50 Best Florida Keys Vacation rentals on Holiday Lettings - House rentals

Close

View larger map

Also consider

Vacation rentals Key Largo
243 properties
Vacation rentals Sugarloaf Key
215 properties
Vacation rentals Key West
202 properties
Vacation rentals Islamorada
144 properties
Vacation rentals Marathon
105 properties
Vacation rentals Key Colony Beach
57 properties
Long Key
21 properties
Stock Island
15 properties
Lower Keys
11 properties
Vacation rentals Big Pine Key
9 properties
Vacation rentals Cudjoe Key
8 properties
Matecumbe Key
6 properties
Sugarloaf
5 properties

Florida Keys

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

1,047 Vacation rentals

(1) Very Good 

26

Vacation apartment in Tavernier

Key Largo / Tavernier

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
!WE WILL REOPEN ON APR 15, 2018 AFTER FULL PROPERTY RENOVATION! 24/7 FRONT DESK AND SECURITY, PRIVATE BEACH AND MARINA, FREE PARKING, SWIMMING POOL, HOT TUB, ON-SITE RESTAURANT, GRILL Travelling with your family or friends and want to stay all together? Prefer to coo …see more

from $325 / night

$2,275 / week

Book View

from $325 / night

26

Vacation apartment rental

Florida Keys / Key Largo

6 18 Min stay varies

  • 6 bedrooms
  • Sleeps 18
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
!WE WILL REOPEN ON APR 15, 2018 AFTER FULL PROPERTY RENOVATION! 24/7 FRONT DESK AND SECURITY, PRIVATE BEACH AND MARINA, FREE PARKING, SWIMMING POOL, HOT TUB, ON-SITE RESTAURANT, GRILL Travelling with your family or friends and want to stay all together? Prefer to coo …see more

from $499 / night

$3,493 / week

Book View

from $499 / night

24

Vacation apartment in Tavernier

Key Largo / Tavernier

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
!WE WILL REOPEN ON APR 15, 2018 AFTER FULL PROPERTY RENOVATION! 24/7 FRONT DESK AND SECURITY, PRIVATE BEACH AND MARINA, FREE PARKING, SWIMMING POOL, HOT TUB, ON-SITE RESTAURANT, GRILL Travelling with your family or friends and want to stay all together? Prefer to coo …see more

from $159 / night

$1,113 / week

Book View

from $159 / night

27

Marathon Shores Vacation home rental

Marathon / Marathon Shores

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning
Beautifully decorated, extra clean, new furniture, fully equipped kitchen brand new hot tub, along with everything you will need to make your stay comfortable. Walking distance to one of the most beautiful beaches in the Florida Keys. Only minutes away from the 7 mile …see more

from $225 / night

$1,295 - $1,420 / week

Book View

Responds fast!
avg. 54 minutes

from $225 / night

(4) Excellent 

29

Marathon Shores Vacation home rental

Marathon / Marathon Shores

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 8 mi
  • Child friendly
  • Air conditioning
The "Mermaid House" sits directly on the ocean with the unobstructed views, gorgeous sunrises and some of the best boating access in the Marathon area. House offers 4 Queen Bedrooms and 2 full bathrooms. 3 bedrooms and a bathroom are located on the ground level. Upstair …see more

from $430 / night

$3,000 - $4,000 / week

Book View

Responds fast!
avg. 2 hours 31 minutes

from $430 / night

26

Tavernier Vacation apartment rental

Key Largo / Tavernier

6 18 1 night min

  • 6 bedrooms
  • Sleeps 18
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
!WE WILL REOPEN ON APR 15, 2018 AFTER FULL PROPERTY RENOVATION! Island View, private beach and marina, free parking, tennis courts, swimming pool Travelling with your family or friends and want to stay all together? Prefer to cook by yourself while on the vacation? Or …see more

from $499 / night

$3,493 / week

Book View

from $499 / night

32

Vacation condo in Key Largo

Florida Keys / Key Largo

1 2 28 nights min

  • 1 bedroom
  • Sleeps 2
  • 28 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
If you have a vision of a Pleasure Filled Vacation, free from the distractions of home and wall to wall people, we know you will love it here on Key Largo, where comfort and privacy come first. Unobstructed breathtaking views of the Florida Bay are yours from the momen …see more

from $75 / night

$525 / week

Book View

from $75 / night

24

Vacation apartment with swimming pool in Key Largo

Florida Keys / Key Largo

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Travelling with your family or friends and want to stay all together? Prefer to cook by yourself while on the vacation? Or maybe you just want to feel yourself like home, not like in a hotel. If you have many people in your party, or big family, or want to have some pri …see more

