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Matecumbe Key Vacation Rentals

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121 rentals in Matecumbe Key.
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WATERFRONT COTTAGE GREAT RATES ! Pet Friendly !, vacation rental in Matecumbe Key
WATERFRONT COTTAGE GREAT RATES ! Pet Friendly !, vacation rental in Matecumbe Key
WATERFRONT COTTAGE GREAT RATES ! Pet Friendly !, vacation rental in Matecumbe Key

WATERFRONT COTTAGE GREAT RATES ! Pet Friendly !

Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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ANGLER'S REEF, ISLAMORADA, KEYS LUXURY- SLIPS, POOL, BEACHES, vacation rental in Matecumbe Key
ANGLER'S REEF, ISLAMORADA, KEYS LUXURY- SLIPS, POOL, BEACHES, vacation rental in Matecumbe Key
ANGLER'S REEF, ISLAMORADA, KEYS LUXURY- SLIPS, POOL, BEACHES, vacation rental in Matecumbe Key

ANGLER'S REEF, ISLAMORADA, KEYS LUXURY- SLIPS, POOL, BEACHES

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Oceanfront, Private Beach, Charming 2 Bed 2 Bath Beach Cottage - Kayaks Included, vacation rental in Matecumbe Key
Oceanfront, Private Beach, Charming 2 Bed 2 Bath Beach Cottage - Kayaks Included, vacation rental in Matecumbe Key
Oceanfront, Private Beach, Charming 2 Bed 2 Bath Beach Cottage - Kayaks Included, vacation rental in Matecumbe Key

Oceanfront, Private Beach, Charming 2 Bed 2 Bath Beach Cottage - Kayaks Included

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Single Family Home In Angler's Reef Gated Community,Beautiful Ground,Resort Pool, vacation rental in Matecumbe Key
Single Family Home In Angler's Reef Gated Community,Beautiful Ground,Resort Pool, vacation rental in Matecumbe Key
Single Family Home In Angler's Reef Gated Community,Beautiful Ground,Resort Pool, vacation rental in Matecumbe Key

Single Family Home In Angler's Reef Gated Community,Beautiful Ground,Resort Pool

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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WALK TO RESTAURANTS | POOL | WATERFRONT | PERSONAL BALCONY | Conch Villa 6, vacation rental in Matecumbe Key
WALK TO RESTAURANTS | POOL | WATERFRONT | PERSONAL BALCONY | Conch Villa 6, vacation rental in Matecumbe Key
WALK TO RESTAURANTS | POOL | WATERFRONT | PERSONAL BALCONY | Conch Villa 6, vacation rental in Matecumbe Key

WALK TO RESTAURANTS | POOL | WATERFRONT | PERSONAL BALCONY | Conch Villa 6

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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WALK TO RESTAURANTS | POOL | SUNSETS | Little Basin Villas | Key Lime Villa 2, vacation rental in Matecumbe Key
WALK TO RESTAURANTS | POOL | SUNSETS | Little Basin Villas | Key Lime Villa 2, vacation rental in Matecumbe Key
WALK TO RESTAURANTS | POOL | SUNSETS | Little Basin Villas | Key Lime Villa 2, vacation rental in Matecumbe Key

WALK TO RESTAURANTS | POOL | SUNSETS | Little Basin Villas | Key Lime Villa 2

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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RELAX in your PRIVATE Oceanfront Cottage!, vacation rental in Matecumbe Key
RELAX in your PRIVATE Oceanfront Cottage!, vacation rental in Matecumbe Key
RELAX in your PRIVATE Oceanfront Cottage!, vacation rental in Matecumbe Key

RELAX in your PRIVATE Oceanfront Cottage!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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5 Star Modern Oceanfront Islamorada Townhome on the Beach!, vacation rental in Matecumbe Key
5 Star Modern Oceanfront Islamorada Townhome on the Beach!, vacation rental in Matecumbe Key
5 Star Modern Oceanfront Islamorada Townhome on the Beach!, vacation rental in Matecumbe Key

