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Islamorada Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
744 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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
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!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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New Rental! Beautiful canal pool home with dockage!, vacation rental in Islamorada
New Rental! Beautiful canal pool home with dockage!, vacation rental in Islamorada
New Rental! Beautiful canal pool home with dockage!, vacation rental in Islamorada

New Rental! Beautiful canal pool home with dockage!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage, vacation rental in Islamorada
Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage, vacation rental in Islamorada
Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage, vacation rental in Islamorada

Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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You will never want to leave, vacation rental in Islamorada
You will never want to leave, vacation rental in Islamorada
You will never want to leave, vacation rental in Islamorada

You will never want to leave

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Islamorada house with waterfront, private dock and beach, vacation rental in Islamorada
Charming Islamorada house with waterfront, private dock and beach, vacation rental in Islamorada
Charming Islamorada house with waterfront, private dock and beach, vacation rental in Islamorada

Charming Islamorada house with waterfront, private dock and beach

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

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

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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3 BR 2 Bath Islamorada home with Private Beach Access, vacation rental in Islamorada
3 BR 2 Bath Islamorada home with Private Beach Access, vacation rental in Islamorada
3 BR 2 Bath Islamorada home with Private Beach Access, vacation rental in Islamorada

3 BR 2 Bath Islamorada home with Private Beach Access

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mini Ray's of Sunshine, vacation rental in Islamorada
Mini Ray's of Sunshine, vacation rental in Islamorada
Mini Ray's of Sunshine, vacation rental in Islamorada

Mini Ray's of Sunshine

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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This is The Oasis, YOUR private Oasis!, vacation rental in Islamorada
This is The Oasis, YOUR private Oasis!, vacation rental in Islamorada
This is The Oasis, YOUR private Oasis!, vacation rental in Islamorada

This is The Oasis, YOUR private Oasis!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Your Retreat in the Heart of Islamorada! Kitchenette, Outdoor Swimming Pool!, vacation rental in Islamorada
Your Retreat in the Heart of Islamorada! Kitchenette, Outdoor Swimming Pool!, vacation rental in Islamorada
Your Retreat in the Heart of Islamorada! Kitchenette, Outdoor Swimming Pool!, vacation rental in Islamorada

Your Retreat in the Heart of Islamorada! Kitchenette, Outdoor Swimming Pool!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Oceanfront Property w/ Outdoor Pools, Pets Allowed, Free Parking Onsite, vacation rental in Islamorada
Oceanfront Property w/ Outdoor Pools, Pets Allowed, Free Parking Onsite, vacation rental in Islamorada
Oceanfront Property w/ Outdoor Pools, Pets Allowed, Free Parking Onsite, vacation rental in Islamorada

Oceanfront Property w/ Outdoor Pools, Pets Allowed, Free Parking Onsite

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Bonefish House at Tarpon Point, vacation rental in Islamorada
The Bonefish House at Tarpon Point, vacation rental in Islamorada
The Bonefish House at Tarpon Point, vacation rental in Islamorada

The Bonefish House at Tarpon Point

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Canal-front home with private dock, wraparound deck, & central AC - snowbirds OK, vacation rental in Islamorada
Canal-front home with private dock, wraparound deck, & central AC - snowbirds OK, vacation rental in Islamorada
Canal-front home with private dock, wraparound deck, & central AC - snowbirds OK, vacation rental in Islamorada

Canal-front home with private dock, wraparound deck, & central AC - snowbirds OK

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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SALT HAVEN - BEAUTIFUL & CLEAN 70' WATERFRONT/CANAL POOL HOME + PRIVATE BEACH, vacation rental in Islamorada
SALT HAVEN - BEAUTIFUL & CLEAN 70' WATERFRONT/CANAL POOL HOME + PRIVATE BEACH, vacation rental in Islamorada
SALT HAVEN - BEAUTIFUL & CLEAN 70' WATERFRONT/CANAL POOL HOME + PRIVATE BEACH, vacation rental in Islamorada

SALT HAVEN - BEAUTIFUL & CLEAN 70' WATERFRONT/CANAL POOL HOME + PRIVATE BEACH

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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This studio makes the best of the space, vacation rental in Islamorada
This studio makes the best of the space, vacation rental in Islamorada
This studio makes the best of the space, vacation rental in Islamorada

