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Islamorada Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
756 rentals in Islamorada.
Executive Bay Club- great unit, great location!,  , vacation rental in Islamorada
Executive Bay Club- great unit, great location!,  , vacation rental in Islamorada
Executive Bay Club- great unit, great location!,  , vacation rental in Islamorada

Executive Bay Club- great unit, great location!,

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Come relax in Islamorada, the tropical jewel of the Florida Keys!!, vacation rental in Islamorada
Come relax in Islamorada, the tropical jewel of the Florida Keys!!, vacation rental in Islamorada
Come relax in Islamorada, the tropical jewel of the Florida Keys!!, vacation rental in Islamorada

Come relax in Islamorada, the tropical jewel of the Florida Keys!!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Manatee Bay, vacation rental in Islamorada
Manatee Bay, vacation rental in Islamorada
Manatee Bay, vacation rental in Islamorada

Manatee Bay

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Islamorada cottage on deep water canal, vacation rental in Islamorada
Islamorada cottage on deep water canal, vacation rental in Islamorada
Islamorada cottage on deep water canal, vacation rental in Islamorada

Islamorada cottage on deep water canal

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Oceanfront Estate on Millionaire's Row with Private 350ft Pier and Heated Pool, vacation rental in Islamorada
Oceanfront Estate on Millionaire's Row with Private 350ft Pier and Heated Pool, vacation rental in Islamorada
Oceanfront Estate on Millionaire's Row with Private 350ft Pier and Heated Pool, vacation rental in Islamorada

Oceanfront Estate on Millionaire's Row with Private 350ft Pier and Heated Pool

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Newly refinished  condo open water views very nice, vacation rental in Islamorada
Newly refinished  condo open water views very nice, vacation rental in Islamorada
Newly refinished  condo open water views very nice, vacation rental in Islamorada

Newly refinished condo open water views very nice

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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3/2 condo Futura Yacht Club Pool, Dockage, Wifi, dockage, beach, vacation rental in Islamorada
3/2 condo Futura Yacht Club Pool, Dockage, Wifi, dockage, beach, vacation rental in Islamorada
3/2 condo Futura Yacht Club Pool, Dockage, Wifi, dockage, beach, vacation rental in Islamorada

3/2 condo Futura Yacht Club Pool, Dockage, Wifi, dockage, beach

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Anglers Reef Islamorada Florida Sleeps 6, vacation rental in Islamorada
Anglers Reef Islamorada Florida Sleeps 6, vacation rental in Islamorada
Anglers Reef Islamorada Florida Sleeps 6, vacation rental in Islamorada

Anglers Reef Islamorada Florida Sleeps 6

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Bayview house with bayviews. Pool with Spa, dock center of town great fishing !!, vacation rental in Islamorada
Bayview house with bayviews. Pool with Spa, dock center of town great fishing !!, vacation rental in Islamorada
Bayview house with bayviews. Pool with Spa, dock center of town great fishing !!, vacation rental in Islamorada

Bayview house with bayviews. Pool with Spa, dock center of town great fishing !!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!, vacation rental in Islamorada
2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!, vacation rental in Islamorada
2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!, vacation rental in Islamorada

2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!

Condo/Apartment
0 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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BAYSIDE Villa, vacation rental in Islamorada
BAYSIDE Villa, vacation rental in Islamorada
BAYSIDE Villa, vacation rental in Islamorada

BAYSIDE Villa

Rental Home
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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This studio makes the best of the space, vacation rental in Islamorada
This studio makes the best of the space, vacation rental in Islamorada
This studio makes the best of the space, vacation rental in Islamorada

This studio makes the best of the space

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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NEW-Summer Sea - Sweet updated 1B Apartment w/ Garden View Apt 125, vacation rental in Islamorada
NEW-Summer Sea - Sweet updated 1B Apartment w/ Garden View Apt 125, vacation rental in Islamorada
NEW-Summer Sea - Sweet updated 1B Apartment w/ Garden View Apt 125, vacation rental in Islamorada

NEW-Summer Sea - Sweet updated 1B Apartment w/ Garden View Apt 125

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Private Tropical Oasis, vacation rental in Islamorada
Private Tropical Oasis, vacation rental in Islamorada
Private Tropical Oasis, vacation rental in Islamorada

