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Browse Select Fleming Key Holiday Homes

LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!
A heated pool
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!
9.6 out of 10, Exceptional, 189 reviews
"This little house is perfect! Everything was clean and the pool was a perfect backyard oasis. 10/10 recommend for a nice little getaway!"
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
Fridge, microwave, oven, stovetop
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
10.0 out of 10, Exceptional, 2 reviews
"Absolutely Fantastic! Place was amazing and the pool was perfect. The house is located in close walking distance to pretty much everything you want to do in Key West. The host was easy to communicate with and we had a great time. Can't wait to go back, and would highly recommend staying here if you are headed to Key West."
The price is £1,162
per night
11 Jul - 12 Jul
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
Fridge, microwave, oven, stovetop
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
9.6 out of 10, Exceptional, 186 reviews
"Great location, you can ride a bike or walk to the beach or anywhere on Duval street. The pool was a nice touch to the property."
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
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TROPICAL RETREAT ~ 3 Bedroom, 3.5 Bath 1/2 Block From Duval St. w/ Pool!
Property grounds
TROPICAL RETREAT ~ 3 Bedroom, 3.5 Bath 1/2 Block From Duval St. w/ Pool!
9.8 out of 10, Exceptional, 59 reviews
"This property is a 10/10 Plenty of room for our party of 7 adults. Super clean and the property manager kept in touch the entire time. Highly recommend"
TROPICAL RETREAT ~ 3 Bedroom, 3.5 Bath 1/2 Block From Duval St. w/ Pool!
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
Interior
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
9.8 out of 10, Exceptional, 102 reviews
"wonderful stay!"
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!
Property grounds
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!
9.8 out of 10, Exceptional, 43 reviews
"Great location, awesome home inside and out, clean, and Grade A communication."
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!
OFF COURSE ~ Adorable 2 BR, 2.5 Ba Townhome in Truman Annex w/ Shared Pool!
TV
OFF COURSE ~ Adorable 2 BR, 2.5 Ba Townhome in Truman Annex w/ Shared Pool!
10.0 out of 10, Exceptional, 21 reviews
"This property was amazing! Upon arrival the host was in contact with all the information and made getting to the property very easy and is exactly as shown on the site. This is a very safe area with everything within walking distance- Duval St, beaches and restaurants. The pool is clean and well maintained. I would highly recommend this VRBO if visiting Key West and if available for my next visit will use it as my spot to stay!"
OFF COURSE ~ Adorable 2 BR, 2.5 Ba Townhome in Truman Annex w/ Shared Pool!
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
Property grounds
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
9.8 out of 10, Exceptional, 156 reviews
"A short walk from the busy docks, the property offered the unexpected pleasure of staying in our own peaceful and private garden enclave. The nature-inspired design of the pool and the lush tropical foliage invited lingering on the lounge chairs and the porch. The patch of grass, although artificial, made great terrain for water fights, a game of beachball soccer, and sunbathing on a towel. Inside, the home was spacious and charming, with island colors punctuating wonderful (original?) wood...
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
A heated pool
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
9.8 out of 10, Exceptional, 76 reviews
"House was great and location is amazing. You can't get any closer to Duvall without being directly on it. Practically the center of Duvall street so everything is walking distance. Parking spot is tight - I would recommend renting a golf cart in lieu of a car - but everything is so close, you don't need either."
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
Property grounds
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
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
Fridge, microwave, oven, stovetop
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
9.8 out of 10, Exceptional, 157 reviews
"Very good for 5 friends. Within walking distance of many great activities Would recommend Queen Size beds for little more room in bedrooms. More chairs by pool area since is the only area large enough for meals Easy communication with property manager"
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
A heated pool
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
9.6 out of 10, Exceptional, 157 reviews
"We had 3 adults varying ages celebrating a 30th birthday. The house couldn't have been more perfect. Charm alongside the perfect layout for personal space as well as areas to be together at the pool family room or dining room. The pool amazing. House immaculate with all amenities needed. Bikes to rent are just a couple blocks away (walking) we had no issue parking for one car. Easy bike ride or nice walk to Duvall. And our host Melanie was a star! Quick to respond but really everything was...
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
ISLE AZURE ~ Charming 3 Bed/3 Bath with Private Pool & Spa in Truman Annex!
Fridge, microwave, oven, stovetop
ISLE AZURE ~ Charming 3 Bed/3 Bath with Private Pool & Spa in Truman Annex!
9.4 out of 10, Exceptional, 68 reviews
"The place is beautiful, inside and out. I read out by the pool, it was the most relaxing vacation I think I’ve ever had. A lot of walking around Key West, I just love it!"
ISLE AZURE ~ Charming 3 Bed/3 Bath with Private Pool & Spa in Truman Annex!
SAILOR HOUSE ~ Charming 2 Bedroom, 1.5 Bathroom Just Steps to Duval St!
Property grounds
SAILOR HOUSE ~ Charming 2 Bedroom, 1.5 Bathroom Just Steps to Duval St!
10.0 out of 10, Exceptional, 57 reviews
"This was our first time visiting Key West and we stayed at the Sailor House at the end of April. The home was very clean and comfortable, the air conditioning worked well and the location was very convenient. The front porch, back patio, upstairs back deck and balcony were nice outside options to read a book or drink a morning coffee. A block away was a shop where we rented bikes for the day and a golf cart for 4 hours another day. Moondog Cafe and El Siboney were two of our favorite restaurants...
SAILOR HOUSE ~ Charming 2 Bedroom, 1.5 Bathroom Just Steps to Duval St!
Feb 3-10 $245 off the rates close beach full kitchen & patio
Interior
Feb 3-10 $245 off the rates close beach full kitchen & patio
9.6 out of 10, Exceptional, 188 reviews
"Stayed here with my 12 year old son and had a great Memorial Day Weekend in Key West! The place is quaint but very tidy and convenient / central to all parts of the island. Just as advertised, and communication with owner was great. We had a blast!"
Feb 3-10 $245 off the rates close beach full kitchen & patio
ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking
Pool
ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking
9.6 out of 10, Exceptional, 42 reviews
"The location of the home was top notch - only a few minutes walk to Duval, but still very quiet and relaxing for when you return. The home has a lot of charm and you can tell the owners have put in updates, while still keeping the island home feel. The private pool was one of my favorite things … spent hours in or around it. There are rafts and other pool toys provided as well. The porch has plenty of seating, and I enjoyed a few late breakfasts outside. Nice place to sit with coffee and a...
The price is £1,723
per night
8 Jul - 9 Jul
ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking
Poolside Cottage #412
Pool | Outdoor pool
Poolside Cottage #412
10.0 out of 10, Exceptional, 6 reviews
"Perfect location. Poolside. Friendly staff, excellent service ~ Brandy!!!"
The price is £297
per night
23 Jun - 24 Jun
Poolside Cottage #412
Duval Street Suite in Key West
Property grounds
Duval Street Suite in Key West
10.0 out of 10, Exceptional, 19 reviews
"The location, overlooking Duval Street, is perfect. The place is huge, comfortably sleeping 6, and is dog friendly. Very clean, with all of the amenities. Just note that, if you have somebody that is disabled with you, there is a steep staircase with no elevator. Also, there is only parking for one vehicle, so if there are six of you staying there, you had better hope that you all came in the very same car. I can't recommend that three groups of 2 meet up there, planning on parking three cars."
Duval Street Suite in Key West
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Property grounds
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
9.4 out of 10, Exceptional, 16 reviews
"Location was awesome. Love the proximity of water with the open deck. AC works really good."
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool!
A heated pool
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool!
10.0 out of 10, Exceptional, 55 reviews
"From the moment we arrived at our Key West retreat, we were enchanted despite the initial hiccup of discovering that two of the bedrooms were situated on the third floor. Yes, the stairs were a bit of a challenge, but what awaited us inside made it all worthwhile. The accommodation was exceptionally cozy, with a delightful small pool that became our little oasis. Cleanliness and comfort were top-notch, and the location could not have been better, placing us right in the heart of Kew West and...
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool!
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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 property types in Fleming Key

