Holiday Homes in Lower Florida Keys

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Featured Holiday Homes in Lower Florida Keys

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Terrace/patio

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

9.0 out of 10, Wonderful, (35)
"Stay was fun and place was clean. Could use a little improvement. Couch was u comfortable and coffeetable broken. The bikes def need some attending to. The table outside is very nice but a little too high; needs adjusting. Hot tub was wonderful and it was quiet for sleeping. "
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Old Florida Style, wrap around porch, boat basin for dockage, open water
Property grounds

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.6 out of 10, Exceptional, (66)
"The house is in a great location and we really enjoyed the porch overlooking the water. The house has some quirks that need attention (lights not working, uneven floors, broken plumbing fixtures, junk outside, etc.), but we spent most of our time outside anyway. "
The price is AU$1,410
includes taxes & fees
10 Mar - 11 Mar
Old Florida Style, wrap around porch, boat basin for dockage, open water
Spec.Feb.24-Mar 1 @229+ w. 3 night stay close beach
Terrace/patio

Spec.Feb.24-Mar 1 @229+ w. 3 night stay close beach

9.0 out of 10, Wonderful, (157)
"The good: convenient location, quiet, bed was comfortable, the little patio in the back is nice. The bad: there is no “on site’ parking but we always found parking on the street about a block away, The communication with property manager was a bit strange, she accused us of still being inside the unit a full day after we had check out on time, despite texting her to tell her we had left (an hour before check out)"
Spec.Feb.24-Mar 1 @229+ w. 3 night stay close beach
Poolside Cottage #411
Outdoor dining

Poolside Cottage #411

9.8 out of 10, Exceptional, (38)
"Quiet area close to everything we were looking for. "
The price is AU$832
includes taxes & fees
3 Mar - 4 Mar
Poolside Cottage #411
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, (33)
"This was a very smooth, perfect 5 night visit. The property offered us everything that we could need. It was a short drive to Duval St and all of the activities in Key West yet the property was very peaceful with a wonderful waterfront patio that we sat out on and enjoyed. The hot tub was a nice treat as well. I have to mention the incredible responsiveness of the property manager. Every question that I had they responded to within minutes which was very much appreciated. "
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Beachside @ Torchview Waterfront Retreat
On the beach, beach towels

Beachside @ Torchview Waterfront Retreat

9.8 out of 10, Exceptional, (40)
"Saw deer and raccoons in the yard, almost daily, one large iguana on the pier, great views"
Beachside @ Torchview Waterfront Retreat
Feb 3-10 $245 off the rates close beach full kitchen & patio
Exterior detail

Feb 3-10 $245 off the rates close beach full kitchen & patio

9.6 out of 10, Exceptional, (209)
"Had enjoyable three day visit in Key West. Stayed in comfortable little VRBO house apartment in southern part of Old Town. "
Feb 3-10 $245 off the rates close beach full kitchen & patio
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
A heated pool

CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

9.6 out of 10, Exceptional, (177)
"This property was perfect. The house itself is lovely and has a great set up. 4 bedrooms (one is in a little attached cottage outside). The pool is a very nice addition. The home is located a little bit off the beaten track, so it is quiet. It is in walking distance of everything. We would definitely stay here again!walkingof "
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
Villa Déjà vu Key West - Steps Off Duval w Private Pool
A heated pool

Villa Déjà vu Key West - Steps Off Duval w Private Pool

9.4 out of 10, Exceptional, (55)
"This house was exactly what our group was looking for. Loved the location and proximity to Duval Street. Also loved the outdoor pool area for hanging out. Would def recommend. "
Villa Déjà vu Key West - Steps Off Duval w Private Pool
Coastal Comfort; Waterfront Luxury Home with private pool!
Property grounds

Coastal Comfort; Waterfront Luxury Home with private pool!

