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

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Vacation rentals Key Largo
228 properties
Vacation rentals Key West
205 properties
Vacation rentals Islamorada
137 properties
Vacation rentals Marathon
96 properties
Vacation rentals Big Pine Key
29 properties
Vacation rentals Cudjoe Key
24 properties
Lower Keys
21 properties
Vacation rentals Key Colony Beach
19 properties
Long Key
17 properties
Ramrod Key
15 properties
Cottages Little Torch Key
14 properties
Matecumbe Key
5 properties

Florida Keys

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819 Vacation rentals

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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avg. 2 hours 15 minutes

from $449 / night

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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avg. 2 hours 15 minutes

from $325 / night

(8) Excellent 

17

Key West Vacation houseboat rental

Florida Keys / Key West

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
  • Air conditioning
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 member only marinas. Take it out for a snorkel or sunset cruise. Breath taking views from your ki …see more

from $406 / night

$2500 - $6650 / week

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avg. 35 minutes

from $406 / night

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

$3000 - $4000 / week

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avg. 1 hour 48 minutes

from $430 / 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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avg. 2 hours 15 minutes

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 - $1550 / week

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avg. 1 hour 35 minutes

from $158 / night

23

Home rental in Tavernier with swimming pool

Key Largo / Tavernier

2 6 6 nights min

  • 2 bedrooms
  • Sleeps 6
  • 6 nights min
  • 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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avg. 2 hours 16 minutes

from $325 / 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

$1385 - $2085 / week

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avg. 2 hours 48 minutes

from $198 / 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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avg. 2 hours 15 minutes

from $162 / night

(12) 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

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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avg. 2 hours 15 minutes

from $149 / 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 $170 / night

$999 - $1349 / week

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from $170 / 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 $219 / night

$1533 / week

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from $219 / night

(34) 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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avg. 2 hours 10 minutes

from $259 / night

(39) 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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avg. 2 hours 10 minutes

from $329 / night

(19) 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
Its all about being newly renovated, on the top floor of the best building with the largest end unit with the most windows - twelve. You will have the most magnificent unobstructed ocean views from the living room, kitchen, master & guest bedrooms and balcony. This cond …see more

Certificate of Excellence

from $200 / night

$1400 / week

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avg. 1 hour 21 minutes

from $200 / night

(1) Excellent 

15

Home rental in Marathon Shores

Marathon / Marathon Shores

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Get ready for some awesome changes, this property is under new ownership, so check back often for new photos! Come enjoy the Florida Keys like a local with a private tropical island & waterfront home!This newly furnished 2B/1B home is located on a quiet street in Mara …see more

from $469 / night

$2995 - $4250 / week

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from $469 / night

(38) 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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avg. 1 hour 41 minutes

from $340 / night

22

Vacation condo in Marathon

Florida Keys / Marathon

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Best Views and most accessible in the Complex! Large one Bedroom Apartment, overlooking the pool, beach and ocean. Furnished, with dishwasher, stove, refrigerator, TV and more. King sized bed in bedroom, full sized sofa sleeper in living room . < …see more

from $115 / night

$800 / week

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from $115 / 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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avg. 3 hours 21 minutes

from $229 / night

16

Marathon Vacation home rental

Florida Keys / Marathon

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Brand new built 2017 beautiful and luxurious, 4 bedroom 3 bath Gulf front private home with private built in heated pool, private beach, with boat and fishing dock. Sleeps up to 10 guests. Impeccable with all new furnishings, including washer, dryer, small appliances …see more

from $500 / night

$2500 - $3500 / week

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from $500 / 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

$926 / week

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avg. 47 minutes

from $158 / night

(3) Very Good 

31

Vacation cottage in Key Largo

Florida Keys / Key Largo

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
Our Private Bay Front Key Largo Cottage is our home away from home. Located in Kings Kamp RV park, we have Spectacular Views of Florida Bay as we are 25′ from the waters edge. Our Large Kitchen and Living area are all one with central air conditioning. The 12’x15′ Scre …see more

from $178 / night

$1205 - $1485 / week

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avg. 47 minutes

from $178 / night

8

Key West Vacation home rental

Florida Keys / Key West

2 6 30 nights min

  • 2 bedrooms
  • Sleeps 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
This fully furnished turn-key two bedroom bungalow is the perfect spot to escape the winter weather in tropical Key West! Full kitchen, luxury shower, high ceilings and washer/dryer in unit! Also has a nice little fenced in outdoor space with a picnic table for enjoying …see more

from $135 / night

$945 / week

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from $135 / night

26

Vacation townhouse in Tavernier

Key Largo / Tavernier

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
There is room for the whole family in this 2,200 sq. ft. townhouse with In-Laws quarters. As you enter the first floor you will find an open floor plan with living room, full bathroom and kitchenette with microwave, toaster, coffee maker, portable induction single-burne …see more

from $295 / night

$2100 / week

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avg. 3 hours 18 minutes

from $295 / night

(4) Very Good 

33

Vacation apartment in Key Largo

Florida Keys / Key Largo

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to your home away from home! “Bel Cielo” is a beautiful two-story condo in the quaint community of Moon Bay, located at mile marker 104 in Key Largo. (Moon Bay was recently featured on HGTV's Beach Front Bargain Hunt!) Featuring 1,146 square feet of living space …see more

from $150 / night

$1050 - $1365 / week

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from $150 / 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 - $1851 / week

