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Islamorada Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
746 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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Southern Diversion Estate  Islamorada Thanksgiving open deep discount, vacation rental in Islamorada
Southern Diversion Estate  Islamorada Thanksgiving open deep discount, vacation rental in Islamorada
Southern Diversion Estate  Islamorada Thanksgiving open deep discount, vacation rental in Islamorada

Southern Diversion Estate Islamorada Thanksgiving open deep discount

Rental Home
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Beautifully Renovated 2 Bedroom Condo, vacation rental in Islamorada
Beautifully Renovated 2 Bedroom Condo, vacation rental in Islamorada
Beautifully Renovated 2 Bedroom Condo, vacation rental in Islamorada

Beautifully Renovated 2 Bedroom Condo

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Better Choice for your Vacation! 2 Pet-Friendly Units, Free Breakfast, Pool, vacation rental in Islamorada
Better Choice for your Vacation! 2 Pet-Friendly Units, Free Breakfast, Pool, vacation rental in Islamorada
Better Choice for your Vacation! 2 Pet-Friendly Units, Free Breakfast, Pool, vacation rental in Islamorada

Better Choice for your Vacation! 2 Pet-Friendly Units, Free Breakfast, Pool

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Prime Location! Onsite Pool, Free Breakfast, Free Parking, vacation rental in Islamorada
Prime Location! Onsite Pool, Free Breakfast, Free Parking, vacation rental in Islamorada
Prime Location! Onsite Pool, Free Breakfast, Free Parking, vacation rental in Islamorada

Prime Location! Onsite Pool, Free Breakfast, Free Parking

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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"Islamorada Waterside Getaway: Prime Fishing, Sunset Views, Beachside Bliss!", vacation rental in Islamorada
"Islamorada Waterside Getaway: Prime Fishing, Sunset Views, Beachside Bliss!", vacation rental in Islamorada
"Islamorada Waterside Getaway: Prime Fishing, Sunset Views, Beachside Bliss!", vacation rental in Islamorada

"Islamorada Waterside Getaway: Prime Fishing, Sunset Views, Beachside Bliss!"

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Private Bayside Waterfront Home 2 acres, Beach, Deep Water Boat Dock, vacation rental in Islamorada
Private Bayside Waterfront Home 2 acres, Beach, Deep Water Boat Dock, vacation rental in Islamorada
Private Bayside Waterfront Home 2 acres, Beach, Deep Water Boat Dock, vacation rental in Islamorada

Private Bayside Waterfront Home 2 acres, Beach, Deep Water Boat Dock

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Paradise Retreat, vacation rental in Islamorada
Paradise Retreat, vacation rental in Islamorada
Paradise Retreat, vacation rental in Islamorada

Paradise Retreat

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Islamorada Hidden Treasure, vacation rental in Islamorada
Islamorada Hidden Treasure, vacation rental in Islamorada
Islamorada Hidden Treasure, vacation rental in Islamorada

Islamorada Hidden Treasure

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Islamorada Luxury Waterfront Condo with Boat Slip, vacation rental in Islamorada
Islamorada Luxury Waterfront Condo with Boat Slip, vacation rental in Islamorada
Islamorada Luxury Waterfront Condo with Boat Slip, vacation rental in Islamorada

Islamorada Luxury Waterfront Condo with Boat Slip

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
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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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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Waterfront Escape: Bayfront Accommodation w/ Kitchen, Onsite Pool, Free Parking, vacation rental in Islamorada
Waterfront Escape: Bayfront Accommodation w/ Kitchen, Onsite Pool, Free Parking, vacation rental in Islamorada
Waterfront Escape: Bayfront Accommodation w/ Kitchen, Onsite Pool, Free Parking, vacation rental in Islamorada

