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Rentals with Pools in Key West, FL

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    1 / 14
    4.5 of 5 stars (26) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 17
    5 of 5 stars (24) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 17
    5 of 5 stars (13) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 14
    5 of 5 stars (19) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Relax of the Island Style front porch and enjoy Key West at it's finest. Centrally located, less than a block from Duval - this Completely updated 2 Bedroom, 1 Bath will simply amaze you! High Ceilings, tall windows, full kitchen with separate dining room and plenty of space to make your Key West... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed August 22, 2015
    Traveled to Key West with my sister and my Mom to celebrate Moms 85th birthday. The house was so close to everything we wanted to do and see. The grocer nearby was great, the...
    4 of 5 stars Reviewed May 2, 2015
    We stayed for three nights in April. Checked in Saturday, and as we were unloading our car owner came by to say hi and ask if we had any questions. She answered the few...
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    1 / 6
    4 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Penthouse unit has designer furniture in this two bedroom (master has king size bed and guest bedroom has a queen) with a comfortable queen sleeper sofa in the living room. Two full bathrooms, full kitchen, dishwasher, microwave, cook top and electric oven, and outside balcony overlooking the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed September 18, 2015
    I would definitely stay here again! It was a great trip with a lot of memories made thanks to the wonderful owner of this apartment. It was the perfect space in the best location...
    4 of 5 stars Reviewed May 25, 2015
    This room had all the comforts of home. A bit dated, but very clean. A bit of a drive to Duvall though. About a 10-12 min cab ride. We were there with 6 people and the cab drivers...
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    1 / 20
    4 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Come down and take part in in Key West's many fishing tournaments! No docking fees at this condo where you can park your boat in the spacious lot and keep your car covered in your reserved spot under the building. Make memories the whole family will cherish in this great family friendly condo in... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed February 10, 2014
    I hosted a bachelor/bachelorette party the weekend of Dec 28th and I stumbled on this space while i was searching. Everything on Duval was booked and around $1300-$1500 for 2...
    5 of 5 stars Reviewed October 25, 2013
    A very nice accommodation. Very well thought out and presented. Faultlessly clean and well maintained. Pauly was quite kind and took great pains to ensure our complete...
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    1 / 14
    5 of 5 stars (8) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Satellite TV
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    • x
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    About this property
    Tropical 2 bedroom, 2 bath condo 1/2 mile from Smather's Beach in Key West. Fully appointed kitchen and living room. Balcony overlooking Salt Ponds and distant ocean view. Large heated pool on property, perfect for sunbathing. Jacuzzi and gym. Tennis court. Small boats on trailer allowed.... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed April 15, 2016
    The condo was clean and equipped with the necessities and a washer/dryer. Location is away from downtown but we knew that when we booked it. Would definitely rent again and price...
    5 of 5 stars Reviewed March 5, 2016
    Condo is a $25 cab ride including tip (2016 prices) from Duval Street area where most bars/restaurants/shopping/tourist sites are located. However all cab companies were familiar...
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    1 / 15
    5 of 5 stars (4) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Upper Duval is the best! A few steps away from the Southernmost pt & beaches,great restaurants,art galleries, Louies backyard,and Blue Heaven. A few more steps from Mallory sq, Sloppy Joes, Smokin tuna, the pier restaurants, entertainment day and night. Have the best of both worlds, be in the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed March 9, 2016
    First time renting from Trip Advisor. The entire process went very smooth & would definitely recommend it. Stayed at this location for a week with spouse and another couple...
    5 of 5 stars Reviewed March 18, 2015
    Wonderful location. Delightful owners. Relaxed and comfortable. Pool area great...sun if you want it and shade if you need it. Would definitely recommend to friends and will stay...
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    1 / 12
    4.5 of 5 stars (13) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 1 week ago
    Two bedroom, two bathroom condo suite with patio, across the street from the water. Each bathroom is connected to a bedroom, with the master bedroom having private access, of...
    5 of 5 stars Reviewed July 17, 2016
    We LOVED this condo for our stay in Key West. The condo was very clean, spacious, absolutely adorable, and most importantly affordable! It was nice to have access to a pool and...
