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Holiday Rentals with Pools in Islamorada

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
43 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, All pools
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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, All pools
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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, All pools
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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, All pools
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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, All pools
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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, All pools
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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, All pools
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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, All pools
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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, All pools
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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, All pools
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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, All pools
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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, All pools
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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, All pools
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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, All pools
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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, All pools
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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, All pools
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, All pools
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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, All pools
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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, All pools
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Majestic estate, 200' of private oceanfront beach & pool, ideal wedding venue, holiday rental in Islamorada
Majestic estate, 200' of private oceanfront beach & pool, ideal wedding venue, holiday rental in Islamorada
Majestic estate, 200' of private oceanfront beach & pool, ideal wedding venue, holiday rental in Islamorada

Majestic estate, 200' of private oceanfront beach & pool, ideal wedding venue

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS, holiday rental in Islamorada
EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS, holiday rental in Islamorada
EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS, holiday rental in Islamorada

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Islamorada trop paradise pool, fishing, 2fls luxury with a filet stationn, holiday rental in Islamorada
Islamorada trop paradise pool, fishing, 2fls luxury with a filet stationn, holiday rental in Islamorada
Islamorada trop paradise pool, fishing, 2fls luxury with a filet stationn, holiday rental in Islamorada

Islamorada trop paradise pool, fishing, 2fls luxury with a filet stationn

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Islamorada Townhome w/Beach View, Pool, Marina,Tennis! Perfect Family Getaway!!, holiday rental in Islamorada
Islamorada Townhome w/Beach View, Pool, Marina,Tennis! Perfect Family Getaway!!, holiday rental in Islamorada
Islamorada Townhome w/Beach View, Pool, Marina,Tennis! Perfect Family Getaway!!, holiday rental in Islamorada

Islamorada Townhome w/Beach View, Pool, Marina,Tennis! Perfect Family Getaway!!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Remodeled Townhome in Waterfront Community - 20% for Spring/Summer!, holiday rental in Islamorada
Remodeled Townhome in Waterfront Community - 20% for Spring/Summer!, holiday rental in Islamorada
Remodeled Townhome in Waterfront Community - 20% for Spring/Summer!, holiday rental in Islamorada

Remodeled Townhome in Waterfront Community - 20% for Spring/Summer!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Oceanfront Anglers Reef Islamorada Florida Keys , holiday rental in Islamorada
Oceanfront Anglers Reef Islamorada Florida Keys , holiday rental in Islamorada

Oceanfront Anglers Reef Islamorada Florida Keys

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Perfect Family Getaway! Waterfront Vacation Home in Islamorada, Florida Keys!, holiday rental in Islamorada
Perfect Family Getaway! Waterfront Vacation Home in Islamorada, Florida Keys!, holiday rental in Islamorada
Perfect Family Getaway! Waterfront Vacation Home in Islamorada, Florida Keys!, holiday rental in Islamorada

Perfect Family Getaway! Waterfront Vacation Home in Islamorada, Florida Keys!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Islamorada Oceanfront Corner Condo, Panoramic Ocean Views, Pool, Wi-Fi, Balcony, holiday rental in Islamorada
Islamorada Oceanfront Corner Condo, Panoramic Ocean Views, Pool, Wi-Fi, Balcony, holiday rental in Islamorada
Islamorada Oceanfront Corner Condo, Panoramic Ocean Views, Pool, Wi-Fi, Balcony, holiday rental in Islamorada

Islamorada Oceanfront Corner Condo, Panoramic Ocean Views, Pool, Wi-Fi, Balcony

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Gorgeous Florida Keys Vacation Home with Beach Access in Islamorada!, holiday rental in Islamorada
Gorgeous Florida Keys Vacation Home with Beach Access in Islamorada!, holiday rental in Islamorada
Gorgeous Florida Keys Vacation Home with Beach Access in Islamorada!, holiday rental in Islamorada

Gorgeous Florida Keys Vacation Home with Beach Access in Islamorada!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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'Irish Ayes' Elegant Waterfront Home with Pool, holiday rental in Islamorada
'Irish Ayes' Elegant Waterfront Home with Pool, holiday rental in Islamorada
'Irish Ayes' Elegant Waterfront Home with Pool, holiday rental in Islamorada

