Fleming Key Vacation Rentals

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Browse Select Fleming Key Vacation Homes

Fridge, microwave, oven, stovetop
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
10.0 out of 10, Exceptional, (1)
"We had a great time at Pagitt House. The location is central to everything you’d want to do in Key West. The rooms are comfortable and well appointed. We didn’t use the kitchen much but it was well stocked with whatever you might need."
The price is CA $820
CA $1,983 total
includes taxes & fees
Jun 18 - Jun 19
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
Pool
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
9.8 out of 10, Exceptional, (191)
"Everything about this place exceeded expectations. The check in was easy and they even let us store our luggage before our check in to make everything more conducive. The house is better than advertised, within walking distance to all the bars and restaurants."
The price is CA $955
CA $2,077 total
includes taxes & fees
May 28 - May 29
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Pool
Duval Square in Key West
10.0 out of 10, Exceptional, (12)
"Great location and nice accommodations. Very enjoyable trip. Located right by Duvall Loop free trolly so no reason to pay for the old Town Trolly. Only negative is I don’t like having to wash dishes and put away, having to strip beds and do their laundry. This is my vacation so I could do these things at home. Manager helped 2 old people with our luggage because we thought the elevator was out of order. He even took it up the stairs to our bedroom. So nice and helpful!"
Duval Square in Key West
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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!
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!
Pool
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
10.0 out of 10, Exceptional, (73)
"The house was as advertised and we had everything we needed. We enjoyed the pool it was very refreshing. We will definitely look To book again on our next Key West trip."
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
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 CA $295
CA $505 total
includes taxes & fees
May 28 - May 29
Poolside Cottage #411
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
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!
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!
Property grounds
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
9.6 out of 10, Exceptional, (91)
"Condo was clean and as advertised. The amenities were great. We used the bikes, the beach chairs and coolers that were provided. We had a plumbing issue but Judy was right on it and it was fixed the same day. We ran out of garbage bags and paper towels but we managed. Not a huge issue but wanted to point it out so it can be addressed with the cleaning company. Overall, a wonderful place to stay."
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Pool
Great Family Vacation Rental.
10.0 out of 10, Exceptional, (3)
"The townhome was nice and is located in a quaint community. The pool area was beautiful. We found that we needed to Uber into Key West since parking is very limited and we were told the bus service is often not on time."
Great Family Vacation Rental.
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!
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!
A heated pool
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
9.6 out of 10, Exceptional, (156)
"The house was clean and well stocked with essentials, had lots of character and nicely decorated. The backyard was beautiful with an amazing pool and lots of lounge chairs and outdoor seating. Wonderful stay for our group of 6 adults."
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
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!
Fridge, microwave, oven, stovetop
**QUEEN OF LOUISA @ DUVAL** Home in Old Town & Private Pool + LAST KEY SERVICES
10.0 out of 10, Exceptional, (32)
"We absolutely loved this house! The check-in process was easy and a team member greeted us upon check-in. You cannot get a better location in Key West than this house. You can walk to everything! We loved it. Highly recommend."
**QUEEN OF LOUISA @ DUVAL** Home in Old Town & Private Pool + LAST KEY SERVICES
Smart TV
**ENDLESS SUMMER @ OLD TOWN** New Villa & Pool + LAST KEY SERVICES...
9.8 out of 10, Exceptional, (73)
"Great place!! Very convenient You get what you see Quiet in the gates but duval street 100 feet"
**ENDLESS SUMMER @ OLD TOWN** New Villa & Pool + LAST KEY SERVICES...
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!
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!
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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

Beach towels
Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, (330)
"My husband and I just got back from Key West. We had a fabulous time and loved where we stayed. Ken, the owner, is terrific. Great communication, excellent tips on things to do and places to eat. It a large house and you have a room to stay in with your own bathroom, small kitchen and bed. It was perfect for us. We will definitely be back next time we visit Key West. Thanks Ken for being a great host!!!"
The price is CA $190
CA $397 total
includes taxes & fees
Jun 20 - Jun 21
Steps from Duval, Pool & Bikes $129-$299 Night!
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 CA $295
CA $505 total
includes taxes & fees
May 28 - May 29
Poolside Cottage #411
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, (228)
"Description and pictures accurate. Clean, got what you need, quick response to my questions. Great for me and my husband in a room. Bikes were awesome to have. Couple blocks off Duval. Each room is good for two. Enjoyed the stay!"
The price is CA $409
CA $796 total
includes taxes & fees
Jun 3 - Jun 4
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 Vacation Homes information

Number of reviews
1,069
Accommodation
619 Vacation Homes
Lowest Price
Highest Price

Recent Reviews in Fleming Key
Expedia verified reviews

Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

5/5 Excellent
"Great stay "
A verified traveller stayed at Hilton Garden Inn Key West / The Keys Collection
Posted 18 hours ago
Hilton Garden Inn Key West / The Keys Collection