Fleming Key Vacation Rentals

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Find properties with these dates

Tonight
May 12 - May 13
Tomorrow
May 13 - May 14
Next weekend
May 17 - May 19

Vacation Rentals in Fleming Key

Poolside Cottage #411
Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (16)
"My son and his new wife stayed here for their honeymoon and they absolutely loved it!"
The price is ￥33,648
￥57,074 total
includes taxes & fees
May 14 - May 15
Poolside Cottage #411
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
Property grounds
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
10.0 out of 10, Exceptional, (9)
"Sunset cruise was amazing around key west with captain lombardi"
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
52' Power Catamaran Yacht at Luxury Resort Marina
Outdoor dining
52' Power Catamaran Yacht at Luxury Resort Marina
10.0 out of 10, Exceptional, (11)
"We had a great time about Blue Jeans! Louie is an amazing host, as responsive as possible, also took us out for a cruise around Key West, AC works great! Easy Golf kart ride from the marina to down town key west. Pool at the marina was nice as well."
52' Power Catamaran Yacht at Luxury Resort Marina
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Bahama Village studio @ the Galleria!
Pool
Bahama Village studio @ the Galleria!
10.0 out of 10, Exceptional, (5)
"It was very clean and nice. The air conditioning worked great. Located close to Duval. The only issue we had was that there was no closet or place to put clothes so after a few days it was hard to keep organized."
The price is ￥33,859
￥66,425 total
includes taxes & fees
May 14 - May 15
Bahama Village studio @ the Galleria!
Luxury 62' Yacht! In a Beautiful Resort
Outdoor pool, a heated pool
Luxury 62' Yacht! In a Beautiful Resort
10.0 out of 10, Exceptional, (6)
"Everything was great and we would love to visit again!"
Luxury 62' Yacht! In a Beautiful Resort
Poolside Cottage #412
Outdoor dining
Poolside Cottage #412
10.0 out of 10, Exceptional, (6)
"Perfect location. Poolside. Friendly staff, excellent service ~ Brandy!!!"
The price is ￥33,648
￥57,074 total
includes taxes & fees
May 16 - May 17
Poolside Cottage #412
The Crystalmarine Suite – Rustic Luxury on the Sea
Interior
The Crystalmarine Suite – Rustic Luxury on the Sea
10.0 out of 10, Exceptional, (1)
"This was such a nice and cozy place to spend the weekend! We took our boat from key largo and docked up next to the houseboat and it was just amazing! I live how you can order food delivered to your door! It had tons of privacy and if your wondering no it does not move a lot at night! The solid pannel powered everything at night and we slept very peaceful! The sunsets from this house boat are 2nd to none would stay here again in the future!"
The price is ￥85,679
￥108,695 total
includes taxes & fees
May 21 - May 22
The Crystalmarine Suite – Rustic Luxury on the Sea
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
A heated pool
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
10.0 out of 10, Exceptional, (52)
"Only a couple of nights but the Scarlet Mango was perfect for our first trip to Key West. Perfectly clean and convenient to Duval St. activities. Five Stars across the board."
The price is ￥26,171
￥58,749 total
includes taxes & fees
May 21 - May 22
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Pool
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
9.8 out of 10, Exceptional, (188)
"We had 10 friends staying in the William Skelton Home this past weekend and the home was perfect. Our hosts were helpful and accommodating in letting us store luggage there on our arrival. The house is so close to so much of the action of Key West and yet it's quiet and peaceful when you're back at the home. It's a special place to stay and perfect for large groups."
The price is ￥116,679
￥246,620 total
includes taxes & fees
May 19 - May 20
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Pool | Outdoor pool, a heated pool
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
9.8 out of 10, Exceptional, (257)
"This property and host exceeded all of our expectations. It was spacious, comfortable, and welcoming with its amazing kitchen, breezy rooms, and friendly neighbors. The hosts were a pleasure to work with and easy to reach whenever we wished to communicate with them. 10/10 would return to this property. I highly recommend it!"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
Beach nearby
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
9.8 out of 10, Exceptional, (100)
"Beautiful property in a great location. I would definitely stay again."
The price is ￥18,849
￥43,542 total
includes taxes & fees
May 20 - May 21
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
A heated pool
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
9.8 out of 10, Exceptional, (103)
"Excellent top drawer"
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo / Pool + LAST KEY SERVICES
Pool
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo / Pool + LAST KEY SERVICES
9.8 out of 10, Exceptional, (148)
