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Islamorada Rentals

From $259 per night (USD)
VRBO
Beautiful Waterfront Pool Home in the Best Location for Your Best Vacation!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Best Home to Share with Family and Friends! This Beautiful Home consists of two levels. The ground level has a 3bedrooms ...
From $259 per night (USD)
VRBO
$2BR\/2.5BA Angler's Reef Cottage 116 With Private Beach and Pool Access$
From $464 per night (USD)
Expedia
2BR\/2.5BA Angler's Reef Cottage 116 With Private Beach and Pool Access
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Check out our video tour! All NEW Anglers Reef Villa 116, a modern beach retreat offering relaxation at its finest. Our ...
From $464 per night (USD)
Expedia
$2BR\/2.5BA Angler's Reef Conch Villa 103 With Private Beach and Pool Access$
From $461 per night (USD)
VRBO
2BR\/2.5BA Angler's Reef Conch Villa 103 With Private Beach and Pool Access
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
In the heart of the Florida Keys - Islamorada - an ancient reef awaits your arrival, where its waters brim with earth's ...
From $461 per night (USD)
VRBO
From $296 per night (USD)
VRBO
Newly Renovated - 2-bedroom state of the art condo Islamorada. Perfect Location!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Palms - Islamorada Brand New - Ripped down to the studs and just completed a $150k remodel with state of the art eve ...
From $296 per night (USD)
VRBO
From $749 per night (USD)
VRBO
Islamorada home, ocean views, playroom, near Tiki Bar, pool, and boat dockage, ultimate Keys getaway
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
PROPERTY NAME: Pirate's Paradise 84745 Old Highway Unit A2, Islamorada, Florida LOCATION: Oceanview home located in an ...
From $749 per night (USD)
VRBO
From $277 per night (USD)
Expedia
Charming Islamorada house with waterfront, private dock and beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in Islamorada, this delightful house offers a peaceful and serene retreat for guests. With 2 bedrooms, including ...
From $277 per night (USD)
Expedia
From $1866 per night (USD)
VRBO
Your Ultimate Keys Getaway Awaits!
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Welcome to your dream getaway at Coastal Cove Villa! Nestled in the heart of downtown Islamorada, this spacious 4-bedroo ...
From $1866 per night (USD)
VRBO
From $315 per night (USD)
Expedia
FULLY RENOVATED piece of paradise. 2 bdrs, 2 king beds, 1 Queen bed 2 full baths
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FULLY RENOVATED piece of paradise. 2 bdrs, 2 king beds, 1 Queen bed 2 full bathrooms and a loft for gaming etc. freshly ...
From $315 per night (USD)
Expedia
$Keys home on water w\/ access to beach *monthly*$
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VRBO
Keys home on water w\/ access to beach *monthly*
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Canal front house in the white marlin beach neighborhood of Lower Matecumbe (Islamorada) The space Three bedroom two bat ...
Click For Pricing
VRBO
$Bayside Home Dock\/Lift quick to ocean perfect spot to enjoy the best of the Keys$
From $295 per night (USD)
VRBO
Bayside Home Dock\/Lift quick to ocean perfect spot to enjoy the best of the Keys
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Waterfront home with dock & lift (6k dry weight max) small ramp for your kayaks & paddle boards has direct access to bay ...
From $295 per night (USD)
VRBO
From $460 per night (USD)
VRBO
Spacious 5-bedroom house with AC and WiFi in welcoming Tavernier
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Enjoy a peaceful stay at this 5-bedroom house in Tavernier. This superb property offers a beautiful blend of comfort and ...
From $460 per night (USD)
VRBO
From $261 per night (USD)
VRBO
Cozy Oceanfront Studio in the Heart of Islamorada.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This property sits directly behind the main oceanfront house on the same property, Your Islamorada adventure begins at t ...
From $261 per night (USD)
VRBO
From $346 per night (USD)
VRBO
Manatee Manor ~ 3 Bedroom Island Home on Plantation Key with Pool & Dockage
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Swim. Sleep. Repeat., at Manatee Manor. This 3-bedroom, 2.5-bath home on Plantation Key has something for everyone. Enjo ...
From $346 per night (USD)
VRBO
From $194 per night (USD)
Expedia
Tropical Oasis Anchor located on the bay side. Community private boat ramp.
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Tropical Oasis Anchor a Beautiful Place To Stay conveniently located just two blocks away from private community boat r ...
