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Key West Florida Vacation Rentals - Home
1 / 12

Key West Home
1 Bedroom / 1 Bathroom / Sleeps 1
Home / 1 Bedroom / Sleeps 1

(28)“ Excellent ”28 Reviews

Bedrooms:1
Bathrooms:1
Sleeps:1
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated...

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Tavernier Florida Vacation Rentals - Home
1 / 30

Tavernier Home
4 Bedrooms / 3 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

from

$225

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Home
Per night:$225 - $259
Per week:$1,575 - $1,809
Pets allowed:No
Internet:No

MINIMUM STAY: 29 DAYS Sensational remodeled single family home on Plantation Key awaits your arrival. The gorgeous POOL, HOT TUB, and TIKI BAR are ready and waiting. Imagine fun filled days and evenings relaxing in the patio and yard area! The patio is spacious and surrounded by...

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Key Largo Florida Vacation Rentals - Home
1 / 28

Key Largo Home
4 Bedrooms / 4 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$332

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$332 - $425
Per week:$2,322 - $2,975
Pets allowed:Yes
Internet:No

MINIMUM STAY: 1 MONTH Looking for a spacious ocean front home but don't need a mansion? The upper two floors of this home offer an elevator from the ground level to the main living areas, 4 bedrooms each with an ensuite bath and a spacious living area with a huge kitchen, formal...

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Key Largo Florida Vacation Rentals - Home
1 / 34

Key Largo Home
5 Bedrooms / 6 Bathrooms / Sleeps 12
Home / 5 Bedrooms / Sleeps 12

from

$484

/ night

Email Owner
Bedrooms:5
Bathrooms:6
Sleeps:12
Type:Home
Per night:$484 - $550
Per week:$3,384 - $3,850
Pets allowed:Yes
Internet:No

MINIMUM RENTAL: 1 MONTH 180 degree ocean views are yours from almost every room in this magnificent ocean front home. This home has over 5962 (not a typo) square feet of living area with 5 bedrooms, 6 and one half baths, and two full kitchens! This home comfortably sleeps 10 in...

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Islamorada Florida Vacation Rentals - Apartment
1 / 21

Islamorada Apartment
3 Bedrooms / 2 Bathrooms / Sleeps 6
Apartment / 3 Bedrooms / Sleeps 6

from

$117

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$117 - $150
Per week:$817 - $1,050
Pets allowed:No
Internet:Yes

MINIMUM STAY: 29 DAYS Enjoy unobstructed and panoramic views of the Atlantic Ocean from your own private balcony! This 3 bedroom/2 bath condo unit features direct ocean views from the living room, balcony and two of the three bedrooms. Tropical furnishings create a warm and inviting...

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Islamorada Florida Vacation Rentals - Apartment
1 / 17

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$134

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$134 - $160
Per week:$934 - $1,120
Pets allowed:No
Internet:Yes

Minimum Rental: 1 Month Extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada. It offers 2 spacious...

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Islamorada Florida Vacation Rentals - Home
1 / 16

Islamorada Home
2 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 2 Bedrooms / Sleeps 6

from

$107

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$107
Per week:$747
Pets allowed:Yes
Internet:No

Minimum Rental: 3 Months Beautifully furnished, this almost new single family stilt home sits on an ocean side canal front lot. Bring your boat and your swim suit! This 2 bedroom, 2 bath home has everything you need, including a laundry room with a clothes washer and dryer and...

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Islamorada Florida Vacation Rentals - Home
1 / 23

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

from

$217

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$217 - $284
Per week:$1,517 - $1,984
Pets allowed:No
Internet:Yes

Minimum Rental: 1 Month Oceanfront - Beach - Protected Dock and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The Florida Keys. From the...

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Islamorada Florida Vacation Rentals - Apartment
1 / 18

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$67

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$67 - $124
Per week:$467 - $864
Pets allowed:No
Internet:Yes

Minimum Rental: 1 Month Gorgeous 2 bedroom, 2 bath condo. This is a gated complex located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master suite and the balcony. Wake up every morning, open the curtains and view a panorama of the Atlantic...

