Holiday Homes in Florida Keys

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan
In one month
23 Jan - 25 Jan
In two months
20 Feb - 22 Feb

Our top choices for Florida Keys holiday homes

Outdoor dining
Waterfront Pool, Beach, Dock, Kayaks

Waterfront Pool, Beach, Dock, Kayaks

Waterfront Pool, Beach, Dock, Kayaks
Key Largo
9.8 out of 10, Exceptional, (80)
"Had a great time property was exactly as described. Would stay again."
United States
Michael S.
The price is NZ$826
includes taxes & fees
11 Jan - 12 Jan 2026
Waterfront Pool, Beach, Dock, Kayaks
Fridge, microwave, oven, stovetop
Charming Home in Key Largo

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (29)
"It was clean and a very nice place to stay. Plenty of room and awesome amenities."
United States
Eric M.
The price is NZ$783
includes taxes & fees
4 Jan - 5 Jan 2026
Charming Home in Key Largo
Marina
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Key Largo
9.6 out of 10, Exceptional, (84)
"Very quiet and cozy "
United States
Stephanie T.
The price is NZ$752
includes taxes & fees
7 Jan - 8 Jan 2026
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Outdoor dining
Poolside Cottage #412

Poolside Cottage #412

Poolside Cottage #412
Key West
9.2 out of 10, Wonderful, (28)
"The property and our place was really nice. Would definitely stay again. "
United States
Sarah M.
The price is NZ$941
includes taxes & fees
3 Jan - 4 Jan 2026
Poolside Cottage #412
Outdoor dining
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (101)
"Great location. "
United States
Davian k.
The price is NZ$1,045
includes taxes & fees
10 Jan - 11 Jan 2026
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Outdoor pool, a heated pool
SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (82)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is NZ$1,059
includes taxes & fees
18 Jan - 19 Jan 2026
SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Interior
4. Cozy Waterfront Apartment in Key Largo!

4. Cozy Waterfront Apartment in Key Largo!

4. Cozy Waterfront Apartment in Key Largo!
Key Largo
9.8 out of 10, Exceptional, (11)
"We loved our stay at the waterfront cabanas! The location is 10/10 with an awesome waterfront bar/restaurant and coffee truck within walking distance. We truly felt like keys locals staying here - highly recommend! "
United States
Brittany M.
4. Cozy Waterfront Apartment in Key Largo!
Beach
Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (66)
"This place was perfect for 9 people. Both the condo and the area had plenty to do "
United States
Ethan
The price is NZ$1,444
includes taxes & fees
20 Jan - 21 Jan 2026
Sunrise Escape - Ocean Front Villa - Sleeps 10
Property grounds
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.6 out of 10, Exceptional, (46)
"Clean property! Great views! Great communication with owner! Perfect location- close to marathon and key west! "
United States
candi b.
The price is NZ$1,089
includes taxes & fees
5 Jan - 6 Jan 2026
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Terrace/patio
Very Low Rates. See dates below avail. PreXmas spec@ And 10% Off wkly stays

Very Low Rates. See dates below avail. PreXmas spec@ And 10% Off wkly stays

Very Low Rates. See dates below avail. PreXmas spec@ And 10% Off wkly stays
Old Town Key West
9.0 out of 10, Wonderful, (180)
"We had such a delightful time staying here! While the space is small, it was absolutely perfect for two people. Everything was clean, comfortable, and conveniently located. We really enjoyed our time in Key West and would definitely stay here again! "
United States
ALISHA
Very Low Rates. See dates below avail. PreXmas spec@ And 10% Off wkly stays
Outdoor dining
Poolside Cottage #411

Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (53)
"Perfect for our family! Recommend 10/10!"
United States
Melissa F.
The price is NZ$941
includes taxes & fees
3 Jan - 4 Jan 2026
Poolside Cottage #411
Terrace/patio
NEW ! Lagoon-front townhouse with Marina in Key Largo