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avg. 2 hours 59 minutes

from $136 / night

14

Vacation home in Islamorada

Florida Keys / Islamorada

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef at mile marker 85 in Islamorada of the Florida Keys. Luxurious beach decor, plush furnishings, spacious accommodations that comfortably sleep 6 adults and children of all ages will feel r …see more

from $129 / night

$903 / week

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from $129 / night

(23) Excellent 

31

Islamorada Vacation apartment rental

Florida Keys / Islamorada

1 4 30 nights min

  • 1 bedroom
  • Sleeps 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Get away from it all in our tranquil waterfront condo at Summer Sea in beautiful Islamorada. Fully equipped, with newly updated kitchen and bathroom, flat screen televisions, and stunning views of Florida Bay from our patio. Located right in the heart of all the Keys …see more

from $94 / night

$654 / week

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from $94 / night

(42) Excellent 

26

Vacation cottage rental

Florida Keys / Marathon

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Air conditioning
BRAND NEW WHISPER QUIET $5300/42,000 BTU'S TRI-ZONE AIR CONDITIONING/HEATING SYSTEM PROFESSIONALLY INSTALLED AND COMPLETED IN MAY 2014. Simple and unpretentious, the Oceanfront Bungalow Hideaway is a mobile home located right on the water at Boot Key Harbor. Only 45 mil …see more

from $125 / night

$875 - $1155 / week

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avg. 2 hours 23 minutes

from $125 / night

19

Vacation home in Marathon Shores

Marathon / Marathon Shores

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Child friendly
  • Pet friendly
Handsome 10,000 sq ft. vacation paradise. Choose a 6 bedroom/5 bath or a 5 bedroom/ 5 bathroom home a few steps away from the one of the best beaches in the Florida Keys, the famous Sombrero Beach. Scenic deep water canal with extra long dock. Fresh water swimming poo …see more

from $540 / night

$3780 - $6545 / week

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from $540 / night

15

Vacation home rental

Florida Keys / Key West

2 6 30 nights min

  • 2 bedrooms
  • Sleeps 6
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Hello prospective guests! Our great little spot is only a monthly rental but I am sure you will find our rate for a month is less expensive than most for a week. Please consider a longer stay on our island while saving some money by doing so. In a great location,nes …see more

from $94 / night

$654 / week

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avg. 1 hour 32 minutes

from $94 / night

15

Vacation apartment with swimming pool in Tavernier

Key Largo / Tavernier

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Property Description Ocean Pointe Suites in Tavernier mile marker 92, is an all-suite resort located directly on the Atlantic Ocean. Our 60 acres in the Florida Keys are part of a protected mangrove forest, entered through a private road and gatehouse. From sunrise to s …see more

from $130 / night

$2254 - $2296 / week

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from $130 / night

(4) 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

(5) Good 

42

Home rental in Tavernier

Key Largo / Tavernier

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Ask about children
  • Air conditioning
This is a beautiful home, you will enjoy every minute of your stay here! There aren't many homes built like this in the Keys. The room for rent is the guest room (the other room is occupied), with 14 foot vaulted ceilings, a comfy, queen sized bed and a ladder leading t …see more

from $129 / night

$903 / week

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from $129 / night

(5) Excellent 

33

Vacation home in Marathon

Florida Keys / Marathon

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
500 Ocean is truly a great value and sells out quickly. We provide luxury level setting in a Coconut Palm Paradise for a great fishing, diving or relaxing family value vacation in Marathon Key Florida. This place is really a Coconut Palm paradise, it is like living in a …see more

from $99 / night

$693 - $2035 / week

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from $99 / night

(2) Excellent 

4

Vacation cottage in Marathon

Florida Keys / Marathon

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
Ocean View Cottages (3) Sea Horse, Horse, Periwinkle 2 bedroom - 2 bath These are ocean view cottages perched in the air 12 feet on pilings open to fabulous views. With a full gourmet kitchen and great attention to detail, this cottage has a warm feel at home ambiance. …see more

from $375 / night

$2432 - $2712 / week

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from $375 / night

(5) Excellent 

24

Vacation home in Key Largo

Florida Keys / Key Largo

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly
Enjoy your own private paradise and have fun in the Keys! This beautiful, clean, spacious and airy vacation rental home is locate in Key Largo "Diving Capital of the World." Key Largo is the first island of the Florida Keys, south of the Florida mainland. The house has …see more

from $250 / night

$1500 / week

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from $250 / night

(28) Excellent 

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

from $189 / night

$1323 / week

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avg. 1 hour 50 minutes

from $189 / night

13

Vacation home in Cudjoe Key

Florida Keys / Cudjoe Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 - $2250 / week

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avg. 2 hours 12 minutes

from $260 / night

1