Private Tropical Oasis

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Oceanfront 2/2 Condo in Beacon Reef - Free boat dock, vacation rental in Islamorada
Oceanfront 2/2 Condo in Beacon Reef - Free boat dock, vacation rental in Islamorada
Oceanfront 2/2 Condo in Beacon Reef - Free boat dock, vacation rental in Islamorada

Oceanfront 2/2 Condo in Beacon Reef - Free boat dock

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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New Listing! Charming Angler's Reef Home with Pool, Dockage, vacation rental in Islamorada
New Listing! Charming Angler's Reef Home with Pool, Dockage, vacation rental in Islamorada
New Listing! Charming Angler's Reef Home with Pool, Dockage, vacation rental in Islamorada

New Listing! Charming Angler's Reef Home with Pool, Dockage

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Modern Studio, recently remodeled, new to the market, Summer Sea 405, vacation rental in Islamorada
Beautiful Modern Studio, recently remodeled, new to the market, Summer Sea 405, vacation rental in Islamorada
Beautiful Modern Studio, recently remodeled, new to the market, Summer Sea 405, vacation rental in Islamorada

Beautiful Modern Studio, recently remodeled, new to the market, Summer Sea 405

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Beautifully Renovated 2 Bedroom Condo, vacation rental in Islamorada
Beautifully Renovated 2 Bedroom Condo, vacation rental in Islamorada
Beautifully Renovated 2 Bedroom Condo, vacation rental in Islamorada

Beautifully Renovated 2 Bedroom Condo

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stunning view from this beautiful 1 bedroom condominium-Summer Sea, Islamorada, vacation rental in Islamorada
Stunning view from this beautiful 1 bedroom condominium-Summer Sea, Islamorada, vacation rental in Islamorada
Stunning view from this beautiful 1 bedroom condominium-Summer Sea, Islamorada, vacation rental in Islamorada

Stunning view from this beautiful 1 bedroom condominium-Summer Sea, Islamorada

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Studio Apartment - Summer Sea Condo #230, vacation rental in Islamorada
Beautiful Studio Apartment - Summer Sea Condo #230, vacation rental in Islamorada
Beautiful Studio Apartment - Summer Sea Condo #230, vacation rental in Islamorada

Beautiful Studio Apartment - Summer Sea Condo #230

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Islamorada Escape - Executive Bay w/Pool, Fishing Dock, Beach, Tennis/Pickleball, vacation rental in Islamorada
Islamorada Escape - Executive Bay w/Pool, Fishing Dock, Beach, Tennis/Pickleball, vacation rental in Islamorada
Islamorada Escape - Executive Bay w/Pool, Fishing Dock, Beach, Tennis/Pickleball, vacation rental in Islamorada

Islamorada Escape - Executive Bay w/Pool, Fishing Dock, Beach, Tennis/Pickleball

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Experience the Florida Keys like never before!!!, vacation rental in Islamorada
Experience the Florida Keys like never before!!!, vacation rental in Islamorada
Experience the Florida Keys like never before!!!, vacation rental in Islamorada

Experience the Florida Keys like never before!!!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Great location in Islamorada, FL., vacation rental in Islamorada
Great location in Islamorada, FL., vacation rental in Islamorada
Great location in Islamorada, FL., vacation rental in Islamorada

Great location in Islamorada, FL.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Bay and Beach Beauty, vacation rental in Islamorada
Bay and Beach Beauty, vacation rental in Islamorada
Bay and Beach Beauty, vacation rental in Islamorada

Bay and Beach Beauty

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!, vacation rental in Islamorada
ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!, vacation rental in Islamorada
ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!, vacation rental in Islamorada

ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Great Townhome with Basin & Bay Views, vacation rental in Islamorada
Great Townhome with Basin & Bay Views, vacation rental in Islamorada
Great Townhome with Basin & Bay Views, vacation rental in Islamorada

Great Townhome with Basin & Bay Views

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Cozy Keys Cottage Islamorada FL., vacation rental in Islamorada
Cozy Keys Cottage Islamorada FL., vacation rental in Islamorada
Cozy Keys Cottage Islamorada FL., vacation rental in Islamorada

