A beach with palm trees, people relaxing on chairs, and colorful kayaks.

Florida Keys Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Florida Keys vacation homes

A resort with a pool, lounge chairs, and a view of the ocean.

1. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
2.5 star property
Marathon
9.2 out of 10, Wonderful, (145 reviews)
"It is an excellent place."
United States
Arianna
The price is CA $240
CA $309 total
includes taxes & fees
Oct 1 - Oct 2
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

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

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (97 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is CA $183
CA $584 total
includes taxes & fees
Oct 1 - Oct 2
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A waterfront property with a covered porch, a boat dock, and a clear sky.

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (112 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
The price is CA $225
CA $637 total
includes taxes & fees
Oct 4 - Oct 5
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A coastal area with clear water, a sandy beach, and a small island with buildings.

4. Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Key Largo
9.6 out of 10, Exceptional, (51 reviews)
"We had a nice stay"
United States
Kevin M.
The price is CA $109
CA $410 total
includes taxes & fees
Oct 1 - Oct 2
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
A wooden deck with a large tree, outdoor seating, and a marina in the background.

5. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Definitely would stay here again. Very smooth process. Property was perfect for our family of 5. We loved having access to the pool right at our doorstep. Very accurate photos and description. Excellent value for the money."
United States
Danielle D.
The price is CA $243
CA $438 total
includes taxes & fees
Oct 10 - Oct 11
Poolside Cottage #412
A building with a red door, a covered porch, and a bamboo plant in the foreground.

6. Road's End | Prime Old Town Location! Updated Home w/ Pool

Road's End | Prime Old Town Location! Updated Home w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (24 reviews)
"The property was very clean with an excellent location. "
United States
Mike T.
The price is CA $200
CA $639 total
includes taxes & fees
Oct 26 - Oct 27
Road's End | Prime Old Town Location! Updated Home w/ Pool
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

7. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (70 reviews)
"Excellent cottage in a quiet location. Our family of 4 enjoyed the stay & plan to return in the future!"
United States
Jennifer W.
The price is CA $236
CA $435 total
includes taxes & fees
Oct 14 - Oct 15
Poolside Cottage #411
A modern kitchen with granite countertops, stainless steel appliances, and light-colored cabinetry.

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

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (128 reviews)
"Very nice place. Centrally located near good restaurants, markets, etc.. Pet friendly which worked for us. Nice long walking trail behind cottage."
United States
John B.
The price is CA $281
CA $722 total
includes taxes & fees
Oct 3 - Oct 4
Kelly's Kabin - Adorable Private Summerland Key Cottage
A wooden deck with a railing, wicker chairs, and a view of greenery.

9. Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
United States
max
The price is CA $323
CA $881 total
includes taxes & fees
Oct 5 - Oct 6
Starlight Serenity - Hideaway w Stunning Views
Pool

10. 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.
The price is CA $223
CA $649 total
includes taxes & fees
Oct 2 - Oct 3
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A two-story building with a blue exterior, white railings, and a staircase leading to the upper floor.

11. Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
9.8 out of 10, Exceptional, (6 reviews)
"Property was perfectly located and very clean and comfortable."
United States
Kiara
The price is CA $262
CA $827 total
includes taxes & fees
Oct 6 - Oct 7
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
A modern living room with a flat-screen TV, a black leather sofa, and a white ottoman.

12. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
10.0 out of 10, Exceptional, (41 reviews)
"Awesome house, convenient to everything we needed. Super clean and everything was pretty modern. I would definitely stay again and would definitely recommend this property"
United States
JOHN P.
The price is CA $204
CA $583 total
includes taxes & fees
Oct 5 - Oct 6
Charming Home in Key Largo
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

13. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
Stock Island
9.6 out of 10, Exceptional, (136 reviews)
"I can't say enough about how wonderful this property is or the host."
United States
Linda
The price is CA $370
CA $830 total
includes taxes & fees
Oct 1 - Oct 2
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with bar stools.

14. Sea Esta Suite | Located On Iconic Duval w/ Pool

Sea Esta Suite | Located On Iconic Duval w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (53 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
United States
Rick H.
The price is CA $262
CA $1,057 total
includes taxes & fees
Oct 7 - Oct 8
Sea Esta Suite | Located On Iconic Duval w/ Pool
A covered outdoor area with a ceiling fan, a view of the sea, and a distant building.

15. 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, (55 reviews)
"Very nice villa "
United States
Grace L.
The price is CA $228
CA $691 total
includes taxes & fees
Oct 1 - Oct 2
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Pool

16. 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.
The price is CA $298
CA $745 total
includes taxes & fees
Oct 4 - Oct 5
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
A modern kitchen with a built-in microwave, stove, and dishwasher.

17. 4. Cozy Key Largo Waterfront Studio | Dive

4. Cozy Key Largo Waterfront Studio | Dive
Key Largo
9.8 out of 10, Exceptional, (13 reviews)
"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.
The price is CA $243
CA $504 total
includes taxes & fees
Oct 1 - Oct 2
4. Cozy Key Largo Waterfront Studio | Dive
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

18. 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.
The price is CA $283
CA $724 total
includes taxes & fees
Oct 2 - Oct 3
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
A swimming pool with a tiled edge, surrounded by lounge chairs and umbrellas, under a cloudy sky.

19. 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.
The price is CA $351
CA $729 total
includes taxes & fees
Oct 2 - Oct 3
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

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

Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
Cudjoe Key
9.4 out of 10, Exceptional, (6 reviews)
"Clean and excellent water access"
United States
Chris P.
The price is CA $283
CA $724 total
includes taxes & fees
Oct 2 - Oct 3
Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
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 Florida Keys Hotel Reviews

Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"Beautiful location, great amenities, and comfortable rooms"
Michael 7-night trip
Posted 13 hours ago
Lime Tree Bay Resort

Find out more about Florida Keys

Florida Keys Vacation Homes information

Number of reviews
758
Accommodation
1052 Vacation Homes
Lowest Price
CA $309
Highest Price
CA $1,057

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