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Islamorada Vacation Rentals

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5 km
814 rentals in Islamorada.
Wonderful 2 Bedroom Condo with Ocean Views, vacation rental in Islamorada
Wonderful 2 Bedroom Condo with Ocean Views, vacation rental in Islamorada
Wonderful 2 Bedroom Condo with Ocean Views, vacation 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, vacation rental in Islamorada
Adorable canal front Pool Home in Plantation Key, vacation rental in Islamorada
Adorable canal front Pool Home in Plantation Key, vacation 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!, vacation rental in Islamorada
ULTIMATE outdoor living area at this 4/4 canal home with pool!, vacation rental in Islamorada
ULTIMATE outdoor living area at this 4/4 canal home with pool!, vacation 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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Ocean Harbour P21 ~ Modern Oceanfront Islamorada Condo with Boat Slip, vacation rental in Islamorada
Ocean Harbour P21 ~ Modern Oceanfront Islamorada Condo with Boat Slip, vacation rental in Islamorada
Ocean Harbour P21 ~ Modern Oceanfront Islamorada Condo with Boat Slip, vacation rental in Islamorada

Ocean Harbour P21 ~ Modern Oceanfront Islamorada Condo with Boat Slip

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Tropical retreat where location meets quintessential Keys vacation home., vacation rental in Islamorada
Tropical retreat where location meets quintessential Keys vacation home., vacation rental in Islamorada
Tropical retreat where location meets quintessential Keys vacation home., vacation 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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A Place You'll Surely Enjoy! 3 Comfortable Units, Onsite Pool, Free Parking, vacation rental in Islamorada
A Place You'll Surely Enjoy! 3 Comfortable Units, Onsite Pool, Free Parking, vacation rental in Islamorada
A Place You'll Surely Enjoy! 3 Comfortable Units, Onsite Pool, Free Parking, vacation rental in Islamorada

A Place You'll Surely Enjoy! 3 Comfortable Units, Onsite Pool, Free Parking

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Vacation Day Is Always A Great Idea! 4 Classy Units, FREE Parking, Pets Allowed!, vacation rental in Islamorada
Vacation Day Is Always A Great Idea! 4 Classy Units, FREE Parking, Pets Allowed!, vacation rental in Islamorada
Vacation Day Is Always A Great Idea! 4 Classy Units, FREE Parking, Pets Allowed!, vacation rental in Islamorada

Vacation Day Is Always A Great Idea! 4 Classy Units, FREE Parking, Pets Allowed!

Condo/Apartment
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Peacock Shores Islamorada - Vacation On The Beach!, vacation rental in Islamorada
Peacock Shores Islamorada - Vacation On The Beach!, vacation rental in Islamorada
Peacock Shores Islamorada - Vacation On The Beach!, vacation rental in Islamorada

Peacock Shores Islamorada - Vacation On The Beach!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Fantastic ocean front conch house on the ocean with 160’ dock., vacation rental in Islamorada
Fantastic ocean front conch house on the ocean with 160’ dock., vacation rental in Islamorada
Fantastic ocean front conch house on the ocean with 160’ dock., vacation rental in Islamorada

Fantastic ocean front conch house on the ocean with 160’ dock.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Keys Villa--Islamorada private beach!, vacation rental in Islamorada
Keys Villa--Islamorada private beach!, vacation rental in Islamorada
Keys Villa--Islamorada private beach!, vacation rental in Islamorada

Keys Villa--Islamorada private beach!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Morada Zen - 4BR/3Bath Waterfront Ocean & Bay Access, Pool, Tiki, Dockage, vacation rental in Islamorada
Morada Zen - 4BR/3Bath Waterfront Ocean & Bay Access, Pool, Tiki, Dockage, vacation rental in Islamorada
Morada Zen - 4BR/3Bath Waterfront Ocean & Bay Access, Pool, Tiki, Dockage, vacation 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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Bayside Tranquility: 3 Relaxing Villa w/ Spacious Living Area & Kitchen, vacation rental in Islamorada
Bayside Tranquility: 3 Relaxing Villa w/ Spacious Living Area & Kitchen, vacation rental in Islamorada
Bayside Tranquility: 3 Relaxing Villa w/ Spacious Living Area & Kitchen, vacation rental in Islamorada

Bayside Tranquility: 3 Relaxing Villa w/ Spacious Living Area & Kitchen

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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Coastal Retreat! Pool, Pets Allowed, Minutes to Indian Key Historic State Park, vacation rental in Islamorada
Coastal Retreat! Pool, Pets Allowed, Minutes to Indian Key Historic State Park, vacation rental in Islamorada
Coastal Retreat! Pool, Pets Allowed, Minutes to Indian Key Historic State Park, vacation rental in Islamorada