From $194 per night (USD)
Expedia
From $1242 per night (USD)
VRBO
Seaside Sanctuary in the Heart of Islamorada
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Nestled between the Cheeca Lodge and Caribbean Resort, discover our exclusive 4-bedroom oceanside sanctuary, delivering ...
From $1242 per night (USD)
VRBO
From $136 per night (USD)
Expedia
Marine Loft at Coconut Palm Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Marine Loft is a unique upstairs 1 bedroom/1 bath efficiency residence that accommodates 2 people. The large king b ...
From $136 per night (USD)
Expedia
From $1953 per night (USD)
VRBO
Your Idyllic Getaway Awaits! Breathtaking Beachfront, Outdoor Pool | 3 Units
Bedrooms:
6
Bathrooms:
6
Sleeps:
18
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $1953 per night (USD)
VRBO
$Three Villa w\/ Living Area & Private Patio | Close to Theater of the Sea$
From $1954 per night (USD)
VRBO
Three Villa w\/ Living Area & Private Patio | Close to Theater of the Sea
Bedrooms:
6
Bathrooms:
6
Sleeps:
18
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $1954 per night (USD)
VRBO
From $633 per night (USD)
VRBO
Southern Comfort - Charming oceanfront private oasis!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Welcome to Southern Comfort, your home away from home! Your ideal oceanfront getaway boasting 3 bedrooms and 4 baths an ...
From $633 per night (USD)
VRBO
From $331 per night (USD)
Expedia
Beautiful Home located in Venetian Shores Neighborhood
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
PROPERTY NAME: Venetian House 101 San Marco Drive, Islamorada, FL LOCATION: Bayside House MINIMUM STAY: 28 Days, All ...
From $331 per night (USD)
Expedia
$Peninsula Villa \/ Heated Pool \/ Sunset Point$
From $2156 per night (USD)
VRBO
Peninsula Villa \/ Heated Pool \/ Sunset Point
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
This grand peninsula retreat is embraced by the Ocean and lush mangroves, offering privacy to the heated pool with its t ...
From $2156 per night (USD)
VRBO
From $279 per night (USD)
VRBO
Brand New Home, Resort Location, Pet Friendly, Oceanview
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This brand new home is sitting quietly behind a controlled access gate with a private balcony overlooking the Atlantic O ...
From $279 per night (USD)
VRBO
$Spectacular 4 bedroom 4 1\/2 bath villa on Tavernier Creek in Florida Keys.$
From $1125 per night (USD)
VRBO
Spectacular 4 bedroom 4 1\/2 bath villa on Tavernier Creek in Florida Keys.
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Incomparable villa directly on Tavernier Creek with immediate access to ocean and bay. Fully fenced and gated. Manatees ...
From $1125 per night (USD)
VRBO
From $258 per night (USD)
VRBO
Brand New Home, Resort Location, Oceanview
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This brand new home is sitting quietly behind a controlled access gate with a personal view of the Atlantic Ocean. Full ...
From $258 per night (USD)
VRBO
From $230 per night (USD)
VRBO
BEAUTIFUL PLACE TO STAY!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
ONE OF "THE BEST" vacation value getaways in the Florida Keys. Packed with amenities, access to gulf side dockage, a g ...
From $230 per night (USD)
VRBO
From $351 per night (USD)
Expedia
Ocean Harbor Paradise in Islamorada
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Talk about an Atlantic Ocean View; you've found it! You will fall in love as soon as you enter the gates at Ocean Harbor ...
From $351 per night (USD)
Expedia
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VRBO
THIS is the ONE!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Perfect for the whole family! Enjoy this spacious and newly remodeled unit in a private community. Beach and pool access ...
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VRBO
From $856 per night (USD)
Expedia
Keys home overlooking the ocean and beautiful sunrises!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Beautiful oceanfront residence with pool, and modern renovations. Located in desirable Islamorada with access to a priva ...
From $856 per night (USD)
Expedia
From $319 per night (USD)
VRBO
Canal-Front Oasis in the Florida Keys
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Escape to paradise in this stunning 3-bedroom, 2-bathroom vacation home in the heart of the Florida Keys. Situated on a ...
From $319 per night (USD)
VRBO
From $212 per night (USD)
VRBO
NEW! Delightful 2 Bedroom Townhouse with Pool, Beach, Tennis Courts & More
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to paradise in this delightful 2-bedroom townhouse, nestled in the peaceful compound of Executive Bay Club. Ste ...
