Top 50 Florida Keys Vacation Rentals

Houses (2,054)
Condos (953)
Townhome (337)
Golf rental (1,921)
Beachfront (1,825)
Ocean view (963)

Explore a selection of Florida Keys vacation rentals

Paradise on the Golf
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$84 avg/night
2 beds
2 Bathrooms
Guests 6
5 reviews
Coco Plum Paradise • Private Bayfront Home • Pool, Hot Tub, Dock...
Guests5
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$241 avg/night
2 beds
1 Bathroom
Guests 5
62 reviews
Oceana Vista - Oceanfront Home w/ Private Beach, Pool...
Guests10
Bedrooms2
Bathrooms2
Wonderful 0 / 5
$250 avg/night
2 beds
2 Bathrooms
Guests 10
Charming Condo in Old Town Key West's Truman Annex
Guests2
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$171 avg/night
1 bed
1 Bathroom
Guests 2
94 reviews
Lazy River Pool and Enchanting Gardens in Old Town Key West
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$103 avg/night
2 beds
2 Bathrooms
Guests 4
16 reviews
Oceanfront Acre Heated Private Pool Sandy Area Dock 15 Min Key...
Guests10
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$285 avg/night
3 beds
2 Bathrooms
Guests 10
115 reviews
The Conch Farmhouse
Guests4
Bedrooms2
Bathroom1
Wonderful 5 / 5
$325 avg/night
2 beds
1 Bathroom
Guests 4
35 reviews
Ocean Perch , Dock 80'Heated Pool Deep Channel Tennis 15 min Key...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.7 / 5
$154 avg/night
2 beds
2 Bathrooms
Guests 6
94 reviews
Captain D's Hideout - Beautiful waterfront home in the heart of a...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$100 avg/night
2 beds
2 Bathrooms
Guests 6
57 reviews
Beautiful Duval St. Condo, Location, Location!!!!
Guests4
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$225 avg/night
2 beds
1 Bathroom
Guests 4
87 reviews
Royal Keys House-Ocean View 20m from Keywest
Guests10
Bedrooms5
Bathrooms3
Wonderful 4.7 / 5
$600 avg/night
5 beds
3 Bathrooms
Guests 10
51 reviews
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.6 / 5
$150 avg/night
2 beds
2 Bathrooms
Guests 6
44 reviews
Key West Condo in Truman Annex with 2 Bikes and Pool!
Guests4
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$318 avg/night
2 beds
1 Bathroom
Guests 4
73 reviews
Quiet, Quaint and 2.5 blocks off of Duval St!
Guests2
Studio
Bathroom1
Wonderful 4.6 / 5
$156 avg/night
Studio
1 Bathroom
Guests 2
44 reviews
Very Nice 3 Bedroom Home With Large Lot! Basketball Court! Rv Hook...
Guests5
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$75 avg/night
3 beds
2 Bathrooms
Guests 5
4 reviews
Mockingbird Pointe - Waterfront Tropical Escape - Private Home...
Guests6
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$271 avg/night
2 beds
1 Bathroom
Guests 6
35 reviews
Beach House with Ocean View
Guests4
Bedroom1
Bathroom1
Wonderful 5 / 5
$213 avg/night
1 bed
1 Bathroom
Guests 4
16 reviews
Enjoy Paradise on our Florida Keys Island Home on the Florida Bay!
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$160 avg/night
3 beds
2 Bathrooms
Guests 8
3 reviews
Luxury Living Inside & Out
Guests4
Bedroom1
Bathrooms2
Wonderful 5 / 5
$159 avg/night
1 bed
2 Bathrooms
Guests 4
69 reviews
Coral Hammock Tropical Getaway 3/3, sleeps 6 to 8, very charming
Guests8
Bedrooms3
Bathrooms3
Wonderful 4.9 / 5
$250 avg/night
3 beds
3 Bathrooms
Guests 8
55 reviews
Quiet, Quaint And Conveniently Located!
Guests2
Studio
Bathroom1
Wonderful 4.3 / 5
$156 avg/night
Studio
1 Bathroom
Guests 2
89 reviews
Dock 80'Heated Pool Deep Channel Tennis 15 Min Key West
Guests4
Bedrooms2
Bathroom1
Wonderful 4.4 / 5
$125 avg/night
2 beds
1 Bathroom
Guests 4
24 reviews
Welcome to Paradise "Sandbar Bungalow Villa" @ Anglers Reef
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.7 / 5
$217 avg/night
2 beds
2 Bathrooms
Guests 6
43 reviews
Relax, Fish, Kayak And Enjoy The Florida Keys
Guests6
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$140 avg/night
2 beds
2 Bathrooms
Guests 6
7 reviews
Beach Chic with a Water View
Guests4
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$363 avg/night
2 beds