Coastal Retreat! Pool, Pets Allowed, Minutes to Indian Key Historic State Park

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Luxury, Elegant, Water Front Home, Heated Pool, Plantation Key, Islamorada, vacation rental in Islamorada
Luxury, Elegant, Water Front Home, Heated Pool, Plantation Key, Islamorada, vacation rental in Islamorada
Luxury, Elegant, Water Front Home, Heated Pool, Plantation Key, Islamorada, vacation rental in Islamorada

Luxury, Elegant, Water Front Home, Heated Pool, Plantation Key, Islamorada

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay, vacation rental in Islamorada
2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay, vacation rental in Islamorada
2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay, vacation rental in Islamorada

2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean  &  Bay Views.  Welcome To Paradise!, vacation rental in Islamorada
Ocean  &  Bay Views.  Welcome To Paradise!, vacation rental in Islamorada
Ocean  &  Bay Views.  Welcome To Paradise!, vacation rental in Islamorada

Ocean & Bay Views. Welcome To Paradise!

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Breezy Beach Waterfront home in Port Antigua, vacation rental in Islamorada
Breezy Beach Waterfront home in Port Antigua, vacation rental in Islamorada
Breezy Beach Waterfront home in Port Antigua, vacation rental in Islamorada

Breezy Beach Waterfront home in Port Antigua

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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House in Islamorada, in exclusive Venetian Shores., vacation rental in Islamorada
House in Islamorada, in exclusive Venetian Shores., vacation rental in Islamorada
House in Islamorada, in exclusive Venetian Shores., vacation rental in Islamorada

House in Islamorada, in exclusive Venetian Shores.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sportfishing in Florida Keys! Large Unit w/ Private Beach Access! Pool, vacation rental in Islamorada
Sportfishing in Florida Keys! Large Unit w/ Private Beach Access! Pool, vacation rental in Islamorada
Sportfishing in Florida Keys! Large Unit w/ Private Beach Access! Pool, vacation rental in Islamorada

Sportfishing in Florida Keys! Large Unit w/ Private Beach Access! Pool

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Exec Bay townhouse w/heated pool, marina, beach, vacation rental in Islamorada
Exec Bay townhouse w/heated pool, marina, beach, vacation rental in Islamorada
Exec Bay townhouse w/heated pool, marina, beach, vacation rental in Islamorada

Exec Bay townhouse w/heated pool, marina, beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Paradise with Free Dockage - Contact us to price your stay!!, vacation rental in Islamorada
Waterfront Paradise with Free Dockage - Contact us to price your stay!!, vacation rental in Islamorada
Waterfront Paradise with Free Dockage - Contact us to price your stay!!, vacation rental in Islamorada

Waterfront Paradise with Free Dockage - Contact us to price your stay!!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Sea Glass Cottage Beautiful Canal Front Home, vacation rental in Islamorada
Sea Glass Cottage Beautiful Canal Front Home, vacation rental in Islamorada
Sea Glass Cottage Beautiful Canal Front Home, vacation 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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Beautiful oceanfront resort located at mile marker 73.8, vacation rental in Islamorada
Beautiful oceanfront resort located at mile marker 73.8, vacation rental in Islamorada
Beautiful oceanfront resort located at mile marker 73.8, vacation rental in Islamorada

Beautiful oceanfront resort located at mile marker 73.8

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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"Our Happy Place" Paradise in Islamorada with Heated Pool and 90 ft Dock, vacation rental in Islamorada
"Our Happy Place" Paradise in Islamorada with Heated Pool and 90 ft Dock, vacation rental in Islamorada
"Our Happy Place" Paradise in Islamorada with Heated Pool and 90 ft Dock, vacation rental in Islamorada

"Our Happy Place" Paradise in Islamorada with Heated Pool and 90 ft Dock

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Infinity Bay Islamorada ~ Luxury 9-bed, 10-bath Bayfront Estate in Islamorada, vacation rental in Islamorada
Infinity Bay Islamorada ~ Luxury 9-bed, 10-bath Bayfront Estate in Islamorada, vacation rental in Islamorada
Infinity Bay Islamorada ~ Luxury 9-bed, 10-bath Bayfront Estate in Islamorada, vacation rental in Islamorada

Infinity Bay Islamorada ~ Luxury 9-bed, 10-bath Bayfront Estate in Islamorada

Holiday Rental House
9 bedrooms
10 bathrooms
Sleeps 18
Match: Sleeps
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Stunning 3 Bedroom Bayfront Home, vacation rental in Islamorada
Stunning 3 Bedroom Bayfront Home, vacation rental in Islamorada
Stunning 3 Bedroom Bayfront Home, vacation rental in Islamorada