Waterfront Escape: Bayfront Accommodation w/ Kitchen, Onsite Pool, Free Parking

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Islamorada Home on Canal with Private Beach Access
/ 4 bedroom  3 bath, vacation rental in Islamorada
Islamorada Home on Canal with Private Beach Access
/ 4 bedroom  3 bath, vacation rental in Islamorada
Islamorada Home on Canal with Private Beach Access
/ 4 bedroom  3 bath, vacation rental in Islamorada

Islamorada Home on Canal with Private Beach Access / 4 bedroom 3 bath

Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Best Place to Unwind! 2 Spacious Units, Free Breakfast, Swimming Pool!, vacation rental in Islamorada
Best Place to Unwind! 2 Spacious Units, Free Breakfast, Swimming Pool!, vacation rental in Islamorada
Best Place to Unwind! 2 Spacious Units, Free Breakfast, Swimming Pool!, vacation rental in Islamorada

Best Place to Unwind! 2 Spacious Units, Free Breakfast, Swimming Pool!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Updated Unit with Beautiful Florida Bay Sunsets, vacation rental in Islamorada
Updated Unit with Beautiful Florida Bay Sunsets, vacation rental in Islamorada
Updated Unit with Beautiful Florida Bay Sunsets, vacation rental in Islamorada

Updated Unit with Beautiful Florida Bay Sunsets

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip., vacation rental in Islamorada
Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip., vacation rental in Islamorada
Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip., vacation rental in Islamorada

Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful sunsets & water views, vacation rental in Islamorada
Beautiful sunsets & water views, vacation rental in Islamorada
Beautiful sunsets & water views, vacation rental in Islamorada

Beautiful sunsets & water views

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bay front 6BDr Private Beach Pickle-ball Ct Game room Sunset Views, vacation rental in Islamorada
Bay front 6BDr Private Beach Pickle-ball Ct Game room Sunset Views, vacation rental in Islamorada
Bay front 6BDr Private Beach Pickle-ball Ct Game room Sunset Views, vacation rental in Islamorada

Bay front 6BDr Private Beach Pickle-ball Ct Game room Sunset Views

Rental Home
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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10 Bedroom Private Ocean Front Estate, vacation rental in Islamorada
10 Bedroom Private Ocean Front Estate, vacation rental in Islamorada
10 Bedroom Private Ocean Front Estate, vacation rental in Islamorada

10 Bedroom Private Ocean Front Estate

Rental Home
10 bedrooms
11 bathrooms
Sleeps 22
Match: Sleeps
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Come Create Memories w/ Fun-filled Adventures at this Paradise! Beachfront, vacation rental in Islamorada
Come Create Memories w/ Fun-filled Adventures at this Paradise! Beachfront, vacation rental in Islamorada
Come Create Memories w/ Fun-filled Adventures at this Paradise! Beachfront, vacation rental in Islamorada

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

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Port Antigua South Islamorada Canal Front Home with Pool Dock & Private Beach, vacation rental in Islamorada
Port Antigua South Islamorada Canal Front Home with Pool Dock & Private Beach, vacation rental in Islamorada
Port Antigua South Islamorada Canal Front Home with Pool Dock & Private Beach, vacation rental in Islamorada

Port Antigua South Islamorada Canal Front Home with Pool Dock & Private Beach

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Isla Lychee: Little Basin Villas, Waterfront Boutique Resort, Walkable, vacation rental in Islamorada
Isla Lychee: Little Basin Villas, Waterfront Boutique Resort, Walkable, vacation rental in Islamorada
Isla Lychee: Little Basin Villas, Waterfront Boutique Resort, Walkable, vacation rental in Islamorada

Isla Lychee: Little Basin Villas, Waterfront Boutique Resort, Walkable

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Coral Harbour Club ~ 2 Bedroom Condo in Islamorada with Pool & Dockage, vacation rental in Islamorada
Coral Harbour Club ~ 2 Bedroom Condo in Islamorada with Pool & Dockage, vacation rental in Islamorada
Coral Harbour Club ~ 2 Bedroom Condo in Islamorada with Pool & Dockage, vacation rental in Islamorada

