Vacation Rentals in Islamorada, Florida

50 Properties Available

Bay front 6BDr Private Beach Pickle-ball Ct Game room Sunset Views Private vacation home
Bay front 6BDr Private Beach Pickle-ball Ct Game room Sunset Views
$6809 / night
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Island Beach House Oasis Your Memory Maker awaits Private vacation home
Island Beach House Oasis Your Memory Maker awaits
$5724 / night
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Sprawling Bayfront Estate in Heart of Islamorada with Deep Dockage, Heated Pool, Kayaks and More! Private vacation home
Sprawling Bayfront Estate in Heart of Islamorada with Deep Dockage, Heated Pool, Kayaks and More!
$2976 / night
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Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10 Private vacation home
Pineapple Beach : 5 BR, 4.5 BA House in Islamorada, Sleeps 10
$2500 / night
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Sensational Ocean Front Villa | Kayak+PBs+Cinema+Fire Pit+Pool Villa
Sensational Ocean Front Villa | Kayak+PBs+Cinema+Fire Pit+Pool
$2452 / night
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PRIVATE BEACH / Heated Pool / Private Dock / Dolphin Key Villa
PRIVATE BEACH / Heated Pool / Private Dock / Dolphin Key
$2424 / night
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Oceanfront Estate with 4 Cozy Cottages Private vacation home
Oceanfront Estate with 4 Cozy Cottages
$2384 / night
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Charming Suite @Islamorada With Pool Access - Twilight Suite Guest house
Charming Suite @Islamorada With Pool Access - Twilight Suite
$2320 / night
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Private Tropical Oceanfront Estate with Pool and Beach Private vacation home
Private Tropical Oceanfront Estate with Pool and Beach
$2183 / night
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7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks Private vacation home
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
$2049 / night
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This is The Oasis, YOUR private Oasis! Private vacation home
This is The Oasis, YOUR private Oasis!
$1991 / night
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Custom-Built Oceanfront Caribbean Home w\/ Gorgeous Ocean & Sunrise Views Hotel resort
Custom-Built Oceanfront Caribbean Home w\/ Gorgeous Ocean & Sunrise Views
$1819 / night
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Custom-Built Oceanfront Caribbean Home w\/ Incredible Ocean & Sunrise Views Hotel resort
Custom-Built Oceanfront Caribbean Home w\/ Incredible Ocean & Sunrise Views
$1819 / night
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4 Guest Room, 2 Queens, Balcony, Free Parking & Pet Friendly Hotel
4 Guest Room, 2 Queens, Balcony, Free Parking & Pet Friendly
$1690 / night
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Flamingo Bay: Stunning 6BR home with breathtaking open water views in Islamorada. Private vacation home
Flamingo Bay: Stunning 6BR home with breathtaking open water views in Islamorada.
$1552 / night
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5 Bedroom Ocean Front Pool Home Villa
5 Bedroom Ocean Front Pool Home
$1551 / night
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Beach Heaven | 6 mi to Robbies | Tarpon Feeding Experience Hotel
Beach Heaven | 6 mi to Robbies | Tarpon Feeding Experience
$1492 / night
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Turtle Beach is an Oasis on the Atlantic Ocean Private vacation home
Turtle Beach is an Oasis on the Atlantic Ocean
$1487 / night
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4 Bedroom Private Oceanfront House - Bahia Private vacation home
4 Bedroom Private Oceanfront House - Bahia
$1461 / night
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Ocean Front 4 Bedroom Estate with Private Beach Villa
Ocean Front 4 Bedroom Estate with Private Beach
$1429 / night
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Casa Del Mar: A spacious 5-bedroom canal retreat in beautiful Islamorada. Private vacation home
Casa Del Mar: A spacious 5-bedroom canal retreat in beautiful Islamorada.
$1312 / night
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3 Guest Room, 2 Queens, Balcony, 3 Outdoor Pools, Free Parking & Pet Friendly Hotel
3 Guest Room, 2 Queens, Balcony, 3 Outdoor Pools, Free Parking & Pet Friendly
$1261 / night
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Islamorada Paradise on Snake Creek with ELEVATOR TO THE ROOF. Private vacation home
Islamorada Paradise on Snake Creek with ELEVATOR TO THE ROOF.