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    1 / 30
    5 of 5 stars (2) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • x
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    About this property
    You are downtown with a pool at Flip Flop Retreat- just 2 blocks from Duval Street in a quiet poolside condo in Truman Annex. We have 33 all 5 Star Reviews on a competing website- our guests are very pleased with their vacations. You are in Old Town for convenient entertainment, shopping,... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 4, 2016
    My wife and I along with our son and daughter have been travelling to Key West for several years now and the past few we have stayed at the Flip Flop. As of now I can not think...
    5 of 5 stars Reviewed December 15, 2015
    My husband and I stayed here from 12/5-12/2015. Flip Flop was immaculate, perfectly located in Old Town Key West and well furnished. The owner took all of the steps to make...
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    1 / 14
    4.5 of 5 stars (8) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Pet-friendly
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    • x
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    About this property
    Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed February 9, 2015
    Loved the condo! Besides a few minor issues the place was everything it promised and more. Nicely and comfortably decorated with lots of room (there were 6 adults). The balcony...
    5 of 5 stars Reviewed December 29, 2014
    The condo comfortably fit out family of 5. It had lovely ocean views, homey updated decor, a pool & jacuzzi, while walking distance to Smather's Beach equipped with all kinds of...
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    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Sauna
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    About this property
    WELCOME to our beachside condo in Key West. Our terrace directly overlooks Smather's Beach and is the focal point of our home; watch the sunrise with coffee; watch the kids on the beach and the parasailors fly by; have a private sunset dinner; enjoy a late night drink and watch the cruise ships... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 44
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    If you have had your fill of hotels and the street scenes of downtown Key West and you don't want to spend another minute on a boat loaded with people but do want to get out on the water, then S/V Tortuga may be the perfect solution for you. Tortuga Sailing Adventures offers a unique, totally... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
    • Satellite TV
    • Ocean Views
    • DVD Player
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    • Air Conditioning
    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The Hyatt Windward Pointe is the most luxurious accommodation in Key West. This is one of a kind unit that is the best in the property with ocean and pool view and largest balcony on the third floor. One- king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Pet-friendly
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    • x
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    About this property
    La Brisa Condominiums is located on S. Roosevelt Blvd. across from Smathers beach the largest beach in Key West. Only 5 minutes from Duval Street & Mallory Square. Our condos' at La Brisa are two bedrooms with two full bathrooms on the third floor. The master bedroom has a king size bed with a walk... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 19
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
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    • ?
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    • x
    About this property
    Note, this is a monthly rental only. We do not rent our home out for less than 30 days. Historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV in 2007 (!), this intimate house boasts many fun and thoughtful features... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed December 8, 2014
    This is a wonderful conch house in Old Town, Key West. The house is just around the middle of Old Town, so you can walk or bike to the harbor, the ocean, and the great music at...
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    1 / 9
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Steps from the Ocean, Esprit du Vent is a spacious catamaran within minutes of Key West on Stock Island in a yacht club setting with a pool, beach and restaurant. The catamaran has 3 cabins, 1 head, and is bright, airy and spacious. Fully equipped with galley kitchen, oven, stove, coffee maker,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Ocean Views from Every Balcony. Expect every Amenity from Hyatt. Come Relax by the water with a cool drink. Come visit Old Town Key West for the Sunset Celebration on Mallory Square while enjoying the entertainment, dining and shopping along Duvall Street. This historical city has much to see &... View all property information
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    Key West, Florida Keys 33040
    1 / 27
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    ***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights***<BR><BR>MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO SMOKING - NO EXCEPTIONS<BR><BR>Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed March 17, 2015
    Stayed here for 2 months while I was having my house remodeled and I was very pleased with the facilities and the unit. The condo has been nicely redone and very well stocked...
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    1 / 24
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Washer
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    • Pet-friendly
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    About this property
    2 Bdrm, 1 Bath, Washer/dryer, Dishwasher, Great Porch View Of Southard St, Pool<BR><BR>Multiple week and military discounts available. Great Fall rates! Queen bed in Master Bedroom, two single beds in second bedroom, fold out queen bed in couch, gated back patio with gas grill, lounge chairs, table... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 14, 2016
    Condo was ideally located for all our activities. Very comfortable and enjoyable! Cindy was a pleasure to work with, can't wait to return to Tiki, Too!
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    1 / 24
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Terrace
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    • Pet-friendly
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    • x
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    About this property
    Great for large groups - 6 bdrms, 3 bathrms, sleeps up to 14 adults, White Ibis Inn just 15/20 minutes drive from Key West. Sometimes we run a special discounted price from our White Ibis Inn. If you are interested to book our place, please let us know how many people in your group, any pets,... View all property information
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    Key West, Florida Keys 33040
    1 / 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • ?
