Search Vacation Homes in Lower Keys

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

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Lower Keys vacation homes

9.4 out of 10, Exceptional, (101)
"Great location. "
United States
Davian k.
$548 nightly
The price is $610
Jan 10 - Jan 11, 2026
Total with taxes and fees
DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Vacation Home in Upper Sugarloaf Key

The Hemingway - Beach Houses Key West
9.6 out of 10, Exceptional, (8)
"Perfect location way off the path if you like seclusion."
United States
Jonathan L.
$2,063 nightly
The price is $2,284
Jan 3 - Jan 4, 2026
Total with taxes and fees
The Hemingway - Beach Houses Key West
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.
$548 nightly
The price is $610
Jan 18 - Jan 19, 2026
Total with taxes and fees
DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
$554 nightly
The price is $615
Jan 4 - Jan 5, 2026
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Vacation Home in Summerland Key

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
$707 nightly
The price is $795
Jan 6 - Jan 7, 2026
Total with taxes and fees
Starlight Serenity - Hideaway w Stunning Views
$633 nightly
The price is $704
Jan 6 - Jan 7, 2026
Total with taxes and fees
Starlight Serenity - Hideaway with Stunning Views
8.8 out of 10, Excellent, (65)
"Excellent secluded location but near everything Thanks!!!!!"
United States
Gary D.
$1,254 nightly
The price is $1,391
Jan 7 - Jan 8, 2026
Total with taxes and fees
One of the very few beach houses with a daily, rental license in the Keys.
$736 nightly
The price is $778
Jan 21 - Jan 22, 2026
Total with taxes and fees
105 - Newly renovated house Oceanside and Pool
9.6 out of 10, Exceptional, (88)
"This place really had it all , one of my best stays yet anywhere. "
United States
Charles M.
$739 nightly
The price is $821
Jan 1 - Jan 2, 2026
Total with taxes and fees
Old Florida Style, wrap around porch, boat basin for dockage, open water
$590 nightly
The price is $655
Jan 4 - Jan 5, 2026
Total with taxes and fees
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
10.0 out of 10, Exceptional, (3)
"Beautiful "
United States
Lisa P.
$920 nightly
The price is $1,021
Jan 3 - Jan 4, 2026
Total with taxes and fees
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Vacation Home in Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
9.4 out of 10, Exceptional, (19)
"This is our third time staying here. It is a great property and works perfectly for a three-person family."
United States
Kimberly G.
$643 nightly
The price is $714
Jan 4 - Jan 5, 2026
Total with taxes and fees
Spanish Queen @Venture Out, Cudjoe Key
$609 nightly
The price is $676
Jan 4 - Jan 5, 2026
Total with taxes and fees
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

Vacation Home in Upper Sugarloaf Key

The Lighthouse - Beach Houses Key West
9.6 out of 10, Exceptional, (11)
"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"
United States
Peter Q.
$1,535 nightly
The price is $1,705
Dec 24 - Dec 25
Total with taxes and fees
The Lighthouse - Beach Houses Key West
6.0 out of 10, (1)
"The house was not thoroughly cleaned. The cabinets and under the place mats were dirty. When we opened the pack and play it had an orange substance caked all over inside. We tried to watch tv and remote had no batteries, we tried the second remote and that didn’t work either. "
United States
Heather H.
$580 nightly
The price is $644
Jan 5 - Jan 6, 2026
Total with taxes and fees
Charming 3-bedroom house in Big Pine Key near Beach and Key West
8.0 out of 10, Very Good, (1)
"It was a short trip but we enjoyed our stay! "
United States
Jennifer S.
$658 nightly
The price is $732
Jan 2 - Jan 3, 2026
Total with taxes and fees
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape
9.6 out of 10, Exceptional, (7)
"We really enjoyed our stay here. We really loved sitting on the back porch by the water and the closeness to the community pool and courts. "
United States
Lindsay C.
$647 nightly
The price is $718
Jan 4 - Jan 5, 2026
Total with taxes and fees
Reel Island Retreat #273 at Venture Out in the Florida Keys
9.2 out of 10, Wonderful, (28)
"Close to Key West and lots of great boating"
United States
Simon S.
$665 nightly
The price is $739
Jan 6 - Jan 7, 2026
Total with taxes and fees
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
$668 nightly
The price is $741
Jan 3 - Jan 4, 2026
Total with taxes and fees
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Vacation Home in Cudjoe Key

Tiki Time in Cudjoe Key 136
2.0 star property
10.0 out of 10, Exceptional, (3)
"Beautiful well maintained property. You just cannot beat the view on the extra large deck. Sit back relax and enjoy a coffee.I absolutely love this property."
Canada
Rachel H.
$855 nightly
The price is $905
Dec 31 - Jan 1, 2026
Total with taxes and fees
Tiki Time in Cudjoe Key 136
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Lower Keys Hotel Reviews

Find out more about Lower Keys

Lower Keys Vacation Homes information

Number of reviews
410
Accommodation
540 Vacation Homes
Lowest Price
$610
Highest Price
$2,284

Explore a world of travel with Expedia