From $212 per night (USD)
VRBO
From $619 per night (USD)
VRBO
Bayfront Townhome with Boat Slip, Pool and Beach
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
PROPERTY NAME: Seas The Day 88540 Overseas Highway TH#701, Plantation Key, Florida LOCATION: End unit townhouse on the ...
From $619 per night (USD)
VRBO
$Seaside Serenity Coral Harbour Club 3\/2 condo, located Oceanside in Islamorada$
From $331 per night (USD)
Expedia
Seaside Serenity Coral Harbour Club 3\/2 condo, located Oceanside in Islamorada
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy gated coastal luxury while staying at “Seaside Serenity” in this beautiful Coral Harbour Club Condo (CHC) . This v ...
From $331 per night (USD)
Expedia
From $428 per night (USD)
VRBO
Ultimate Keys Oasis! 4 Bedroom, Poolside Retreat!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Indulge in the ultimate waterfront getaway at this 4-bedroom canal front, pool side oasis, conveniently located at mile ...
From $428 per night (USD)
VRBO
From $524 per night (USD)
Expedia
Isla Mamey: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $524 per night (USD)
Expedia
From $497 per night (USD)
VRBO
Isla Key Acaí: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $497 per night (USD)
VRBO
From $613 per night (USD)
Expedia
Isla Lychee: Little Basin Villas, Waterfront Boutique Resort, Walkable
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $613 per night (USD)
Expedia
From $528 per night (USD)
VRBO
Isla Kiwi: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $528 per night (USD)
VRBO
From $613 per night (USD)
Expedia
Isla Guava: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $613 per night (USD)
Expedia
From $604 per night (USD)
VRBO
Isla Key Lime: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $604 per night (USD)
VRBO
From $879 per night (USD)
VRBO
Heart of Islamorada Dream Getaway Awaits!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Get ready to experience an incredible Islamorada vacation at Maison 305, located in the heart of Islamorada, FL. This wa ...
From $879 per night (USD)
VRBO
From $3053 per night (USD)
VRBO
A Premier Oceanfront Estate in Islamorada
Bedrooms:
9
Bathrooms:
6
Sleeps:
14
Welcome to Ocean’s Edge, a premier oceanfront estate in Islamorada. Nestled along the pristine shores of the Atlantic Oc ...
From $3053 per night (USD)
VRBO
$Leisure Inn Islamorada - 3\/2 canal home on a double lot, bring all of the toys!$
From $303 per night (USD)
Expedia
Leisure Inn Islamorada - 3\/2 canal home on a double lot, bring all of the toys!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This charming Florida home is situated on a double lot with a full sea basin on an ocean side, deep water canal...second ...
From $303 per night (USD)
Expedia
From $454 per night (USD)
VRBO
Cosy Cottage in Islamorada with private garden & pool - 6 pers.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Flamingo Cottage! The pretty cottage is located in Islamorada, the heart of the Keys. A part of the interior ...
From $454 per night (USD)
VRBO
From $553 per night (USD)
Expedia
Bayberry Key: Waterfront Htd Pool, Dock, Walkable, Direct Water views!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $553 per night (USD)
Expedia
From $619 per night (USD)
VRBO
Isla Mirabelle: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $619 per night (USD)
VRBO
From $1422 per night (USD)
VRBO
Waterfront, dock, private oasis in the heart of Islamorada! Pool & Sunsets!
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
You don’t want to miss this! Old Florida charm in the heart of Islamorada on a half-acre private oasis. The Butterfly Ho ...
From $1422 per night (USD)
VRBO
From $319 per night (USD)
VRBO
The Finn in the Keys
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Finn houseboat has 1 Queen bed. This houseboat has 2 SMART flat-screen TVs and complimentary Wi-Fi. The kitchen feat ...
From $319 per night (USD)
VRBO
From $610 per night (USD)
VRBO
Islamorada Cay ~ Resort Style 4 Bed Plantation Key Home with Pool & 100' Dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Chill out in style at Islamorada Cay! This resort style, 4-bedroom, 3-bathroom canal-front property is nestled in the id ...
From $610 per night (USD)
VRBO
From $3276 per night (USD)
VRBO
Voted best boutique resort in Islamorada! Beach, dockage, pool + more!
Bedrooms:
8
Bathrooms:
8
Sleeps:
22
Located in the heart of Islamorada, Mermaid’s Bay Boutique Estate is a secluded oasis situated directly on the bay. Secu ...
