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Holiday Rentals in Islamorada

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
805 rentals in Islamorada.
Wonderful 2 Bedroom Condo with Ocean Views, holiday rental in Islamorada
Wonderful 2 Bedroom Condo with Ocean Views, holiday rental in Islamorada
Wonderful 2 Bedroom Condo with Ocean Views, holiday rental in Islamorada

Wonderful 2 Bedroom Condo with Ocean Views

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Adorable canal front Pool Home in Plantation Key, holiday rental in Islamorada
Adorable canal front Pool Home in Plantation Key, holiday rental in Islamorada
Adorable canal front Pool Home in Plantation Key, holiday rental in Islamorada

Adorable canal front Pool Home in Plantation Key

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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ULTIMATE outdoor living area at this 4/4 canal home with pool!, holiday rental in Islamorada
ULTIMATE outdoor living area at this 4/4 canal home with pool!, holiday rental in Islamorada
ULTIMATE outdoor living area at this 4/4 canal home with pool!, holiday rental in Islamorada

ULTIMATE outdoor living area at this 4/4 canal home with pool!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Luxury Waterfront Home with Sandy Beach, Hot Tub and Theater, holiday rental in Islamorada
Luxury Waterfront Home with Sandy Beach, Hot Tub and Theater, holiday rental in Islamorada
Luxury Waterfront Home with Sandy Beach, Hot Tub and Theater, holiday rental in Islamorada

Luxury Waterfront Home with Sandy Beach, Hot Tub and Theater

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Dive Into Your Dream Vacation! Beachfront, Outdoor Pool, Near Hurricane Monument, holiday rental in Islamorada
Dive Into Your Dream Vacation! Beachfront, Outdoor Pool, Near Hurricane Monument, holiday rental in Islamorada
Dive Into Your Dream Vacation! Beachfront, Outdoor Pool, Near Hurricane Monument, holiday rental in Islamorada

Dive Into Your Dream Vacation! Beachfront, Outdoor Pool, Near Hurricane Monument

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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" Endless Summer" Awaits!, holiday rental in Islamorada
" Endless Summer" Awaits!, holiday rental in Islamorada
" Endless Summer" Awaits!, holiday rental in Islamorada

" Endless Summer" Awaits!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
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
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Poolside Maison Matecumbe #302 - Great 3 Bedroom Condo, holiday rental in Islamorada
Poolside Maison Matecumbe #302 - Great 3 Bedroom Condo, holiday rental in Islamorada
Poolside Maison Matecumbe #302 - Great 3 Bedroom Condo, holiday rental in Islamorada

Poolside Maison Matecumbe #302 - Great 3 Bedroom Condo

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful bayfront house, private pool and dock, right in Downtown Islamorada, holiday rental in Islamorada
Beautiful bayfront house, private pool and dock, right in Downtown Islamorada, holiday rental in Islamorada
Beautiful bayfront house, private pool and dock, right in Downtown Islamorada, holiday rental in Islamorada

Beautiful bayfront house, private pool and dock, right in Downtown Islamorada

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage, holiday rental in Islamorada
Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage, holiday rental in Islamorada
Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage, holiday rental in Islamorada

Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities, holiday rental in Islamorada
Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities, holiday rental in Islamorada
Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities, holiday rental in Islamorada

Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Your Blissful Haven in Islamorada! Beach, Swimming Pool, Pets Allowed!, holiday rental in Islamorada
Your Blissful Haven in Islamorada! Beach, Swimming Pool, Pets Allowed!, holiday rental in Islamorada
Your Blissful Haven in Islamorada! Beach, Swimming Pool, Pets Allowed!, holiday rental in Islamorada

Your Blissful Haven in Islamorada! Beach, Swimming Pool, Pets Allowed!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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FULLY RENOVATED piece of paradise. 2 bdrs, 2 king beds, 1 Queen bed 2 full baths, holiday rental in Islamorada
FULLY RENOVATED piece of paradise. 2 bdrs, 2 king beds, 1 Queen bed 2 full baths, holiday rental in Islamorada
FULLY RENOVATED piece of paradise. 2 bdrs, 2 king beds, 1 Queen bed 2 full baths, holiday rental in Islamorada

FULLY RENOVATED piece of paradise. 2 bdrs, 2 king beds, 1 Queen bed 2 full baths

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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RELAX in your PRIVATE Oceanfront Cottage!, holiday rental in Islamorada
RELAX in your PRIVATE Oceanfront Cottage!, holiday rental in Islamorada
RELAX in your PRIVATE Oceanfront Cottage!, holiday rental in Islamorada

