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Islamorada
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Vacation Rentals
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World
>
USA
>
Florida
>
Florida Keys
>
Upper Florida Keys
>
Islamorada
4
BR /
Sleeps
12
Featured
1
BR /
Sleeps
4
Featured
4
BR /
4
BA /
Sleeps
8
Featured
2
BR /
2
BA /
1
HF BA /
Sleeps
6
From $2,100/wk
Featured
3
BR /
2
BA /
1
HF BA /
Sleeps
8
Featured
Islamorada with Pools
(177)
sort by
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Special Offers First
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
(17)
Compare
Cocomo's
3 Bedrooms,
4
Bathrooms
, Sleeps 14
$857
per night
Cocomo's
3
BR,
4
BA,
Sleeps
14
Upper Florida Keys
>
Islamorada House
#969325
(4)
Compare
Oceanfront End Unit, Internet, Pool, Tennis, PANORAMIC OCEAN VIEWS
2 Bedrooms,
2
Bathrooms
, Sleeps 5
Oceanfront End Unit, Internet, Pool, Tennis, PANORAMIC OCEAN VIEWS
2
BR,
2
BA,
Sleeps
5
Upper Florida Keys
>
Islamorada Condo
#151910
(8)
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
Your Florida Keys Getaway.....
4 Bedrooms,
4
Bathrooms
, Sleeps 8
Your Florida Keys Getaway.....
4
BR,
4
BA,
Sleeps
8
Upper Florida Keys
>
Islamorada Estate
#453867vb
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
1 Review
Compare
Ocean Front - Catch Bonefish &Tarpon from our 450-foot fishing pier.
4 Bedrooms,
3
Bathrooms
, Sleeps 8
Ocean Front - Catch Bonefish &Tarpon from our 450-foot fishing pier.
4
BR,
3
BA,
Sleeps
8
Upper Florida Keys
>
Islamorada Lodge
#294142
Compare
Angler's Reef Coastal Conch Style Vacation Home in Islamorada, Fl.
2 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 6
$195 - $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
(14)
Compare
27 steps to Paradise Bay
2 Bedrooms,
1
Bathroom
,
1
Half Bath
, Sleeps 6
$135 - $168
per night
27 steps to Paradise Bay
Book it Now!
6 night Minimum Stay
2
BR,
1
BA,
1
HF BA,
Sleeps
6
Upper Florida Keys
>
Islamorada Condo
#3488586
1 Review
Compare
Magnificent Ocean View from Private Roof Top Sundeck!
2 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 6
Magnificent Ocean View from Private Roof Top Sundeck!
2
BR,
2
BA,
1
HF BA,
Sleeps
6
Upper Florida Keys
>
Islamorada Townhome
#153551
(18)
Compare
Tropically Furnished Condo with Ocean Views
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$750 - $1,050
per week
Tropically Furnished Condo with Ocean Views
7 night Minimum Stay
2
BR,
2
BA,
Sleeps
6
Upper Florida Keys
>
Islamorada Condo
#301565
(11)
Compare
Luxurious Home at Anglers Reef Oceanfront Resort with Boat Dock
2 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 5
Luxurious Home at Anglers Reef Oceanfront Resort with Boat Dock
2
BR,
2
BA,
1
HF BA,
Sleeps
5
Upper Florida Keys
>
Islamorada House
#426200vb
(11)
Compare
Ocean Front Heated Pool w/Stunning ocean views,Tiki Hut Bar, 90' of Dockage
3 Bedrooms,
3
Bathrooms
, Sleeps 8
Ocean Front Heated Pool w/Stunning ocean views,Tiki Hut Bar, 90' of Dockage
3
BR,
3
BA,
Sleeps
8
Upper Florida Keys
>
Islamorada House
#423195vb
(11)
Compare
Spectacular 3 Story Pool Home On Deep Dockage Minutes Ocean& Bay Tavernier Creek
4 Bedrooms,
3
Bathrooms
, Sleeps 8
$700
per night
Spectacular 3 Story Pool Home On Deep Dockage Minutes Ocean& Bay Tavernier Creek
1 - 14 night Minimum Stay
4
BR,
3
BA,
Sleeps
8
Upper Florida Keys
>
Islamorada House
#3014301
Compare
Waterfront Rental at Florida Keys Resort!
1 Bedrooms,
1
Bathroom
, Sleeps 4
$209 - $259
per night
Waterfront Rental at Florida Keys Resort!