From $3276 per night (USD)
VRBO
From $422 per night (USD)
Expedia
1.5 Bedroom, 1 bath with back deck. Pet friendly with 2 Queen and 2 twin beds.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Quaint Aqua Lodge located in Mangrove Marina. 1.5 bedroom, 1 bath with a back deck. With 4 beds, 2 Queens and 2 twins, ...
From $422 per night (USD)
Expedia
From $117 per night (USD)
VRBO
Charming 1 Bedroom Condo on Plantation Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Sit back and relax at Port o Palms. Experience the ultimate Florida Keys getaway at this light and bright one-bedroom, ...
From $117 per night (USD)
VRBO
From $2359 per night (USD)
VRBO
Infinity Bay Islamorada ~ Luxury 9-bed, 10-bath Bayfront Estate in Islamorada
Bedrooms:
10
Bathrooms:
9
Sleeps:
18
Welcome to Infinity Bay Islamorada, an infinite paradise with infinite possibilities in the heart of the Florida Keys. T ...
From $2359 per night (USD)
VRBO
From $1457 per night (USD)
VRBO
Luxury Oceanfront Estate in Islamorada - Your Tropical Paradise Awaits!
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Welcome to Orchid Beach, your ultimate oceanside escape! Nestled directly on the beach, this gated estate greets you wit ...
From $1457 per night (USD)
VRBO
From $570 per night (USD)
VRBO
Welcome to Our Beautiful Spacious 2 BR Home in the Heart of Islamorada, Florida
Bedrooms:
3
Bathrooms:
2
Sleeps:
8
Experience the perfect getaway in our stunning 2-bedroom home located in the vibrant heart of Islamorada, Florida. Nestl ...
From $570 per night (USD)
VRBO
From $699 per night (USD)
VRBO
Tut's Cay: 4 BR, 5.5 BA House in Tavernier, Sleeps 10
Bedrooms:
6
Bathrooms:
4
Sleeps:
10
Welcome to Tut’s Cay, an opulent 4-bedroom, 5.5-bathroom sanctuary nestled in the heart of Islamorada within the captiva ...
From $699 per night (USD)
VRBO
From $437 per night (USD)
VRBO
Port Antigua Home in a Private Beach & Golf Cart Community
Bedrooms:
4
Bathrooms:
5
Sleeps:
15
Our relaxing 3 STORY, 4 bedroom, 3.5 bathroom home is located in Islamorada, Florida within the Private Beach community ...
From $437 per night (USD)
VRBO
From $238 per night (USD)
VRBO
Gorgeous Beach Bungalow Just Steps from Private Sandy Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
You have found a sandy beach paradise in the Florida Keys! Located just 4 houses from a secret, sandy beach, Little Pea ...
From $238 per night (USD)
VRBO
From $241 per night (USD)
Expedia
Islamorada Slice of Paradise with private beach and glorious sunsets!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautifully decorated townhome community located right next door to Founder’s Park in Islamorada. This community offer ...
From $241 per night (USD)
Expedia
From $520 per night (USD)
VRBO
Sunset Peninsula—a multi-family, original, Florida Keys waterfront retreat!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Welcome to the Sunset Peninsula! This gated, multi-family compound is perfect for those traveling in larger groups with ...
From $520 per night (USD)
VRBO
From $694 per night (USD)
Expedia
PARADISE SHORES
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
You won't be disappointed once you arrive at Paradise Shores. This completely remodeled Venetian Shores 4 BD / 3 BA cana ...
From $694 per night (USD)
Expedia
From $432 per night (USD)
VRBO
Islamorada's Premier Boating Neighborhood; Venetian Shores. A boaters paradise.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled within the serene surroundings of Islamorada, Florida, awaits a charming oasis at 116 Stromboli Drive. This sing ...
From $432 per night (USD)
VRBO
From $562 per night (USD)
Expedia
Isla Honeydew: 3 En-Suite Bedrooms! Waterfront Resort, Pool, Dock!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $562 per night (USD)
Expedia
Click For Pricing
VRBO
Luxury One Bedroom Condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
One Bedroom, One Bathroom Condo, Separate Living Space and Fully Equipped Kitchen. Outdoor Fire pit under palm trees w ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Luxury One Bedroom Condo #3
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
One Bedroom, One Bathroom Condo, Separate Living Space and Fully Equipped Kitchen. Outdoor Fire pit under palm trees w ...