1 Bathroom
Guests 4
43 reviews
Ocean front property
Guests6
Bedrooms2
Bathrooms2
Wonderful 0 / 5
$83 avg/night
2 beds
2 Bathrooms
Guests 6
Oceanfront Home on Deep Water Canal w/Dock, Pool, Hot Tub, Kayaks...
Guests10
Bedrooms4
Bathrooms3
Wonderful 5 / 5
$829 avg/night
4 beds
3 Bathrooms
Guests 10
30 reviews
Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and...
Guests4
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$312 avg/night
2 beds
1 Bathroom
Guests 4
98 reviews
Simonton Studio, an Old Town get-away for 2
Guests2
Studio
Bathroom1
Wonderful 4.8 / 5
$152 avg/night
Studio
1 Bathroom
Guests 2
91 reviews
Simonton Studio, an Old Town get-away for 2
Guests2
Studio
Bathroom1
Wonderful 4.8 / 5
$152 avg/night
Studio
1 Bathroom
Guests 2
91 reviews
Oceanfront Sandy Beach Vacation Rental Unit 1
Guests8
Bedroom1
Bathroom1
Wonderful 4.4 / 5
$156 avg/night
1 bed
1 Bathroom
Guests 8
10 reviews
Conch Retreat in Beautiful Truman Annex with 2 Bikes
Guests4
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$300 avg/night
2 beds
1 Bathroom
Guests 4
81 reviews
Luxury Gulf front Heated Pool Hot tub kayaks bikes Open water...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$414 avg/night
2 beds
2 Bathrooms
Guests 6
35 reviews
Luxurious 4 bedroom/3 full bath home with private pool in Old Town...
Guests8
Bedrooms4
Bathrooms3
Wonderful 4.9 / 5
$429 avg/night
4 beds
3 Bathrooms
Guests 8
53 reviews
Kawama Yacht Club Townhouse Renovated in December of 2015!
Guests10
Bedrooms3
Bathrooms3
Wonderful 4.8 / 5
$236 avg/night
3 beds
3 Bathrooms
Guests 10
60 reviews
Oceanfront Escape--Reserve Your Sunsets Now!
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.5 / 5
$155 avg/night
2 beds
2 Bathrooms
Guests 6
36 reviews
Beautiful 3/3 Family Tropical Beach Key West Home Get Away in...
Guests8
Bedrooms3
Bathrooms3
Wonderful 4.8 / 5
$288 avg/night
3 beds
3 Bathrooms
Guests 8
40 reviews
🌴SUPER SALE💎Aquamarine💎OCEANVIEW+Dock+Pool+Spa+2...
Guests6
Bedrooms2
Bathrooms3
Wonderful 5 / 5
$197 avg/night
2 beds
3 Bathrooms
Guests 6
27 reviews
Beautiful Tropical House 3 bedrooms - 2 King Beds! Sleeps 8
Guests8
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$343 avg/night
3 beds
3 Bathrooms
Guests 8
138 reviews
Conch Get Enough! - Old Town's Truman Annex
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$261 avg/night
2 beds
2 Bathrooms
Guests 4
48 reviews
TICKET TO PARADISE !!! NEW PRIVATE POOL, OCEAN SIDE/VIEW...
Guests8
Bedrooms3
Bathrooms2
Wonderful 0 / 5
$200 avg/night
3 beds
2 Bathrooms
Guests 8
SUMMER SALE SPECTACULAR ~ Remaining Open Aug/Sept Nights $220****
Guests6
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$268 avg/night
2 beds
1 Bathroom
Guests 6
17 reviews
Tropical Paradise at #1 Rated Resort in Marathon - Coral Lagoon
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.8 / 5
$283 avg/night
3 beds
2 Bathrooms
Guests 8
70 reviews
David and Christopher Welcome You To Gracie's Place
Guests2
Bedroom1
Bathroom1
Wonderful 0 / 5
$125 avg/night
1 bed
1 Bathroom
Guests 2
Southernmost Retreat: 1 Block from Duval in Old Town.
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.5 / 5
$338 avg/night
3 beds
2 Bathrooms
Guests 8
70 reviews
Islamorada Keys Home In Anglers Reef With Ocean View, Dock, Pool...
Guests6
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$264 avg/night
2 beds
2 Bathrooms
Guests 6
20 reviews
OCEANFRONT 5th Flr End Unit, FREE WiFi, Pool, Tennis, Ocean View...
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$150 avg/night
2 beds
2 Bathrooms
Guests 4
49 reviews
Island Escape Condo in Beautiful Truman Annex
Guests2
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$171 avg/night
1 bed
1 Bathroom
Guests 2
52 reviews
Luxury living @ great low rates - Truman Annex 2/2 1/2 WIFI 2 blks...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$333 avg/night
2 beds
2 Bathrooms
Guests 6
13 reviews
One of the Best Private Beaches in US! Great Location for fun...
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$185 avg/night
2 beds
2 Bathrooms
Guests 4
46 reviews