5 Star Modern Oceanfront Islamorada Townhome on the Beach!

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Location. Location. Location., vacation rental in Matecumbe Key
Location. Location. Location., vacation rental in Matecumbe Key
Location. Location. Location., vacation rental in Matecumbe Key

Location. Location. Location.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!, vacation rental in Matecumbe Key
Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!, vacation rental in Matecumbe Key
Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!, vacation rental in Matecumbe Key

Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Serene Home in Beautiful Anglers Reef!!, vacation rental in Matecumbe Key
Serene Home in Beautiful Anglers Reef!!, vacation rental in Matecumbe Key
Serene Home in Beautiful Anglers Reef!!, vacation rental in Matecumbe Key

Serene Home in Beautiful Anglers Reef!!

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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WALK TO RESTAURANTS | POOL | SUNSETS | Little Basin Villas | Key Lime Villa 3, vacation rental in Matecumbe Key
WALK TO RESTAURANTS | POOL | SUNSETS | Little Basin Villas | Key Lime Villa 3, vacation rental in Matecumbe Key
WALK TO RESTAURANTS | POOL | SUNSETS | Little Basin Villas | Key Lime Villa 3, vacation rental in Matecumbe Key

WALK TO RESTAURANTS | POOL | SUNSETS | Little Basin Villas | Key Lime Villa 3

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Bayside Paradise in the Heart of Islamorada with Private Boat Dockage, vacation rental in Matecumbe Key
Bayside Paradise in the Heart of Islamorada with Private Boat Dockage, vacation rental in Matecumbe Key
Bayside Paradise in the Heart of Islamorada with Private Boat Dockage, vacation rental in Matecumbe Key

Bayside Paradise in the Heart of Islamorada with Private Boat Dockage

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Truly OceanFRONT Home 3BR 2.5BA, Panoramic Ocean Views, Lg Wraparound Decks, vacation rental in Matecumbe Key
Truly OceanFRONT Home 3BR 2.5BA, Panoramic Ocean Views, Lg Wraparound Decks, vacation rental in Matecumbe Key
Truly OceanFRONT Home 3BR 2.5BA, Panoramic Ocean Views, Lg Wraparound Decks, vacation rental in Matecumbe Key

Truly OceanFRONT Home 3BR 2.5BA, Panoramic Ocean Views, Lg Wraparound Decks

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Little Basin Villas | Bay Villa 7 | WALK TO RESTAURANTS | POOL | SUNSETS, vacation rental in Matecumbe Key
Little Basin Villas | Bay Villa 7 | WALK TO RESTAURANTS | POOL | SUNSETS, vacation rental in Matecumbe Key
Little Basin Villas | Bay Villa 7 | WALK TO RESTAURANTS | POOL | SUNSETS, vacation rental in Matecumbe Key

Little Basin Villas | Bay Villa 7 | WALK TO RESTAURANTS | POOL | SUNSETS

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Sunrise Haven at Maison Matecumbe #306 - 3Bd, 3Ba Condo - Beach, Pool & Hot Tub, vacation rental in Matecumbe Key
Sunrise Haven at Maison Matecumbe #306 - 3Bd, 3Ba Condo - Beach, Pool & Hot Tub, vacation rental in Matecumbe Key
Sunrise Haven at Maison Matecumbe #306 - 3Bd, 3Ba Condo - Beach, Pool & Hot Tub, vacation rental in Matecumbe Key

Sunrise Haven at Maison Matecumbe #306 - 3Bd, 3Ba Condo - Beach, Pool & Hot Tub

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Anglers Reef Islamorada Home Oceanview Dock Beach Com Pool Boat Slip - 2/2.5, vacation rental in Matecumbe Key
Anglers Reef Islamorada Home Oceanview Dock Beach Com Pool Boat Slip - 2/2.5, vacation rental in Matecumbe Key
Anglers Reef Islamorada Home Oceanview Dock Beach Com Pool Boat Slip - 2/2.5, vacation rental in Matecumbe Key

Anglers Reef Islamorada Home Oceanview Dock Beach Com Pool Boat Slip - 2/2.5

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Deep Dockage & Heated Pool in Islamorada.

