Holiday Rentals in Fleming Key

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Holiday Rentals in Fleming Key

Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, 331 reviews
"Beautiful studio and great location. Communication with the owner was excellent."
The price is €237
per night
20 Jun - 21 Jun
Steps from Duval, Pool & Bikes $129-$299 Night!
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
9.4 out of 10, Exceptional, 99 reviews
"We loved it here. Great location and very clean. Would highly recommend if you are visiting key west."
The price is €257
per night
2 Jun - 3 Jun
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, 88 reviews
"Everyone was extremely nice and helpful."
Aqua Lodges at Hurricane Hole Marina
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FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
9.8 out of 10, Exceptional, 103 reviews
"Beautiful property in a great location. I would definitely stay again."
The price is €265
per night
2 Jun - 3 Jun
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
Poolside Cottage #411
10.0 out of 10, Exceptional, 17 reviews
"Clean. Everything we needed in a key west stay."
The price is €341
per night
4 Jun - 5 Jun
Poolside Cottage #411
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
9.8 out of 10, Exceptional, 56 reviews
"Perfect, loved the pool area, very peaceful, beautiful property"
The price is €418
per night
2 Jun - 3 Jun
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
Salvador's Studio by Brightwild | Heated Pool!
8.0 out of 10, Very good, 20 reviews
"So enjoyed it ! Had never stayed in this part of Old Town , and this introduced me to so much. Would absolutely return."
The price is €261
per night
16 Jun - 17 Jun
Salvador's Studio by Brightwild | Heated Pool!
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
10.0 out of 10, Exceptional, 10 reviews
"The Yacht was beautiful. The marina was amazing. The marina and resort had excellent restaurants and bars. It was very cool to see all of the boats coming and going. It was an easy Uber ride to Key West and enjoy the fast pace life. Then it was wonderful to come back to the quiet of the marina. Would highly recommend a stay here."
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
10.0 out of 10, Exceptional, 55 reviews
"My husband and I really enjoyed our time at Scarlet Mango Inn! Communication with the hosts was super easy with the convenience of reaching them via text. Our room was very clean and the property was so cute! It was a little noisy in the morning as staff cleaned outside, otherwise it was quiet. There is plenty to do within walking distance - food, bars, shopping, etc. We would definitely stay here again!"
The price is €388
per night
8 Jun - 9 Jun
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
9.0 out of 10, Wonderful, 214 reviews
"Very enjoyable"
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
9.2 out of 10, Wonderful, 94 reviews
"Wonderful stay. Was not in the room much, except to sleep and used the pool and common areas a few times and, overall, Azul was just beautiful and should I return, I would stay here again."
The price is €258
per night
2 Jun - 3 Jun
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
Key West Beachfront Luxury 2/2 Condo A212
9.8 out of 10, Exceptional, 119 reviews
"Nice property with great furnishings; really liked that it felt more like a residence than a resort. I would stay here again if I had the chance."
Key West Beachfront Luxury 2/2 Condo A212
CORONA ~ Adults Only, Historic Azul Mansion Suite with Community Pool!
9.8 out of 10, Exceptional, 106 reviews
"My wife and I stayed for a long weekend (Thurs - Sunday) and we had a great time. We will definitely stay again and highly recommend this location. If you are going, rent a golf cart as it is much easier to get around."
The price is €260
per night
5 Jun - 6 Jun
CORONA ~ Adults Only, Historic Azul Mansion Suite with Community Pool!
Penthouse Level Ocean Views- Live the Dream
9.6 out of 10, Exceptional, 208 reviews
"Condo was as good as the pictures showed and everything you needed. Views were amazing and pool was great! Thanks for sharing with us."
Penthouse Level Ocean Views- Live the Dream
34’ Catamaran Sailboat
9.4 out of 10, Exceptional, 25 reviews
"Friendly, easy access and close to desired destination "
34’ Catamaran Sailboat
ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking
9.6 out of 10, Exceptional, 40 reviews
"I recently had the pleasure of staying at Elizabeth's Secret in Old Town Key West, and it was an absolutely delightful experience. The property offers the perfect blend of comfort, convenience, and charm, making it an ideal choice for anyone looking to immerse themselves in the vibrant atmosphere of Key West. Accommodations: Elizabeth's Secret features two well-appointed bedrooms along with a cozy loft bedroom. The space is tastefully decorated, providing a warm and inviting ambiance that made...
The price is €2,024
per night
15 Jun - 16 Jun
ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
8.8 out of 10, Excellent, 18 reviews
"Good location as far walking distance to a Cuban food truck- Luna. Hogfish is a good restaurant, good seafood and good service, short walk. Property was clean. Beds comfortable. Mostly quiet. It’s about 3 miles from Key West."
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
9.6 out of 10, Exceptional, 159 reviews
"Lovely room. Very clean. Property mgt responded immediately when i had a request."
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
9.8 out of 10, Exceptional, 258 reviews
"We really enjoyed our stay at this property. The condo was clean and well supplied with essentials. The property is well maintained and safe. We were able to use the included bicycles to get to most locations we wanted to go in old town. Southernmost point was a leisurely 15 min bike ride away. The property owner communicated well with us and answered all of our questions. The only thing we were not prepared for was the traffic noise. The unit does face a busy street, so you can hear vehicles...
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
TIDES ON SIMONTON ~ Perfectly located just off Duval and all the fun!
9.2 out of 10, Wonderful, 157 reviews
"Property was not as clean as I expected. Information in downloaded info said check-in info would be emailed about a week ahead, did not get check-in info unit I called the day before check-in."
TIDES ON SIMONTON ~ Perfectly located just off Duval and all the fun!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Fleming Key you may be interested in

Oceans Edge Key West Resort, Hotel & Marina
4.0 star property
9.0 out of 10, Wonderful, 1,520 reviews
"I paid for ocean view but was assigned a view of the pool and harbor. This problem was corrected and I was reassigned an ocean view."
The price is €167
per night
9 Jun - 10 Jun
Oceans Edge Key West Resort, Hotel & Marina
Margaritaville Beach House Key West
4.0 star property
8.6 out of 10, Excellent, 1,772 reviews
"Great place to stay "
The price is €240
per night
4 Jun - 5 Jun
Margaritaville Beach House Key West
Southernmost Beach Resort
4.0 star property
8.2 out of 10, Very good, 1,897 reviews
"Overall, great experience would definitely stay there again"
The price is €254
per night
19 Jun - 20 Jun
Southernmost Beach Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Fleming Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Fleming Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Fleming Key holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Fleming Key holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Fleming Key. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Fleming Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Fleming Key holiday rentals we have selected for you start as low as €237 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Fleming Key rentals

At Expedia, we put the best Fleming Key holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Fleming Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Fleming Key holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Fleming Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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