    About this property
    The Hyatt Windward Pointe is the most luxurious accommodation in Key West. One king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full kitchen, balcony with ocean views, W/D in unit, TV in every room, large pool and hot tub, volleyball court, amazing landscaping.... View all property information
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    Key West, Florida Keys 33040
    1 / 17
    4 of 5 stars (1) Very good
    2 Bedrooms, 5 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
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    • Pet-friendly
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    • x
    About this property
    This property is located on the north side of Key West 4 miles from downtown.It is available from Dec. 27th to January 3rd. A great venue for the holiday season. This is a great two bedroom two bath unit with master bedroom and en suite. Private balcony which overlooks outdoor infinity pool. Also a... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed January 29, 2016
    I own at this hyatt timeshare. The units are spacious. Very clean and nice grounds. Only problem is away from downtown and car is needed. Hyatt working on new shuuttle service to...
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    1 / 11
    4.5 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The resort all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just minutes from Smathers Beach and 2 miles from Key West Airport. This location is also two miles from popular Higgs Beach and between 4 miles from the Key West Lighthouse... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed October 14, 2015
    Location, while good very close to Airport which was noisy at times. Bedrooms good size. However, plastic mattress protectors were uncomfortably hot, unnecessary and had to be...
    5 of 5 stars Reviewed June 26, 2015
    Very lovely condo!!! Close to everything you need! It was our first time to key west and when we return we will definitely try to stay here again!!!! We really enjoyed our time.
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    1 / 21
    4 of 5 stars (4) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    ***PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN*** CASA ROSA is a four bedroom, four bath classic "eyebrow" style home located in historic Old Town Key West. This home is just 1 block off Duval Street and a short walk to Harbor Walk & Mallory Square. Enjoy Simonton... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed April 11, 2016
    4 bed/4 bath older/historical home. Some of the rooms lacked storage space but they were clean and beds/bathrooms were good. Two good size bedrooms and the other two not much...
    5 of 5 stars Reviewed April 4, 2016
    I rarely get on sites to complete a review. However, I felt that this review needed to happen, as I was looking for current reviews of the property when we were looking for that...
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    1 / 23
    4 of 5 stars (19) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • x
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed December 15, 2015
    Could be a great place . Needs a good deep cleaning and friendlier and more helpful women working in the office. Was there for 4 days with kids in November with no pool heater...
    5 of 5 stars Reviewed July 18, 2013
    I used to live in Key West and have had friends stay here before. I was excited to see the new renovations they had done. The room was beautiful and clean and our stay was great...
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    1 / 26
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Beautifully renovated duplex in Old Town. 2 bed/1.5 bath. Sleeps 4-6. There is a private stairway to apartment/loft upstairs. Upstairs unit is a massive 1100 sq ft with cathedral ceilings and loft (2nd bdrm). There is a king bed in the master, full bed in the loft and a pull-out sofa. Fully... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    4.5 of 5 stars (25) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Shared Outdoor Pool...
    • DVD Player
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    • Terrace
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed June 30, 2015
    This is our second time staying at Pelican Landing. Our group comes up yearly for the Swim Around Key West race and we love the penthouse suites where we can all stay together...
    5 of 5 stars Reviewed June 11, 2013
    Pleasantly surprised at the cleanliness of the unit. Check in time was limited to 1 hour time frame, not so convenient. Liked the fact that I could take my small dog along, but...
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    1 / 28
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    * This vacation home is available to rent on a monthly basis only * Dating all the way back to 1884, this delightful 3BR home is located in Bahama Village, part of Key West's prominent Old Town neighborhood. This single-family home is available to rent on a monthly basis. If you'd like more... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 8
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Yard
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    • Pet-friendly
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    • x
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    • x
    About this property
    <BR> KEY WEST VACATION CONDO RENTAL DESCRIPTION<BR><BR> Our beautiful deluxe one bedroom condo in Key West Florida on<BR>Southard Street is just blocks from the ocean and Duval street.<BR>Located in historic old town, the condo is enclosed in a beautiful<BR>garden on the ground floor. It is... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed September 24, 2015
    We've stayed in this condo multiple trips to Key West. It sets back from the street behind a locked gate and you can feel safe and secure in this quiet condo community which also...
