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Vacation Rentals
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Florida
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Florida Keys
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Upper Florida Keys
4
BR /
3
BA /
Sleeps
8
Featured
2
BR /
1
BA /
1
HF BA /
Sleeps
6
From $115/nt
Featured
7
BR /
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BA /
Sleeps
24
From $1,200/nt
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BR /
Sleeps
8
Featured
6
BR /
6
BA /
2
HF BA /
Sleeps
14
From $28,000/month
Featured
Upper Florida Keys Vacation Home Rentals with Cable Tv
(362)
sort by
HomeAway Sort
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Availability Last Updated
Accepts Online Payments
Bedrooms: Least to Most
Bedrooms: Most to Least
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Price: Low to High
Number of Reviews
Special Offers First
Waterfront Luxury Home with An Incredible View on a Full Acre, Free Secured WiFi
4 Bedrooms,
3
Bathrooms
, Sleeps 8
$2,400 - $2,550
per week
Waterfront Luxury Home with An Incredible View on a Full Acre, Free Secured WiFi
7 night minimum stay
4
BR,
3
BA,
Sleeps
8
Upper Florida Keys
>
Key Largo House
#332253
(26)
Compare
A Magnificent, Luxurious 7 Bedrooms, 5 Bath Rent All or Part
7 Bedrooms,
5
Bathrooms
, Sleeps 24
$1,200
per night
A Magnificent, Luxurious 7 Bedrooms, 5 Bath Rent All or Part
3 night minimum stay
7
BR,
5
BA,
Sleeps
24
Upper Florida Keys
>
Key Largo House
#937436
(14)
Compare
Meagan's Beach House - Bayfront Home with spectacular Sunrises and Sunsets
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$1,600
per week
Meagan's Beach House - Bayfront Home with spectacular Sunrises and Sunsets
7 night minimum stay
2
BR,
2
BA,
Sleeps
6
Upper Florida Keys
>
Key Largo House
#265117
(21)
Compare
Beach House with Open Water views! Dockage Included!
3 Bedrooms,
2
Bathrooms
, Sleeps 10
$200 - $300
per night
Beach House with Open Water views! Dockage Included!
3 night minimum stay
3
BR,
2
BA,
Sleeps
10
Upper Florida Keys
>
Key Largo House
#314828
(10)
Compare
Affordable Key Largo Beach Cottage! Open water location
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$125 - $185
per night
Affordable Key Largo Beach Cottage! Open water location
3 night minimum stay
2
BR,
2
BA,
Sleeps
6
Upper Florida Keys
>
Key Largo House
#107982
(6)
Compare
Bayfront and Beautiful, A Boater's Dream
3 Bedrooms,
3
Bathrooms
, Sleeps 8
Bayfront and Beautiful, A Boater's Dream
3
BR,
3
BA,
Sleeps
8
Upper Florida Keys
>
Key Largo House
#191669
8 Reviews
Compare
Oceanfront Home Adjacent to Pennecamp Coral Reef State Park
4 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 8
Oceanfront Home Adjacent to Pennecamp Coral Reef State Park
4
BR,
3
BA,
1
HF BA,
Sleeps
8
Upper Florida Keys
>
Key Largo House
#312507
6 Reviews
Compare
Paradise for Rent in the Florida Keys!! Designer Vacation Home on Deep Water
3 Bedrooms,
2
Bathrooms
, Sleeps 7
$1,375 - $1,450
per week
Paradise for Rent in the Florida Keys!! Designer Vacation Home on Deep Water
7 night minimum stay
3
BR,
2
BA,
Sleeps
7
Upper Florida Keys
>
Islamorada House
#330045
(19)
Compare
Waterfront Cottage - Beach and Dockage! Sunset Views!
2 Bedrooms,
1
Bathroom
, Sleeps 4
$114 - $150
per night
Waterfront Cottage - Beach and Dockage! Sunset Views!
