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

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Vacation rentals Key Largo
240 properties
Vacation rentals Key West
216 properties
Vacation rentals Islamorada
135 properties
Vacation rentals Marathon
106 properties
Vacation rentals Key Colony Beach
55 properties
Vacation rentals Big Pine Key
29 properties
Vacation rentals Cudjoe Key
24 properties
Long Key
24 properties
Lower Keys
21 properties
Ramrod Key
16 properties
Cottages Little Torch Key
14 properties
Matecumbe Key
7 properties
Sugarloaf
5 properties

Florida Keys

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901 Vacation rentals

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
Ocean 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 maybe you just want to feel yourself like home, not like in a hot …see more

from $325 / night

$2275 / week

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from $325 / night

26

Tavernier Vacation apartment rental

Key Largo / Tavernier

6 18 Min stay varies

  • 6 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 maybe you just want to feel yourself like home, not like in a ho …see more

from $449 / night

$3143 / week

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from $449 / 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
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 $485 / night

$3395 / week

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from $485 / 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 $158 / night

$1100 - $1200 / week

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avg. 1 hour 21 minutes

from $158 / night

(2) 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

$2000 - $4000 / week

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Responds fast!
avg. 1 hour 23 minutes

from $430 / 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
Ocean 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 maybe you just want to feel yourself like home, not like in a hot …see more

from $162 / night

$1134 / week

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from $162 / night

23

Vacation apartment in Tavernier

Key Largo / Tavernier

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 halfway between Miami and Key West. 60 acres in the Florida Keys ar …see more

from $149 / night

$1043 / week

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from $149 / night

(2) Excellent 

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

$1386 - $2085 / week

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Responds fast!
avg. 2 hours 48 minutes

from $198 / night

(1)  

15

Houseboat rental in Key West

Florida Keys / Key West

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Pet friendly
Rosie is at anchor in harbor just off the bustling downtown life of Key West. She has a very comfortable queen size V berth bed, a cozy saloon (living room) great for curling up, amazing sunset views, and in a very friendly neighborhood of boats! Rosie is a 33ft Pears …see more

from $169 / night

$999 - $1350 / week

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from $169 / night

80

Key Largo Vacation home rental

Florida Keys / Key Largo

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
Our Key Largo Holiday Vacation Rental home is fully air conditioned and all on one level with Tiled floors for hygiene throughout. We have a Queen size bed in the master bedroom, 2 x full size doubles in the second bedroom. All beds have quality posture-pedic mattresses …see more

from $117 / night

$774 - $1407 / week

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from $117 / night

(2) Excellent 

24

Home rental in Tavernier with swimming pool

Key Largo / Tavernier

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Charming doesn't even begin to describe this modern, tastefully appointed waterfront 2 bedroom 2 bathroom house. Plush bedding, upgraded kitchen and bath, and a breezy terrace perfect for bbq's and relaxing. This home features a private pool, and dock and direct canal …see more

from $325 / night

$2659 / week

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Responds fast!
avg. 2 hours 8 minutes

from $325 / night

(14) Very Good 

14

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 t …see more

from $195 / night

$985 / week

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from $195 / night

4

Key West Vacation boathouse rental

Florida Keys / Key West

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
2 private bedrooms, plus pullout bed. Immaculate cabin interior. Approximately 100 yards off shore is where your adventure begins! Enjoy key west sunshine on your own private sundeck with comfortable upholstered seating & outdoor table for drinks/snacks. After you've wo …see more

from $189 / night

$1323 / week

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from $189 / night

(23) Excellent 

Certificate of Excellence

55

Vacation condo in Tavernier

Key Largo / Tavernier

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
We just received Trip Advisor's 2017 Certificate of Excellence "Best Condo in the Keys" award! Its all about being tastefully decorated, on the top floor of the best building with the largest end unit with the most windows - twelve. See a UTube walk through video of …see more

Certificate of Excellence

from $200 / night

$1400 / week

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Responds fast!
avg. 22 minutes

from $200 / night

13

Vacation home in Cudjoe Key

Florida Keys / Cudjoe Key

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful home overlooking the Atlantic Ocean is part of the Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes, is located right in the center of the Lower Keys. Key West is only 16 miles in one direction and Marathon 25 mi …see more

from $260 / night

$1495 - $2100 / week

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Responds fast!
avg. 1 hour 45 minutes

from $260 / night

26

Marathon Vacation home rental

Florida Keys / Marathon

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
Get your fishing buddies together for an unforgettable Florida Keys adventure from this Marathon vacation rental. It has all the home essentials, a private dock, an unbeatable location for ocean access via Boot Key Harbor, and offers space for four guests. This home sit …see more

from $107 / night

$749 / week

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Responds fast!
avg. 2 hours 39 minutes

from $107 / night

(37) Very Good 

Certificate of Excellence

17

Key West Vacation apartment rental

Florida Keys / Key West

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary
Located in the heart of Old Town, this split 2 Bedroom plan is just blocks from everything Key West has to offer. The famous Southernmost Point, Hemingway House, Lighthouse, Beaches and more. Just 1/2 block from Duval Street. Completely updated for your comfort and c …see more

