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Matecumbe Key Holiday Rentals

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73 rentals in Matecumbe Key.
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The Caribbean Resort - Malayan Palm North, holiday rental in Matecumbe Key

The Caribbean Resort - Malayan Palm North

2 bedrooms
1 bathroom
Sleeps 6
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Oceanfront, Private Beach, Charming 2 Bed 2 Bath Beach Cottage - Kayaks Included, holiday rental in Matecumbe Key

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

2 bedrooms
2 bathrooms
Sleeps 6
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Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!, holiday rental in Matecumbe Key

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

5 bedrooms
3 bathrooms
Sleeps 10
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5 Star Modern Oceanfront Islamorada Townhome on the Beach!, holiday rental in Matecumbe Key

5 Star Modern Oceanfront Islamorada Townhome on the Beach!

2 bedrooms
3 bathrooms
Sleeps 6
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Sunrise Haven at Maison Matecumbe #306 - 3Bd, 3Ba Condo - Beach, Pool & Hot Tub, holiday rental in Matecumbe Key

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

3 bedrooms
3 bathrooms
Sleeps 8
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Anglers Reef Oceanfront Complex w Pool & Beach-Islamorada, holiday rental in Matecumbe Key

Anglers Reef Oceanfront Complex w Pool & Beach-Islamorada

2 bedrooms
3 bathrooms
Sleeps 6
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Location. Location. Location., holiday rental in Matecumbe Key

Location. Location. Location.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Secluded Stunning Oceanview Townhome, holiday rental in Matecumbe Key

Secluded Stunning Oceanview Townhome

2 bedrooms
3 bathrooms
Sleeps 6
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Beautiful Bayfront Home with Amazing Sunsets, holiday rental in Matecumbe Key

Beautiful Bayfront Home with Amazing Sunsets

4 bedrooms
3 bathrooms
Sleeps 10
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ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE, holiday rental in Matecumbe Key

ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Ocean  &  Bay Views.  Welcome To Paradise!, holiday rental in Matecumbe Key

Ocean & Bay Views. Welcome To Paradise!

1 bedroom
2 bathrooms
Sleeps 4
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Islamorada-Anglers Reef-Spacious/updated Ocean View DOCKAGE INCLUDED, holiday rental in Matecumbe Key

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

2 bedrooms
3 bathrooms
Sleeps 6
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75130 Overseas Highway, holiday rental in Matecumbe Key

75130 Overseas Highway

2 bedrooms
2 bathrooms
Sleeps 4
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Anglers Reef Islamorada Vacation Rental 2/2.5 updated 131 Anglers Way, holiday rental in Matecumbe Key

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

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

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

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

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

1 bedroom
2 bathrooms
Sleeps 4
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Captain's Quarters Piece of Peace, holiday rental in Matecumbe Key

Captain's Quarters Piece of Peace

2 bedrooms
2 bathrooms
Sleeps 8
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Paradise * Islamorada, holiday rental in Matecumbe Key

Paradise * Islamorada

2 bedrooms
2 bathrooms
Sleeps 8
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2 Bedroom, 3 bathroom Townhouse in Executive Bay complex Islamorada FL, holiday rental in Matecumbe Key

2 Bedroom, 3 bathroom Townhouse in Executive Bay complex Islamorada FL

2 bedrooms
3 bathrooms
Sleeps 6
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Islamorada Bungalow In the Heart of the Florida Keys, holiday rental in Matecumbe Key

Islamorada Bungalow In the Heart of the Florida Keys

2 bedrooms
2 bathrooms
Sleeps 4
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BEACON REEF 522, holiday rental in Matecumbe Key

BEACON REEF 522

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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New listing! Bayfront townhouse in yacht club w/ shared pool & private boat slip, holiday rental in Matecumbe Key

New listing! Bayfront townhouse in yacht club w/ shared pool & private boat slip

2 bedrooms
3 bathrooms
Sleeps 6
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Oceanfront condo in Islamorada, amazing sunrise views, just renovated in 2019!, holiday rental in Matecumbe Key

Oceanfront condo in Islamorada, amazing sunrise views, just renovated in 2019!