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Bayfront Home with Amazing Sunsets, vacation rental in Matecumbe Key
Beautiful Bayfront Home with Amazing Sunsets, vacation rental in Matecumbe Key
Beautiful Bayfront Home with Amazing Sunsets, vacation rental in Matecumbe Key

Beautiful Bayfront Home with Amazing Sunsets

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Gated Oceanfront 1.8 acre Estate on Millionaire's Row, Private Saltwater Pool, vacation rental in Matecumbe Key
Gated Oceanfront 1.8 acre Estate on Millionaire's Row, Private Saltwater Pool, vacation rental in Matecumbe Key
Gated Oceanfront 1.8 acre Estate on Millionaire's Row, Private Saltwater Pool, vacation rental in Matecumbe Key

Gated Oceanfront 1.8 acre Estate on Millionaire's Row, Private Saltwater Pool

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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The Perfect Getaway with Heated Swimming Pool, Jacuzzi and Boat Slip, vacation rental in Matecumbe Key
The Perfect Getaway with Heated Swimming Pool, Jacuzzi and Boat Slip, vacation rental in Matecumbe Key
The Perfect Getaway with Heated Swimming Pool, Jacuzzi and Boat Slip, vacation rental in Matecumbe Key

The Perfect Getaway with Heated Swimming Pool, Jacuzzi and Boat Slip

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Ocean  &  Bay Views.  Welcome To Paradise!, vacation rental in Matecumbe Key
Ocean  &  Bay Views.  Welcome To Paradise!, vacation rental in Matecumbe Key
Ocean  &  Bay Views.  Welcome To Paradise!, vacation rental in Matecumbe Key

Ocean & Bay Views. Welcome To Paradise!

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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WATERFRONT | POOL | WALK TO RESTAURANTS | Little Basin Villas | Conch Villa 4, vacation rental in Matecumbe Key
WATERFRONT | POOL | WALK TO RESTAURANTS | Little Basin Villas | Conch Villa 4, vacation rental in Matecumbe Key
WATERFRONT | POOL | WALK TO RESTAURANTS | Little Basin Villas | Conch Villa 4, vacation rental in Matecumbe Key

WATERFRONT | POOL | WALK TO RESTAURANTS | Little Basin Villas | Conch Villa 4

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Anglers Reef Oceanfront Complex w Pool & Beach-Islamorada, vacation rental in Matecumbe Key
Anglers Reef Oceanfront Complex w Pool & Beach-Islamorada, vacation rental in Matecumbe Key
Anglers Reef Oceanfront Complex w Pool & Beach-Islamorada, vacation rental in Matecumbe Key

Anglers Reef Oceanfront Complex w Pool & Beach-Islamorada

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Anglers Reef Islamorada Vacation Rental 2/2.5 updated 131 Anglers Way, vacation rental in Matecumbe Key
Anglers Reef Islamorada Vacation Rental 2/2.5 updated 131 Anglers Way, vacation rental in Matecumbe Key
Anglers Reef Islamorada Vacation Rental 2/2.5 updated 131 Anglers Way, vacation rental in Matecumbe Key

Anglers Reef Islamorada Vacation Rental 2/2.5 updated 131 Anglers Way

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Anglers Reef Islamorada  home with ocean views, private marina, beach & pool, vacation rental in Matecumbe Key
Anglers Reef Islamorada  home with ocean views, private marina, beach & pool, vacation rental in Matecumbe Key
Anglers Reef Islamorada  home with ocean views, private marina, beach & pool, vacation rental in Matecumbe Key