Click For Pricing
Expedia
$\Luxurious Open Bay Retreat: Expansive Dockage & Private Pool Oasis!$
From $1865 per night (USD)
VRBO
\"Luxurious Open Bay Retreat: Expansive Dockage & Private Pool Oasis!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Discover your dream vacation at Pirate's Chateau, nestled in the pristine Venetian Shores on the open bay. This luxuriou ...
From $1865 per night (USD)
VRBO
From $1415 per night (USD)
VRBO
Coastal Retreat in the Heart of Islamorada
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Nestled between the Cheeca Lodge and Caribbean Resort, our 4-bedroom oceanside home offers a unique beachfront experienc ...
From $1415 per night (USD)
VRBO
From $405 per night (USD)
VRBO
4-bedroom airport community house in Tavernier
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
*MORE PHOTOS TO COME AFTER RENOVATIONS* Experience Tavernier like a local in this 4-bedroom house. Step into a wonderful ...
From $405 per night (USD)
VRBO
From $1138 per night (USD)
VRBO
Maison 402 Island Charm
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Welcome to Maison 402 Island Charm, your perfect vacation retreat in the heart of Islamorada! This charming 3-bedroom, 3 ...
From $1138 per night (USD)
VRBO
From $136 per night (USD)
VRBO
Ocean front property
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
2 bedroom, 1 and a half two story Condo. Kitchen, living area, private parking, barbecue area, recreational room, in a ...
From $136 per night (USD)
VRBO
From $1558 per night (USD)
VRBO
Oceanfront Estate in the Heart of Islamorada
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Welcome to Morada Shores, an exquisite estate where every detail has been carefully crafted for the ultimate vacation ex ...
From $1558 per night (USD)
VRBO
From $694 per night (USD)
VRBO
4-bedroom house in Islamorada, The Sportfishing Capital of the World
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
You won't be disappointed once you arrive at Paradise Shores. This completely remodeled Venetian Shores 4 BD / 3 BA cana ...
From $694 per night (USD)
VRBO
From $1449 per night (USD)
VRBO
Luxury Oceanfront Oasis With Deep Water Dockage!
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Experience the ultimate coastal getaway at this spectacular 5 bedroom, 5.5 bathroom oceanfront home, complete with deep ...
From $1449 per night (USD)
VRBO
From $1255 per night (USD)
VRBO
Casa del Mar - MONTHLY RENTALS AND DISCOUNTS FOR LONGER STAYS AUG-DEC
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Nestled in the heart of Islamorada you will find large outdoor spaces with outdoor dining and private lounge areas with ...
From $1255 per night (USD)
VRBO
From $342 per night (USD)
VRBO
Beachside Topsider Octagon Pad
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
At Topsider Resort, you’ll be staying in our unique octagonal stilted homes nestled in a lush tropical setting facing di ...
From $342 per night (USD)
VRBO
From $452 per night (USD)
VRBO
The Reef House, Waterfront, Oceanside, 70' Dock, Heated Pool and Spa Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Reef House! This ideal location allows for direct, bridge-free access to the Atlantic Ocean or bayside via Ta ...
From $452 per night (USD)
VRBO
$Exec Bay 3 Bedroom townhouse w\/heated pool, marina, tennis & more$
From $244 per night (USD)
Expedia
Exec Bay 3 Bedroom townhouse w\/heated pool, marina, tennis & more
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Come and experience the beauty and tranquility of the Florida Keys at Executive Bay Club! Enjoy gorgeous sunsets from th ...
From $244 per night (USD)
Expedia
$Islamorada waterfront gem: Total reno ‘24: 3\/3.5, pool, spa & deep water dock.$
From $696 per night (USD)
VRBO
Islamorada waterfront gem: Total reno ‘24: 3\/3.5, pool, spa & deep water dock.
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Lower Matecumbe generally, and Sapodilla Drive specifically, is an idyllic location in Islamorada. Only five miles to ev ...
From $696 per night (USD)
VRBO
$Ocean View Beautifully Remodeled 2\/2 at Seagulls$
Click For Pricing
Expedia
Ocean View Beautifully Remodeled 2\/2 at Seagulls
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful ocean views, spacious interior, and recent renovations of the condo make it the perfect place for Florida Keys ...
Click For Pricing
Expedia
From $231 per night (USD)
VRBO
Charming 2-bedroom townhome with WiFi, AC in enjoyable Islamorada
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Your Islamorada adventure begins at this 2-bedroom townhome. Inside, guests will find a delightful mix of comfort and st ...