Coral Harbour Club ~ 2 Bedroom Condo in Islamorada with Pool & Dockage

Condo/Apartment
2 bedrooms
2 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!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming and Cozy  Townhouse in the Fl Keys with Pool and Beach Access, vacation rental in Islamorada
Charming and Cozy  Townhouse in the Fl Keys with Pool and Beach Access, vacation rental in Islamorada
Charming and Cozy  Townhouse in the Fl Keys with Pool and Beach Access, vacation rental in Islamorada

Charming and Cozy Townhouse in the Fl Keys with Pool and Beach Access

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Brand New Home, Resort Location, Ocean View, vacation rental in Islamorada
Brand New Home, Resort Location, Ocean View, vacation rental in Islamorada
Brand New Home, Resort Location, Ocean View, vacation rental in Islamorada

Brand New Home, Resort Location, Ocean View

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Sportfishing in Florida Keys! Elegant Villa w/ Beach Access and Pool! Breakfast, vacation rental in Islamorada
Sportfishing in Florida Keys! Elegant Villa w/ Beach Access and Pool! Breakfast, vacation rental in Islamorada
Sportfishing in Florida Keys! Elegant Villa w/ Beach Access and Pool! Breakfast, vacation rental in Islamorada

Sportfishing in Florida Keys! Elegant Villa w/ Beach Access and Pool! Breakfast

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Oceanside Resort... Oceanview unit with kayaks, paddleboards and walk in beach!, vacation rental in Islamorada
Oceanside Resort... Oceanview unit with kayaks, paddleboards and walk in beach!, vacation rental in Islamorada
Oceanside Resort... Oceanview unit with kayaks, paddleboards and walk in beach!, vacation rental in Islamorada

Oceanside Resort... Oceanview unit with kayaks, paddleboards and walk in beach!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Off the beaten path in one of Islamorada’s hidden gem of a community!., vacation rental in Islamorada
Off the beaten path in one of Islamorada’s hidden gem of a community!., vacation rental in Islamorada
Off the beaten path in one of Islamorada’s hidden gem of a community!., vacation rental in Islamorada

Off the beaten path in one of Islamorada’s hidden gem of a community!.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property, vacation rental in Islamorada
Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property, vacation rental in Islamorada
Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property, vacation rental in Islamorada

Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Beachy 3 Bedroom Condo with Ocean Views, vacation rental in Islamorada
Beachy 3 Bedroom Condo with Ocean Views, vacation rental in Islamorada
Beachy 3 Bedroom Condo with Ocean Views, vacation rental in Islamorada

Beachy 3 Bedroom Condo with Ocean Views

Rental Home
3 bedrooms
3 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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Your Majestic View in Islamorada! Swimming Pool, Kitchenette, Pets Allowed!, vacation rental in Islamorada
Your Majestic View in Islamorada! Swimming Pool, Kitchenette, Pets Allowed!, vacation rental in Islamorada
Your Majestic View in Islamorada! Swimming Pool, Kitchenette, Pets Allowed!, vacation rental in Islamorada

Your Majestic View in Islamorada! Swimming Pool, Kitchenette, Pets Allowed!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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This condo is located in one of Islamorada's most prestigious condo complexes., vacation rental in Islamorada
This condo is located in one of Islamorada's most prestigious condo complexes., vacation rental in Islamorada
This condo is located in one of Islamorada's most prestigious condo complexes., vacation rental in Islamorada

This condo is located in one of Islamorada's most prestigious condo complexes.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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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Gated canal-front retreat with pool water access, grill, AC & 2 kitchens, vacation rental in Islamorada
Gated canal-front retreat with pool water access, grill, AC & 2 kitchens, vacation rental in Islamorada
Gated canal-front retreat with pool water access, grill, AC & 2 kitchens, vacation rental in Islamorada

Gated canal-front retreat with pool water access, grill, AC & 2 kitchens

Rental Home
6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Florida Keys Chic, vacation rental in Islamorada
Florida Keys Chic, vacation rental in Islamorada
Florida Keys Chic, vacation rental in Islamorada

