Updating...

Enter dates for more accurate prices

Florida Keys Rentals

Filter

Florida Keys Rentals

1,529 house rentals

Open for business after Irma. Private home with Beach Access

Key Largo house

2 bedrooms / 2 bathrooms / Sleeps 6

“Perfectly located between Miami and the keys !” We stayed at the house during Dec 2013 and enjoyed the house and location very much. The house is clean, spacious and has everything you need to spend a lovely time with friends or family. Lots of games

$149

1 / 68

Coco Plum Beach 2 BR/ BA Fantastic Condo

Marathon condo

2 bedrooms / 2 bathrooms / Sleeps 6

$150

1 / 14

New, Luxury 4/3 Single Family Home w/Pool , 40 ft BoatDock, short walk to Beach

Marathon Shores house

4 bedrooms / 3 bathrooms / Sleeps 8

$397

1 / 36

Sunrise At Seaside Condo 2 bedroom 2 bath

Key West apartment

2 bedrooms / 2 bathrooms / Sleeps 5

“Amamzing” First time to Key West and fell in love! The condo was truly a home away from home. We will be going back to make many more memories!

$158

1 / 12

Direct Atlantic Ocean front private boat ramp dock

Summerland Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$139

1 / 14

Oceanfront 2 Bedroom/2 Bathroom Well Maintained Condo with Large Balcony

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 5

$125

1 / 14

Gorgeous, dog-friendly, waterfront home with beach, pool, dock, & kayaks

Marathon house

4 bedrooms / 3 bathrooms / Sleeps 8

$371

1 / 37

2 Great Waterfront FL Keys Homes - 1 Low Price

Marathon house

4 bedrooms / 4 bathrooms / Sleeps 12

“Excellent Stay!” We rented out both sides for the week and we couldn't have asked for a better location! Great fishing, lobstering, and diving. We took the boat out almost everyday right from the house. Just enough room for our 9 people plus 1 baby. I

$256

1 / 26

SPRING SPECIAL! Hurry, couple weeks left!! Kayak, Dock, Bikes, Pool, 2 Beaches

Key Colony Beach house

2 bedrooms / 2 bathrooms / Sleeps 6

“Paradise Found” This is an adorable property. It is so "keysie"! The decor is just lovely with all the amenities you need. The kitchen is fully equipped, there was a new set of pots and pans, crockpot, blender and anything else I needed. The grill

$157

1 / 70

Dog-friendly half-duplex w/ a 30-ft dock including Cabana Club pool and beach

Key Colony Beach house

2 bedrooms / 2 bathrooms / Sleeps 4

$130

1 / 24

Sip your coffee looking out to a tropical sunrise

Marathon house

4 bedrooms / 3 bathrooms / Sleeps 10

$600

1 / 46

Casa Del Sol, a Key West Vacation (Truman Annex)

Key West house

2 bedrooms / 3 bathrooms / Sleeps 6

“awesome” the condo was beautiful. very good location. 2 suggestions. the grill did not have gas . the bed that opens up to king. not so much, mattress is 2 different heights and slides if you try to sleep on it. very very uncomfortable.

$263

1 / 26

Islamorada Luxury Waterfront Condo with Boat Slip

Islamorada apartment

2 bedrooms / 3 bathrooms / Sleeps 6

$228

1 / 21

Coral Hammock 34- 3 Bedroom Townhouse with a Shared Pool

Key West house

3 bedrooms / 3 bathrooms / Sleeps 6

“New Years Vacation” We had a great time at Coral Hammock, it was a nice community town home with a lovely pool and in a great location. Our rental agent, Brian, was very helpful and personable. We look forward to returning.

$300

1 / 24

Beautiful Beachfront Condo

Dry Tortugas National Park apartment

3 bedrooms / 2 bathrooms / Sleeps 7

$333

1 / 14

2 Bed 2 Bath Condo with Beautiful Ocean views

Key Largo apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$249

1 / 25

Marathon Key Beach Club

Marathon Shores condo

2 bedrooms / 2 bathrooms / Sleeps 6

$249

1 / 7

Key Largo 2/2 Tropical Daze Oceanfront Condo

Key Largo apartment

2 bedrooms / 2 bathrooms / Sleeps 4

“Couldn't be better!!!” If you are looking to rest and relax, look no further.