3 night minimum stay
2
BR,
1
BA,
Sleeps
4
Upper Florida Keys
>
Key Largo House
#225990
(3)
Compare
The Views...Water Water Everywhere...Key Largo Home.
4 Bedrooms,
4
Bathrooms
,
1
Half Bath
, Sleeps 10
The Views...Water Water Everywhere...Key Largo Home.
4
BR,
4
BA,
1
HF BA,
Sleeps
10
Upper Florida Keys
>
Key Largo House
#980977
(3)
Compare
Elegant Beach Home With Dockage and WIFI in Key Largo! Pet friendly!
4 Bedrooms,
3
Bathrooms
, Sleeps 12
$250 - $350
per night
Elegant Beach Home With Dockage and WIFI in Key Largo! Pet friendly!
3 night minimum stay
4
BR,
3
BA,
Sleeps
12
Upper Florida Keys
>
Key Largo House
#916757
Compare
Quite, charming, elegant, tropical, a beautiful setting on the bay
5 Bedrooms,
3
Bathrooms
, Sleeps 16
$900
per night
Quite, charming, elegant, tropical, a beautiful setting on the bay
3 night minimum stay
5
BR,
3
BA,
Sleeps
16
Upper Florida Keys
>
Key Largo House
#338473
(23)
Compare
Bay Front Home With Magnificent Views
3 Bedrooms,
3
Bathrooms
, Sleeps 8
$425 - $500
per night
Bay Front Home With Magnificent Views
3 night minimum stay
3
BR,
3
BA,
Sleeps
8
Upper Florida Keys
>
Plantation Key House
#452120vb
(3)
Compare
The Markeysa, the Ultimate Keys Experience - Private Beach
4 Bedrooms,
4
Bathrooms
, Sleeps 10
$1,200
per night
The Markeysa, the Ultimate Keys Experience - Private Beach
4 night minimum stay
4
BR,
4
BA,
Sleeps
10
Upper Florida Keys
>
Islamorada House
#40210vb
(18)
Compare
Cocomo's
3 Bedrooms,
4
Bathrooms
, Sleeps 14
$857 - $19,000
per night
Cocomo's
3
BR,
4
BA,
Sleeps
14
Upper Florida Keys
>
Islamorada House
#969325
(4)
Compare
Islamorada Waterfront-Great Dockage! Wonderful Views! WiFi & More!
3 Bedrooms, Sleeps 8
Islamorada Waterfront-Great Dockage! Wonderful Views! WiFi & More!
3
BR,
Sleeps
8
Upper Florida Keys
>
Islamorada House
#223571
(6)
Compare
Islamorada - Private Oceanfront Estate - Heated Pool & Dockage
4 Bedrooms,
4
Bathrooms
, Sleeps 8
Islamorada - Private Oceanfront Estate - Heated Pool & Dockage
4
BR,
4
BA,
Sleeps
8
Upper Florida Keys
>
Islamorada House
#43902vb
(10)
Compare
Private / Oceanfront Estate / Contemporary Interior Design
5 Bedrooms,
5
Bathrooms
,
1
Half Bath
, Sleeps 12
$700 - $1,500
per night
Private / Oceanfront Estate / Contemporary Interior Design
3 - 7 night minimum stay
5
BR,
5
BA,
1
HF BA,
Sleeps
12
Upper Florida Keys
>
Key Largo House
#333821
(3)
Compare
Relaxing Home in the Florida Keys
2 Bedrooms,
2
Bathrooms
, Sleeps 4
$1,650 - $1,850
per week
Relaxing Home in the Florida Keys
7 night minimum stay
2
BR,
2
BA,
Sleeps
4
Upper Florida Keys
>
Tavernier House
#328833
(5)
Compare
Waterfront Key Largo luxury home with Bay access!!
3 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 6
$210 - $310
per night
Waterfront Key Largo luxury home with Bay access!!