RELAX in your PRIVATE Oceanfront Cottage!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Peninsula Villa / Heated Pool / Sunset Point, holiday rental in Islamorada
Peninsula Villa / Heated Pool / Sunset Point, holiday rental in Islamorada
Peninsula Villa / Heated Pool / Sunset Point, holiday rental in Islamorada

Peninsula Villa / Heated Pool / Sunset Point

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Deep Water Canalfront Home W/ Boat Ramp, holiday rental in Islamorada
Deep Water Canalfront Home W/ Boat Ramp, holiday rental in Islamorada
Deep Water Canalfront Home W/ Boat Ramp, holiday rental in Islamorada

Deep Water Canalfront Home W/ Boat Ramp

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New Caribbean home.  Resort access to pool, holiday rental in Islamorada
New Caribbean home.  Resort access to pool, holiday rental in Islamorada
New Caribbean home.  Resort access to pool, holiday rental in Islamorada

New Caribbean home. Resort access to pool

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Come Create Memories w/ Fun-filled Adventures at this Paradise! Free Parking, holiday rental in Islamorada
Come Create Memories w/ Fun-filled Adventures at this Paradise! Free Parking, holiday rental in Islamorada
Come Create Memories w/ Fun-filled Adventures at this Paradise! Free Parking, holiday rental in Islamorada

Come Create Memories w/ Fun-filled Adventures at this Paradise! Free Parking

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Relax and Recharge! Pets Allowed, Outdoor Swimming Pool, Free Parking!, holiday rental in Islamorada
Relax and Recharge! Pets Allowed, Outdoor Swimming Pool, Free Parking!, holiday rental in Islamorada
Relax and Recharge! Pets Allowed, Outdoor Swimming Pool, Free Parking!, holiday rental in Islamorada

Relax and Recharge! Pets Allowed, Outdoor Swimming Pool, Free Parking!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Anglers Reef Islamorada 2/2.5 dock available Bikes, Kayak available, Pool, holiday rental in Islamorada
Anglers Reef Islamorada 2/2.5 dock available Bikes, Kayak available, Pool, holiday rental in Islamorada
Anglers Reef Islamorada 2/2.5 dock available Bikes, Kayak available, Pool, holiday rental in Islamorada

Anglers Reef Islamorada 2/2.5 dock available Bikes, Kayak available, Pool

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Tranquil One Bedroom Cottage with Pool and Boat Basin, holiday rental in Islamorada
Tranquil One Bedroom Cottage with Pool and Boat Basin, holiday rental in Islamorada
Tranquil One Bedroom Cottage with Pool and Boat Basin, holiday rental in Islamorada

Tranquil One Bedroom Cottage with Pool and Boat Basin

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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BRAND NEW HOME, pet friendly, resort location!, holiday rental in Islamorada
BRAND NEW HOME, pet friendly, resort location!, holiday rental in Islamorada
BRAND NEW HOME, pet friendly, resort location!, holiday rental in Islamorada

BRAND NEW HOME, pet friendly, resort location!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Morada Zen - 4BR/3Bath Waterfront Ocean & Bay Access, Pool, Tiki, Dockage, holiday rental in Islamorada
Morada Zen - 4BR/3Bath Waterfront Ocean & Bay Access, Pool, Tiki, Dockage, holiday rental in Islamorada
Morada Zen - 4BR/3Bath Waterfront Ocean & Bay Access, Pool, Tiki, Dockage, holiday rental in Islamorada

Morada Zen - 4BR/3Bath Waterfront Ocean & Bay Access, Pool, Tiki, Dockage

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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4 Family-friendly Rooms w/ Balcony | Refreshing Outdoor Pool & Free Parking, holiday rental in Islamorada
4 Family-friendly Rooms w/ Balcony | Refreshing Outdoor Pool & Free Parking, holiday rental in Islamorada
4 Family-friendly Rooms w/ Balcony | Refreshing Outdoor Pool & Free Parking, holiday rental in Islamorada

4 Family-friendly Rooms w/ Balcony | Refreshing Outdoor Pool & Free Parking

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Maseri's Hideaway - Beautiful Newly Renovated Townhome in Gorgeous Islamorada, holiday rental in Islamorada
Maseri's Hideaway - Beautiful Newly Renovated Townhome in Gorgeous Islamorada, holiday rental in Islamorada
Maseri's Hideaway - Beautiful Newly Renovated Townhome in Gorgeous Islamorada, holiday rental in Islamorada