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    1 / 15
    4.5 of 5 stars (40) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Great, popular, quiet townhouse in the well-liked Duval Square complex in the heart of Old Town. One off-street parking space per unit. Easy walking distance to all downtown attractions. Bank, convenience store, health club, hair salon and fine restaurants in the complex. Families are... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 3 weeks ago
    My family and I stayed for 6 days and had a great time. As it was very hot in Florida this time of year the location was great to stop for a quick snack and break. Centrally...
    5 of 5 stars Reviewed April 27, 2016
    We had a great time, the house was nice, but the dishwasher was broken on the bottom rack, the electrical outlet upstairs blew and they had to come fix it, the faucet in the...
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    1 / 4
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Nestled behind hisbiscus and stands of bamboo Lone Palm welcomes you to a tropical oasis in the heart of Old Town. Located just a block off Duval at the corner of Truman & Simonton in Windward Park a gated community consisting of 13 privately owned homes around a sparkling 20 x 60 ft. pool; a... View all property information
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    Key West, Florida Keys 33040
    1 / 21
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    EASY LIVIN' -- The name says it all! This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman Annex is a gated community located in the historic Old Town neighborhood, in walking distance of anything you'll want to do during your visit. The formal entrance... View all property information
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    Key West, Florida Keys 33040
    1 / 9
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Secure Parking
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    • x
    About this property
    Why stay in a cramped hotel when you can relax in a private, quiet, and peaceful 2-acre estate! We are now running an special discounted offer for the Fall of 2016 WHITE IBIS INN - LOCATED ONLY A 15 MINUTE DRIVE FROM KEY WEST OR THE WORLD-FAMOUS BAHIA HONDA BEACH. Sometimes we run a special... View all property information
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    Key West, Florida Keys 33040
    1 / 37
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    AMELIA HOME - A 2 bedroom 2.5 bath private home with sparkling private pool that is only four blocks from the Atlantic Ocean and one block from all the Duval Street entertainment is the Key West vacation you have been seeking. Tucked away in one of the most interesting neighborhoods in the historic... View all property information
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    Key West, Florida Keys 33040
    1 / 54
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • x
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    About this property
    CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street with room to park 2 vehicles off-street -- a bonus in Old Town where parking is worth its weight in gold. Casa... View all property information
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    Key West, Florida Keys 33040
    1 / 15
    4.5 of 5 stars (47) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • x
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    • x
    About this property
    Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer.... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 2, 2013
    I selected this cottage via computer. The location is excellent for seeing ALL the sights of Key West. This cottage is as represented. The kitchen was spacious and nicely...
    5 of 5 stars Reviewed August 1, 2012
    The location is excellently placed in Key West. My girlfriend and I were never more than a 15 minute walk to anything that we needed and the kitchen had many of the things we...
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    1 / 14
    4.5 of 5 stars (7) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the mature tropical tree garden in the hidden back yard, you would never know you're just 1/2 block off Duval Street in Old Town Key West. It is indeed rare to find a cottage property... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 12, 2016
    If you want to be near the heart of Duval, but never hear it when you choose to take a break, then this is your place. The backyard garden is amazing with gorgeous landscaping and...
    5 of 5 stars Reviewed February 15, 2016
    Great little cottage for 2 couples; clean and comfy. Great pool, it was warm and felt wonderful (it was a bit cool during week we visited); great location. King bed mattress...
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    1 / 26
    4 of 5 stars (15) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. The huge oceanfront balcony can be accessed from both the living/dining... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed January 24, 2013
    We spent 2 weeks at this condo, it was beautiful. We were right on the ocean and spent numerous hours on the large lani. The condo was very roomy and well kept. Our only problem...
    3 of 5 stars Reviewed July 2, 2012
    Going downtown to pick up the key at the rental place was a major pain, and we had to set there for a long while before someone even acknowledge us. The beach club #204 should of...
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    1 / 22
    4 of 5 stars (20) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Terrace
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 20, 2013
    I chose the Pelican Landing due its proximity to Duvall Street and the ability to secure the rental for daily rates. The unit was spacious and had a lot of accommodations within...
    4 of 5 stars Reviewed May 21, 2013
    We stayed in a two bedroom unit, and had other friends in a separate unit. When we first pulled up we were a little worried because the outside is rather plain. We were...
