Search Vacation Homes in Fleming Key

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

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
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 ￥101,257
per night
Jun 10 - Jun 11
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, (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
per night
May 19 - May 20
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
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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
per night
May 14 - May 15
Poolside Cottage #411
Property grounds
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
9.6 out of 10, Exceptional, (89)
"Condo was clean and orderly and as-advertised. Host was easy to deal with. Would've hoped for more paper products for the price we paid! Overall enjoyed our stay. Pool was lovely."
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Pool
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
10.0 out of 10, Exceptional, (72)
"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
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.
Property grounds
Mother Ocean: Waterfront 4 Bedroom 3 Bath luxury Oceanfront home with pool
9.4 out of 10, Exceptional, (44)
"Wonderful place. We rented 7 bikes and were able to store them in the garage and ride wherever we needed to go. Didn’t need to go much since the place was so great, between the pool and the spacious open kitchen and decks we were able to cook and make cocktails."
Mother Ocean: Waterfront 4 Bedroom 3 Bath luxury Oceanfront home with pool
Property grounds
Seaside Retreat: Waterfront Home with private heated pool & lush landscaping
9.6 out of 10, Exceptional, (45)
"This was a beautiful house in a great location. Very large, easily fit everyone comfortably. Awesome."
Seaside Retreat: Waterfront Home with private heated pool & lush landscaping
Property grounds
Duval Street Suite in Key West
10.0 out of 10, Exceptional, (17)
"The house was spectacular!! The stairs were tough but when the hard work was done we had a great stay!!! Dave, Liz, Jeff and wendy"
Duval Street Suite in Key West
Property grounds
Spacious home with pool & balcony - 1 block from Duval Street
9.2 out of 10, Wonderful, (66)
"Had an absolute blast in Key West! From the vibrant sunset celebrations at Mallory Square to exploring the historic streets of Old Town, every moment was a treasure. Bars on Duval Street, and the laid-back island vibes made it an unforgettable."
Spacious home with pool & balcony - 1 block from Duval Street
A heated pool
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
9.6 out of 10, Exceptional, (63)
"Enjoyed our stay…..Dan was very helpful with the smart tv issue…."
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
A heated pool
Boli Townhouse - Luxury Rental in gated Truman Annex - Saturday to Saturday only
10.0 out of 10, Exceptional, (158)
"Boli Townhouse was perfect for our stay. Close to Duval Street, but quiet for relaxing. Great patio with grill. We loved morning coffee out there. Pool was perfect with plenty of chairs. Kitchen is very small, but has everything you need. Would stay there again for sure."
Boli Townhouse - Luxury Rental in gated Truman Annex - Saturday to Saturday only
Interior
May 20-23 or 27-30 ngt. mid-wk..spec. beach kitchen & patio 142.ngt + ext
9.6 out of 10, Exceptional, (185)
"This was our third time staying at this location. It is as described and the location is fantastic."
May 20-23 or 27-30 ngt. mid-wk..spec. beach kitchen & patio 142.ngt + ext
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
per night
May 16 - May 17
Poolside Cottage #412
Terrace/patio
Spec. April.19-24 155.00 night plus extras Near beach& Full Kitchen & Patio
9.0 out of 10, Wonderful, (139)
"What a great location! The apartment is close to the heart of Key West and the majority of attractions on the island, so we were able to walk everywhere during our stay. We had a variety of restaurants, grocers, and shops to choose from, and when we were exhausted, it didn't take long to walk back. While the apartment is small, it's perfect for those wishing to not be surrounded by hoards of tourists. Calm, comfortable, and secluded. The back patio was a nice area to enjoy without distractions...
Spec. April.19-24 155.00 night plus extras Near beach& Full Kitchen & Patio
Exterior
Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location
9.0 out of 10, Wonderful, (163)
"This home is perfectly located. It was a great get away weekend to celebrate a birthday with family and friends."
Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location
Fridge, microwave, oven, stovetop
**QUEEN OF LOUISA @ DUVAL** Home in Old Town & Private Pool + LAST KEY SERVICES
10.0 out of 10, Exceptional, (31)
"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
A heated pool
**DUCHESS OF CATHERINE @ DUVAL** Brand New Home & Pool + LAST KEY SERVICES…
10.0 out of 10, Exceptional, (1)
"The house is beautiful! Great set up and so well equipped and stocked! Highly recommend."
**DUCHESS OF CATHERINE @ DUVAL** Brand New Home & Pool + LAST KEY SERVICES…
Property grounds
Family home in gated community w/great amenities, shared pool, fitness center
8.8 out of 10, Excellent, (119)
"Very clean. Good size for a family with older kids who want their own space. We enjoyed reading and drinking coffee on the porches."
Family home in gated community w/great amenities, shared pool, fitness center
Don't see what you're looking for?
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, (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
per night
May 20 - May 21
Steps from Duval, Pool & Bikes $129-$299 Night!
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, (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 ￥46,578
per night
Jun 3 - Jun 4
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St
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
per night
May 14 - May 15
Poolside Cottage #411
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.