2 bedrooms
2 bathrooms
Sleeps 4
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Oceanfront Islamorada Condo with Boat Slip, holiday rental in Matecumbe Key

Oceanfront Islamorada Condo with Boat Slip

3 bedrooms
2 bathrooms
Sleeps 6
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BEACON REEF 406, holiday rental in Matecumbe Key

BEACON REEF 406

2 bedrooms
2 bathrooms
Sleeps 4
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Fall Special-Recently Renovated Executive Bay Club Luxury Townhome in Islamorada, holiday rental in Matecumbe Key

Fall Special-Recently Renovated Executive Bay Club Luxury Townhome in Islamorada

2 bedrooms
2 bathrooms
Sleeps 6
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Martin Family Fish Camp, holiday rental in Matecumbe Key

Martin Family Fish Camp

4 bedrooms
3 bathrooms
Sleeps 12
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Palms of Islamorada #403, holiday rental in Matecumbe Key

Palms of Islamorada #403

2 bedrooms
2 bathrooms
Sleeps 5
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Beautiful Key West Townhome, holiday rental in Matecumbe Key

Beautiful Key West Townhome

2 bedrooms
2 bathrooms
Sleeps 6
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Cypress House 3bed/2bath with 40ft of dockage, holiday rental in Matecumbe Key

Cypress House 3bed/2bath with 40ft of dockage

3 bedrooms
2 bathrooms
Sleeps 6
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75691 Overseas Highway, holiday rental in Matecumbe Key

75691 Overseas Highway

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Caribbean Resort - Jamaican Palm House, holiday rental in Matecumbe Key

The Caribbean Resort - Jamaican Palm House

3 bedrooms
2 bathrooms
Sleeps 9
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The Caribbean Resort - Royal Palm North, holiday rental in Matecumbe Key

The Caribbean Resort - Royal Palm North

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Angler's Reef #118, holiday rental in Matecumbe Key

Angler's Reef #118

2 bedrooms
3 bathrooms
Sleeps 4
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The Caribbean Resort - Bird of Paradise - One Bedroom One Bath, holiday rental in Matecumbe Key

The Caribbean Resort - Bird of Paradise - One Bedroom One Bath

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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BEACON REEF 301, holiday rental in Matecumbe Key

BEACON REEF 301

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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194 Airstream Lane, holiday rental in Matecumbe Key

194 Airstream Lane

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Caribbean Resort - Malayan Palm East, holiday rental in Matecumbe Key

The Caribbean Resort - Malayan Palm East

1 bedroom
1 bathroom
Sleeps 4
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Coral Cove Resort - Fisherman's Dream, holiday rental in Matecumbe Key

Coral Cove Resort - Fisherman's Dream

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Caribbean Resort - Hemingway House North, holiday rental in Matecumbe Key

The Caribbean Resort - Hemingway House North

2 bedrooms
2 bathrooms
Sleeps 8
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Port of Call C-2, holiday rental in Matecumbe Key

Port of Call C-2

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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The Caribbean Resort - Canary Island Palm South, holiday rental in Matecumbe Key

The Caribbean Resort - Canary Island Palm South

2 bedrooms
2 bathrooms
Sleeps 8
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The Caribbean Resort - Harbor House, holiday rental in Matecumbe Key

The Caribbean Resort - Harbor House

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Caribbean Resort - Royal Palm South, holiday rental in Matecumbe Key

The Caribbean Resort - Royal Palm South

3 bedrooms
3 bathrooms
Sleeps 8
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Beautiful Venetian Shores, Cozy home, Heated pool, Tiki, Boat Lift, Fish & Dive., holiday rental in Matecumbe Key

Beautiful Venetian Shores, Cozy home, Heated pool, Tiki, Boat Lift, Fish & Dive.

3 bedrooms
3 bathrooms
Sleeps 8
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Summer Sea #420, holiday rental in Matecumbe Key

Summer Sea #420

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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BEACON REEF 503, holiday rental in Matecumbe Key

BEACON REEF 503

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The Caribbean Resort - Hemingway House South, holiday rental in Matecumbe Key

The Caribbean Resort - Hemingway House South

2 bedrooms
2 bathrooms
Sleeps 8
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Island Conch Cottage, holiday rental in Matecumbe Key

Island Conch Cottage

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Townhouse Islamorada Florida / Excecutive Bay Club, holiday rental in Matecumbe Key

Beautiful Townhouse Islamorada Florida / Excecutive Bay Club

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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