Stunning 3 Bedroom Bayfront Home

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Isla Mamey: Waterfront Boutique Resort, Htd Pool, Dock, Walkable, vacation rental in Islamorada
Isla Mamey: Waterfront Boutique Resort, Htd Pool, Dock, Walkable, vacation rental in Islamorada
Isla Mamey: Waterfront Boutique Resort, Htd Pool, Dock, Walkable, vacation rental in Islamorada

Isla Mamey: Waterfront Boutique Resort, Htd Pool, Dock, Walkable

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Better Choice for your Vacation! 2 Comfortable Units, Beachfront, Outdoor Pool, vacation rental in Islamorada
Better Choice for your Vacation! 2 Comfortable Units, Beachfront, Outdoor Pool, vacation rental in Islamorada
Better Choice for your Vacation! 2 Comfortable Units, Beachfront, Outdoor Pool, vacation rental in Islamorada

Better Choice for your Vacation! 2 Comfortable Units, Beachfront, Outdoor Pool

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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3 bedroom, 3.5 bath luxurious condo 402  at Maison  in Islamorada, vacation rental in Islamorada
3 bedroom, 3.5 bath luxurious condo 402  at Maison  in Islamorada, vacation rental in Islamorada
3 bedroom, 3.5 bath luxurious condo 402  at Maison  in Islamorada, vacation rental in Islamorada

3 bedroom, 3.5 bath luxurious condo 402 at Maison in Islamorada

Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Executive Bay - Next to Beach and Pool!, vacation rental in Islamorada
Executive Bay - Next to Beach and Pool!, vacation rental in Islamorada
Executive Bay - Next to Beach and Pool!, vacation rental in Islamorada

Executive Bay - Next to Beach and Pool!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Islamorada waterfront gem: Total reno ‘24: 3/3.5, pool, spa & deep water dock., vacation rental in Islamorada
Islamorada waterfront gem: Total reno ‘24: 3/3.5, pool, spa & deep water dock., vacation rental in Islamorada
Islamorada waterfront gem: Total reno ‘24: 3/3.5, pool, spa & deep water dock., vacation rental in Islamorada

Islamorada waterfront gem: Total reno ‘24: 3/3.5, pool, spa & deep water dock.

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Your Idyllic Getaway Awaits! Breathtaking Beachfront, Outdoor Pool | 3 Units, vacation rental in Islamorada
Your Idyllic Getaway Awaits! Breathtaking Beachfront, Outdoor Pool | 3 Units, vacation rental in Islamorada
Your Idyllic Getaway Awaits! Breathtaking Beachfront, Outdoor Pool | 3 Units, vacation rental in Islamorada

Your Idyllic Getaway Awaits! Breathtaking Beachfront, Outdoor Pool | 3 Units

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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Ultimate Beach Relaxation: Resort w/ Marina and Outdoor Pool | Free Parking, vacation rental in Islamorada
Ultimate Beach Relaxation: Resort w/ Marina and Outdoor Pool | Free Parking, vacation rental in Islamorada
Ultimate Beach Relaxation: Resort w/ Marina and Outdoor Pool | Free Parking, vacation rental in Islamorada

Ultimate Beach Relaxation: Resort w/ Marina and Outdoor Pool | Free Parking

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Harbor Hideaway | Island style beach house with pool, dockage & bay views!, vacation rental in Islamorada
Harbor Hideaway | Island style beach house with pool, dockage & bay views!, vacation rental in Islamorada
Harbor Hideaway | Island style beach house with pool, dockage & bay views!, vacation rental in Islamorada

Harbor Hideaway | Island style beach house with pool, dockage & bay views!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Charming Condo in Paradise!, vacation rental in Islamorada
Charming Condo in Paradise!, vacation rental in Islamorada
Charming Condo in Paradise!, vacation rental in Islamorada

Charming Condo in Paradise!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Perfect Home for a get away! Private homeowners beach,  enjoy Islamorada., vacation rental in Islamorada
Perfect Home for a get away! Private homeowners beach,  enjoy Islamorada., vacation rental in Islamorada
Perfect Home for a get away! Private homeowners beach,  enjoy Islamorada., vacation rental in Islamorada

Perfect Home for a get away! Private homeowners beach, enjoy Islamorada.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Delightful 2 Bedroom Townhouse with Pool, Beach, Tennis Courts & More, vacation rental in Islamorada
NEW! Delightful 2 Bedroom Townhouse with Pool, Beach, Tennis Courts & More, vacation rental in Islamorada
NEW! Delightful 2 Bedroom Townhouse with Pool, Beach, Tennis Courts & More, vacation rental in Islamorada