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Islamorada Florida Vacation Rentals - Apartment
1 / 18

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$134

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$134 - $167
Per week:$934 - $1,167
Pets allowed:No
Internet:Yes

Minimum Rental: 1 Month This is a very special unit in a premier condominium complex located directly on the Atlantic Ocean and in the heart of Islamorada. This unit provides spectacular ocean views. It is one of the few units that offer spiral stairs to the ground level directly ...

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Islamorada Florida Vacation Rentals - Apartment
1 / 14

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$74

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$74 - $120
Per week:$514 - $840
Pets allowed:No
Internet:Yes

Minimum Rental: 1 Month Pure pleasure will be yours in this beautifully remodeled and immaculate condo. You'll love the uncluttered and modern décor along with the recent renovations. Enjoy the picturesque views of Alligator Reef and the Atlantic Ocean from this 4th floor balcony....

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Islamorada Florida Vacation Rentals - Apartment
1 / 23

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$107

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$107 - $157
Per week:$747 - $1,097
Pets allowed:No
Internet:Yes

MINIMUM STAY: ONE MONTH. Exceptional 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Ocean views from the open air balcony. You'll be so glad you have chosen to spend your holiday here. The kitchen was remodeled in 2013 - granite counters, stainless steel appliances,...

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Islamorada Florida Vacation Rentals - Apartment
1 / 14

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$67

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$67 - $114
Per week:$467 - $794
Pets allowed:No
Internet:No

Minimum Rental: 1 Month Comfortably furnished and ready for you. Conveniently located just steps from a full service marina and 2 highly acclaimed restaurants. Watch the sun rise over the ocean as fishing boats leave on their daily charters, or watch the spectacular sunsets over ...

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Islamorada Florida Vacation Rentals - Apartment
1 / 20

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$80

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$80 - $127
Per week:$560 - $887
Pets allowed:No
Internet:Yes

Minimum Rental: 1 Month This exceptional 2 bedroom and 2 bath condo is located in one of the most popular Islamorada condo complexes - The Palms. The balcony is large enough to dine or recline and offers fabulous open water ocean views. Watching the sunrise over the Atlantic Ocean...

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Tavernier Florida Vacation Rentals - Home
1 / 24

Tavernier Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$140

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$140 - $165
Per week:$980 - $1,155
Pets allowed:Yes
Internet:Yes

MINIMUM STAY: 30 DAYS NEW HOME (2013) Spend the fall or winter in the Florida Keys! You will love this wonderful 2013 built stilt home. Features include an open living area with gourmet kitchen, stainless steel appliances, including a wine refrigerator and granite counters. The...

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Islamorada Florida Vacation Rentals - Home
1 / 26

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$140

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$140 - $175
Per week:$980 - $1,225
Pets allowed:Yes
Internet:No

MINIMUM RENTAL: 1 MONTH BEAUTIFUL CANAL FRONT STILT HOME WITH HEATED POOL - For the guest who expects perfection this is it. This is a completely remodeled 3 bedroom/2 bath (2/1 up and 1/1 down) single family home - perfect for one couple or a smaller family. It is conveniently ...

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Islamorada Florida Vacation Rentals - Villa
1 / 19

Islamorada Villa
1 Bedroom / 1 Bathroom / Sleeps 3
Villa / 1 Bedroom / Sleeps 3

(2)“ Excellent ”2 Reviews

from

$149

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:3
Type:Villa
Per night:$149 - $177
Per week:$1,040 - $1,235
Pets allowed:Yes
Internet:Yes

Minimum Rental: 7 Nights You can have it all – privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people who ...

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Islamorada Florida Vacation Rentals - Apartment
1 / 26

Islamorada Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

from

$92

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$92 - $127
Per week:$642 - $887
Pets allowed:No
Internet:Yes

Minimum Rental: 1 Month A Diamond! Be among the first to rent this gorgeous two bedroom condo. It has been completely renovated from floor to ceiling. The floors have been replaced with tile and the old popcorn ceilings are gone. You'll adore the comfortable living room furnishings...

