private Vacation Home

ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!

Key West, Florida, United States

YOUR SOUTHERN SANCTUARY...brFind your serenity in this stylish and cheery townhome, just a short distance away from the stunning beaches of Key West and all the fun on Duval St. This tropical refuge hosts the right amount of southern hospitality to wash away your real world worries. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES...brStep in to find this sweet surprise of nautical decor with comfortable furnishings in a fun-loving space infused with natural lighting all around. This cheery space greets you with a cozy sectional surrounding a flat screen TV to gather around for lazy evenings together. A fully equipped kitchen allows for seamless meal prep that can be enjoyed around the dining table for 6. Open the large sliders to take advantage of this incredible indoor/outdoor space. brbrSLEEPING ARRANGEMENTS...brHead up to the 2nd level to find the primary suite with a king bed, flat screen TV and en suite bathroom with a shower and double sink vanity. Just down the hall is a room with 2 twin beds that can convert to a king upon request, a flat screen TV and en suite bathroom with a shower. There is a sleeper sofa in the great room for additional sleeping arrangements with the convenience of a powder room steps away. brbrOUTDOOR LIVING...brIndulge in your private island oasis out on the back pool deck as you catch some rays and enjoy the sweet breeze. Rinse off the day in the refreshing private pool (comes heated in the cooler months) and enjoy a good book out on the covered porch with seating. A gas grill, wet bar and outdoor shower complete your tranquil escape. brbrPARKING...brAlthough perfectly located within walking distance of most everything, this home comes with a parking spot for those wanting to head out for a scenic drive.brbrPETS...brDogs are permitted and a pet fee is required.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.brbrCOME STAY A WHILE...
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$1002.32

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Private Vacation Home

BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!

Key West, Florida, United States

BEGIN YOUR ISLAND ESCAPE...brCome get lost in the magic of this captivating island retreat offering modern amenities within this old-world, historic setting. Savor sweet moments with your loved ones while enjoying a simple agenda, lounging indoors or tooling around town by foot to all the highly sought-after Key West attractions. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES... brStep off your private porch into your peaceful escape boasting rich, hardwood flooring, inviting you inside. A homey living room featuring beautiful wooden beams is outfitted with cozy furnishings around a flat screen TV for your movie or game nights together. A cheerful and fully equipped kitchen lies steps away to whip up your home cooked meals at the casual indoor bistro table for 2 or out with the whole gang on the covered porch dining table for 6. brbrSLEEPING ARRANGEMENTS...brSettle into a good night’s rest in the guest room with two twins, which can convert to a king upon request. A comfortable queen guestroom is just down the hall. Follow the stairs to the 2nd floor king suite with an en suite bathroom with a shower/tub combination. Each guest room comes with a flat screen TV for your daily dose of media. A sofa sleeper resides in the living room with convenience to an adjacent bathroom with a shower.brbrOUTDOOR LIVING...brCatch some rays out on your back deck in one of the loungers as you soak up your serene surroundings with lush vegetation swaying in the breeze. Grill up your fresh catch of the day after your refreshing swim in the private pool(comes heated in the cooler months) as you plan out your evening on the town. Located in an incredibly diverse and upbeat hotspot, this home is just a stone’s throw to all the favorite bars, restaurants, the local's favorite grocery spot and and all the sights to see!brbrPARKING...brEnjoy the perk of a parking space for a small to medium sized vehicle. brbrPETS…brDogs are considered at this home and a pet fee is required. brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.brbrTHERE’S NO PLACE LIKE KEY WEST...
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$904.5

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Hotel Resort

Hyatt Vacation Club at Windward Pointe Resort. 2 Bedroom/2 Bath Villa

Key West, Florida, United States

Relax in a tropical retreat overlooking the Atlantic Ocean, Windward Pointe captures the essence of Key West. The resort, located at the southeastern tip of the island’s southernmost point, boasts a freeform infinity-edge pool with a poolside restaurant, a hammock overlooking the ocean, and an array of games. Nearby, enjoy Smathers Beach and the iconic Southernmost Point landmark. On-site, get involved with Inspired Experiences for unforgettable moments together during your Key West stay.brThe spacebrPartial ocean views and lavish décor welcome you to a two-bedroom condominium offering a primary suite with king bed and adjoining bath with walk-in shower and jetted tub, and guest bedroom with queen bed and full bath. Deluxe amenities include full kitchen, dining area, living room with TV, Blu-ray disc player, furnished balcony featuring partial ocean views, and wireless Internet.brbrRoom AmenitiesbrbrBlu-ray disc playerbr55 flat-screen TV in living room and primary bedroombr43 flat-screen TV in guest bedroombrCable/satellite TV channelsbrHairdryerbrIron and ironing boardbrWasher and dryerbrDining areabrRefrigeratorbrMicrowavebrCoffee makerbrDishwasherbrConventional oven with stove topbrFully equipped kitchenbrThree telephonesbrVoicemailbrDataportbrComplimentary Wi-Fi and high-speed Internet accessbrConcierge during regular hoursbrIn-room safebrWalk-in showerbrSpa tubbrSeparate sitting areabrBalconybrIndividual climate controlbriHomebrMaximum guests per room: 6brOther things to notebrA resort fee of approximately $29/day applies.
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Exceptional(26)