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    1 / 15
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Private Luxury Home surrounded by lush tropical landscaping. The fusion of a mid-century Florida home with dramatic Caribbean design, has created an ideal contemporary "Floribbean" style villa in the Casa Marina district of Key West. Walking distance to all Old Town has to offer, as well as a... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed August 28, 2014
    We were told about this magnificent property by very good friends. The location is in a quiet residential area, but it is easy to access all the activities of Key West. The...
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    1 / 32
    4.5 of 5 stars (8) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Waterfront
    • Hot Tub
    • Sauna
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Paradise found reservations must begin and end on a Saturday. You feel it the moment you arrive. It's a rhythm. A rhythm set into motion over a century ago by pirates, artists, writers and other champions of leisure. Today that same rhythm beckons you to discover the charm and grace of Old Key... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed January 24, 2016
    The property was great. A few issues with C120. The fridge had rust. The TV in the living room was computer monitor sized. We like to catch a game now and then and it was like...
    5 of 5 stars Reviewed January 4, 2016
    The onsite property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the...
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    1 / 22
    4.5 of 5 stars (16) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    The Pineapple Cottage is tucked away and totally private, yet it is only a half a block from Duval Street. This two story "cottage" offers a first floor bedroom that opens through french doors to the private pool and gardens. A second floor suite includes a bedroom and bath plus a seperate living... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 27, 2016
    We recently stayed 4 nights at the Pineapple cottage and it was everything we hoped for and more. The place had plenty of room and is even better than advertised. Both bedrooms...
    5 of 5 stars Reviewed June 25, 2015
    This beautiful house was situated in the center of downtown although hidden and quiet we never used our car during our stay. The backyard and private pool were amazing. We ate...
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    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can't be beat. The home's history is rich; neighboring the historic Gato Cigar factory which is now... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 12
    5 of 5 stars (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Tucked away near the upper end of Duval Street you'll find this stylish, newly renovated three bedroom, three bath home. Thoughtful details are luxuriously appointed to suit the vacation guest looking for privacy and high design. Walk up the brick drive and enter the gate to the palm tree lined... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed October 31, 2015
    My husband, college-aged son and I stayed at Louisa's Hideaway at spring break 2014. From the moment we opened the gate to this tucked-away property, we were in love. The...
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    1 / 23
    4.5 of 5 stars (27) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
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    • Shared Outdoor Pool...
    • Grill
    • Balcony
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    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 13, 2015
    The actual unit was really nice and accommodating for us (a party of six). However, from the time of check in and a few times afterwards, the management official working at the...
    4 of 5 stars Reviewed January 24, 2014
    Nice location looking out on Garrison Bight Marina and close enough to Old Town. Super spacious unit was very nice and clean. Completely equipped and has washer/dryer stack. A...
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    1 / 35
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Our unit is a 2 bedroom 2 bathroom condominium with a full kitchen. Located in Key West, FL for Nightly, Weekly, vacation rental. The price of a hotel with the comforts of home. Sunrise Suite Key West is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 28, 2016
    First time using a Vacation Rental & forst time in Florida so wasn't sure what to expect, walked into the Condo and it was beautiful, well kept, and tastefully decorated. Loved...
    5 of 5 stars Reviewed April 23, 2016
    This condo was like being at home. The attention to detail for items you need when traveling were there for our use. Beach towels, beach chairs, and even beach toys for children...
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    1 / 20
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderful home, which has recently been completely renovated, boasts 4 bedrooms, 3-1/2 bathrooms, a new modern kitchen, a living room, a dining room, an office nook, a 270 degree wrap... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 stars (12) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
    • Satellite TV
    • Internet Access
    • Terrace
    • Grill
    • Shared Outdoor Pool...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 13, 2013
    Everything was as promised , great location , very nice and helpful staff .
    5 of 5 stars Reviewed January 5, 2013
    Very spacious with great balcony with dock/pool access. Would definitely stay again
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    1 / 9
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other traveler has booked this property
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    • Pet-friendly
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    • x
    • x
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    • x
    About this property
    ***CHECK IN DATES FOR THIS RESORT ARE FRI/SAT/SUN. RATES ARE SUBJECT TO CHANGE UNTIL RESERVATION IS CONFIRMED*** Situated on the Atlantic Ocean, the property captures Key West style with modern convenience. Conveniently located near Key West Int'l airport and only a short distance to beaches,... View all property information
    Location Information
    Key West, Florida Keys 33040