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Key West Florida Vacation Rentals - Apartment
1 / 21

Key West Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$77

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$77 - $110
Per week:$537 - $770
Pets allowed:No
Internet:Yes

HIDDEN TREASURE (monthly rental): You could easily pass by this jewel of a home without ever knowing it was there. Located down Wong Song Alley behind a private fence, just a few steps from the pool and you've reached your sanctuary. Comfortable open floor space includes living, ...

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Islamorada Florida Vacation Rentals - Apartment
1 / 15

Islamorada Apartment
1 Bedroom / 2 Bathrooms / Sleeps 4
Apartment / 1 Bedroom / Sleeps 4

(1)“ Excellent ”1 Review

from

$60

/ night

Email Owner
Bedrooms:1
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$60 - $89
Per week:$420 - $619
Pets allowed:No
Internet:Yes

Minimum Rental: 1 Month Everything in this unit is exquisite - furnishings, linens, updated kitchen, appliances, and bathrooms. Great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and 2 highly acclaimed...

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Islamorada Florida Vacation Rentals - Home
1 / 23

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

from

$130

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$130 - $164
Per week:$910 - $1,144
Pets allowed:Yes
Internet:Yes

Minimum Rental: 1 Month Bring your boat your dog and the kids! Relax on the patio or swim in the canal. You will love this ground level single family home located in prestigious Venetian Shores. It has been completely renovated and awaits your arrival. The large open kitchen with...

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Islamorada Florida Vacation Rentals - Home
1 / 24

Islamorada Home
3 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

(1)“ Excellent ”1 Review

from

$175

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$175 - $240
Per week:$1,225 - $1,680
Pets allowed:Yes
Internet:Yes

Minimum Rental: 1 Month Location, location, location! This home has it all - ocean side Lower Matecumbe location, totally remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost every room in...

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Key West Florida Vacation Rentals - Home
1 / 24

Key West Home
5 Bedrooms / 6 Bathrooms / Sleeps 12
Home / 5 Bedrooms / Sleeps 12

from

$785

/ night

Email Owner
Bedrooms:5
Bathrooms:6
Sleeps:12
Type:Home
Per night:$785 - $1,658
Per month:$23,550 - $49,740
Pets allowed:Yes
Internet:Yes

CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street with room to park 2 vehicles off- street - - a bonus in Old Town where parking is worth its weight in...

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Key West Florida Vacation Rentals - Home
1 / 27

Key West Home
3 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$180

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$180 - $275
Per week:$1,260 - $1,925
Pets allowed:No
Internet:Yes

HELICONIA HOUSE (monthly rental): Beautiful and exotic as the plant itself, Heliconia House is an exceptional example of luxurious living in its simplest form. This pristine 3 bedroom private home has been lovingly restored with meticulous attention to detail bringing it to its stunning...

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Key West Florida Vacation Rentals - Apartment
1 / 25

Key West Apartment
2 Bedrooms / 3 Bathrooms / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

(13)“ Very Good ”13 Reviews

from

$175

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Apartment
Per night:$175 - $338
Per month:$5,250 - $10,140
Pets allowed:Yes
Internet:No

CORAL SUITE: If you're looking for a home away from home that will leave you with money in your pocket, Coral Suite is the place for you. This 2 bedroom 3 bath townhome accommodates up to 6 people, and your pet! Both bedrooms (ensuite) are on the 2nd floor of this stilt home. Master...

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Key West Florida Vacation Rentals - Home
1 / 24

Key West Home
2 Bedrooms / 3 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$90

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:4
Type:Home
Per night:$90 - $140
Per week:$630 - $980
Pets allowed:Yes
Internet:Yes

GREEN ORCHID: Dreaming of living like a local in Key West? Dream no more. Green Orchid offers a true Conch experience situated on a narrow lane in one of the last historic Old Town neighborhoods. Furnished for comfort, decorated to soothe your senses, equipped with the most up- ...

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Key West Florida Vacation Rentals - Home
1 / 25

Key West Home
1 Bedroom / 1 Bathroom / Sleeps 2
Home / 1 Bedroom / Sleeps 2

from

$100

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Home
Per night:$100
Per week:$700
Pets allowed:No
Internet:Yes

CONCH CABANA: Check into Conch Cabana and leave your worries behind. Simple yet so comfortable for just the two of you in this lovely historic Conch studio cottage. Situated steps away from Ernest Hemingway's Key West residence and the Key West Lighthouse Museum, easy walking or ...