$198

1 / 32

Beautiful 2 bedroom 2.5 bath townhome fully furnis

Key Largo townhouse

2 bedrooms / 2 bathrooms / Sleeps 10

$132

1 / 14

$134

1 / 8

Cozy Couples Houseboat with an Amazing Sunset

Tavernier boathouse

1 bedroom / 1 bathroom / Sleeps 2

$174

1 / 19

Come relax in Islamorada, the tropical jewel of the Florida Keys!!

Islamorada apartment

1 bedroom / 1 bathroom / Sleeps 4

$174

1 / 9

Private and Immaculate 2 Bedroom Home with Private Fenced Yard

Key West house

2 bedrooms / 1 bathroom / Sleeps 4

$115

1 / 13

Atlantic Paradise

Key West apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$230

1 / 24

BAYSIDE CONDO MARINA,POOL,TENNIS AND DOCKAGE

Islamorada apartment

3 bedrooms / 2 bathrooms / Sleeps 6

“Phenomenal keys experience!” This bay front condo is the perfect destination for the entire family! The fishing ranks up with the best in the world, there are plenty of other activities, and Key West is just a short trip down the beautiful HWY 1. I'

$170

1 / 39

~ POTTER'S COTTAGE ~ Perfect Home w/ Pvt Heated Pool Just 1 Block to Duval!

Key West house

2 bedrooms / 2 bathrooms / Sleeps 6

“Found what we were looking for” Cute cottage with a great master bedroom loft suite, well appointed throughout, furnishings look new. The private pool and really cool poolside seating area were perfect for sun or shade. Location couldn't have been b

$593

1 / 26

Escape to Paradise in a Gated Tropical Bayfront Estate (Free Wifi)

Tavernier house

2 bedrooms / 2 bathrooms / Sleeps 4

$224

1 / 19

Futura Yacht Club Bay View Condo with 36' Deeded Boat Slip (Min. 28 Day Rental)

Islamorada condo

2 bedrooms / 2 bathrooms / Sleeps 6

$142

1 / 9

New Rental Like New - Sombrero Beach Gem

Marathon house

3 bedrooms / 3 bathrooms / Sleeps 6

$426

1 / 14

Luxury 2 Bedroom 2.5 Bath Townhouse on Duval Street. Great Location

Key West apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$340

1 / 32

Shipyard 106-2 1 Bedroom newly renovated Condo

Key West apartment

1 bedroom / 1 bathroom / Sleeps 4

“Lovely condo in fantastic location.” Condo amenities were even more complete than described, with nice "extra" touches like beach towels,soaps,hairdryer,a few board games,etc. A tiny part of the write-up we found a bit misleading was the claim that th

$214

1 / 18

Mediterranean styling, oceanview, pool, dockage, hot tub

Marathon house

4 bedrooms / 4 bathrooms / Sleeps 10

$571

1 / 70

Coral Hammock 36- 3 Bedroom 3 Bathroom Townhouse with Shared Pool Pool View

Key West house

3 bedrooms / 3 bathrooms / Sleeps 6

“Fun week for the family” We spent a week in key west, the property was perfect . Lots of room for all in our group. Nice pool to enjoy. Very clean and had everything we needed.

$300

1 / 24

WOW – waterfront, boat lift, private heated pool, walk to beach and shops!

Marathon house

2 bedrooms / 2 bathrooms / Sleeps 6

$249

1 / 27

Breezy half-duplex w/35 ft dock. Includes Cabana Club access w/ pool & beach

Key Colony Beach house

4 bedrooms / 4 bathrooms / Sleeps 9

$162

1 / 36

Waterfront Keys Home - Spectacular View, 37' Dock

Marathon house

2 bedrooms / 2 bathrooms / Sleeps 6

“Enjoyable vacation rental and location” All is as advertised. The view is awesome. Rental unit has everything that one would need for a week or several weeks stay. Washer/dryer, comfortable beds, towels, kitchen stuff, TV, Wi-Fi, etc. All we had t

$136

1 / 22

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / Sleeps 6

$298

1 / 25

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

2 bedrooms / 3 bathrooms / Sleeps 6

$277

1 / 25
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more