Cozy Keys Cottage Islamorada FL.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Fabulous ' Sea Breeze 41 ', 3 / 2 Condo located Oceanside in Islamorada, vacation rental in Islamorada
Fabulous ' Sea Breeze 41 ', 3 / 2 Condo located Oceanside in Islamorada, vacation rental in Islamorada
Fabulous ' Sea Breeze 41 ', 3 / 2 Condo located Oceanside in Islamorada, vacation rental in Islamorada

Fabulous ' Sea Breeze 41 ', 3 / 2 Condo located Oceanside in Islamorada

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Discover the Charm of Island Living, vacation rental in Islamorada
Discover the Charm of Island Living, vacation rental in Islamorada
Discover the Charm of Island Living, vacation rental in Islamorada

Discover the Charm of Island Living

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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WATERFRONT TOWNHOME IN ISLAMORADA K1, vacation rental in Islamorada
WATERFRONT TOWNHOME IN ISLAMORADA K1, vacation rental in Islamorada
WATERFRONT TOWNHOME IN ISLAMORADA K1, vacation rental in Islamorada

WATERFRONT TOWNHOME IN ISLAMORADA K1

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Keys Kottage , vacation rental in Islamorada
Keys Kottage , vacation rental in Islamorada
Keys Kottage , vacation rental in Islamorada

Keys Kottage

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning 1st floor 2 bedroom Condo at Summer Sea, vacation rental in Islamorada
Stunning 1st floor 2 bedroom Condo at Summer Sea, vacation rental in Islamorada
Stunning 1st floor 2 bedroom Condo at Summer Sea, vacation rental in Islamorada

Stunning 1st floor 2 bedroom Condo at Summer Sea

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sea Glass Cottage Beautiful Canal Front Home, vacation rental in Islamorada
Sea Glass Cottage Beautiful Canal Front Home, vacation rental in Islamorada
Sea Glass Cottage Beautiful Canal Front Home, vacation rental in Islamorada

Sea Glass Cottage Beautiful Canal Front Home

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bay Views from this Charming 2 Bedroom Condo, vacation rental in Islamorada
Bay Views from this Charming 2 Bedroom Condo, vacation rental in Islamorada
Bay Views from this Charming 2 Bedroom Condo, vacation rental in Islamorada

Bay Views from this Charming 2 Bedroom Condo

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Islamorada 3/2 condo. Dockage, swimming pool, sunsets, vacation rental in Islamorada
Islamorada 3/2 condo. Dockage, swimming pool, sunsets, vacation rental in Islamorada
Islamorada 3/2 condo. Dockage, swimming pool, sunsets, vacation rental in Islamorada

Islamorada 3/2 condo. Dockage, swimming pool, sunsets

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Paradise at Islamorada, vacation rental in Islamorada
Paradise at Islamorada, vacation rental in Islamorada
Paradise at Islamorada, vacation rental in Islamorada

Paradise at Islamorada

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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POPULAR BAYFRONT Townhouse Futura Yacht Club, Pool, Dockage, vacation rental in Islamorada
POPULAR BAYFRONT Townhouse Futura Yacht Club, Pool, Dockage, vacation rental in Islamorada
POPULAR BAYFRONT Townhouse Futura Yacht Club, Pool, Dockage, vacation rental in Islamorada

POPULAR BAYFRONT Townhouse Futura Yacht Club, Pool, Dockage

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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☀️Islamorada Luxury Canal Front 3 Bedroom 2 Bath Fully Remodeled, vacation rental in Islamorada
☀️Islamorada Luxury Canal Front 3 Bedroom 2 Bath Fully Remodeled, vacation rental in Islamorada
☀️Islamorada Luxury Canal Front 3 Bedroom 2 Bath Fully Remodeled, vacation rental in Islamorada

☀️Islamorada Luxury Canal Front 3 Bedroom 2 Bath Fully Remodeled

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning 3 Bedroom Bayfront Home, vacation rental in Islamorada
Stunning 3 Bedroom Bayfront Home, vacation rental in Islamorada
Stunning 3 Bedroom Bayfront Home, vacation rental in Islamorada