$361.65

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Condo

**THE LARK’S LANDING @ SUNRISE SUITES** Condo & Pool + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrLooking to land at the perfect vacation rental to explore Key West and the Lower Keys Then look no further than THE LARK’S LANDING. Found on the top floor of Sunrise Suites, THE LARK’S LANDING features all new furniture and TVs, a private balcony, Two Bedroom Suites, a comfortable living room, and a full kitchen. With a location near the entrance to Key West and close to the airport, THE LARK’S LANDING is a convenient starting point for exploring the Florida Keys. Pair this home with Last Key Realty’s Five Star Guest Services and in-house concierge, THE LARK’S LANDING has all the right pieces to put together a fantastic vacation.brbrTHE LIVING AREA & KITCHEN...brbrWhen you touch down at THE LARK’S LANDING, you will have your ideal island vacation easily within reach! The living area and its recent updates give your group a great space to unwind after exploring downtown Key West or island hopping. Relax and enjoy the flat-screen TV from the comfort of the living room sofa, which pulls out to a queen sleeper. The fully equipped kitchen has all the appliances and tools for the chef in your group to prepare a delicious, home cooked meal. Keep the chef company or grab a quick bite at the kitchen bar with seating for four. The private balcony offers an outdoor dining table with seating for four, and is the perfect space to start your day sipping coffee with the sunrise or toasting as a group to the sunset.brbrTHE ACCOMMODATIONS...brbr** Primary Suite: King bed, flat screen TV, closet, and en suite bathroom. brbr** Second Suite: Two Twins OR One King bed, flat screen TV, closet, and en suite bathroom.brbr** Living room has a queen size sleeper sofa.brbrTHE COMMUNITY POOL & GROUNDS...brbrSunrise Suites is about 3 miles from Duval Street and provides a community pool and hot tub, as well as free parking. Smathers Beach, Key West's largest public beach, is just 2 miles away. Need to get to the airport for your flight home or to hop on the seaplane to the Dry Tortugas National Park The Key West International Airport is only half a mile away!brbrWhen you’re ready to take a dip, Sunrise Suites offers a large community pool and a hot tub. Work on your tan using the chaise lounges that sit poolside. There’s also an outdoor shower and public restrooms next to the pool. Guests have access to the on-site gym and tennis court, as well as the charcoal grill and picnic tables if you are looking to BBQ. Conveniently, this unit has its own designated covered parking spot, plus first-come visitor parking in the lot.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** In-home Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen Smart TVs in Living Room & All Bedroomsbr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Designated covered parkingbr** Community Poolbr** Community Hot Tubbr** Grilling Area w/ Picnic Tablesbr** Gymbr** Tennis CourtbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.
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Exceptional(21)

$957.05

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Apartment

KAMP - Rooftop Penthouse Overlooking Duval

Key West, Florida, United States

Summary:brbrStay in this one-of-a-kind penthouse and Jimmy Buffet's former Margaritaville Headquarters as well as David Mr. Key West Wolkowsky's exclusive pad. brbrbrbrKAMP embodies the history of Duval Street and Old Time Key West where many parties were had. brbrbrbrThis penthouse provides a large contemporary and trendy footprint perfect for entertaining, enjoying Old Town Key West's sights and sounds while also being the perfect place to catch a few ZZZs before the next day’s activities.brbrbrbrThe Space:brbrWelcome to KAMP–a luxurious penthouse located in the heart of Key West right on Duval Street. This modern and charming space offers rare island views from your private rooftop.brbrbrbrLocated four stories above street level, the rooftop offers panoramic views of many Key West attractions and is steps away from your favorite bars, restaurants and shops.brbrbrbrStep inside and immerse yourself in the open-concept living area, seamlessly combining contemporary design with the charm of cozy Key West. The living space is surrounded by floor-to-ceiling windows and sliding glass doors that flood the room with natural light, creating a bright and airy atmosphere.brbrbrbrBedroom 1: King-size bed, blackout curtains creating a quiet ambiance, a desk for a dedicated workspace and an extensive library filled with novels for your reading pleasure.brbrbrbrBedroom 2: King-size bed, an attached full bathroom and access to a private section of the rooftop deck.brbrbrbrAs you explore the penthouse, you'll discover a combined dining and game room, where you can enjoy a friendly game of ping pong or play some classic tunes on the record player.brbrbrbrThe galley kitchen is fully equipped to cater to all your entertaining needs, whether you're hosting a dinner party or preparing a simple home-cooked meal.brbrbrbrMake KAMP your home for your next unforgettable vacation!brbrbrbrGuest Access:brbrOur self check-in makes the process seamless. brbrbrbrGuests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager (GEM) for any questions, needs, or recommendations during their stay.brbrbrbrThe Neighborhood:brbrOn the 400/500 block of Duval, this Penthouse is centralized to everything Key West. brbrbrbrOn Duval street you can find many local favorites such as Fausto's Food Market, Keys Coffee Co., Cuban Coffee Queen and tourist attractions such as: The Ernest Hemingway house, Mallory Square and Key West Lighthouse, all walking distance from your front door! brbrbrbrLooking for a night out Find Willy T's, Fogarty's and Fat Tuesday's within 1 block. And be sure to not forget the world famous Sloppy Joe's Bar which is 3 blocks away!brbrbrbrBeing in the heart of everything does come with the noise of Duval street, but alas, you can slip away to your rooftop hideout when you are ready to relax!brbrbrbrGetting Around:brbrThere are a variety of great ways to explore Key West including by bicycle, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance.brbrbrbrUnfortunately, there is no on-site parking for this unit. Feel free to ask us for recommendations.brbrbrbrOther Things to Note:brbr- This property is a historic penthouse and accessible via elevator or stairs.brbr- No pets allowedbrbr- No parking is provided: we are happy to provide you with nearby recommendations!
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