This studio makes the best of the space

Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Escape to Paradise! Beachfront, Outdoor Pool, Near Theater of the Sea, vacation rental in Islamorada
Escape to Paradise! Beachfront, Outdoor Pool, Near Theater of the Sea, vacation rental in Islamorada
Escape to Paradise! Beachfront, Outdoor Pool, Near Theater of the Sea, vacation rental in Islamorada

Escape to Paradise! Beachfront, Outdoor Pool, Near Theater of the Sea

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful 3 Bedroom Condo - Bay Harbour A101, vacation rental in Islamorada
Beautiful 3 Bedroom Condo - Bay Harbour A101, vacation rental in Islamorada
Beautiful 3 Bedroom Condo - Bay Harbour A101, vacation rental in Islamorada

Beautiful 3 Bedroom Condo - Bay Harbour A101

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming 2 Bedroom House with Peekaboo Views, vacation rental in Islamorada
Charming 2 Bedroom House with Peekaboo Views, vacation rental in Islamorada
Charming 2 Bedroom House with Peekaboo Views, vacation rental in Islamorada

Charming 2 Bedroom House with Peekaboo Views

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Oceanfront Oasis in Angler’s Reef with Private Boat Slip, vacation rental in Islamorada
Oceanfront Oasis in Angler’s Reef with Private Boat Slip, vacation rental in Islamorada
Oceanfront Oasis in Angler’s Reef with Private Boat Slip, vacation rental in Islamorada

Oceanfront Oasis in Angler’s Reef with Private Boat Slip

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming Escape in Islamorada! 2 Modern Units, Swimming Pool, Pets Allowed!, vacation rental in Islamorada
Charming Escape in Islamorada! 2 Modern Units, Swimming Pool, Pets Allowed!, vacation rental in Islamorada
Charming Escape in Islamorada! 2 Modern Units, Swimming Pool, Pets Allowed!, vacation rental in Islamorada

Charming Escape in Islamorada! 2 Modern Units, Swimming Pool, Pets Allowed!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Steps Away from the Beach | Spacious 1BR Suite w/ Kitchenette, vacation rental in Islamorada
Steps Away from the Beach | Spacious 1BR Suite w/ Kitchenette, vacation rental in Islamorada
Steps Away from the Beach | Spacious 1BR Suite w/ Kitchenette, vacation rental in Islamorada

Steps Away from the Beach | Spacious 1BR Suite w/ Kitchenette

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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" Endless Summer" Awaits!, vacation rental in Islamorada
" Endless Summer" Awaits!, vacation rental in Islamorada
" Endless Summer" Awaits!, vacation rental in Islamorada

" Endless Summer" Awaits!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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La Casita White Marlin, vacation rental in Islamorada
La Casita White Marlin, vacation rental in Islamorada
La Casita White Marlin, vacation rental in Islamorada

La Casita White Marlin

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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A True Islamorada Oasis with Breathtaking Bay Views, vacation rental in Islamorada
A True Islamorada Oasis with Breathtaking Bay Views, vacation rental in Islamorada
A True Islamorada Oasis with Breathtaking Bay Views, vacation rental in Islamorada

A True Islamorada Oasis with Breathtaking Bay Views

Rental Home
6 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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Royal Palm South 3 Bedrooms, 3 Baths, Ocean Front, Marina, vacation rental in Islamorada
Royal Palm South 3 Bedrooms, 3 Baths, Ocean Front, Marina, vacation rental in Islamorada
Royal Palm South 3 Bedrooms, 3 Baths, Ocean Front, Marina, vacation rental in Islamorada

Royal Palm South 3 Bedrooms, 3 Baths, Ocean Front, Marina

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Snorkeling in Islamorada! Premium Villa, Bike Rentals & Water Sports Equipment!, vacation rental in Islamorada
Snorkeling in Islamorada! Premium Villa, Bike Rentals & Water Sports Equipment!, vacation rental in Islamorada
Snorkeling in Islamorada! Premium Villa, Bike Rentals & Water Sports Equipment!, vacation rental in Islamorada