Anglers Reef Islamorada home with ocean views, private marina, beach & pool

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Breathtaking ocean views for your Paradise vacations

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Islamorada's Finest Canal Front 'One Story' Vacation Home  WiFi-HDTV-NO STAIRS, vacation rental in Matecumbe Key
Islamorada's Finest Canal Front 'One Story' Vacation Home  WiFi-HDTV-NO STAIRS, vacation rental in Matecumbe Key
Islamorada's Finest Canal Front 'One Story' Vacation Home  WiFi-HDTV-NO STAIRS, vacation rental in Matecumbe Key

Islamorada's Finest Canal Front 'One Story' Vacation Home WiFi-HDTV-NO STAIRS

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Islamorada-Anglers Reef-Spacious/updated Ocean View DOCKAGE INCLUDED, vacation rental in Matecumbe Key
Islamorada-Anglers Reef-Spacious/updated Ocean View DOCKAGE INCLUDED, vacation rental in Matecumbe Key
Islamorada-Anglers Reef-Spacious/updated Ocean View DOCKAGE INCLUDED, vacation rental in Matecumbe Key

Islamorada-Anglers Reef-Spacious/updated Ocean View DOCKAGE INCLUDED

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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4 Bedroom House In Angler's Reef, Includes 31' Boat Slip

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Secluded Stunning Oceanview Townhome, vacation rental in Matecumbe Key
Secluded Stunning Oceanview Townhome, vacation rental in Matecumbe Key
Secluded Stunning Oceanview Townhome, vacation rental in Matecumbe Key

Secluded Stunning Oceanview Townhome

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Discover the Charm of Island Living, vacation rental in Matecumbe Key
Discover the Charm of Island Living, vacation rental in Matecumbe Key
Discover the Charm of Island Living, vacation rental in Matecumbe Key

Discover the Charm of Island Living

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool, vacation rental in Matecumbe Key
Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool, vacation rental in Matecumbe Key
Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool, vacation rental in Matecumbe Key

Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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4 Bedroom Private Oceanfront House - Bahia, vacation rental in Matecumbe Key
4 Bedroom Private Oceanfront House - Bahia, vacation rental in Matecumbe Key
4 Bedroom Private Oceanfront House - Bahia, vacation rental in Matecumbe Key

4 Bedroom Private Oceanfront House - Bahia

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Bayside: 1st Floor Apartment in Native Hammock on Florida Bay, vacation rental in Matecumbe Key
Bayside: 1st Floor Apartment in Native Hammock on Florida Bay, vacation rental in Matecumbe Key
Bayside: 1st Floor Apartment in Native Hammock on Florida Bay, vacation rental in Matecumbe Key

Bayside: 1st Floor Apartment in Native Hammock on Florida Bay

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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PERSONAL PORCH AND BALCONY | WATERFRONT | POOL | Conch Villa 4 | Little Basin, vacation rental in Matecumbe Key
PERSONAL PORCH AND BALCONY | WATERFRONT | POOL | Conch Villa 4 | Little Basin, vacation rental in Matecumbe Key
PERSONAL PORCH AND BALCONY | WATERFRONT | POOL | Conch Villa 4 | Little Basin, vacation rental in Matecumbe Key

PERSONAL PORCH AND BALCONY | WATERFRONT | POOL | Conch Villa 4 | Little Basin

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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You will love my 'Fl Keys Luxury Home', vacation rental in Matecumbe Key
You will love my 'Fl Keys Luxury Home', vacation rental in Matecumbe Key
You will love my 'Fl Keys Luxury Home', vacation rental in Matecumbe Key

You will love my 'Fl Keys Luxury Home'

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Caribbean Villa in Islamorada Resort Community with Dedicated Boat Slip, vacation rental in Matecumbe Key
Caribbean Villa in Islamorada Resort Community with Dedicated Boat Slip, vacation rental in Matecumbe Key
Caribbean Villa in Islamorada Resort Community with Dedicated Boat Slip, vacation rental in Matecumbe Key