Certificate of Excellence

from $259 / night

$1813 / week

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Responds fast!
avg. 3 hours 13 minutes

from $259 / night

13

Key West Vacation condo rental

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom and twin beds in the guest bedroom that can be converted into a king bed. Living room sofa with queen sleeper. Nicely decorated with a Key West Flai …see more

from $299 / night

$1400 - $2500 / week

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Responds fast!
avg. 3 hours 30 minutes

from $299 / night

(8) Excellent 

30

Vacation villa rental

Florida Keys / Marathon

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Come to the Florida Keys and enjoy living in luxury at 'Blue Heaven'. There are blue skies, crystal clear blue water, calm tropical breezes at 'Blue Heaven' every day. This beautiful new three bedroom, three bath villa has 2,000 square feet on 2 levels with under cover …see more

from $200 / night

$1200 - $2300 / week

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Responds fast!
avg. 2 hours 3 minutes

from $200 / night

(1) Very Good 

43

Vacation apartment in Key Largo

Florida Keys / Key Largo

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Air conditioning
This 1 Bedroom Apartment is located upstairs overlooking direct views to Florida Bay. It is furnished in white with tile floors, air conditioning, WIFI, cable Television with 75 channels. Linens are provided and the kitchen is fully stocked for cooking. You have private …see more

from $158 / night

$925 / week

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Responds fast!
avg. 2 hours 53 minutes

from $158 / night

(41) Very Good 

Certificate of Excellence

11

Apartment rental in Key West

Florida Keys / Key West

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary
Just steps away from shops, restaurants, and the excitement of Duval Street, yet set on a quiet side street in a world of its own. With 3 bedrooms and 2 Baths, The Grand Bahama Suite has plenty of room for a large gathering or group of friends. Experience endless sun …see more

Certificate of Excellence

from $329 / night

$2303 / week

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Responds fast!
avg. 3 hours 13 minutes

from $329 / night

21

Marathon Vacation condo rental

Florida Keys / Marathon

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to paradise! Dolphin Bay in Marathon is close to all the Keys has to offer and more! It is located at the friendly Gulf Pointe II complex. We have great views, breezes and impeccably kept grounds. There are only 20 units, so our place is quiet, uncrowded and …see more

from $136 / night

$950 - $1850 / week

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Responds fast!
avg. 2 hours 59 minutes

from $136 / night

(39) Excellent 

Certificate of Excellence

39

Vacation apartment rental

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 40 foot deck which encompasses the whole unit. Every room has a spectacular view of the tropical Nature Preserve and the Atlantic Ocean. The complex i …see more

Certificate of Excellence

from $340 / night

$2143 - $3800 / week

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Responds fast!
avg. 1 hour 14 minutes

from $340 / night

27

Vacation home in Marathon

Florida Keys / Marathon

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Gather some friends or the extended family together at this bright and breezy, dog-friendly home in the Florida Keys with a well-appointed back patio and ocean views from every room. You can also spend your day lounging at the exclusive, members-only Cabana Club just fi …see more

from $193 / night

$1345 / week

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Responds fast!
avg. 2 hours 40 minutes

from $193 / night

32

Vacation home in Key Colony Beach

Florida Keys / Key Colony Beach

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Air conditioning
The Florida Keys await in this glittering waterfront Key Colony Beach getaway with its own 35-foot dock, Cabana Club membership, and a shaded porch! This home is a gateway to your personal paradise. It's right across the street from the Key Colony Beach Golf Course, as …see more

from $85 / night

$595 / week

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Responds fast!
avg. 2 hours 40 minutes

from $85 / night

(5) Excellent 

20

Islamorada Vacation condo rental

Florida Keys / Islamorada

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Luxurious end unit in Bay Harbour with a boat slip. Upon entering the unit you are greeted with the tranquil views of the harbor and ocean. Enjoy the ocean breeze from the large screen porch. Beautiful Bay Harbour gated condo community on lower Matecumbe, mm 74 1/2. …see more

from $250 / night

$1800 - $3800 / week

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Responds fast!
avg. 47 minutes

from $250 / night

(2) Excellent 

13

Condo rental in Key Largo

Florida Keys / Key Largo

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
THE MOON BAY PENTHOUSE located beautiful Key Largo. This beautiful Penthouse condo is on the Florida Bay side of Key Largo at Moon Bay Condos just one mile from John Pennekamp State Park. The Penthouse condo is 1 of 2 original, top floor, large Penthouse units that inc …see more

from $200 / night

$1400 - $2400 / week

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from $200 / night

35

Key Largo Vacation private room rental

Florida Keys / Key Largo

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Air conditioning
Enjoy this private air conditioned room with 75 channels of cable TV, Wi Fi, coffee pot. Guest uses the bathrooms/showers that are common to the RV Park wherein this private room is located. Clean Linens and towel provided by our housekeeping staff. "We enjoyed our time …see more

from $64 / night

$390 - $500 / week

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Responds fast!
avg. 2 hours 53 minutes

from $64 / night

(3) Very Good 

14

Vacation condo in Marathon

Florida Keys / Marathon

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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