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Key West Florida Vacation Rentals - Apartment
1 / 30

Key West Apartment
3 Bedrooms / 3 Bathrooms / Sleeps 8
Apartment / 3 Bedrooms / Sleeps 8

(10)“ Excellent ”10 Reviews

from

$215

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Apartment
Per night:$215 - $394
Per month:$6,450 - $11,820
Pets allowed:No
Internet:Yes

CORAL VILLA - - Located right in the middle of the action, Coral Villa is a beautiful 3- bedroom townhome in the gated community of Coral Hammock. Just off U. S. 1, across the street from the golf course, and minutes from some of Key West locals' favorite restaurants, marinas,...

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Key West Florida Vacation Rentals - Home
1 / 16

Key West Home
3 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

(1)“ Excellent ”1 Review

from

$400

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$400 - $791
Per month:$12,000 - $23,730
Pets allowed:Yes
Internet:No

SOUTHARD CHARM (formerly Garden House): A lovely jewel, Southard Charm is a quaint Conch house nestled in the center of historic Old Town Key West. Sit on the front porch and while away the hours with a good book. Duval Street is a short block away, so close to all the activity ...

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Key West Florida Vacation Rentals - Apartment
1 / 27

Key West Apartment
2 Bedrooms / 3 Bathrooms / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

(25)“ Excellent ”25 Reviews

from

$175

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Apartment
Per night:$175 - $338
Per month:$5,250 - $10,140
Pets allowed:No
Internet:Yes

CORAL GARDEN: A 2- bedroom 2. 5 bath townhome in the private gated community of Coral Hammock, this home offers the finest accommodations for you and your family. Furnished with comfort in mind with a fully- equipped kitchen for preparing your fresh catch or a quick breakfast to ...

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Key West Florida Vacation Rentals - Apartment
1 / 23

Key West Apartment
2 Bedrooms / 3 Bathrooms / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

(4)“ Excellent ”4 Reviews

from

$240

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Apartment
Per night:$240 - $479
Per month:$7,200 - $14,370
Pets allowed:No
Internet:No

SPA ON DUVAL - Is a tropical two story, 2 bedroom 2. 5 bath townhome located in the rooftop community of Duval Square where you only have to walk downstairs to great restaurants, speciality shops and the action of Duval Street. Spa On Duval is truly a Key West experience to enjoy!...

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Key West Florida Vacation Rentals - Home
1 / 26

Key West Home
2 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 2 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

from

$107

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Home
Per night:$107 - $217
Per week:$747 - $1,517
Pets allowed:No
Internet:Yes

CAYO HUESO SUNSHINE: Awaken your senses with tropical breezes, tourquoise waters and Key West Sunshine in this brand new 2- bedroom, den, 3- bath home. A secluded location yet the best of both worlds allows you an easy stroll over to the sandy shores of Smather's Beach or just ...

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Key West Florida Vacation Rentals - Home
1 / 28

Key West Home
2 Bedrooms / 2 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$70

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$70 - $110
Per week:$490 - $770
Pets allowed:No
Internet:Yes

BOGEY'S RETREAT: Welcome to Bogey's Retreat, your home away from home in Key West. This lovely townhome is located in the exclusive Golf Course community, and allows you to enjoy all that Key West has to offer while staying in a relaxing environment. If you're a golfer, this house...

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Key West Florida Vacation Rentals - Apartment
1 / 25

Key West Apartment
1 Bedroom / 1 Bathroom / Sleeps 2
Apartment / 1 Bedroom / Sleeps 2

from

$150

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Apartment
Per night:$150 - $353
Per week:$1,050 - $2,465
Pets allowed:No
Internet:Yes

CITY CAY: Looking for a cozy, quiet spot for just the two of you with all the modern conveniences of home? This is the place! City Cay is our 1- bedroom 1- bath upstairs condo in Truman Annex that has been lovingly renovated and furnished in a sleek modern style of the most hip ...