Caribbean Villa in Islamorada Resort Community with Dedicated Boat Slip

Rental Home
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE, vacation rental in Matecumbe Key
ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE, vacation rental in Matecumbe Key
ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE, vacation rental in Matecumbe Key

ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Payment Protection
Coral Cove Resort - Fisherman's Dream, vacation rental in Matecumbe Key
Coral Cove Resort - Fisherman's Dream, vacation rental in Matecumbe Key
Coral Cove Resort - Fisherman's Dream, vacation rental in Matecumbe Key

Coral Cove Resort - Fisherman's Dream

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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3 Bedroom Private Oceanfront House - Sol, vacation rental in Matecumbe Key
3 Bedroom Private Oceanfront House - Sol, vacation rental in Matecumbe Key
3 Bedroom Private Oceanfront House - Sol, vacation rental in Matecumbe Key

3 Bedroom Private Oceanfront House - Sol

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The PERFECT ESCAPE with Private Pool and Dock, vacation rental in Matecumbe Key
The PERFECT ESCAPE with Private Pool and Dock, vacation rental in Matecumbe Key
The PERFECT ESCAPE with Private Pool and Dock, vacation rental in Matecumbe Key

The PERFECT ESCAPE with Private Pool and Dock

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular Ocean Front Home, In the heart of  beautiful Islamorada!, vacation rental in Matecumbe Key
Spectacular Ocean Front Home, In the heart of  beautiful Islamorada!, vacation rental in Matecumbe Key
Spectacular Ocean Front Home, In the heart of  beautiful Islamorada!, vacation rental in Matecumbe Key

Spectacular Ocean Front Home, In the heart of beautiful Islamorada!

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Getaway for Spring and  Summer, vacation rental in Matecumbe Key
Getaway for Spring and  Summer, vacation rental in Matecumbe Key
Getaway for Spring and  Summer, vacation rental in Matecumbe Key

Getaway for Spring and Summer

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Spring and  Summer at  Paradise, vacation rental in Matecumbe Key
Spring and  Summer at  Paradise, vacation rental in Matecumbe Key
Spring and  Summer at  Paradise, vacation rental in Matecumbe Key

Spring and Summer at Paradise

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The 'Nest' villa - 2Bed /2Bath, Stunning Bay Views, private sun deck, boat dock!, vacation rental in Matecumbe Key
The 'Nest' villa - 2Bed /2Bath, Stunning Bay Views, private sun deck, boat dock!, vacation rental in Matecumbe Key
The 'Nest' villa - 2Bed /2Bath, Stunning Bay Views, private sun deck, boat dock!, vacation rental in Matecumbe Key

The 'Nest' villa - 2Bed /2Bath, Stunning Bay Views, private sun deck, boat dock!

Rental Home
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Captain's Quarters Piece of Peace

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Oceanfront Islamorada Condo with Boat Slip, vacation rental in Matecumbe Key
Oceanfront Islamorada Condo with Boat Slip, vacation rental in Matecumbe Key
Oceanfront Islamorada Condo with Boat Slip, vacation rental in Matecumbe Key

Oceanfront Islamorada Condo with Boat Slip

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Key West Townhome, vacation rental in Matecumbe Key
Beautiful Key West Townhome, vacation rental in Matecumbe Key
Beautiful Key West Townhome, vacation rental in Matecumbe Key

Beautiful Key West Townhome

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Oceanfront Islamorada Condo with T-Dock FREE boat dockage, vacation rental in Matecumbe Key
Oceanfront Islamorada Condo with T-Dock FREE boat dockage, vacation rental in Matecumbe Key
Oceanfront Islamorada Condo with T-Dock FREE boat dockage, vacation rental in Matecumbe Key

Oceanfront Islamorada Condo with T-Dock FREE boat dockage

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Frequently Asked Questions about Matecumbe Key