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Our top choices for Fleming Key holiday homes
1. Poolside Cottage #411
Poolside Cottage #411Key West
9.8 out of 10, Exceptional, (72 reviews)
"Excellent cottage in a quiet location. Our family of 4 enjoyed the stay & plan to return in the future!"
Jennifer W.
The price is €280
includes taxes & fees
1 Dec - 2 Dec
2. Poolside Cottage #412
Poolside Cottage #412Key West
9.4 out of 10, Exceptional, (37 reviews)
"Wonderful stay. Thank you."
shannon b.
The price is €271
includes taxes & fees
29 Nov - 30 Nov
3. Casa Havana | Old Town Condo w/ Pool & Balcony
Casa Havana | Old Town Condo w/ Pool & BalconyOld Town Key West
9.2 out of 10, Wonderful, (12 reviews)
"Wonderful location, clean, quiet. All around it was a great experience staying here!"
Kim T.
The price is €655
includes taxes & fees
16 Nov - 17 Nov
4. Andros Suite | Perfect Location with Pool!
Andros Suite | Perfect Location with Pool!Old Town Key West
10.0 out of 10, Exceptional, (6 reviews)
"Great little place 1 block off Duval. A nice quiet oasis from everything a street away. Moon Dog restaurant is around the block and was great for breakfast and dinner. Great kitchen! The mattress upstairs could use a firmer replacement IMHO…overall very good spot!"
Robert J.
5. Road's End | Prime Old Town Location! Updated Home w/ Pool
Road's End | Prime Old Town Location! Updated Home w/ PoolOld Town Key West
9.6 out of 10, Exceptional, (28 reviews)
"Charming, clean accommodations in a conveniently located area of Key West for walking to sites and renting bicycles"
BARBARA Y.
The price is €377
includes taxes & fees
15 Nov - 16 Nov
6. Sea Esta Suite | Located On Iconic Duval w/ Pool
Sea Esta Suite | Located On Iconic Duval w/ PoolOld Town Key West
9.8 out of 10, Exceptional, (58 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
Rick H.
The price is €690
includes taxes & fees
7 Dec - 8 Dec
7. Shared Pool & Near Duval - Curry House Room 9
Shared Pool & Near Duval - Curry House Room 9Old Town Key West
7.4 out of 10, Good, (20 reviews)
"Nice and clean.Quiet and convenient to Duval.We will be back!"
Deborah L.
8. Slice of Paradise
Slice of ParadiseStock Island
10.0 out of 10, Exceptional, (5 reviews)
"House was clean, what we expected, host responded promptly and accurately, pool was great."
Cathy S.
The price is €491
includes taxes & fees
10 Nov - 11 Nov
9. Capmar House at Lunara Bay
Capmar House at Lunara BayRaccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"The Best VRBO I have stayed in "
Wilbert C.
The price is €1,247
includes taxes & fees
10 Nov - 11 Nov
10. The Seagate Estate at Lunara Bay
The Seagate Estate at Lunara BayRaccoon Key
10.0 out of 10, Exceptional, (30 reviews)
"Great property, terrific hosts - amazing location!"
Jason T.
The price is €1,474
includes taxes & fees
16 Nov - 17 Nov
11. Poolside Paradise
Poolside ParadiseStock Island
The price is €516
includes taxes & fees
9 Nov - 10 Nov
12. Waterlane House at Lunara Bay
Waterlane House at Lunara BayRaccoon Key
9.8 out of 10, Exceptional, (38 reviews)
"Everything was great"
Justin S.
The price is €1,255
includes taxes & fees
8 Nov - 9 Nov
13. Luxury two floor apartment in prime location of famous Duval Street
Luxury two floor apartment in prime location of famous Duval StreetOld Town Key West
9.6 out of 10, Exceptional, (104 reviews)
"Great stay at a great location. Apartment was very clean. Enjoyed the balcony overlooking Duval St. "
Gregory L.
14. The Greenmoor House at Lunara Bay
The Greenmoor House at Lunara BayRaccoon Key
10.0 out of 10, Exceptional, (4 reviews)
"We flew into Key West only to find our original host had ghosted us. This host responded immediately to our inquiry for a replacement property. We arrived to find a beautiful home, in perfect condition. The hot tub and pool were awesome, the fire pit and grill made for a great evening with friends. We rented bikes and explored local restaurants which were excellent. The local french bakery was visited often. It is near the Marine Air Station, and you will be able to experience the sights...
Jim M.
The price is €1,965
includes taxes & fees
19 Nov - 20 Nov
15. The Shellstone House at Solaire Lunara Bay
The Shellstone House at Solaire Lunara BayRaccoon Key
10.0 out of 10, Exceptional, (7 reviews)
"Great property / location. Perfect house with wonderful amenities!!!"
Dudley S.
16. Suncoast House at Lunara Bay
Suncoast House at Lunara BayRaccoon Key
9.6 out of 10, Exceptional, (44 reviews)
"Beautiful House, super clean, perfect location "
carlos s.
The price is €1,403
includes taxes & fees
9 Nov - 10 Nov
17. Capmar House by Brightwild Huge Home Pool
Capmar House by Brightwild Huge Home PoolRaccoon Key
10.0 out of 10, Exceptional, (1 review)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
Karen
The price is €1,387
includes taxes & fees
10 Nov - 11 Nov
18. The Sunray Home at Lunara Bay
The Sunray Home at Lunara BayRaccoon Key
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful and well maintained "
Dr. T.
The price is €1,935
includes taxes & fees
11 Nov - 12 Nov
19. Mastway House at Lunara Bay - Wellness Home
Mastway House at Lunara Bay - Wellness HomeRaccoon Key
9.6 out of 10, Exceptional, (36 reviews)
"My family and I had a very nice stay."
Robert L.
The price is €1,247
includes taxes & fees
10 Nov - 11 Nov
20. Starlight Serenity - Hideaway with Stunning Views
Starlight Serenity - Hideaway with Stunning ViewsSummerland Key
10.0 out of 10, Exceptional, (1 review)
"This place was everything we needed. The location was the perfect combination of secluded but with accessibility to Marathon and Key West. The house had everything we needed. We loved the appliances, the bed, the shower and the wrap-around porch with the swing. And the people managing the property made our visit the best experience from booking to departure. Will book again!"
Tom H.
The price is €582
includes taxes & fees
19 Nov - 20 Nov
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.