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Holiday Rentals in Islamorada

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
800 rentals in Islamorada.
Executive Bay Club- great unit, great location!,  , holiday rental in Islamorada
Executive Bay Club- great unit, great location!,  , holiday rental in Islamorada
Executive Bay Club- great unit, great location!,  , holiday rental in Islamorada

Executive Bay Club- great unit, great location!,

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Come relax in Islamorada, the tropical jewel of the Florida Keys!!, holiday rental in Islamorada
Come relax in Islamorada, the tropical jewel of the Florida Keys!!, holiday rental in Islamorada
Come relax in Islamorada, the tropical jewel of the Florida Keys!!, holiday 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, holiday rental in Islamorada
Manatee Bay, holiday rental in Islamorada
Manatee Bay, holiday rental in Islamorada

Manatee Bay

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Vacation Condo at Futura Yacht Club, holiday rental in Islamorada
Vacation Condo at Futura Yacht Club, holiday rental in Islamorada
Vacation Condo at Futura Yacht Club, holiday rental in Islamorada

Vacation Condo at Futura Yacht Club

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

Islamorada cottage on deep water canal

Holiday Rental House
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, holiday rental in Islamorada
Oceanfront Estate on Millionaire's Row with Private 350ft Pier and Heated Pool, holiday rental in Islamorada
Oceanfront Estate on Millionaire's Row with Private 350ft Pier and Heated Pool, holiday rental in Islamorada

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
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Newly refinished  condo open water views very nice, holiday rental in Islamorada
Newly refinished  condo open water views very nice, holiday rental in Islamorada
Newly refinished  condo open water views very nice, holiday 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, holiday rental in Islamorada
3/2 condo Futura Yacht Club Pool, Dockage, Wifi, dockage, beach, holiday rental in Islamorada
3/2 condo Futura Yacht Club Pool, Dockage, Wifi, dockage, beach, holiday 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, holiday rental in Islamorada
Anglers Reef Islamorada Florida Sleeps 6, holiday rental in Islamorada
Anglers Reef Islamorada Florida Sleeps 6, holiday rental in Islamorada

Anglers Reef Islamorada Florida Sleeps 6

Holiday Rental House
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 !!, holiday rental in Islamorada
Bayview house with bayviews. Pool with Spa, dock center of town great fishing !!, holiday rental in Islamorada
Bayview house with bayviews. Pool with Spa, dock center of town great fishing !!, holiday rental in Islamorada

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!, holiday rental in Islamorada
2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!, holiday rental in Islamorada
2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!, holiday 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, holiday rental in Islamorada
BAYSIDE Villa, holiday rental in Islamorada
BAYSIDE Villa, holiday rental in Islamorada

BAYSIDE Villa

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

This studio makes the best of the space

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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NEW-Summer Sea - Sweet updated 1B Apartment w/ Garden View Apt 125, holiday rental in Islamorada
NEW-Summer Sea - Sweet updated 1B Apartment w/ Garden View Apt 125, holiday rental in Islamorada
NEW-Summer Sea - Sweet updated 1B Apartment w/ Garden View Apt 125, holiday 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, holiday rental in Islamorada
Private Tropical Oasis, holiday rental in Islamorada
Private Tropical Oasis, holiday 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, holiday rental in Islamorada
Oceanfront 2/2 Condo in Beacon Reef - Free boat dock, holiday rental in Islamorada
Oceanfront 2/2 Condo in Beacon Reef - Free boat dock, holiday 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, holiday rental in Islamorada
New Listing! Charming Angler's Reef Home with Pool, Dockage, holiday rental in Islamorada
New Listing! Charming Angler's Reef Home with Pool, Dockage, holiday rental in Islamorada

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

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Modern Studio, recently remodeled, new to the market, Summer Sea 405, holiday rental in Islamorada
Beautiful Modern Studio, recently remodeled, new to the market, Summer Sea 405, holiday rental in Islamorada
Beautiful Modern Studio, recently remodeled, new to the market, Summer Sea 405, holiday 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, holiday rental in Islamorada
Beautifully Renovated 2 Bedroom Condo, holiday rental in Islamorada
Beautifully Renovated 2 Bedroom Condo, holiday rental in Islamorada

Beautifully Renovated 2 Bedroom Condo

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Stunning view from this beautiful 1 bedroom condominium-Summer Sea, Islamorada, holiday rental in Islamorada
Stunning view from this beautiful 1 bedroom condominium-Summer Sea, Islamorada, holiday rental in Islamorada
Stunning view from this beautiful 1 bedroom condominium-Summer Sea, Islamorada, holiday 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, holiday rental in Islamorada
Beautiful Studio Apartment - Summer Sea Condo #230, holiday rental in Islamorada
Beautiful Studio Apartment - Summer Sea Condo #230, holiday rental in Islamorada