$1192 / night
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Oceanfront 4BR Retreat w/ Private 31' Boat Slip, Pool & Beach, gourmet kitchen Private vacation home
Oceanfront 4BR Retreat w/ Private 31' Boat Slip, Pool & Beach, gourmet kitchen
$1191 / night
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Seaside Sanctuary in the Heart of Islamorada Private vacation home
Seaside Sanctuary in the Heart of Islamorada
$1190 / night
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Islamorada Getaway in beautiful Port Antigua Private vacation home
Islamorada Getaway in beautiful Port Antigua
$1180 / night
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Beautifully Renovated Home w\/ Custom Furnishings, Chef's Kitchen, & Veranda Hotel resort
Beautifully Renovated Home w\/ Custom Furnishings, Chef's Kitchen, & Veranda
$1173 / night
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NEW LISTING! | Walkable Islamorada Townhome with Private Pool & Dockage Private vacation home
NEW LISTING! | Walkable Islamorada Townhome with Private Pool & Dockage
$1124 / night
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Alligator Reef Conch & Lobster Homes, a special slice of paradise Private vacation home
Alligator Reef Conch & Lobster Homes, a special slice of paradise
$1082 / night
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Peaceful Palms #15 ~ 3 Bed \/ 3 Bath Islamorada Villa W\/ Unobstructed Ocean Views Villa
Peaceful Palms #15 ~ 3 Bed \/ 3 Bath Islamorada Villa W\/ Unobstructed Ocean Views
$1075 / night
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Marlin House @ Tarpon Point Private vacation home
Marlin House @ Tarpon Point
$992 / night
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Charming cottage on the Florida Bay in the heart of Islamorada with pool, dockage, beach + more Cottage
Charming cottage on the Florida Bay in the heart of Islamorada with pool, dockage, beach + more
$991 / night
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New~Pools~Dock~Bikes~3 King Beds~Kayaks~EV charger Private vacation home
New~Pools~Dock~Bikes~3 King Beds~Kayaks~EV charger
$982 / night
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Beautifully decorated 3-bedroom condo in Islamorada, steps from the pool with beautiful views! Condo
Beautifully decorated 3-bedroom condo in Islamorada, steps from the pool with beautiful views!
$936 / night
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Estate Home with Private Beach, Dock & Bay\/Ocean Access Private vacation home
Estate Home with Private Beach, Dock & Bay\/Ocean Access
$917 / night
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Lobster Tales: A stunning 5-bedroom, 5-bath home in Islamorada with bay views. Private vacation home
Lobster Tales: A stunning 5-bedroom, 5-bath home in Islamorada with bay views.
$897 / night
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Tropical Haven in the Heart of Islamorada Private vacation home
Tropical Haven in the Heart of Islamorada
$893 / night
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Spacious Caribbean-Style Home w\/ Kitchen, WiFi, Grill, & Outdoor Veranda Hotel resort
Spacious Caribbean-Style Home w\/ Kitchen, WiFi, Grill, & Outdoor Veranda
$881 / night
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Spectacular Coastal Paradise with outstanding outdoor living spaces Private vacation home
Spectacular Coastal Paradise with outstanding outdoor living spaces
$843 / night
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ISLAMORADA DREAM Private vacation home
ISLAMORADA DREAM
$813 / night
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Ultimate Islamorada Oasis with Pool, Dock, & More Private vacation home
Ultimate Islamorada Oasis with Pool, Dock, & More
$795 / night
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ISLAND DREAM- Fantastic 5-bedroom house with dockage in peaceful Islamorada. Private vacation home
ISLAND DREAM- Fantastic 5-bedroom house with dockage in peaceful Islamorada.
$790 / night
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The Salt & Light House Sleeps 24 dock, pool, beach Private vacation home
The Salt & Light House Sleeps 24 dock, pool, beach
$781 / night
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Gorgeous Keys Vacation Home in Prestigious Neighborhood of Port Antigua Private vacation home
Gorgeous Keys Vacation Home in Prestigious Neighborhood of Port Antigua
$779 / night
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Gulf access, private dock and private neighborhood beach! Private vacation home
Gulf access, private dock and private neighborhood beach!
$772 / night
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Paradise Just Found : Ocean Front Views : Heated Pool : YOU MUST SEE TO BELIEVE Private vacation home
Paradise Just Found : Ocean Front Views : Heated Pool : YOU MUST SEE TO BELIEVE
$767 / night
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Breezy Caribbean-Style Home w\/ Kitchen, WiFi, & Wraparound Outdoor Veranda Hotel resort
Breezy Caribbean-Style Home w\/ Kitchen, WiFi, & Wraparound Outdoor Veranda
$763 / night
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Caribbean-Style Family Home w\/ Full Kitchen, WiFi, Veranda, & Full Washer-Dryer Hotel resort
Caribbean-Style Family Home w\/ Full Kitchen, WiFi, Veranda, & Full Washer-Dryer
$763 / night
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Large Caribbean-Style Home w\/ Full Kitchen, WiFi, Grill, & Outdoor Veranda Hotel resort
Large Caribbean-Style Home w\/ Full Kitchen, WiFi, Grill, & Outdoor Veranda
$763 / night
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Off The Charts-Waterfront Tiki Bar & Private Dock Private vacation home
Off The Charts-Waterfront Tiki Bar & Private Dock
$754 / night
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