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Key West Florida Vacation Rentals - Home
1 / 32

Key West Home
2 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 2 Bedrooms / Sleeps 6

from

$70

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$70 - $110
Per week:$490 - $770
Pets allowed:Yes
Internet:Yes

A LITTLE SLICE OF PARADISE (monthly rental): Imagine yourself in a secluded, gated community steps from the golf course, minutes from the beach, airport and some of the local's favorite restaurants. Spend a month (or two) in A Slice of Paradise and you may never return home. Two...

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Key West Florida Vacation Rentals - Home
1 / 17

Key West Home
3 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

from

$107

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$107 - $184
Per week:$747 - $1,284
Pets allowed:No
Internet:Yes

ISLAND BREEZE - - Located in the exclusive Sanctuary within the Key West Golf Club, this spacious home allows for lots of visitors with 3 bedrooms and a sleeper sofa. Enter an open floor plan of kitchen, dining room, half- bath and living room, with French doors leading outside...

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Key West Florida Vacation Rentals - Apartment
1 / 24

Key West Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 5
Apartment / 2 Bedrooms / Sleeps 5

(9)“ Excellent ”9 Reviews

from

$272

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:5
Type:Apartment
Per night:$272 - $539
Per week:$1,900 - $3,770
Pets allowed:No
Internet:Yes

TRUMAN'S HIDEAWAY: It's hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House. This lovely condo in the exclusive Harbour Place condominium complex in Truman Annex offers all the comforts of home and...

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Key West Florida Vacation Rentals - Apartment
1 / 24

Key West Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 5
Apartment / 2 Bedrooms / Sleeps 5

(9)“ Excellent ”9 Reviews

from

$272

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:5
Type:Apartment
Per night:$272 - $539
Per week:$1,900 - $3,770
Pets allowed:No
Internet:Yes

SUNDOWN REFUGE: Balmy breezes, brilliant sunshine and magnificent sunsets await you at Sundown Refuge, located in the exclusive Harbour Place condominium complex in Truman Annex. You'll spend most of your time overlooking Florida Bay in one direction and Truman's Little White House...

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Key West Florida Vacation Rentals - Home
1 / 23

Key West Home
1 Bedroom / 2 Bathrooms / Sleeps 2
Home / 1 Bedroom / Sleeps 2

from

$82

/ night

Email Owner
Bedrooms:1
Bathrooms:2
Sleeps:2
Type:Home
Per night:$82 - $100
Per week:$572 - $700
Pets allowed:Yes
Internet:Yes

ROBIN'S ROOST (monthly rental): Tucked away in a quiet local neighborhood, Robin's Roost sits pretty in its own little world. Step through the front entry into an open living space that leads to your private backyard with jacuzzi to soothe your mind and soul. Bright, tropical colors...

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Key West Florida Vacation Rentals - Home
1 / 27

Key West Home
2 Bedrooms / 2 Bathrooms / Sleeps 7
Home / 2 Bedrooms / Sleeps 7

(1)“ Excellent ”1 Review

from

$100

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:7
Type:Home
Per night:$100 - $217
Per week:$700 - $1,517
Pets allowed:Yes
Internet:Yes

REJUVENATE! ! ! : This is a Key West experience you don't often find. This spacious 2- bedroom 2- bath cottage is part of a small compound with shared pool, but has its own jacuzzi within a private lanai. RECREATE: Master bedroom with king bed, brand new extra firm mattress, and...

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Key West Florida Vacation Rentals - Home
1 / 32

Key West Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$100

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$100 - $204
Per week:$700 - $1,424
Pets allowed:Yes
Internet:Yes

FIRST BREATH: Lovely 3- bedroom 2- bath Conch home with pool located right in the middle of the action in Old Town Key West. Fenced in and lushly landscaped for the ultimate in privacy. Back gate opens onto Elgin Lane. Two bedrooms upstairs, one with king and one with queen bed, ...

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Key West Florida Vacation Rentals - Home
1 / 24

Key West Home
3 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$180

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$180 - $275
Per week:$1,260 - $1,925
Pets allowed:Yes
Internet:Yes

FAN- tastic GETAWAY: This home has everything, including a bit of Key West history. Formerly owned by actress and fan dancer, Sally Rand, this spacious, fully renovated 3- bedroom, 2. 5 bath home offers the perfect Key West experience. Newly- furnished spacious living room with...