$1000 - $1400 / week

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from $150 / night

(9) Very Good 

Certificate of Excellence

19

Vacation apartment in Conch Key

Florida Keys / Conch Key

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 38 mi
  • Child friendly
If Comfort, Fun, Fishing and Views Are on Your List, Stay Here! We have ground level or second floor units. We provide outside table and chairs, and just around the corner the barbecue grill is located to grill up those freshly caught Florida Keys' lobster or our wonde …see more

Certificate of Excellence

from $150 / night

$945 - $975 / week

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Responds fast!
avg. 2 hours 24 minutes

from $150 / night

25

Vacation home accommodation

Florida Keys / Islamorada

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This magnificent oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool are …see more

from $229 / night

$1600 - $2500 / week

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Responds fast!
avg. 3 hours 22 minutes

from $229 / night

(8) Excellent 

Certificate of Excellence

21

Vacation condo 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 are offering for rent our beautiful, 2/2 condominium located directly on the ocean in Key Largo (Tavernier), Florida. As this is 4th floor "END" unit there are many windows that provide an open, bright feel and offer views of the ocean throughout. Our location provi …see more

Certificate of Excellence

from $175 / night

$1075 - $1675 / week

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Responds fast!
avg. 2 hours 55 minutes

from $175 / night

24

Vacation home in Marathon

Florida Keys / Marathon

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
The location of this home offers the best in Florida Keys living: boating, sailing, sport fishing, and many more exciting activities are just steps from your door! It's also only a short walk to Dolphin Connection where kids can interact with playful dolphins and learn …see more

from $122 / night

$854 / week

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from $122 / night

15

Vacation apartment in Key Largo

Florida Keys / Key Largo

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0 mi
  • Child friendly
  • Air conditioning
Located in beautiful Key Largo, Florida (MM99.2), Zappie's Place is truly an unique property. Enjoy your own private beach situated on the bayside on nearly an acre of tropical property. Fishermen, bring you small boat and launch from our bayside ramp and have direc …see more

from $195 / night

$1300 - $1450 / week

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Responds fast!
avg. 2 hours 40 minutes

from $195 / night

(5) Very Good 

27

Apartment rental in Tavernier

Key Largo / Tavernier

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • 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 $162 / night

$1175 / week

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from $162 / night

(16) Very Good 

24

Home rental in Islamorada

Florida Keys / Islamorada

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
This is a neat house! It sits right on the ocean with a large yard (by keys standards!). Very nicely landscaped (hibiscus, palm trees, tall pine trees, green grass)with statues from all over the world. Very private with a big gate. The house is decorated with pictures t …see more

from $214 / night

$1500 - $1650 / week

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from $214 / night

(3) Excellent 

22

Condo rental in Islamorada

Florida Keys / Islamorada

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Huge screened in terrace. Spacious and extremely clean.. Peaceful and away from the highway. Sleeps 4-6 people. Enjoy the tennis courts, large pool on the ocean, beach-side BBQ grills. Relax, dine and drink under one of the tiki huts or visit one of the many water-front …see more

from $142 / night

$994 - $1500 / week

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from $142 / night

(2) Excellent 

43

Townhouse rental in Key Largo

Florida Keys / Key Largo

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Mariner's Club 606 in Key Largo is one of a kind with it's resorts style pools and amenities that will meet the expectations of anyone looking for a high end, high quality place to stay and truly enjoy this beautiful part of the world! It is a private community tucked a …see more

from $375 / night

$2625 / week

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from $375 / night

(1) Excellent 

22

Vacation home rental

Florida Keys / Key Colony Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to our Key Colony Beach vacation home. We are located at the end of the canal between 8th and 9th streets and enjoy an unobstructed views from the kitchen, sitting area, dining room, and living room directly down our beautiful canal. Our home is bright, much w …see more

from $171 / night

$1050 - $1400 / week

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from $171 / night

(6) Very Good 

24

Marathon Vacation apartment rental

Florida Keys / Marathon

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Location, Location, Location, mile marker 54 on the ocean side. We're located in a quiet location right next to the Marathon public beach. This is one of the few places you can stroll the beach, kayak and snorkle right from your very own beach. Sit on your private sc …see more

from $172 / night

$1200 - $2000 / week

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Responds fast!
avg. 2 hours 2 minutes

from $172 / night