NEW ! Lagoon-front townhouse with Marina in Key Largo

NEW ! Lagoon-front townhouse with Marina in Key Largo
2.0 star property
Key Largo
10.0 out of 10, Exceptional, (46)
"Good location. Lagoon and pool right outside door. "
United States
Debra C.
The price is NZ$1,044
includes taxes & fees
11 Jan - 12 Jan 2026
NEW ! Lagoon-front townhouse with Marina in Key Largo
Pool
Capmar House at Lunara Bay

Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29)
"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"
United States
Anonymous traveller
The price is NZ$2,713
includes taxes & fees
5 Jan - 6 Jan 2026
Capmar House at Lunara Bay
Terrace/patio
The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (18)
"The perfect House , everything was good "
United States
CARLOS G.
The price is NZ$2,713
includes taxes & fees
4 Jan - 5 Jan 2026
The Seagate Estate at Lunara Bay
Fridge, microwave, oven, stovetop
Springtide House at Lunara Bay

Springtide House at Lunara Bay

Springtide House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (43)
"It was great. House was amazing"
United States
Ernest H.
The price is NZ$2,625
includes taxes & fees
4 Jan - 5 Jan 2026
Springtide House at Lunara Bay
Indoor pool, outdoor pool
Ohana Cay 2brm/2bth - Book your getaway!

Ohana Cay 2brm/2bth - Book your getaway!

Ohana Cay 2brm/2bth - Book your getaway!
Rock Harbor
10.0 out of 10, Exceptional, (92)
"Perfect location and great community. Easy docking at the marina and nice amenities. "
United States
Gene Z.
Ohana Cay 2brm/2bth - Book your getaway!
Exterior
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA
Duck Key
9.4 out of 10, Exceptional, (32)
"A short weekend getaway was made perfect in this villa. The location is idyllic; especially the balcony overlooking the bay with a perfect sunset view. The home was well-appointed, simple yet all the necessities were covered. Communication with the property manager was excellent. Definitely will book again. "
United States
Natasha A.
The price is NZ$1,074
includes taxes & fees
4 Jan - 5 Jan 2026
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA
Property grounds
Old Florida Style, wrap around porch, boat basin for dockage, open water

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

Old Florida Style, wrap around porch, boat basin for dockage, open water
Little Torch Key
9.6 out of 10, Exceptional, (88)
"Nice house in a great location. "
United States
Jarrod L.
The price is NZ$1,424
includes taxes & fees
1 Jan - 2 Jan 2026
Old Florida Style, wrap around porch, boat basin for dockage, open water
Living area
Kingfish Keep | Lively Escape on Duval! Balcony!

Kingfish Keep | Lively Escape on Duval! Balcony!

Kingfish Keep | Lively Escape on Duval! Balcony!
Old Town Key West
9.8 out of 10, Exceptional, (25)
"Awesome location with excellent communication. "
United States
Gary W.
The price is NZ$962
includes taxes & fees
6 Jan - 7 Jan 2026
Kingfish Keep | Lively Escape on Duval! Balcony!
Outdoor pool
One of the very few beach houses with a daily, rental license in the Keys.

One of the very few beach houses with a daily, rental license in the Keys.

One of the very few beach houses with a daily, rental license in the Keys.
Summerland Key
8.8 out of 10, Excellent, (65)
"Excellent secluded location but near everything Thanks!!!!!"
United States
Gary D.
The price is NZ$2,042
includes taxes & fees
7 Jan - 8 Jan 2026
One of the very few beach houses with a daily, rental license in the Keys.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Florida Keys Hotel Reviews

Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina

10/10 Excellent
"Excellent staff! Breakfast was outstanding!"
David 3-night trip
Posted 2 days ago
Marina Del Mar Resort and Marina

Find out more about Florida Keys

Florida Keys Holiday Homes information

Number of reviews
1,142
Accommodation
971 Holiday Homes
Lowest Price
NZ$752
Highest Price
NZ$2,713