from $159 / night

$1,113 / week

Book View

from $159 / night

(3) Very Good 

41

Vacation apartment in Islamorada

Florida Keys / Islamorada

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from home surrounded by the tropical beauty of the Florida Keys. The location is in the perfect proximity for visiting Key West & Miami. With its exceptional location and gated …see more

from $198 / night

$1,385 - $2,085 / week

Book View

from $198 / night

(14) Very Good 

15

Vacation condo in Key Largo

Florida Keys / Key Largo

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
A view of the pool off your patio and the Florida Bay sunset glows at your front door. Tropical breezes and gardens grace the gated condo community. Yes, laptops do work in the apartment! At Moon Bay condominium you will have the opportunity to relax in the heated po …see more

from $195 / night

$985 / week

Inquire View

from $195 / night

(1) Excellent 

17

Yacht rental in Key West

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
This yacht is very spacious and bright with windows surrounding it making views of the ocean amazing. The marina and its grounds are meticulous and located in the middle of a turquoise paradise with amazing water clarity. Your stay will include free access to the mari …see more

from $200 / night

$1,400 / week

Book View

Responds fast!
avg. 1 hour 54 minutes

from $200 / night

29

Key Largo Vacation home rental

Florida Keys / Key Largo

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.05 mi
  • Swimming pool
Welcome from Sally and Andrew We look forward to sharing warm tropical breezes and beautiful clear turquoise seas set amid our little slice of Keys Paradise. Feel a sense of Life, Light and Love in our modern, spacious and well maintained Home. Set in an Oceanside locat …see more

from $149 / night

$892 - $2,270 / week

Book View

from $149 / night

23

Vacation apartment in Tavernier

Key Largo / Tavernier

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
!WE WILL REOPEN ON APR 15, 2018 AFTER FULL PROPERTY RENOVATION! Ocean view, private beach and marina, free parking, tennis courts, swimming pool This beautiful 1 bedroom apartment is located in an Oceanfront hotel style building in the heart of Key Largo, which is ha …see more

from $149 / night

$1,043 / week

Book View

from $149 / night

27

Vacation apartment with swimming pool in Key Largo

Florida Keys / Key Largo

4 12 2 nights min

  • 4 bedrooms
  • Sleeps 12
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Travelling with your family or friends and want to stay all together? Prefer to cook by yourself while on the vacation? Or maybe you just want to feel yourself like home, not like in a hotel. If you have many people in your party, or big family, or want to have some pri …see more

from $319 / night

$2,233 / week

Book View

from $319 / night

(27) Excellent 

31

Key West Vacation houseboat rental

Florida Keys / Key West

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
Ocean view yacht with beautiful sunsets and sunrises. Underwater windows in the forward cabins makes this yacht unbelievable. Located in the finest most elegant first class marinas giving you full access to its restaurant and private pool during your stay. The marina i …see more

from $385 / night

$2,875 - $3,925 / week

Book View

Responds fast!
avg. 1 hour 54 minutes

from $385 / night

(1) Excellent 

16

Stock Island Vacation yacht rental

Florida Keys / Stock Island

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
You will not find a cleaner or newer yacht in Key West! This yacht was featured in the 2018 edition of Sail Magazine. This catamaran is a high performance sailing yacht with average sailing speeds at 10 knots. It has a large great room and cockpit with views of the oc …see more

from $200 / night

$1,400 / week

Book View

Responds fast!
avg. 1 hour 54 minutes

from $200 / night

36

Vacation apartment in Tavernier

Key Largo / Tavernier

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Air conditioning
Located directly on the Atlantic Ocean in a 24 hectare (60 acre) protected Mangrove forest. This 6 building complex contains 160 apartments amidst well-landscaped grounds with tropical palm trees and plants. Boardwalk. Marina. Large Olympic-size pool. Beach volleyball. …see more

from $170 / night

$1,092 - $3,219 / week

Book View

from $170 / night

37

Apartment rental in Tavernier

Key Largo / Tavernier

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Air conditioning
Located directly on the Atlantic Ocean in a 24 hectare (60 acre) protected Mangrove forest. This 6 building complex contains 160 apartments amidst well-landscaped grounds with tropical palm trees and plants. Boardwalk. Marina. Large Olympic-size pool. Beach volleyball. …see more

from $170 / night

$1,092 - $3,219 / week

Book View

from $170 / night

47

Vacation apartment in Tavernier

Key Largo / Tavernier

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Air conditioning
Located directly on the Atlantic Ocean in a 24 hectare (60 acre) protected Mangrove forest. This 6 building complex contains 160 apartments amidst well-landscaped grounds with tropical palm trees and plants. Boardwalk. Marina. Large Olympic-size pool. Beach volleyball. …see more