Stunning 3 Bedroom Bayfront Home

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Penthouse 360 degree view of Ocean and Bay from Rooftop Lounge, vacation rental in Islamorada
Penthouse 360 degree view of Ocean and Bay from Rooftop Lounge, vacation rental in Islamorada
Penthouse 360 degree view of Ocean and Bay from Rooftop Lounge, vacation rental in Islamorada

Penthouse 360 degree view of Ocean and Bay from Rooftop Lounge

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Vacation in Tropical Paradise with the Family! Waterfront Townhome in Islamorada, vacation rental in Islamorada
Vacation in Tropical Paradise with the Family! Waterfront Townhome in Islamorada, vacation rental in Islamorada
Vacation in Tropical Paradise with the Family! Waterfront Townhome in Islamorada, vacation rental in Islamorada

Vacation in Tropical Paradise with the Family! Waterfront Townhome in Islamorada

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Stunning Penthouse 3 bedroom Apartment, New, vacation rental in Islamorada
Stunning Penthouse 3 bedroom Apartment, New, vacation rental in Islamorada
Stunning Penthouse 3 bedroom Apartment, New, vacation rental in Islamorada

Stunning Penthouse 3 bedroom Apartment, New

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Waterfront Townhome in Islamorada! Perfect for Florida Keys Vacation!, vacation rental in Islamorada
Beautiful Waterfront Townhome in Islamorada! Perfect for Florida Keys Vacation!, vacation rental in Islamorada
Beautiful Waterfront Townhome in Islamorada! Perfect for Florida Keys Vacation!, vacation rental in Islamorada

Beautiful Waterfront Townhome in Islamorada! Perfect for Florida Keys Vacation!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury condo overlooking harbor with ocean view, vacation rental in Islamorada
Luxury condo overlooking harbor with ocean view, vacation rental in Islamorada
Luxury condo overlooking harbor with ocean view, vacation rental in Islamorada

Luxury condo overlooking harbor with ocean view

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Islamorada Waterfront Townhome w Priv. Beach! Comfortable Family Vacation Rental, vacation rental in Islamorada
Islamorada Waterfront Townhome w Priv. Beach! Comfortable Family Vacation Rental, vacation rental in Islamorada
Islamorada Waterfront Townhome w Priv. Beach! Comfortable Family Vacation Rental, vacation rental in Islamorada

Islamorada Waterfront Townhome w Priv. Beach! Comfortable Family Vacation Rental

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Harbor Front Oceanside Home on the Atlantic Ocean, vacation rental in Islamorada
Beautiful Harbor Front Oceanside Home on the Atlantic Ocean, vacation rental in Islamorada
Beautiful Harbor Front Oceanside Home on the Atlantic Ocean, vacation rental in Islamorada

Beautiful Harbor Front Oceanside Home on the Atlantic Ocean

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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New Upscale, private pool, Dockage, kayaks, bikes, downtown Islamorada locale, vacation rental in Islamorada
New Upscale, private pool, Dockage, kayaks, bikes, downtown Islamorada locale, vacation rental in Islamorada
New Upscale, private pool, Dockage, kayaks, bikes, downtown Islamorada locale, vacation rental in Islamorada

New Upscale, private pool, Dockage, kayaks, bikes, downtown Islamorada locale

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Gorgeous Vacation Home with Beach Access!, vacation rental in Islamorada
Gorgeous Vacation Home with Beach Access!, vacation rental in Islamorada
Gorgeous Vacation Home with Beach Access!, vacation rental in Islamorada

Gorgeous Vacation Home with Beach Access!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Lazy Daze Beach House 5 Star Modern Oceanfront Islamorada Townhome on the Beach!, vacation rental in Islamorada
Lazy Daze Beach House 5 Star Modern Oceanfront Islamorada Townhome on the Beach!, vacation rental in Islamorada
Lazy Daze Beach House 5 Star Modern Oceanfront Islamorada Townhome on the Beach!, vacation rental in Islamorada

Lazy Daze Beach House 5 Star Modern Oceanfront Islamorada Townhome on the Beach!

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Come to Paradise, vacation rental in Islamorada
Come to Paradise, vacation rental in Islamorada
Come to Paradise, vacation rental in Islamorada

Come to Paradise

Rental Home
4 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Showing results 1-50 of 756
Frequently Asked Questions about Islamorada