3 night minimum stay
3
BR,
2
BA,
1
HF BA,
Sleeps
6
Upper Florida Keys
>
Key Largo House
#935531
2 Reviews
Compare
Bayfront Pool Home Views Views Views! Christmas & Springbreak
4 Bedrooms,
3
Bathrooms
, Sleeps 10
$1,400 - $3,500
per week
Bayfront Pool Home Views Views Views! Christmas & Springbreak
7 night minimum stay
4
BR,
3
BA,
Sleeps
10
Upper Florida Keys
>
Key Largo House
#5123vb
Compare
Harbor House In Tavernier
Studio,
6
Bathrooms
, Sleeps 27
Harbor House In Tavernier
Studio,
6
BA,
Sleeps
27
Upper Florida Keys
>
Plantation Key House
#469428vb
2 Reviews
Compare
Islamorada Oceanfront Estate 2 Lush Acres with Dockage Private
4 Bedrooms,
4
Bathrooms
,
1
Half Bath
, Sleeps 12
Islamorada Oceanfront Estate 2 Lush Acres with Dockage Private
4
BR,
4
BA,
1
HF BA,
Sleeps
12
Upper Florida Keys
>
Islamorada House
#73619vb
2 Reviews
Compare
Islamorada Oceanfront Vacation Rental Home
4 Bedrooms,
3
Bathrooms
, Sleeps 10
Islamorada Oceanfront Vacation Rental Home
4
BR,
3
BA,
Sleeps
10
Upper Florida Keys
>
Islamorada House
#114644vb
1 Review
Compare
Elegant Deep Water Ocean Canal Home Cheaper Than A Hotel
3 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 8
$150 - $250
per night
Elegant Deep Water Ocean Canal Home Cheaper Than A Hotel
Book it Now!
2 night minimum stay
3
BR,
3
BA,
1
HF BA,
Sleeps
8
Upper Florida Keys
>
Key Largo House
#387623
(8)
Compare
Angler's Reef Coastal Conch Style Vacation Home in Islamorada, Fl.
2 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 6
$170 - $285
per night
Angler's Reef Coastal Conch Style Vacation Home in Islamorada, Fl.
2 - 4 night minimum stay
2
BR,
2
BA,
1
HF BA,
Sleeps
6
Upper Florida Keys
>
Islamorada House
#944148
(15)
Compare
Escape to Paradise! Oceanfront, Private Sandy Beach, Swimming Pool
2 Bedrooms,
2
Bathrooms
, Sleeps 7
$1,633 - $2,500
per week
Escape to Paradise! Oceanfront, Private Sandy Beach, Swimming Pool
7 night minimum stay
2
BR,
2
BA,
Sleeps
7
Upper Florida Keys
>
Key Largo House
#427049vb
(11)
Compare
Mitchell's Keys Villa - Private, Secluded House on the Bay
2 Bedrooms, Sleeps 4
Mitchell's Keys Villa - Private, Secluded House on the Bay
2
BR,
Sleeps
4
Upper Florida Keys
>
Islamorada House
#236873
(61)
Compare
Canal Waterfront 3/2- 75' Dock-Fisherman Bring Ur 1st Mate
3 Bedrooms,
2
Bathrooms
, Sleeps 6
$1,633 - $1,975
per week
Canal Waterfront 3/2- 75' Dock-Fisherman Bring Ur 1st Mate
7 night minimum stay
3
BR,
2
BA,
Sleeps
6
Upper Florida Keys
>
Key Largo House
#251100vb
(6)
Compare
Best Islamorada Vacation Rental
3 Bedrooms, Sleeps 6
$225 - $300
per night
Best Islamorada Vacation Rental
5 - 7 night minimum stay
3
BR,
Sleeps
6
Upper Florida Keys
>
Islamorada House
#153876
(26)
Compare
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Upper Florida Keys
Islamorada (113)
Key Largo (162)
Ocean Reef Club (7)
Plantation Key (35)
Tavernier (45)