Snorkeling in Islamorada! Premium Villa, Bike Rentals & Water Sports Equipment!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Amazing Sunsets+Sandy Beach+Pier+Heated Pool+Bikes+Kayak+2 Offices Quiet Home, vacation rental in Islamorada
Amazing Sunsets+Sandy Beach+Pier+Heated Pool+Bikes+Kayak+2 Offices Quiet Home, vacation rental in Islamorada
Amazing Sunsets+Sandy Beach+Pier+Heated Pool+Bikes+Kayak+2 Offices Quiet Home, vacation rental in Islamorada

Amazing Sunsets+Sandy Beach+Pier+Heated Pool+Bikes+Kayak+2 Offices Quiet Home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities, vacation rental in Islamorada
Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities, vacation rental in Islamorada
Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities, vacation 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 Oceanfront Islamorada Retreat with Pool & Private Boat Basin!, vacation rental in Islamorada
Your Oceanfront Islamorada Retreat with Pool & Private Boat Basin!, vacation rental in Islamorada
Your Oceanfront Islamorada Retreat with Pool & Private Boat Basin!, vacation rental in Islamorada

Your Oceanfront Islamorada Retreat with Pool & Private Boat Basin!

Rental Home
2 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
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Cosy Cottage in Islamorada with private garden & pool - 6 pers., vacation rental in Islamorada
Cosy Cottage in Islamorada with private garden & pool - 6 pers., vacation rental in Islamorada
Cosy Cottage in Islamorada with private garden & pool - 6 pers., vacation rental in Islamorada

Cosy Cottage in Islamorada with private garden & pool - 6 pers.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Oceanview 2b/2b w/ Boatslip, vacation rental in Islamorada
Oceanview 2b/2b w/ Boatslip, vacation rental in Islamorada
Oceanview 2b/2b w/ Boatslip, vacation rental in Islamorada

Oceanview 2b/2b w/ Boatslip

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

Discover the Charm of Island Living

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful vacation home in the heart of Islamorada , Florida Keys, vacation rental in Islamorada
Beautiful vacation home in the heart of Islamorada , Florida Keys, vacation rental in Islamorada
Beautiful vacation home in the heart of Islamorada , Florida Keys, vacation rental in Islamorada

Beautiful vacation home in the heart of Islamorada , Florida Keys

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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4 Units Perfect for Big Groups! Beachfront Property with Outdoor Pools!, vacation rental in Islamorada
4 Units Perfect for Big Groups! Beachfront Property with Outdoor Pools!, vacation rental in Islamorada
4 Units Perfect for Big Groups! Beachfront Property with Outdoor Pools!, vacation rental in Islamorada

4 Units Perfect for Big Groups! Beachfront Property with Outdoor Pools!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Your Charming Stay in Islamorada! Beach, Swimming Pool, Pets Allowed!, vacation rental in Islamorada
Your Charming Stay in Islamorada! Beach, Swimming Pool, Pets Allowed!, vacation rental in Islamorada
Your Charming Stay in Islamorada! Beach, Swimming Pool, Pets Allowed!, vacation rental in Islamorada

Your Charming Stay in Islamorada! Beach, Swimming Pool, Pets Allowed!

Rental Home
1 bedroom
1 bathroom
Sleeps 3
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

Rental Home
6 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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Peaceful 2 Bedroom Oceanfront Cottage with Pool and Dock, vacation rental in Islamorada
Peaceful 2 Bedroom Oceanfront Cottage with Pool and Dock, vacation rental in Islamorada
Peaceful 2 Bedroom Oceanfront Cottage with Pool and Dock, vacation rental in Islamorada

Peaceful 2 Bedroom Oceanfront Cottage with Pool and Dock

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Enjoy a Hassle-Free Stay! Free Parking, Onsite Pool, Near Anne's Beach, vacation rental in Islamorada
Enjoy a Hassle-Free Stay! Free Parking, Onsite Pool, Near Anne's Beach, vacation rental in Islamorada
Enjoy a Hassle-Free Stay! Free Parking, Onsite Pool, Near Anne's Beach, vacation rental in Islamorada