2 night Minimum Stay
1
BR,
1
BA,
Sleeps
4
Upper Florida Keys
>
Islamorada Cottage
#3491207
2 Reviews
Compare
Ocean Harbour- It Has It All for Your Keys Adventure MONTLY RENTAL
3 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 8
$7,000
per month
Ocean Harbour- It Has It All for Your Keys Adventure MONTLY RENTAL
28 night Minimum Stay
3
BR,
2
BA,
1
HF BA,
Sleeps
8
Upper Florida Keys
>
Islamorada Condo
#3478902
Compare
Luxury! Bayside - 3 BR - Paradise in the Keys with Boat Slip
3 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 8
Luxury! Bayside - 3 BR - Paradise in the Keys with Boat Slip
3
BR,
2
BA,
1
HF BA,
Sleeps
8
Upper Florida Keys
>
Islamorada Townhome
#108057vb
Compare
Dream Home in the Keys with Heated Pool Legal Weekly Rental
5 Bedrooms, Sleeps 12
Dream Home in the Keys with Heated Pool Legal Weekly Rental
5
BR,
Sleeps
12
Upper Florida Keys
>
Islamorada House
#12740vb
(8)
Compare
Peaceful Bay front with pool, jacuzzi and outdoor sports. Relax by the pool!
3 Bedrooms,
3
Bathrooms
, Sleeps 8
Peaceful Bay front with pool, jacuzzi and outdoor sports. Relax by the pool!
3
BR,
3
BA,
Sleeps
8
Upper Florida Keys
>
Islamorada Estate
#383318
Compare
Keys home in Anglers Reef with ocean view, dock, comm. pool & beach
2 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 6
$1,800 - $2,100
per week
Keys home in Anglers Reef with ocean view, dock, comm. pool & beach
7 night Minimum Stay
2
BR,
2
BA,
1
HF BA,
Sleeps
6
Upper Florida Keys
>
Islamorada House
#3000700
(7)
Compare
Beautiful New Waterfront Home In Port Antigua
3 Bedrooms,
3
Bathrooms
, Sleeps 8
Beautiful New Waterfront Home In Port Antigua
3
BR,
3
BA,
Sleeps
8
Upper Florida Keys
>
Islamorada House
#178832
(3)
Compare
Oceanfront Anglers Reef, Islamorada, Florida Keys, Video Tour
2 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 6
$228
per night
Oceanfront Anglers Reef, Islamorada, Florida Keys, Video Tour
Book it Now!
5 - 7 night Minimum Stay
2
BR,
2
BA,
1
HF BA,
Sleeps
6
Upper Florida Keys
>
Islamorada House
#224013
(12)
Compare
OCEANFRONT Pool 30'Dock GatedPeninsula Water3Sides VeryPrivate 7niteMin 6ppl max
3 Bedrooms,
2
Bathrooms
,
2
Half Baths
, Sleeps 6
$2,975 - $3,500
per week
OCEANFRONT Pool 30'Dock GatedPeninsula Water3Sides VeryPrivate 7niteMin 6ppl max
7 night Minimum Stay
3
BR,
2
BA,
2
HF BA,
Sleeps
6
Upper Florida Keys
>
Islamorada House
#341722
(18)
Compare
Islamorada – Simply Beautiful with Free Wifi & Many Extras
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$180
per night
Islamorada – Simply Beautiful with Free Wifi & Many Extras
5 night Minimum Stay
2
BR,
2
BA,
Sleeps
6
Upper Florida Keys
>
Islamorada Townhome
#397581vb
(8)
Compare
Ocean Harbor MONTHLY rental - Luxury condo with pool and ocean views
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$5,000 - $5,500
per month
Ocean Harbor MONTHLY rental - Luxury condo with pool and ocean views
28 night Minimum Stay
2
BR,
2
BA,
Sleeps
6
Upper Florida Keys
>
Islamorada Condo
#252746
Compare
Gorgeous Oceanfront with heated pool, 350' pier, free wifi
3 Bedrooms,
3
Bathrooms
, Sleeps 8
Gorgeous Oceanfront with heated pool, 350' pier, free wifi
3
BR,
3
BA,
Sleeps
8
Upper Florida Keys
>
Islamorada House
#207249
(20)
Compare
Islamorada Luxury Ocean View Townhouse w/private beach & dock
2 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 6
Islamorada Luxury Ocean View Townhouse w/private beach & dock
2
BR,
2
BA,
1
HF BA,
Sleeps
6
Upper Florida Keys
>
Islamorada Townhome
#223915
(7)
Compare
Luxurious Bay Harbour - Ocean View, Boat Dock, Pool, Jacuzzi & Tennis Courts!
3 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 6
Luxurious Bay Harbour - Ocean View, Boat Dock, Pool, Jacuzzi & Tennis Courts!
3
BR,
2
BA,
1
HF BA,
Sleeps
6
Upper Florida Keys
>
Islamorada Condo
#158151
(4)
Compare
Ocean View Luxury Completely Renovated home on the water!
3 Bedrooms,
3
Bathrooms
, Sleeps 8
Ocean View Luxury Completely Renovated home on the water!
3
BR,
3
BA,
Sleeps
8
Upper Florida Keys
>
Islamorada House
#423687vb
(6)
Compare
Executive Bay Club - Beautiful Unit - Beautiful Sunsets!
2 Bedrooms,
2
Bathrooms
, Sleeps 4
$2,500 - $2,800
per month
Executive Bay Club - Beautiful Unit - Beautiful Sunsets!
28 night Minimum Stay
2
BR,
2
BA,
Sleeps
4
Upper Florida Keys
>
Islamorada Condo
#327300
Compare
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