NEW! Delightful 2 Bedroom Townhouse with Pool, Beach, Tennis Courts & More

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Pool, Completely Renovated Lovely Cottage Home in Islamorada, vacation rental in Islamorada
Private Pool, Completely Renovated Lovely Cottage Home in Islamorada, vacation rental in Islamorada
Private Pool, Completely Renovated Lovely Cottage Home in Islamorada, vacation rental in Islamorada

Private Pool, Completely Renovated Lovely Cottage Home in Islamorada

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Deluxe upper apartment with pool, canal-view balcony, water access, grill, & AC, vacation rental in Islamorada
Deluxe upper apartment with pool, canal-view balcony, water access, grill, & AC, vacation rental in Islamorada
Deluxe upper apartment with pool, canal-view balcony, water access, grill, & AC, vacation rental in Islamorada

Deluxe upper apartment with pool, canal-view balcony, water access, grill, & AC

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Pool | Sunsets | Walk to restaurants | Little Basin Villas | Conch Villa 6, vacation rental in Islamorada
Pool | Sunsets | Walk to restaurants | Little Basin Villas | Conch Villa 6, vacation rental in Islamorada
Pool | Sunsets | Walk to restaurants | Little Basin Villas | Conch Villa 6, vacation rental in Islamorada

Pool | Sunsets | Walk to restaurants | Little Basin Villas | Conch Villa 6

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Studio on Oceanfront Property with Pool, vacation rental in Islamorada
Cozy Studio on Oceanfront Property with Pool, vacation rental in Islamorada
Cozy Studio on Oceanfront Property with Pool, vacation rental in Islamorada

Cozy Studio on Oceanfront Property with Pool

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Spectacular Coastal Paradise with outstanding outdoor living spaces, vacation rental in Islamorada
Spectacular Coastal Paradise with outstanding outdoor living spaces, vacation rental in Islamorada
Spectacular Coastal Paradise with outstanding outdoor living spaces, vacation rental in Islamorada

Spectacular Coastal Paradise with outstanding outdoor living spaces

Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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Captain's Quarters Piece of Peace, vacation rental in Islamorada
Captain's Quarters Piece of Peace, vacation rental in Islamorada
Captain's Quarters Piece of Peace, vacation rental in Islamorada

Captain's Quarters Piece of Peace

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast, vacation rental in Islamorada
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast, vacation rental in Islamorada
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast, vacation rental in Islamorada

Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Modern ground-floor apartment with pool, water views, patio, grill, & central AC, vacation rental in Islamorada
Modern ground-floor apartment with pool, water views, patio, grill, & central AC, vacation rental in Islamorada
Modern ground-floor apartment with pool, water views, patio, grill, & central AC, vacation rental in Islamorada

Modern ground-floor apartment with pool, water views, patio, grill, & central AC

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Fabulous " Sea Breeze 41 ", 3 / 2 Condo located Oceanside in Islamorada, vacation rental in Islamorada
Fabulous " Sea Breeze 41 ", 3 / 2 Condo located Oceanside in Islamorada, vacation rental in Islamorada
Fabulous " Sea Breeze 41 ", 3 / 2 Condo located Oceanside in Islamorada, vacation 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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Island Oasis in Islamorada: Your Private Paradise Awaits!, vacation rental in Islamorada
Island Oasis in Islamorada: Your Private Paradise Awaits!, vacation rental in Islamorada
Island Oasis in Islamorada: Your Private Paradise Awaits!, vacation rental in Islamorada

Island Oasis in Islamorada: Your Private Paradise Awaits!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards, vacation rental in Islamorada
OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards, vacation rental in Islamorada
OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards, vacation rental in Islamorada

OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Relax and Unwind in Islamorada! Swimming Pool, Pet-friendly Property!, vacation rental in Islamorada
Relax and Unwind in Islamorada! Swimming Pool, Pet-friendly Property!, vacation rental in Islamorada
Relax and Unwind in Islamorada! Swimming Pool, Pet-friendly Property!, vacation rental in Islamorada

Relax and Unwind in Islamorada! Swimming Pool, Pet-friendly Property!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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You Don’t Want to Miss This! Beachfront, Onsite Pool, Near Coral Bay Marina, vacation rental in Islamorada
You Don’t Want to Miss This! Beachfront, Onsite Pool, Near Coral Bay Marina, vacation rental in Islamorada
You Don’t Want to Miss This! Beachfront, Onsite Pool, Near Coral Bay Marina, vacation rental in Islamorada

You Don’t Want to Miss This! Beachfront, Onsite Pool, Near Coral Bay Marina

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Showing results 1-50 of 814
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