Beautiful Studio Apartment - Summer Sea Condo #230

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

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Experience the Florida Keys like never before!!!, holiday rental in Islamorada
Experience the Florida Keys like never before!!!, holiday rental in Islamorada
Experience the Florida Keys like never before!!!, holiday 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., holiday rental in Islamorada
Great location in Islamorada, FL., holiday rental in Islamorada
Great location in Islamorada, FL., holiday rental in Islamorada

Great location in Islamorada, FL.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Bay and Beach Beauty, holiday rental in Islamorada
Bay and Beach Beauty, holiday rental in Islamorada
Bay and Beach Beauty, holiday rental in Islamorada

Bay and Beach Beauty

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!, holiday rental in Islamorada
ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!, holiday rental in Islamorada
ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!, holiday 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, holiday rental in Islamorada
Great Townhome with Basin & Bay Views, holiday rental in Islamorada
Great Townhome with Basin & Bay Views, holiday rental in Islamorada

Great Townhome with Basin & Bay Views

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Cozy Keys Cottage Islamorada FL., holiday rental in Islamorada
Cozy Keys Cottage Islamorada FL., holiday rental in Islamorada
Cozy Keys Cottage Islamorada FL., holiday rental in Islamorada

Cozy Keys Cottage Islamorada FL.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Fabulous ' Sea Breeze 41 ', 3 / 2 Condo located Oceanside in Islamorada, holiday rental in Islamorada
Fabulous ' Sea Breeze 41 ', 3 / 2 Condo located Oceanside in Islamorada, holiday rental in Islamorada
Fabulous ' Sea Breeze 41 ', 3 / 2 Condo located Oceanside in Islamorada, holiday 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, holiday rental in Islamorada
Discover the Charm of Island Living, holiday rental in Islamorada
Discover the Charm of Island Living, holiday rental in Islamorada

Discover the Charm of Island Living

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

WATERFRONT TOWNHOME IN ISLAMORADA K1

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

Keys Kottage

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

Stunning 1st floor 2 bedroom Condo at Summer Sea

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

Sea Glass Cottage Beautiful Canal Front Home

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bay Views from this Charming 2 Bedroom Condo, holiday rental in Islamorada
Bay Views from this Charming 2 Bedroom Condo, holiday rental in Islamorada
Bay Views from this Charming 2 Bedroom Condo, holiday rental in Islamorada

Bay Views from this Charming 2 Bedroom Condo

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

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

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
More info
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Paradise at Islamorada, holiday rental in Islamorada
Paradise at Islamorada, holiday rental in Islamorada
Paradise at Islamorada, holiday rental in Islamorada

Paradise at Islamorada

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

POPULAR BAYFRONT Townhouse Futura Yacht Club, Pool, Dockage

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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☀️Islamorada Luxury Canal Front 3 Bedroom 2 Bath Fully Remodeled, holiday rental in Islamorada
☀️Islamorada Luxury Canal Front 3 Bedroom 2 Bath Fully Remodeled, holiday rental in Islamorada
☀️Islamorada Luxury Canal Front 3 Bedroom 2 Bath Fully Remodeled, holiday rental in Islamorada

☀️Islamorada Luxury Canal Front 3 Bedroom 2 Bath Fully Remodeled

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

Stunning 3 Bedroom Bayfront Home

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

Penthouse 360 degree view of Ocean and Bay from Rooftop Lounge

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

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

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Stunning Penthouse 3 bedroom Apartment, New, holiday rental in Islamorada
Stunning Penthouse 3 bedroom Apartment, New, holiday rental in Islamorada
Stunning Penthouse 3 bedroom Apartment, New, holiday rental in Islamorada

Stunning Penthouse 3 bedroom Apartment, New

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

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury condo overlooking harbor with ocean view, holiday rental in Islamorada
Luxury condo overlooking harbor with ocean view, holiday rental in Islamorada
Luxury condo overlooking harbor with ocean view, holiday rental in Islamorada

Luxury condo overlooking harbor with ocean view

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

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

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

Beautiful Harbor Front Oceanside Home on the Atlantic Ocean

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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New Upscale, private pool, Dockage, kayaks, bikes, downtown Islamorada locale, holiday rental in Islamorada
New Upscale, private pool, Dockage, kayaks, bikes, downtown Islamorada locale, holiday rental in Islamorada
New Upscale, private pool, Dockage, kayaks, bikes, downtown Islamorada locale, holiday rental in Islamorada

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

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

Gorgeous Vacation Home with Beach Access!

Holiday Rental House
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!, holiday rental in Islamorada
Lazy Daze Beach House 5 Star Modern Oceanfront Islamorada Townhome on the Beach!, holiday rental in Islamorada
Lazy Daze Beach House 5 Star Modern Oceanfront Islamorada Townhome on the Beach!, holiday rental in Islamorada

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

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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