9.4 out of 10, Exceptional, (64)
"This property was awsome! The area is quiet and close to grocery stores. And a.short drive to down townlpve it, love it, love it. Definitely coming back!!"
Coastal Comfort; Waterfront Luxury Home with private pool!
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location
A heated pool

Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location

10.0 out of 10, Exceptional, (5)
"We enjoyed our stay here. The location was great. We even walked the mile to the dock to board the Yankee Freedom III for a trip to the Dry Tortugas.The apartment was comfortable and had plenty of room for the 5 of us adults. We didn’t use the kitchen much, only to make coffee, so we can’t speak to anything in regards to that."
The price is AU$1,371
includes taxes & fees
26 Feb - 27 Feb
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location
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, (90)
"Clean, roomy, comfortable. Adequate seating and dishes for 6 adults. Great mattresses and pillows. "
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
Terrace/patio

HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

9.6 out of 10, Exceptional, (26)
"Very comfortable unit to stay near Key West.Beautiful water view.Just 15-20 min from downtown .Will stay again . "
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
3 night minimum! Spectacular Ocean Views!
A heated pool

3 night minimum! Spectacular Ocean Views!

8.4 out of 10, Very good, (19)
"Venture out is a great location for being on the water. This rental was reasonable, spacious and clean! We had an amazing stay with no issues!"
3 night minimum! Spectacular Ocean Views!
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Exterior

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

9.8 out of 10, Exceptional, (234)
"Clean, easy access, friendly complex/neighborhood. "
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
The Flower Power House - Boho Beautiful
A heated pool

The Flower Power House - Boho Beautiful

2.5 star property
8.8 out of 10, Excellent, (25)
"We truly enjoyed our stay at the Flower Power House! The house was awesome, in a great neighborhood and had everything we needed! The property manager was very pleasant, responsive and accommodating! We will definitely return the next time we are in Key West! Thank you! "
The Flower Power House - Boho Beautiful
Conch Cove - 3br/3ba with private heated pool and private parking
A heated pool

Conch Cove - 3br/3ba with private heated pool and private parking

10.0 out of 10, Exceptional, (4)
"Rick and team were awesome and exceptional throughout the whole stay! Nice house!! "
The price is AU$2,757
includes taxes & fees
23 Feb - 24 Feb
Conch Cove - 3br/3ba with private heated pool and private parking
Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!
Miscellaneous

Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!

2.0 star property
6.0 out of 10, (2)
"Plenty of room indoors and outdoors to live in. Comfortable beds. Clean and tidy"
Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Outdoor dining

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

9.4 out of 10, Exceptional, (29)
"Excellent views, very quiet, pool was outstanding "
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
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, (201)
"All in all, this property was 100 out of 100. There were only two minor issues. One the stopper for the tub was missing which I replaced, and two the auto stop on the coffee pot was broke. Very very minor issues. The privacy, the pool, the rooms were terrific. The location was also great and very convenient to all that we needed. We loved our stay and hated to leave. Almost forgot, the sunshine near the pool is perfect as this property is perfectly positioned to capture the sun while sunbathing...
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
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.
Don't see what you're looking for?
See all available properties in Lower Florida Keys
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Lower Florida Keys

Charming cottages, dockage, pool, just minutes to Key West
Fridge, microwave, oven, stovetop

Charming cottages, dockage, pool, just minutes to Key West

8.6 out of 10, Excellent, (106)
"Drove From CLE to The Keys with my dog and enjoyed the quietness of the property. 30 an hour from Key West. Great rate. Would recommend. "
The price is AU$657
includes taxes & fees
26 Feb - 27 Feb
Charming cottages, dockage, pool, just minutes to Key West
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Outdoor dining

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

9.0 out of 10, Wonderful, (194)
"We loved the house! Thank you for being so flexible with us. We thought the second bedroom had 2 beds when we booked online but it only has 1."
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Direct Oceanfront Cottage-Sunrise View- #2,
On the beach

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (170)
"The location and views are great. It was a comfortable stay. There were some deferred maintenance items which were shared with the property manager. Completion of these items will greatly enhance the experience at the property and make it a '10' rating."
The price is AU$652
includes taxes & fees
23 Mar - 24 Mar
Direct Oceanfront Cottage-Sunrise View- #2,
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.