"A beautiful place to stay! So clean and spacious! Felt like home! We really enjoyed the pool, the reading room, and fitness room. We also loved being so close to Smathers Beach! We had a wonderful vacation!"
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo / Pool + LAST KEY SERVICES
CORONA ~ Adults Only, Historic Azul Mansion Suite with Community Pool!
Beach nearby
CORONA ~ Adults Only, Historic Azul Mansion Suite with Community Pool!
9.8 out of 10, Exceptional, (103)
"Quaint inn with a lovely “at home” feel. Great location close to downtown. The manager came every morning to fill a large water container with ice and sliced fruit. The pool was sparkling clean."
The price is ￥21,809
￥47,182 total
includes taxes & fees
May 21 - May 22
CORONA ~ Adults Only, Historic Azul Mansion Suite with Community Pool!
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!
Property grounds
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!
9.8 out of 10, Exceptional, (79)
"Carpets were soiled, floors seemed not mopped and the refrigerator was dented."
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!
Steps from Duval, Pool & Bikes $129-$299 Night!
Beach towels
Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, (329)
"First off the communication with Ken was amazing. Always got back to me right away. The property was very clean and just what was needed. Location. Was amazing and having the bikes was awesome. We rode them all over. Would definitely rent here again."
The price is ￥15,422
￥37,329 total
includes taxes & fees
May 20 - May 21
Steps from Duval, Pool & Bikes $129-$299 Night!
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
Beach nearby
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
9.6 out of 10, Exceptional, (156)
"Couldn’t have asked for a better stay!! Comfy bed, quiet, great AC! Loved it all."
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
40'yacht in Paradise Awaits You!
Property grounds
40'yacht in Paradise Awaits You!
9.6 out of 10, Exceptional, (23)
"This was our first time staying on a boat, no a yacht! Michael was extremely helpful when meeting up to check us in. All of his tips and advice was helpful during our stay. The boat itself is amazing - clean, spacious, comfortable and in a beautiful location. The marina was quiet, easy to access and walk around, well maintained and had friendly people. We had the beach to ourselves during our stay. It's absolutely stunning. The pool overlooked the channel and more boats - so gorgeous! We would...
40'yacht in Paradise Awaits You!
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Fridge, microwave, oven, stovetop
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
9.4 out of 10, Exceptional, (198)
"Beautiful home, well equipped and close to everything. The bed was comfortable and the cottage was very clean. You can’t go wrong with this lovely place."
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
34’ Catamaran Sailboat
Fridge, cookware/dishes/utensils, dining tables
34’ Catamaran Sailboat
9.4 out of 10, Exceptional, (23)
"So glad we stayed here! It is exactly what I was looking for. A unique way to visit Key West. It was nice to open the hatches and have a nice breeze and great view of the stars. He has a nice bathroom with shower in the car port. The host was great with communication and was really cool. Definitely recommend"
34’ Catamaran Sailboat
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See all available properties in Fleming Key
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
View from property
Oceans Edge Key West Resort, Hotel & Marina
4.0 star property
9.0 out of 10, Wonderful, (1523)
"Liked watching the Navy Fighters flying overhead. Disliked people smoking on balconies."
The price is ￥33,466
￥46,789 total
includes taxes & fees
Jun 6 - Jun 7
Oceans Edge Key West Resort, Hotel & Marina
Havana Cabana at Key West - Adults Only
Outdoor pool, sun loungers
Havana Cabana at Key West - Adults Only
4.0 star property
8.8 out of 10, Excellent, (1454)
"Truly amazing staff and property! It’s super clean , people are friendly and the pool is amazing. The staff were so accommodating. I’d recommend everyone to stay here. They truly made my first visit to Florida amazing. Complementary snacks by the pool, a free shuttle down town. Just overall great experience! Thank you !"
The price is ￥29,785
￥43,482 total
includes taxes & fees
Jun 11 - Jun 12
Havana Cabana at Key West - Adults Only
Margaritaville Beach House Key West
Beach nearby, white sand
Margaritaville Beach House Key West
4.0 star property
8.6 out of 10, Excellent, (1748)
"Nice place to sleep , eat and relax. Walking distance to the beach. "
The price is ￥35,674
￥49,997 total
includes taxes & fees
May 27 - May 28
Margaritaville Beach House Key West
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.

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Recent reviews of Fleming Key properties
Expedia verified reviews

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

5/5 Excellent
"Was so beautiful!"
A verified traveler stayed at Winslow's Bungalows - Key West Historic Inns
Posted 1 day ago
Winslow's Bungalows - Key West Historic Inns