Florida Keys, USA Vacation Rentals

Paradise on the Golf

Coco Plum Paradise • Private Bayfront Home • Pool, Hot Tub, Dock...

Oceana Vista - Oceanfront Home w/ Private Beach, Pool...

Charming Condo in Old Town Key West's Truman Annex

Lazy River Pool and Enchanting Gardens in Old Town Key West

Oceanfront Acre Heated Private Pool Sandy Area Dock 15 Min Key...

The Conch Farmhouse

Ocean Perch , Dock 80'Heated Pool Deep Channel Tennis 15 min Key...

Captain D's Hideout - Beautiful waterfront home in the heart of a...

Beautiful Duval St. Condo, Location, Location!!!!

Royal Keys House-Ocean View 20m from Keywest

Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West

Key West Condo in Truman Annex with 2 Bikes and Pool!

Quiet, Quaint and 2.5 blocks off of Duval St!

Very Nice 3 Bedroom Home With Large Lot! Basketball Court! Rv Hook...

Mockingbird Pointe - Waterfront Tropical Escape - Private Home...

Beach House with Ocean View

Enjoy Paradise on our Florida Keys Island Home on the Florida Bay!

Luxury Living Inside & Out

Coral Hammock Tropical Getaway 3/3, sleeps 6 to 8, very charming

Quiet, Quaint And Conveniently Located!

Dock 80'Heated Pool Deep Channel Tennis 15 Min Key West

Welcome to Paradise "Sandbar Bungalow Villa" @ Anglers Reef

Relax, Fish, Kayak And Enjoy The Florida Keys

Beach Chic with a Water View

Ocean front property

Oceanfront Home on Deep Water Canal w/Dock, Pool, Hot Tub, Kayaks...

Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and...

Simonton Studio, an Old Town get-away for 2

Simonton Studio, an Old Town get-away for 2

Oceanfront Sandy Beach Vacation Rental Unit 1

Conch Retreat in Beautiful Truman Annex with 2 Bikes

Luxury Gulf front Heated Pool Hot tub kayaks bikes Open water...

Luxurious 4 bedroom/3 full bath home with private pool in Old Town...

Kawama Yacht Club Townhouse Renovated in December of 2015!

Oceanfront Escape--Reserve Your Sunsets Now!

Beautiful 3/3 Family Tropical Beach Key West Home Get Away in...

🌴SUPER SALE💎Aquamarine💎OCEANVIEW+Dock+Pool+Spa+2...

Beautiful Tropical House 3 bedrooms - 2 King Beds! Sleeps 8

Conch Get Enough! - Old Town's Truman Annex

TICKET TO PARADISE !!! NEW PRIVATE POOL, OCEAN SIDE/VIEW...

SUMMER SALE SPECTACULAR ~ Remaining Open Aug/Sept Nights $220****

Tropical Paradise at #1 Rated Resort in Marathon - Coral Lagoon

David and Christopher Welcome You To Gracie's Place

Southernmost Retreat: 1 Block from Duval in Old Town.

Islamorada Keys Home In Anglers Reef With Ocean View, Dock, Pool...

OCEANFRONT 5th Flr End Unit, FREE WiFi, Pool, Tennis, Ocean View...

Island Escape Condo in Beautiful Truman Annex

Luxury living @ great low rates - Truman Annex 2/2 1/2 WIFI 2 blks...

One of the Best Private Beaches in US! Great Location for fun...