Florida Keys Chic

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Islamorada Island Getaway, vacation rental in Islamorada
Islamorada Island Getaway, vacation rental in Islamorada
Islamorada Island Getaway, vacation rental in Islamorada

Islamorada Island Getaway

Rental Home
5 bedrooms
5 bathrooms
Sleeps 8
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

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Isla Sunset Collection: Sleeps 18, All Ensuite Bedrooms, Waterfront, vacation rental in Islamorada
Isla Sunset Collection: Sleeps 18, All Ensuite Bedrooms, Waterfront, vacation rental in Islamorada
Isla Sunset Collection: Sleeps 18, All Ensuite Bedrooms, Waterfront, vacation rental in Islamorada

Isla Sunset Collection: Sleeps 18, All Ensuite Bedrooms, Waterfront

Rental Home
9 bedrooms
12 bathrooms
Sleeps 18
Match: Sleeps
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Water-view house with private dock, washer/dryer & grill - snowbird-friendly, vacation rental in Islamorada
Water-view house with private dock, washer/dryer & grill - snowbird-friendly, vacation rental in Islamorada
Water-view house with private dock, washer/dryer & grill - snowbird-friendly, vacation rental in Islamorada

Water-view house with private dock, washer/dryer & grill - snowbird-friendly

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Luxury Home with 60' Deep Water Dock, Waterfall Pool,  HotTub, A/C and WiFi, vacation rental in Islamorada
Luxury Home with 60' Deep Water Dock, Waterfall Pool,  HotTub, A/C and WiFi, vacation rental in Islamorada
Luxury Home with 60' Deep Water Dock, Waterfall Pool,  HotTub, A/C and WiFi, vacation rental in Islamorada

Luxury Home with 60' Deep Water Dock, Waterfall Pool, HotTub, A/C and WiFi

Rental Home
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL, vacation rental in Islamorada
4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL, vacation rental in Islamorada
4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL, vacation rental in Islamorada

4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Relaxation at its Finest in Islamorada! Swimming Pool, Beach, Pet-friendly!, vacation rental in Islamorada
Relaxation at its Finest in Islamorada! Swimming Pool, Beach, Pet-friendly!, vacation rental in Islamorada
Relaxation at its Finest in Islamorada! Swimming Pool, Beach, Pet-friendly!, vacation rental in Islamorada

Relaxation at its Finest in Islamorada! Swimming Pool, Beach, Pet-friendly!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Premium Units w/ Ocean Views & Balcony! Marina, Pets Allowed, Beach Access!, vacation rental in Islamorada
Premium Units w/ Ocean Views & Balcony! Marina, Pets Allowed, Beach Access!, vacation rental in Islamorada
Premium Units w/ Ocean Views & Balcony! Marina, Pets Allowed, Beach Access!, vacation rental in Islamorada

Premium Units w/ Ocean Views & Balcony! Marina, Pets Allowed, Beach Access!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Dive Into Your Dream Vacation! Beachfront, Outdoor Pool, Near Hurricane Monument, vacation rental in Islamorada
Dive Into Your Dream Vacation! Beachfront, Outdoor Pool, Near Hurricane Monument, vacation rental in Islamorada
Dive Into Your Dream Vacation! Beachfront, Outdoor Pool, Near Hurricane Monument, vacation rental in Islamorada

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

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Relax, Play, and Soak in Islamorada! Swimming Pool, Pets Allowed, Free Parking!, vacation rental in Islamorada
Relax, Play, and Soak in Islamorada! Swimming Pool, Pets Allowed, Free Parking!, vacation rental in Islamorada
Relax, Play, and Soak in Islamorada! Swimming Pool, Pets Allowed, Free Parking!, vacation rental in Islamorada

Relax, Play, and Soak in Islamorada! Swimming Pool, Pets Allowed, Free Parking!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
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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Showing results 1-50 of 746
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