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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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, (147 reviews)
"It is an excellent place."
United States
Arianna
The price is CA $229
CA $298 total
includes taxes & fees
Oct 25 - Oct 26
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 $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (98 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is CA $212
CA $619 total
includes taxes & fees
Oct 12 - Oct 13
SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A wooden deck with lounge chairs, a pool, and a dock with boats.

3. Waterfront Tiny House w Pool, Beach, and Boat Dock

Waterfront Tiny House w Pool, Beach, and Boat Dock
Key Largo
9.6 out of 10, Exceptional, (70 reviews)
"We were really impressed with the house - it had all the little things that made the stay so comfortable - reclining chairs in the living room, A/C in every room, a great outside deck complete with a big TV and clean, clean, clean."
United States
Ann
The price is CA $171
CA $490 total
includes taxes & fees
Oct 27 - Oct 28
Waterfront Tiny House w Pool, Beach, and Boat Dock
A wooden deck with a large tree, outdoor seating, and a marina in the background.

4. 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 $237
CA $436 total
includes taxes & fees
Oct 18 - Oct 19
Poolside Cottage #412
A waterfront property with a covered porch, a boat dock, and a clear sky.

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

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (112 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
The price is CA $226
CA $636 total
includes taxes & fees
Oct 13 - Oct 14
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A modern living room with a flat-screen TV, a black leather sofa, and a white ottoman.

6. 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 $160
CA $528 total
includes taxes & fees
Oct 15 - Oct 16
Charming Home in Key Largo
Pool

7. 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 $224
CA $654 total
includes taxes & fees
Oct 11 - Oct 12
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
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, (129 reviews)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
The price is CA $282
CA $727 total
includes taxes & fees
Oct 11 - Oct 12
Kelly's Kabin - Adorable Private Summerland Key Cottage
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

9. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (70 reviews)
"I loved having the pool right outside the door! It was extremely clean and perfectly located for our needs. I really enjoyed sitting outside in the evenings. I would absolutely stay here again and recommend it to others!"
United States
Cristy D.
The price is CA $237
CA $436 total
includes taxes & fees
Oct 14 - Oct 15
Poolside Cottage #411
A two-story building with a blue exterior, white railings, and a staircase leading to the upper floor.

10. 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
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with bar stools.

11. 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, (55 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
United States
Rick H.
The price is CA $321
CA $1,141 total
includes taxes & fees
Oct 29 - Oct 30
Sea Esta Suite | Located On Iconic Duval w/ Pool
A clear swimming pool with lounge chairs and palm trees.

12. Slice of Paradise

Slice of Paradise
Stock Island
10.0 out of 10, Exceptional, (4 reviews)
"House was clean, what we expected, host responded promptly and accurately, pool was great."
United States
Cathy S.
The price is CA $384
CA $847 total
includes taxes & fees
Oct 11 - Oct 12
Slice of Paradise
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 $301
CA $742 total
includes taxes & fees
Oct 12 - Oct 13
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A spacious living area with a sliding glass door leading to a deck, a sofa, a coffee table, and a kitchen area with wooden cabinets and appliances.

14. Charming 3-bedroom house featuring a heated private pool.

Charming 3-bedroom house featuring a heated private pool.
Duck Key
10.0 out of 10, Exceptional, (45 reviews)
"We had a great stay!!"
United States
lissa h.
The price is CA $512
CA $1,100 total
includes taxes & fees
Oct 13 - Oct 14
Charming 3-bedroom house featuring a heated private pool.
Pool

15. 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 $299
CA $748 total
includes taxes & fees
Oct 14 - Oct 15
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
A bedroom with a large bed, a desk with a chair, a mirror, and a wall-mounted artwork.

16. Tranquility Bungalow at Largo Resort

Tranquility Bungalow at Largo Resort
Key Largo
9.6 out of 10, Exceptional, (8 reviews)
"Very Zen atmosphere. Alex and the rest of the staff very friendly and welcoming. "
United States
Becky M.
The price is CA $341
CA $529 total
includes taxes & fees
Oct 21 - Oct 22
Tranquility Bungalow at Largo Resort
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.
The price is CA $284
CA $727 total
includes taxes & fees
Oct 15 - Oct 16
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
A covered outdoor area with a ceiling fan, a view of the sea, and a distant building.

18. 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)
"Great location. Pretty views of Bay. Comfortable rooms. Enjoyed our brief stay for July 4th."
United States
Jorge D.
The price is CA $255
CA $730 total
includes taxes & fees
Oct 12 - Oct 13
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

19. Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views

Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
Cudjoe Key
9.4 out of 10, Exceptional, (16 reviews)
"Great water view and comfortable for four adults "
United States
Kyle F.
The price is CA $321
CA $777 total
includes taxes & fees
Oct 26 - Oct 27
Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
Pool

20. Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (4 reviews)
"Pool area was nice but only visited it once as so much to see and do!"
United States
Karen
The price is CA $322
CA $776 total
includes taxes & fees
Nov 9 - Nov 10
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
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

Islander Resort

Islander Resort

10/10 Excellent
"Our room was very clean. Resort staff was super nice and accommodating. Amenities were nice. Pools were clean. Resort was very peaceful."
Grayson 5-night trip
Posted 4 hours ago
Islander Resort

Find out more about Florida Keys

Florida Keys Vacation Homes information

Number of reviews
793
Accommodation
1052 Vacation Homes
Lowest Price
CA $298
Highest Price
CA $1,141

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