Maseri's Hideaway - Beautiful Newly Renovated Townhome in Gorgeous Islamorada

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lush Tropical Waterfront Oasis With Heated Pool, Dock And WiFi, holiday rental in Islamorada
Lush Tropical Waterfront Oasis With Heated Pool, Dock And WiFi, holiday rental in Islamorada
Lush Tropical Waterfront Oasis With Heated Pool, Dock And WiFi, holiday rental in Islamorada

Lush Tropical Waterfront Oasis With Heated Pool, Dock And WiFi

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Beach Front Home in Lower Matecumbe, holiday rental in Islamorada
Charming Beach Front Home in Lower Matecumbe, holiday rental in Islamorada
Charming Beach Front Home in Lower Matecumbe, holiday rental in Islamorada

Charming Beach Front Home in Lower Matecumbe

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Tarpon Bend ocean view with boat lifts, holiday rental in Islamorada
Tarpon Bend ocean view with boat lifts, holiday rental in Islamorada
Tarpon Bend ocean view with boat lifts, holiday rental in Islamorada

Tarpon Bend ocean view with boat lifts

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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All the feels... tranquility and relaxation, holiday rental in Islamorada
All the feels... tranquility and relaxation, holiday rental in Islamorada
All the feels... tranquility and relaxation, holiday rental in Islamorada

All the feels... tranquility and relaxation

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Beautifully Renovated 2 Bedroom Oceanfront Home, holiday rental in Islamorada
Beautifully Renovated 2 Bedroom Oceanfront Home, holiday rental in Islamorada
Beautifully Renovated 2 Bedroom Oceanfront Home, holiday rental in Islamorada

Beautifully Renovated 2 Bedroom Oceanfront Home

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sunset Reef - 4 bdrm, Bayside Private Gated Estate, Pool, Spa, Deep Water Dock, holiday rental in Islamorada
Sunset Reef - 4 bdrm, Bayside Private Gated Estate, Pool, Spa, Deep Water Dock, holiday rental in Islamorada
Sunset Reef - 4 bdrm, Bayside Private Gated Estate, Pool, Spa, Deep Water Dock, holiday rental in Islamorada

Sunset Reef - 4 bdrm, Bayside Private Gated Estate, Pool, Spa, Deep Water Dock

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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New Ground Level Caribbean Cottage, holiday rental in Islamorada
New Ground Level Caribbean Cottage, holiday rental in Islamorada
New Ground Level Caribbean Cottage, holiday rental in Islamorada

New Ground Level Caribbean Cottage

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Ocean Front Pool Home with dockage & pool, holiday rental in Islamorada
Charming Ocean Front Pool Home with dockage & pool, holiday rental in Islamorada
Charming Ocean Front Pool Home with dockage & pool, holiday rental in Islamorada

Charming Ocean Front Pool Home with dockage & pool

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Charming 2 bed, 2 bath cottage 100 feet from private sandy ocean beach, holiday rental in Islamorada
Charming 2 bed, 2 bath cottage 100 feet from private sandy ocean beach, holiday rental in Islamorada
Charming 2 bed, 2 bath cottage 100 feet from private sandy ocean beach, holiday rental in Islamorada

Charming 2 bed, 2 bath cottage 100 feet from private sandy ocean beach

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast, holiday rental in Islamorada
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast, holiday rental in Islamorada
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast, holiday rental in Islamorada

Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Beach House-Luxury Oceanfront Home, Unobstructed Views, Pool, Sandy Beach, holiday rental in Islamorada
The Beach House-Luxury Oceanfront Home, Unobstructed Views, Pool, Sandy Beach, holiday rental in Islamorada
The Beach House-Luxury Oceanfront Home, Unobstructed Views, Pool, Sandy Beach, holiday rental in Islamorada

The Beach House-Luxury Oceanfront Home, Unobstructed Views, Pool, Sandy Beach

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Serenity by the Sea!!  Anglers Reef with Boat Slip Available!!, holiday rental in Islamorada
Serenity by the Sea!!  Anglers Reef with Boat Slip Available!!, holiday rental in Islamorada
Serenity by the Sea!!  Anglers Reef with Boat Slip Available!!, holiday rental in Islamorada

Serenity by the Sea!! Anglers Reef with Boat Slip Available!!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Gulf View Retreat * Bay Harbor, holiday rental in Islamorada
Gulf View Retreat * Bay Harbor, holiday rental in Islamorada
Gulf View Retreat * Bay Harbor, holiday rental in Islamorada

