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Lower Keys Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Lower Keys vacation rentals

A cozy room with a brown leather sofa, a white table, and a ceiling fan.

1. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (375 reviews)
"Best stop over before going to Key west. We enjoyed here a lot, parking our trailer was never a problem."
United States
Daisybel
$222 nightly
The price is $250
Oct 25 - Oct 26
Total with taxes and fees
Old Wooden Bridge Resort and Marina
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

2. Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"This property was meticulously clean and perfect for us. The property was decorated well-very home-like feel. The communication with the host was prompt and they answered all questions asked. In addition, we loved that we could bring our fur-babies (dogs) to the property with us. We highly recommend this property!"
United States
Elena S.
$376 nightly
The price is $417
Oct 27 - Oct 28
Total with taxes and fees
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Property grounds

3. Cozy 1-bedroom apartment with WiFi, AC in charming Cudjoe Key large outdoor

Cozy 1-bedroom apartment with WiFi, AC in charming Cudjoe Key large outdoor
Cudjoe Key
$109 nightly
The price is $120
Oct 20 - Oct 21
Total with taxes and fees
Cozy 1-bedroom apartment with WiFi, AC in charming Cudjoe Key large outdoor
A modern kitchen with granite countertops, stainless steel appliances, and light-colored cabinetry.

4. Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (129 reviews)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
$458 nightly
The price is $508
Oct 25 - Oct 26
Total with taxes and fees
Kelly's Kabin - Adorable Private Summerland Key Cottage
A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

5. SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (99 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
$391 nightly
The price is $434
Oct 21 - Oct 22
Total with taxes and fees
SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Pool

6. Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Excellent location - clean, quiet, well-kept community. Boat launch was key for us. Pool and beach looked very nice, but we didn't use. The unit is as described and has a nice patio out back that we used every day."
United States
Cheryl V.
$412 nightly
The price is $457
Nov 2 - Nov 3
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A waterfront property with a covered porch, a boat dock, and a clear sky.

7. SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (113 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
$387 nightly
The price is $431
Oct 20 - Oct 21
Total with taxes and fees
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

8. Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Cudjoe Key
9.6 out of 10, Exceptional, (5 reviews)
"Stayed with family and good location for family vacations. "
United States
Phani U.
$474 nightly
The price is $526
Oct 20 - Oct 21
Total with taxes and fees
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Pool

9. Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Cudjoe Key
8.8 out of 10, Excellent, (11 reviews)
"We loved our stayed and booked again for next year. Its in our price range, plenty of space and we were all so comfortable. Its our favorite house we have rented in the area and hope to be able to continue to enjoy it years to come. "
United States
Alisa M.
$469 nightly
The price is $521
Oct 20 - Oct 21
Total with taxes and fees
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

10. Canal-Front Retreat with Dock, Pool & Open Ocean Views

Canal-Front Retreat with Dock, Pool & Open Ocean Views
Cudjoe Key
9.0 out of 10, Wonderful, (13 reviews)
"This property is convenient to food and fun. It was very clean, comfortable and we felt safe to walk around the resort. We had a wonderful stay here."
United States
Catherine C.
$460 nightly
The price is $510
Oct 22 - Oct 23
Total with taxes and fees
Canal-Front Retreat with Dock, Pool & Open Ocean Views
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

11. 2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.

2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
Cudjoe Key
$498 nightly
The price is $553
Oct 20 - Oct 21
Total with taxes and fees
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

12. Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Cudjoe Key
9.0 out of 10, Wonderful, (2 reviews)
"This was a sweet little modular home that gave us a clean and comfortable place to stay… away from the tourist scene."
United States
Nora Kay F.
$439 nightly
The price is $487
Oct 20 - Oct 21
Total with taxes and fees
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Pool

13. Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
8.6 out of 10, Excellent, (4 reviews)
" 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.
$427 nightly
The price is $475
Oct 20 - Oct 21
Total with taxes and fees
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

14. Canalfront Coastal Retreat w/Open Water Views & Fishing Dock

Canalfront Coastal Retreat w/Open Water Views & Fishing Dock
Cudjoe Key
9.8 out of 10, Exceptional, (6 reviews)
"Beautiful home with an amazing view friendly community my family and I will definitely be back highly recommend Elma’s escape "
United States
Mary T.
$469 nightly
The price is $521
Oct 20 - Oct 21
Total with taxes and fees
Canalfront Coastal Retreat w/Open Water Views & Fishing Dock
A swimming pool with a tiled edge, surrounded by lounge chairs and umbrellas, under a cloudy sky.

15. Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key
8.0 out of 10, Very good, (21 reviews)
"Heated pool was very nice, and location of rental."
United States
Angela C.
$461 nightly
The price is $511
Oct 20 - Oct 21
Total with taxes and fees
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Pool

16. Florida Keys Waterfront Escape w/35' Seawall & Seconds to Open Water

Florida Keys Waterfront Escape w/35' Seawall & Seconds to Open Water
Cudjoe Key
9.4 out of 10, Exceptional, (3 reviews)
"Good location to stay with family. "
United States
Phani U.
$463 nightly
The price is $513
Oct 20 - Oct 21
Total with taxes and fees
Florida Keys Waterfront Escape w/35' Seawall & Seconds to Open Water
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

17. Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
9.4 out of 10, Exceptional, (18 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
$460 nightly
The price is $510
Oct 21 - Oct 22
Total with taxes and fees
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

18. Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart

Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
Cudjoe Key
9.6 out of 10, Exceptional, (7 reviews)
"Clean and excellent water access"
United States
Chris P.
$457 nightly
The price is $507
Oct 20 - Oct 21
Total with taxes and fees
Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
Pool

19. Ground Level Waterfront 2BR in Venture Out - 23' Seawall, Pool, Marina & Pet Friendly

Ground Level Waterfront 2BR in Venture Out - 23' Seawall, Pool, Marina & Pet Friendly
Cudjoe Key
8.0 out of 10, Very good, (1 review)
$457 nightly
The price is $507
Oct 20 - Oct 21
Total with taxes and fees
Ground Level Waterfront 2BR in Venture Out - 23' Seawall, Pool, Marina & Pet Friendly
A beachfront property with a pool, palm trees, and a two-story building.

20. Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
8.0 out of 10, Very good, (1 review)
$243 nightly
The price is $261
Oct 20 - Oct 21
Total with taxes and fees
Seabreeze Escape WF RV Lot 489
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.
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Top Lower Keys Hotel Reviews

Sugar Loaf Lodge

Sugar Loaf Lodge

10/10 Excellent
"Very cute place, like at home, the lady on the desk is very sweet and helpful. Good price and close to Kea West."
Mariia 1-night trip
Posted 12 hours ago
Sugar Loaf Lodge

Find out more about Lower Keys

Everything you need to know about Lower Keys vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Lower Keys vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Lower Keys vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Lower Keys vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Lower Keys. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Lower Keys in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $250 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Lower Keys rentals

At Expedia, we put the best Lower Keys vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Lower Keys rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Lower Keys vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Lower Keys. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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