Steps from Duval, Pool & Bikes $129-$299 Night!
Beach towels
Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, 334 reviews
"Listing was accurate. Scuba masks were available and beach chairs which was a great surprise. Room was very clean. Great location and great communication. We will definitely stay again. Thank you!"
The price is £190
per night
25 Jun - 26 Jun
Steps from Duval, Pool & Bikes $129-$299 Night!
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
Beach nearby
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
9.4 out of 10, Exceptional, 100 reviews
"Nice spot away from the crowd but close enough to walk/scoot/bike to. If you plan on parking its first come first serve and not a lot of room for vehicles in the gravel driveway. Maybe 5 cars max if guests know how to park efficiently. If not then youll have to scout the street for a spare spot. I rented a scooter so no issue for finding parking in the driveway. Easy check in and the room( I stayed in the Havana) was small but big enough for one person; two if your spouse packs light and is easy...
The price is £225
per night
30 Jun - 1 Jul
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
Aqua Lodges at Hurricane Hole Marina
Restaurant
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, 92 reviews
"We received info on how to check in via self-service. Very easy to check in and get our key to the lodge. Lodge itself was clean and adorable. We loved sitting on the deck watching the water and the floating tikis. Would go back for sure"
The price is £207
per night
24 Jun - 25 Jun
Aqua Lodges at Hurricane Hole Marina
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.

Fleming Key Holiday Homes information

Number of reviews
1,155
Accommodation
624 Holiday Homes
Lowest Price
£297
Highest Price
£1,723

Fleming Key Hotel Reviews
Expedia verified reviews

Southernmost Beach Resort

Southernmost Beach Resort

5/5 Excellent
"Great location around delicious spots to eat, and the hotels beach restaurant/bar is fantastic!! Clean and friendly "
A verified traveller stayed at Southernmost Beach Resort
Posted 3 days ago
Southernmost Beach Resort