from $205 / night

$1,313 - $3,920 / week

Book View

Responds fast!
avg. 3 hours 38 minutes

from $205 / night

38

Vacation apartment in Tavernier

Key Largo / Tavernier

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Air conditioning
Located directly on the Atlantic Ocean in a 24 hectare (60 acre) protected Mangrove forest. This 6 building complex contains 160 apartments amidst well-landscaped grounds with tropical palm trees and plants. Boardwalk. Marina. Large Olympic-size pool. Beach volleyball. …see more

from $186 / night

$1,195 - $3,450 / week

Book View

from $186 / night

44

Tavernier Vacation apartment rental

Key Largo / Tavernier

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Air conditioning
Located directly on the Atlantic Ocean in a 24 hectare (60 acre) protected Mangrove forest. This 6 building complex contains 160 apartments amidst well-landscaped grounds with tropical palm trees and plants. Boardwalk. Marina. Large Olympic-size pool. Beach volleyball. …see more

from $187 / night

$1,201 - $3,581 / week

Book View

from $187 / night

39

Vacation apartment in Tavernier

Key Largo / Tavernier

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Air conditioning
Located directly on the Atlantic Ocean in a 24 hectare (60 acre) protected Mangrove forest. This 6 building complex contains 160 apartments amidst well-landscaped grounds with tropical palm trees and plants. Boardwalk. Marina. Large Olympic-size pool. Beach volleyball. …see more

from $187 / night

$1,201 - $3,581 / week

Book View

from $187 / night

39

Vacation apartment in Tavernier

Key Largo / Tavernier

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Air conditioning
Located directly on the Atlantic Ocean in a 24 hectare (60 acre) protected Mangrove forest. This 6 building complex contains 160 apartments amidst well-landscaped grounds with tropical palm trees and plants. Boardwalk. Marina. Large Olympic-size pool. Beach volleyball. …see more

from $186 / night

$1,195 - $3,450 / week

Book View

from $186 / night

44

Vacation apartment in Tavernier

Key Largo / Tavernier

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Air conditioning
Located directly on the Atlantic Ocean in a 24 hectare (60 acre) protected Mangrove forest. This 6 building complex contains 160 apartments amidst well-landscaped grounds with tropical palm trees and plants. Boardwalk. Marina. Large Olympic-size pool. Beach volleyball. …see more

from $203 / night

$1,306 - $3,920 / week

Book View

from $203 / night

39

Tavernier Vacation apartment rental

Key Largo / Tavernier

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Air conditioning
Located directly on the Atlantic Ocean in a 24 hectare (60 acre) protected Mangrove forest. This 6 building complex contains 160 apartments amidst well-landscaped grounds with tropical palm trees and plants. Boardwalk. Marina. Large Olympic-size pool. Beach volleyball. …see more

from $187 / night

$1,201 - $3,469 / week

Book View

from $187 / night

38

Vacation apartment in Tavernier

Key Largo / Tavernier

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Air conditioning
Located directly on the Atlantic Ocean in a 24 hectare (60 acre) protected Mangrove forest. This 6 building complex contains 160 apartments amidst well-landscaped grounds with tropical palm trees and plants. Boardwalk. Marina. Large Olympic-size pool. Beach volleyball. …see more

from $170 / night

$1,092 - $3,219 / week

Book View

from $170 / night

48

Tavernier Vacation apartment rental

Key Largo / Tavernier

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Air conditioning
Located directly on the Atlantic Ocean in a 24 hectare (60 acre) protected Mangrove forest. This 6 building complex contains 160 apartments amidst well-landscaped grounds with tropical palm trees and plants. Boardwalk. Marina. Large Olympic-size pool. Beach volleyball. …see more

from $204 / night

$1,306 - $3,898 / week

Book View

from $204 / night

44

Vacation apartment in Tavernier

Key Largo / Tavernier

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Air conditioning
Located directly on the Atlantic Ocean in a 24 hectare (60 acre) protected Mangrove forest. This 6 building complex contains 160 apartments amidst well-landscaped grounds with tropical palm trees and plants. Boardwalk. Marina. Large Olympic-size pool. Beach volleyball. …see more

from $186 / night

$1,195 - $3,562 / week

Book View

from $186 / night

48

Vacation apartment in Tavernier

Key Largo / Tavernier

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Air conditioning
Located directly on the Atlantic Ocean in a 24 hectare (60 acre) protected Mangrove forest. This 6 building complex contains 160 apartments amidst well-landscaped grounds with tropical palm trees and plants. Boardwalk. Marina. Large Olympic-size pool. Beach volleyball. …see more

from $204 / night

$1,306 - $3,898 / week

Book View

from $204 / night

39

Vacation apartment in Tavernier

Key Largo / Tavernier

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Air conditioning
Located directly on the Atlantic Ocean in a 24 hectare (60 acre) protected Mangrove forest. This 6 building complex contains 160 apartments amidst well-landscaped grounds with tropical palm trees and plants. Boardwalk. Marina. Large Olympic-size pool. Beach volleyball. …see more

