Search Vacation Homes in Lower Keys

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Lower Keys vacation homes

Vacation Home in Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
9.4 out of 10, Exceptional, (19 reviews)
"This is our third time staying here. It is a great property and works perfectly for a three-person family."
United States
Kimberly G.
The price is ¥55,356
¥108,102 total
includes taxes & fees
Mar 17 - Mar 18
Spanish Queen @Venture Out, Cudjoe Key
8.8 out of 10, Excellent, (162 reviews)
"Great location , clear communications and listing accuracy. Will be coming back again "
United States
Kirk D.
The price is ¥49,820
¥103,338 total
includes taxes & fees
Mar 25 - Mar 26
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
8.8 out of 10, Excellent, (6 reviews)
"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.
The price is ¥52,035
¥117,909 total
includes taxes & fees
Mar 26 - Mar 27
Charming 3-bedroom house in Big Pine Key near Beach and Key West
7.8 out of 10, Good, (14 reviews)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
The price is ¥39,145
¥81,522 total
includes taxes & fees
Mar 20 - Mar 21
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
9.8 out of 10, Exceptional, (123 reviews)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
The price is ¥33,940
¥83,113 total
includes taxes & fees
Apr 5 - Apr 6
Kelly's Kabin - Adorable Private Summerland Key Cottage
8.8 out of 10, Excellent, (153 reviews)
"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "
United States
bryan c.
The price is ¥59,198
¥115,061 total
includes taxes & fees
Apr 5 - Apr 6
Cudjoe Cottages, swimming pool, just 20 miles from Key West
9.2 out of 10, Wonderful, (9 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is ¥31,553
¥96,233 total
includes taxes & fees
Mar 29 - Mar 30
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
8.0 out of 10, Very Good, (1 review)
" Great 2 bedroom home in a lovely vacation community . We enjoyed the 2 recliners to relax after a full day of exploring as well as in the morning with our coffee. The screened in patio was a nice perk as well . At check in , a calendar of events was provided and the staff were friendly and helpful. FYI : We enjoyed a gorgeous sunrise right by the beach near the pool ."
United States
jim b.
The price is ¥35,637
¥101,185 total
includes taxes & fees
Apr 6 - Apr 7
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
The price is ¥41,438
¥107,397 total
includes taxes & fees
Apr 1 - Apr 2
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
10.0 out of 10, Exceptional, (3 reviews)
"Absolutely love it here… Randy is great to work with and always available. "
United States
Jeannine R.
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Very clean! Good location. "
United States
January M.
The price is ¥45,582
¥113,795 total
includes taxes & fees
Apr 6 - Apr 7
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
9.4 out of 10, Exceptional, (104 reviews)
"Janet was great; quick to respond and very kind. Also the kayaks were fun and the beds were super comfy. "
United States
Lauren D.
The price is ¥47,200
¥97,676 total
includes taxes & fees
Mar 30 - Mar 31
SAVE BIG $$$ MARCH! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Vacation Home in Upper Sugarloaf Key

Private and Exclusive Florida Keys Getaway
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
The price is ¥173,106
¥297,303 total
includes taxes & fees
Mar 24 - Mar 25
Private and Exclusive Florida Keys Getaway
9.4 out of 10, Exceptional, (12 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is ¥37,294
¥102,102 total
includes taxes & fees
Apr 1 - Apr 2
Island Time #110 Ocean Views - Cudjoe Key
9.6 out of 10, Exceptional, (97 reviews)
"Loved the location, good communication!"
United States
Cindy P.
The price is ¥71,037
¥140,101 total
includes taxes & fees
Mar 29 - Mar 30
Old Florida Style, wrap around porch, boat basin for dockage, open water
9.2 out of 10, Wonderful, (29 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is ¥41,438
¥107,397 total
includes taxes & fees
Apr 2 - Apr 3
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
9.8 out of 10, Exceptional, (85 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is ¥61,408
¥115,554 total
includes taxes & fees
Apr 3 - Apr 4
SAVE BIG $$$ MARCH! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Vacation Home in Cudjoe Key

House of the Rising Sun - VO479
8.8 out of 10, Excellent, (12 reviews)
"We rented a boat, fished and snorkeled. Really enjoyed the patio right on the sea wall. One of the best parts of property was the stunning view of the morning sunrise!"
United States
Matt W.
House of the Rising Sun - VO479

Vacation Home in Summerland Key

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
The price is ¥70,253
¥135,198 total
includes taxes & fees
Mar 12 - Mar 13
Starlight Serenity - Hideaway w Stunning Views
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful "
United States
Lisa P.
The price is ¥87,020
¥164,515 total
includes taxes & fees
Mar 30 - Mar 31
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
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
600
Accommodation
540 Vacation Homes
Lowest Price
¥81,522
Highest Price
¥297,303

Explore a world of travel with Expedia