Enjoy a Hassle-Free Stay! Free Parking, Onsite Pool, Near Anne's Beach

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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3 Bedroom Private Oceanfront House - Sol, vacation rental in Islamorada
3 Bedroom Private Oceanfront House - Sol, vacation rental in Islamorada
3 Bedroom Private Oceanfront House - Sol, vacation rental in Islamorada

3 Bedroom Private Oceanfront House - Sol

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Little Piece of Paradise (AVAIL Oct-Dec), vacation rental in Islamorada
Little Piece of Paradise (AVAIL Oct-Dec), vacation rental in Islamorada
Little Piece of Paradise (AVAIL Oct-Dec), vacation rental in Islamorada

Little Piece of Paradise (AVAIL Oct-Dec)

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Seaside Villas w/ Ocean Views & Front Porch! Marina, Pets Allowed, Bike Rental, vacation rental in Islamorada
Seaside Villas w/ Ocean Views & Front Porch! Marina, Pets Allowed, Bike Rental, vacation rental in Islamorada
Seaside Villas w/ Ocean Views & Front Porch! Marina, Pets Allowed, Bike Rental, vacation rental in Islamorada

Seaside Villas w/ Ocean Views & Front Porch! Marina, Pets Allowed, Bike Rental

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Luxurious Caribbean 2 Bedroom 2 Bath Home, vacation rental in Islamorada
Luxurious Caribbean 2 Bedroom 2 Bath Home, vacation rental in Islamorada
Luxurious Caribbean 2 Bedroom 2 Bath Home, vacation rental in Islamorada

Luxurious Caribbean 2 Bedroom 2 Bath Home

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Maison Matecumbe.... the heart of Islamorada!, vacation rental in Islamorada
Maison Matecumbe.... the heart of Islamorada!, vacation rental in Islamorada
Maison Matecumbe.... the heart of Islamorada!, vacation rental in Islamorada

Maison Matecumbe.... the heart of Islamorada!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Your Keys Getaway - A, vacation rental in Islamorada
Your Keys Getaway - A, vacation rental in Islamorada
Your Keys Getaway - A, vacation rental in Islamorada

Your Keys Getaway - A

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Tropical Paradise Retreat in Islamorada! Pool, Pet-friendly, Free Parking!, vacation rental in Islamorada
Tropical Paradise Retreat in Islamorada! Pool, Pet-friendly, Free Parking!, vacation rental in Islamorada
Tropical Paradise Retreat in Islamorada! Pool, Pet-friendly, Free Parking!, vacation rental in Islamorada

Tropical Paradise Retreat in Islamorada! Pool, Pet-friendly, Free Parking!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Luxurious PH 5BR 3.5BA Gym/ Pool & Jacuzzi/ Sauna, vacation rental in Islamorada
Luxurious PH 5BR 3.5BA Gym/ Pool & Jacuzzi/ Sauna, vacation rental in Islamorada
Luxurious PH 5BR 3.5BA Gym/ Pool & Jacuzzi/ Sauna, vacation rental in Islamorada

Luxurious PH 5BR 3.5BA Gym/ Pool & Jacuzzi/ Sauna

Condo/Apartment
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Sun, Ocean and a Luxury Oasis with a  discount
Flexible stays contact host, vacation rental in Islamorada
Sun, Ocean and a Luxury Oasis with a  discount
Flexible stays contact host, vacation rental in Islamorada
Sun, Ocean and a Luxury Oasis with a  discount
Flexible stays contact host, vacation rental in Islamorada

Sun, Ocean and a Luxury Oasis with a discount Flexible stays contact host

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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AQUAMARINE OCEANVIEW<-WALL to WALL->+143 BEST 5 STAR REVIEWS+DOCK+POOL+GYM++++++, vacation rental in Islamorada
AQUAMARINE OCEANVIEW<-WALL to WALL->+143 BEST 5 STAR REVIEWS+DOCK+POOL+GYM++++++, vacation rental in Islamorada
AQUAMARINE OCEANVIEW<-WALL to WALL->+143 BEST 5 STAR REVIEWS+DOCK+POOL+GYM++++++, vacation rental in Islamorada

AQUAMARINE OCEANVIEW<-WALL to WALL->+143 BEST 5 STAR REVIEWS+DOCK+POOL+GYM++++++

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Showing results 1-50 of 744
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