from $186 / night

$1,195 - $3,450 / week

Book View

from $186 / night

40

Vacation apartment in Tavernier

Key Largo / Tavernier

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Air conditioning
Located directly on the Atlantic Ocean in a 24 hectare (60 acre) protected Mangrove forest. This 6 building complex contains 160 apartments amidst well-landscaped grounds with tropical palm trees and plants. Boardwalk. Marina. Large Olympic-size pool. Beach volleyball. …see more

from $187 / night

$1,201 - $3,581 / week

Book View

from $187 / night

37

Vacation apartment in Tavernier

Key Largo / Tavernier

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Air conditioning
Located directly on the Atlantic Ocean in a 24 hectare (60 acre) protected Mangrove forest. This 6 building complex contains 160 apartments amidst well-landscaped grounds with tropical palm trees and plants. Boardwalk. Marina. Large Olympic-size pool. Beach volleyball. …see more

from $171 / night

$1,098 - $3,236 / week

Book View

Responds fast!
avg. 3 hours 38 minutes

from $171 / night

(3) Very Good 

14

Vacation condo in Marathon

Florida Keys / Marathon

2 6 6 nights min

  • 2 bedrooms
  • Sleeps 6
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautifully furnished and newly renovated condo is airy and offers all the comforts of your own home. Walk in to a spacious living room with an adjacent dining area and then onto a full kitchen with everything necessary to prepare and serve your meals. The kitchen …see more

from $150 / night

$900 - $1,200 / week

Book View

from $150 / night

(2) Excellent 

22

Vacation home rental

Florida Keys / Marathon

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
Vaca Cove is an exclusive compound with Bonefish Bay Views, a fantastic pool and beach area for the kids (and adults) to play i!. Brand new 4 bedroom homes with 3 baths, and deep water dockage. The pool and beach area is breathtaking, with palm trees and a large tiki hu …see more

from $450 / night

$3,000 / week

Book View

from $450 / night

(38) Excellent 

Certificate of Excellence

20

Cottage rental in Key Largo

Florida Keys / Key Largo

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Charming and secluded CBS construction seaside cottage with all of the comforts. Two bedrooms each with queen size bed and private bath. Also a third bathroom in the main area for your convenience. Fully equipped kitchen/dining room with a bar cabinet and a washer/drye …see more

Certificate of Excellence

from $223 / night

$1,561 / week

Book View

Responds fast!
avg. 1 hour 33 minutes

from $223 / night

37

Vacation home rental

Florida Keys / Marathon

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
In search of tropical views and blissful privacy in the Florida Keys? This beautiful four-bedroom Marathon home provides guests with their very own beach, swimming pool, and dock on serene Florida Bay. And two dogs are welcome, too, for a small nightly fee! Scenically …see more

from $371 / night

$2,597 / week

Book View

Responds fast!
avg. 29 minutes

from $371 / night

(19) Excellent 

17

Tavernier Vacation apartment rental

Key Largo / Tavernier

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Ocean Pointe Suites is located directly on the Atlantic Ocean. This unit is completely renovated and is located in building 4 which is the most desirable building. Featuring magnificent ocean views from the living room, master bedroom and porch. This unit offers 1 Ki …see more

from $235 / night

$1,645 / week

Book View

from $235 / night

(2) Excellent 

14

Vacation condo in Islamorada

Florida Keys / Islamorada

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This condo has been completely restored after Hurricane Irma’s d is now ready for guests to return. There is new drywall, paint, carpets and new furniture and is safe to stay in. Paradise by the Atlantic Ocean and only 50' front the waters edge. Beautiful condominium …see more

from $150 / night

$1,000 - $1,200 / week

Book View

from $150 / night

(1) Very Good 

47

Vacation home rental

Florida Keys / Marathon

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
Enjoy the unobstructed open water view from anywhere on this acre-sized, Gulf-front estate. Enjoy fruiting palm trees, a private hot tub, pool, a boat ramp, and, coming soon, a private dock, which will be available for all 2018 rentals! Enjoy the unobstructed open wate …see more

from $370 / night

$2,590 / week

Book View

Responds fast!
avg. 24 minutes

from $370 / night

16

Vacation condo with shared pool in Key Colony Beach

Florida Keys / Key Colony Beach

2 6 14 nights min

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our unit is a two bedroom, two and one-half bath, washer/dryer, and private balcony with spiral staircases leading into the courtyard. We are an Oceanfront condominium with our own private beach, beautiful heated pool, tiki hut on the beach, and Oceanfront deck that ca …see more

from $200 / night

$1,400 - $1,600 / week

Book View

from $200 / night