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Browse Select Fleming Key Holiday Homes

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)
"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!
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)
"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 14 364 kr
per night
6 Jun - 7 Jun
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, (185)
"The stay was excellent, a beautiful home with lovely touches to make you feel comfortable. Overall I gave the highest rating, but the TV didn’t work. The manager was attentive but still took a few days to resolve the issue. Also, pool guy arrived unannounced to service the pool, I would have preferred notice. As I said it was overall perfect in terms of location, cleanliness and charm, would recommend it!"
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
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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, (192)
"This house was great. We had an amazing time. No complaints at all. It was walking distance to all the fun places. It was equipped with everything you need and the pool was an added plus. Cant say enough good things about it. The owner was also great to work with. We loved it!"
The price is 15 084 kr
per night
5 Jun - 6 Jun
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
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, (154)
"Loved this home! (even asked to buy it) plenty of room comfortable beds, great pool and grounds. I have stayed at dozens of properties in Key West and this is hands down my favorite. Location doesn't get much better as well. Overall fantastic"
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!
Property grounds
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!
9.2 out of 10, Wonderful, (172)
"Thank you for sharing your great house. It was perfect. It had everything we needed and was very comfortable. Its in a great location. The bus stops we very close and we used the bus to get around."
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!
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, (15)
"Nice, clean property with new appliances. Convenient to Key West. Great deck for hanging out in the morning with coffee or with a cocktail in the evening. Hogfish Bar, a great sandwich shop and French bakery all close and convenient to the property."
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
SALTY KISSES ~ Charming 2 Bedroom, 1.5 Bath Townhome in Truman Annex!
TV
SALTY KISSES ~ Charming 2 Bedroom, 1.5 Bath Townhome in Truman Annex!
10.0 out of 10, Exceptional, (16)
"Everything about this was perfect. Location is great. Having a parking spot right at the rear of unit was a huge plus. Communication with property manager was a breeze (and he even got us in early!) Unit was super clean, updated and well stocked. Having the concierge service was definitely an added plus"
SALTY KISSES ~ Charming 2 Bedroom, 1.5 Bath Townhome in Truman Annex!
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Property grounds
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
8.8 out of 10, Excellent, (18)
"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!
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
A heated pool
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
10.0 out of 10, Exceptional, (69)
"Dan was the best host! The house was perfect for our group, the pool was awesome & we were able to walk to many places! We'll be back!"
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
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, (54)
"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!
Tropical Dreaming by AvantStay | 4 BLKS to Beach! Private Pool!
Beach nearby
Tropical Dreaming by AvantStay | 4 BLKS to Beach! Private Pool!
9.6 out of 10, Exceptional, (85)
"great location. would stay in this cozy little house again."
Tropical Dreaming by AvantStay | 4 BLKS to Beach! Private Pool!
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, (58)
"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!
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
A heated pool
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
9.6 out of 10, Exceptional, (64)
"Enjoyed our stay…..Dan was very helpful with the smart tv issue…."
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
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)
"Very enjoyable"
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Pool
Beach nearby
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Pool
9.8 out of 10, Exceptional, (166)
"The property was in a great location. Two glitches when we arrived. We did not receive the code to get into the property and had to call at 4:00 to get it. Also, the sofa bed had not been made up and we could not find the sheets to make it up that night. Otherwise, the property was excellent and just as described on the website. These were minor annoyances and fairly easily resolved."
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Pool
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, (75)
"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!
KATE'S KRAWL OFF DUVAL ~ 1 BR, 1 Ba Home w/ Outdoor Area Steps to Duval!
Outdoor dining
KATE'S KRAWL OFF DUVAL ~ 1 BR, 1 Ba Home w/ Outdoor Area Steps to Duval!
9.8 out of 10, Exceptional, (59)
"If you like being right downtown in the middle of shops, restaurants and entertainment this place is for you. We parked our car upon arrival and never used it until check out. This is the perfect house for two or maybe three people. We really had a great time."
KATE'S KRAWL OFF DUVAL ~ 1 BR, 1 Ba Home w/ Outdoor Area Steps to Duval!
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, (41)
"This a lovely property. Upstairs bedrooms each have their own bathroom. Washer and dryer in upstairs hallway. Clean and bright. Downstairs has a lovely sitting room and dining area. Fully stocked kitchen with many utensils, even a blender. Small closet 1/2 bath on first floor. Outside covered patio area has a small wet bar. Pool is steps away and has shady and sunny spots throughout the day. Two delicious restaurants walking distance (longest 2 blocks). Try The Garden Cafe or Cafelito, both are...
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!
SAPODILLA HOUSE ~ Spectacular 3B/3.5Ba Home in Desirable Downtown Location!
A heated pool
SAPODILLA HOUSE ~ Spectacular 3B/3.5Ba Home in Desirable Downtown Location!
10.0 out of 10, Exceptional, (75)
"The Sapodilla house was fantastic and the perfect location! We would absolutely stay here again. Truman Annex is beautiful and quiet, but only a block from all the action. We've been to Key West many times visiting family, but never stayed in Truman Annex before. I will not stay anywhere else after this. We have two children, 6 and 8, and this was the perfect house. The pool was very good-sized for Key West and the house was spacious with a well-stocked kitchen. We stayed home and grilled by the...
SAPODILLA HOUSE ~ Spectacular 3B/3.5Ba Home in Desirable Downtown Location!
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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, (331)
"Beautiful studio and great location. Communication with the owner was excellent."
The price is 2 717 kr
per night
20 Jun - 21 Jun
Steps from Duval, Pool & Bikes $129-$299 Night!
Poolside Cottage #411
Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (17)
"Clean. Everything we needed in a key west stay."
The price is 3 914 kr
per night
4 Jun - 5 Jun
Poolside Cottage #411
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St
Sun-loungers, beach towels
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St
9.2 out of 10, Wonderful, (229)
"Great open communication with the property owner! Property located in quaint area of key west nearest Ram’s head restaurant, and the world famous blue heaven!!"
The price is 6 277 kr
per night
3 Jun - 4 Jun
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St
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
1,166
Accommodation
525 Holiday Homes
Lowest Price
14 364 kr
Highest Price
15 084 kr

Fleming Key Hotel Reviews
Expedia verified reviews

Margaritaville Beach House Key West

Margaritaville Beach House Key West

5/5 Excellent
Margaritaville
"Room was nice and large had all amenities need for a family stay. Restaurant on premises was good, staff was friendly and knowledgeable."
A verified traveller stayed at Margaritaville Beach House Key West
Posted 18 hours ago
Margaritaville Beach House Key West