'Irish Ayes' Elegant Waterfront Home with Pool

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Townhome in Beachfront Community: Perfect for Florida Keys Vacation!, holiday rental in Islamorada
Townhome in Beachfront Community: Perfect for Florida Keys Vacation!, holiday rental in Islamorada
Townhome in Beachfront Community: Perfect for Florida Keys Vacation!, holiday rental in Islamorada

Townhome in Beachfront Community: Perfect for Florida Keys Vacation!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps, All pools
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Bayside Condo, marina, pool and beach, holiday rental in Islamorada
Bayside Condo, marina, pool and beach, holiday rental in Islamorada
Bayside Condo, marina, pool and beach, holiday rental in Islamorada

Bayside Condo, marina, pool and beach

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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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, All pools
More info
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San Roc - Private 150 Ft Oceanfront 2.5 Acre Millionaire Row Estate, Pool, Spa, , holiday rental in Islamorada
San Roc - Private 150 Ft Oceanfront 2.5 Acre Millionaire Row Estate, Pool, Spa, , holiday rental in Islamorada
San Roc - Private 150 Ft Oceanfront 2.5 Acre Millionaire Row Estate, Pool, Spa, , holiday rental in Islamorada

San Roc - Private 150 Ft Oceanfront 2.5 Acre Millionaire Row Estate, Pool, Spa,

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
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LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF , holiday rental in Islamorada
LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF , holiday rental in Islamorada
LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF , holiday rental in Islamorada

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Blue Dolphin  Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool, holiday rental in Islamorada
Blue Dolphin  Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool, holiday rental in Islamorada
Blue Dolphin  Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool, holiday rental in Islamorada

Blue Dolphin Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, All pools
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Ocean Front Town House With Breath Taking Views From all 3 Balconies, holiday rental in Islamorada
Ocean Front Town House With Breath Taking Views From all 3 Balconies, holiday rental in Islamorada
Ocean Front Town House With Breath Taking Views From all 3 Balconies, holiday rental in Islamorada

Ocean Front Town House With Breath Taking Views From all 3 Balconies

Condo/Apartment
0 bedrooms
0 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
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A Piece of Paradise Islamorada, Fl. On the water 3/2, 90 Ft of dock New Pool, holiday rental in Islamorada
A Piece of Paradise Islamorada, Fl. On the water 3/2, 90 Ft of dock New Pool, holiday rental in Islamorada
A Piece of Paradise Islamorada, Fl. On the water 3/2, 90 Ft of dock New Pool, holiday rental in Islamorada

A Piece of Paradise Islamorada, Fl. On the water 3/2, 90 Ft of dock New Pool

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Luxury Oceanfront Home, Views, Pool, Sandy Beach, holiday rental in Islamorada
Luxury Oceanfront Home, Views, Pool, Sandy Beach, holiday rental in Islamorada
Luxury Oceanfront Home, Views, Pool, Sandy Beach, holiday rental in Islamorada

Luxury Oceanfront Home, Views, Pool, Sandy Beach

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
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Reel Paradise Islamorada, holiday rental in Islamorada
Reel Paradise Islamorada, holiday rental in Islamorada
Reel Paradise Islamorada, holiday rental in Islamorada

Reel Paradise Islamorada

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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ISLAND DREAM, holiday rental in Islamorada
ISLAND DREAM, holiday rental in Islamorada
ISLAND DREAM, holiday rental in Islamorada

ISLAND DREAM

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Beautiful Captain's Cove, holiday rental in Islamorada
Beautiful Captain's Cove, holiday rental in Islamorada
Beautiful Captain's Cove, holiday rental in Islamorada

Beautiful Captain's Cove

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental , holiday rental in Islamorada
Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental , holiday rental in Islamorada
Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental , holiday rental in Islamorada

Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Bay Front Beauty/ Summer Sea Must See!!!! , holiday rental in Islamorada
Bay Front Beauty/ Summer Sea Must See!!!! , holiday rental in Islamorada
Bay Front Beauty/ Summer Sea Must See!!!! , holiday rental in Islamorada

Bay Front Beauty/ Summer Sea Must See!!!!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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The following properties match some of your filters:
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
More info
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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
More info
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As seen on
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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
More info
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As seen on
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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
More info
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As seen on
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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
More info
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