Gulf View Retreat * Bay Harbor

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Incredible Bayside Home in the Florida Keys!, holiday rental in Islamorada
Incredible Bayside Home in the Florida Keys!, holiday rental in Islamorada
Incredible Bayside Home in the Florida Keys!, holiday rental in Islamorada

Incredible Bayside Home in the Florida Keys!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Best location 3BR house in Islamorada! Pool and beach; walk or bike everywhere., holiday rental in Islamorada
Best location 3BR house in Islamorada! Pool and beach; walk or bike everywhere., holiday rental in Islamorada
Best location 3BR house in Islamorada! Pool and beach; walk or bike everywhere., holiday rental in Islamorada

Best location 3BR house in Islamorada! Pool and beach; walk or bike everywhere.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Little Piece of Paradise (AVAIL Oct-Dec), holiday rental in Islamorada
Little Piece of Paradise (AVAIL Oct-Dec), holiday rental in Islamorada
Little Piece of Paradise (AVAIL Oct-Dec), holiday rental in Islamorada

Little Piece of Paradise (AVAIL Oct-Dec)

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Tropical retreat where location meets quintessential Keys vacation home., holiday rental in Islamorada
Tropical retreat where location meets quintessential Keys vacation home., holiday rental in Islamorada
Tropical retreat where location meets quintessential Keys vacation home., holiday rental in Islamorada

Tropical retreat where location meets quintessential Keys vacation home.

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Making The Best Memories Along The Way! 4 Comfortable Units, FREE Parking, holiday rental in Islamorada
Making The Best Memories Along The Way! 4 Comfortable Units, FREE Parking, holiday rental in Islamorada
Making The Best Memories Along The Way! 4 Comfortable Units, FREE Parking, holiday rental in Islamorada

Making The Best Memories Along The Way! 4 Comfortable Units, FREE Parking

Condo/Apartment
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Beautiful Islamorada Home in he heart of the keys, boat-slip, pool, and gated., holiday rental in Islamorada
Beautiful Islamorada Home in he heart of the keys, boat-slip, pool, and gated., holiday rental in Islamorada
Beautiful Islamorada Home in he heart of the keys, boat-slip, pool, and gated., holiday rental in Islamorada

Beautiful Islamorada Home in he heart of the keys, boat-slip, pool, and gated.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Just What You Were Looking For! Free Breakfast, Onsite Pool, Free Parking, holiday rental in Islamorada
Just What You Were Looking For! Free Breakfast, Onsite Pool, Free Parking, holiday rental in Islamorada
Just What You Were Looking For! Free Breakfast, Onsite Pool, Free Parking, holiday rental in Islamorada

Just What You Were Looking For! Free Breakfast, Onsite Pool, Free Parking

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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End of Summer Paradise at Anglers Reef, holiday rental in Islamorada
End of Summer Paradise at Anglers Reef, holiday rental in Islamorada
End of Summer Paradise at Anglers Reef, holiday rental in Islamorada

End of Summer Paradise at Anglers Reef

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Mitchell's Bayview Villa - Islamorada House on the Bay, holiday rental in Islamorada
Mitchell's Bayview Villa - Islamorada House on the Bay, holiday rental in Islamorada
Mitchell's Bayview Villa - Islamorada House on the Bay, holiday rental in Islamorada

Mitchell's Bayview Villa - Islamorada House on the Bay

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Your Dream Getaway at Anglers Reef, holiday rental in Islamorada
Your Dream Getaway at Anglers Reef, holiday rental in Islamorada
Your Dream Getaway at Anglers Reef, holiday rental in Islamorada

Your Dream Getaway at Anglers Reef

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Enjoy Sunset Views from Your Villa with Pool & Beach Access in FL, holiday rental in Islamorada
Enjoy Sunset Views from Your Villa with Pool & Beach Access in FL, holiday rental in Islamorada
Enjoy Sunset Views from Your Villa with Pool & Beach Access in FL, holiday rental in Islamorada

Enjoy Sunset Views from Your Villa with Pool & Beach Access in FL

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bayside Retreat - Adorable 3 Bedroom Bayfront Duplex with Dockage, holiday rental in Islamorada
Bayside Retreat - Adorable 3 Bedroom Bayfront Duplex with Dockage, holiday rental in Islamorada
Bayside Retreat - Adorable 3 Bedroom Bayfront Duplex with Dockage, holiday rental in Islamorada

Bayside Retreat - Adorable 3 Bedroom Bayfront Duplex with Dockage

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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