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Key West Florida Vacation Rentals - Apartment
1 / 30

Key West Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$84

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$84 - $160
Per week:$584 - $1,120
Pets allowed:No
Internet:Yes

SEASIDE ESCAPE (monthly rental): The name says it all. Stay for a month at Seaside Escape and enjoy the ocean views, balmy breezes and casual lifestyle that is the essence of Key West living. Open living space includes the living room, dining area and kitchen. Kitchen is stocked...

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Key West Florida Vacation Rentals - Home
1 / 25

Key West Home
1 Bedroom / 2 Bathrooms / Sleeps 4
Home / 1 Bedroom / Sleeps 4

(25)“ Excellent ”25 Reviews

from

$210

/ night

Email Owner
Bedrooms:1
Bathrooms:2
Sleeps:4
Type:Home
Per night:$210 - $414
Per month:$6,300 - $12,420
Pets allowed:No
Internet:Yes

TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked. Fabulous artwork, fun collectables, beautiful stained glass all give this cottage the unique feel that keeps bringing visitors back...

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Islamorada Florida Vacation Rentals - Home
1 / 17

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:Yes
Internet:Yes

Minimum Rental: 1 Month You will love jewel of a home! Located in Lower Matecumbe, this charming canal front home offers a swimming pool, dockage, direct access to the ocean, covered fish cleaning station, a screened lanai, inviting décor and comfortable accommodations. It...

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Key West Florida Vacation Rentals - Home
1 / 1

Key West Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi- private deck and lounge area with steps into a large kidney ...

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Key West Florida Vacation Rentals - Home
1 / 10

Key West Home
4 Bedrooms / 4 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Completely surrounded by luscious tropical greenery in beautiful quiet gated community of Truman Annex yet only one block away from Duval and Mallory Square. Covered porches overlooking private swimming pool. Beautiful hardwood and tiled floors with high ceilings and lots of ceiling...

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About Florida Keys

Florida Keys Travel Tips

The Florida Keys are a wonderful vacation spot for families in search of a little relaxation or adventure. Made up of Key Largo, Islamorada, Marathon, Key West, and Big Pine Key and the lower keys, these islands have plenty of family-friendly activities. The best way to visit this beautiful area is by choosing to stay in vacation rentals by owner. Florida Keys tourists can choose from a variety of different sized properties designed to make your time in the Keys comfortable and memorable. For families visiting the Florida Keys, vacation rentals by owner offer the maximum amount of space and privacy for the price. Your entire family will love exploring the islands and coming home to a private, spacious home or condo.

Beaches and Parks

While staying in one of the area's beautiful vacation rentals, Florida Keys tourists can enjoy a leisurely day at one of the best parks in the nation. These are just a few of the Keys most popular destinations:
  • John Pennekamp Coral Reef State Park is the oldest underwater park in the world. Located in Key Largo, families can explore the 47 campsites located on 67,845 acres, split between land and underwater areas. Nature trails, beaches, kayak and canoe rentals, and glass-bottom boat tours are available.
  • Everglades National Park has many fun activities for families. Kids can become Junior Rangers or go on a wildlife hike.
  • Bahia Honda State Park is known for its beautiful beaches and crystal clear water. Visitors can book a snorkeling tour online and enjoy over an hour of snorkeling in the Looe Key National Marine Sanctuary, where swimmers will explore the gorgeous Elkhorn and Star coral.

Things to Do

The Keys have plenty of fun things to do for every activity level. Families who enjoy the outdoors can take advantage of the wide availability of Florida Keys condo rentals and stay right on the beach!
  • Fishing enthusiasts visiting the Florida Keys will be very excited to hear that Islamorada is known as the sport fishing capital of the world, offering a variety of game fish.
  • Water sports are also very popular in the Keys. Hang gliding, parasailing, kayaking, and paddle boarding are great choices for adventurous families.
  • Swimming with dolphins is a unique experience that every tourist of the Florida Keys should try! Through Dolphins Plus in Key Largo, visitors can go on a structured or natural swim with the dolphins or visit the sea lions through the Sea ...

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