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Compare 513 Vacation Homes in Fleming Key with updated reviews, rates, and availability.

Exterior
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 AED 1,837
AED 4,865 total
includes taxes & fees
5 Jun - 6 Jun
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 AED 2,567
AED 5,564 total
includes taxes & fees
27 May - 28 May
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Private Spa Patio
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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Welcome to Mango Margarita!
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!
Welcome to your island home!
TROPICAL RETREAT ~ 3 Bedroom, 3.5 Bath 1/2 Block From Duval St. w/ Pool!
9.8 out of 10, Exceptional, (57)
"We had a very positive stay at Tropical Retreat. The property is in a great location and was very comfortable. It was as presented on the website and the property managers were great to work with."
TROPICAL RETREAT ~ 3 Bedroom, 3.5 Bath 1/2 Block From Duval St. w/ Pool!
CASA SERENDIPITY is the perfect combination of quintessential charm and the conveniences of modern amenities...
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
10.0 out of 10, Exceptional, (73)
"This home was wonderful! House had all we needed and was very comfortable. Fully gated yard which was perfect for our dog. It was in such a quiet and peaceful part of town that we sat on the deck and enjoyed the small pool every day. We walked into town each day and we explored all of Old Town from the North end (great marina, restaurants and view) to the South end (great views, restaurants and shopping). Would absolutely recommend this home and would we definitely would rent here next time!"
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
Pool
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 AED 793
AED 1,357 total
includes taxes & fees
28 May - 29 May
Poolside Cottage #411
Nassau Suite Entrance
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
Welcome home!
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!
Your outdoor Paradise
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!
Huge pool (heated in winter) with clubhouse in background that has bathrms, deck
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
9.6 out of 10, Exceptional, (90)
"House was exactly as stated. We enjoyed it there. Close enough to downtown to enjoy it. Nice touch having the bikes there to use! Condo pool was great too. We enjoyed the amenities! Would stay again if we came back to the area!"
The price is AED 1,102
AED 2,312 total
includes taxes & fees
22 Jun - 23 Jun
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Exterior
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.
Welcome to 2 Cool Fish!
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!
Grill up your fresh catch (Kayaks not included)
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
8.8 out of 10, Excellent, (18)
"Great property, great views on the water."
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Private home with Old Town Charm
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!!
Pool (In Season)
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!
Welcome to the QUEEN OF LOUISA...
**QUEEN OF LOUISA @ DUVAL** Home in Old Town & Private Pool + LAST KEY SERVICES
10.0 out of 10, Exceptional, (32)
"We had an amazing time! The house is within walking distance of everything! Really cool layout, and we all had our own bedroom and bath. The pool is great as well!"
**QUEEN OF LOUISA @ DUVAL** Home in Old Town & Private Pool + LAST KEY SERVICES
ENDLESS SUMMER is a 5 bedroom private home that was designed to accommodate a large group just half a block from Duval Street...
**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...
Welcome to OFF CALL
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!
Welcome to your island home!
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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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

Pool
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 AED 364
AED 880 total
includes taxes & fees
30 May - 31 May
Steps from Duval, Pool & Bikes $129-$299 Night!
Pool
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 AED 793
AED 1,357 total
includes taxes & fees
28 May - 29 May
Poolside Cottage #411
Room
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St
9.2 out of 10, Wonderful, (227)
"This property is no frills but provides everything you need. The location is great, the two room split provides privacy, pool was great and the bikes provided allow for cruising around the island. Tanya was very responsive. Would stay here again."
The price is AED 1,098
AED 2,139 total
includes taxes & fees
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.

Recent reviews of Fleming Key hotels
Expedia verified reviews

Southernmost Beach Resort

Southernmost Beach Resort

5/5 Excellent
"This report was perfect for a three day trip. Nice beach and just a walk away from the crowds. "
A verified traveler stayed at Southernmost Beach Resort
Posted 2 days ago
Southernmost Beach Resort