From $231 per night (USD)
VRBO
From $230 per night (USD)
Expedia
Charming 2-bedroom house in welcoming Islamorada with WiFi, AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This brilliant house in Islamorada is a wonderful choice for guests seeking a cozy retreat. With 2 bedrooms, 2 bathrooms ...
From $230 per night (USD)
Expedia
From $304 per night (USD)
VRBO
NEW! Boater's Paradise with Boat Lift, Ice Machine, and Screened Porch
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This cozy haven is perfect for a laid-back Keys getaway centered around boating and fishing. Nestled in the heart of Tav ...
From $304 per night (USD)
VRBO
From $286 per night (USD)
VRBO
NEW! Canal-Front with Tropical Charm & Private Guest Apartment on Plantation Key
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Manatee Manor! Nestled in the desirable Indian Waterways neighborhood on Plantation Key, this charming canal- ...
From $286 per night (USD)
VRBO
$Executive Bay Club R8 ~ 3 Bed \/ 3 Bath + Loft Townhouse on Plantation Key$
From $238 per night (USD)
VRBO
Executive Bay Club R8 ~ 3 Bed \/ 3 Bath + Loft Townhouse on Plantation Key
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Discover your ideal getaway at this charming seascape in Islamorada! This lovely 3-bedroom, 3-bathroom townhome, complet ...
From $238 per night (USD)
VRBO
From $379 per night (USD)
Expedia
Escape to beautiful Islamorada!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Located 90 minutes from Miami and 20 minutes to the world-famous Tiki Bar sandbar (dock to anchor) one of the best in ...
From $379 per night (USD)
Expedia
From $201 per night (USD)
VRBO
Charming 3-bedroom house with private beach access in beautiful Islamorada
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bask in the warmth of Islamorada Florida with this 3-bedroom, 2-bath home. 90 minutes from Miami and ½ way down the Flor ...
From $201 per night (USD)
VRBO
From $366 per night (USD)
VRBO
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $366 per night (USD)
VRBO
From $213 per night (USD)
VRBO
Amazing new 2-bedroom, 2-bathroom apartment in the heart of Islamorada!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Islamorada apartment boasts 2 inviting bedrooms with 2 queen beds. The cozy living room also offers an extra queen ...
From $213 per night (USD)
VRBO
$Canal front pool home in Florida key's Islamorada! Access to ocean w\/boat lift!!$
From $628 per night (USD)
Expedia
Canal front pool home in Florida key's Islamorada! Access to ocean w\/boat lift!!
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Luxury Waterfront Vacation Home in Islamorada Escape to paradise in this stunning waterfront vacation home located in t ...
From $628 per night (USD)
Expedia
From $276 per night (USD)
VRBO
Coral Harbour Club ~ 2 Bedroom Condo in Islamorada with Pool & Dockage
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Coral Harbour Club! Find your escape, experience relaxing days at this oceanside getaway! Located on Planta ...
From $276 per night (USD)
VRBO
From $399 per night (USD)
Expedia
Modern ground-floor apartment with pool, water views, patio, grill, & central AC
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Treasure Harbor Hideaway - Lower Our calendar is updated in real-time & our nightly rates are accurately displayed. Sim ...
From $399 per night (USD)
Expedia
From $649 per night (USD)
VRBO
Deluxe upper apartment with pool, canal-view balcony, water access, grill, & AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Treasure Harbor Hideaway - Upper Our calendar is updated in real-time & our nightly rates are accurately displayed. Sim ...
From $649 per night (USD)
VRBO
From $875 per night (USD)
VRBO
Oceanfront Oasis in Angler’s Reef with Private Boat Slip
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Escape to this laid-back, oceanfront townhouse in Angler’s Reef, where coastal vibes and easy living come together in th ...
From $875 per night (USD)
VRBO
From $284 per night (USD)
VRBO
Charming canal front with Ocean access 2-bedroom house in peaceful Tavernier
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located in Tavernier, enjoy what this 2-bedroom, 2 bathrooms house has to offer. This perfect and peaceful retreat featu ...
From $284 per night (USD)
VRBO
From $251 per night (USD)
Expedia
Beautiful Home located in Downtown Islamorada
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
PROPERTY NAME: Mango House 81212 Old Highway Islamorada, Florida Location: Ocean side located on the Old Road by Gree ...
From $251 per night (USD)
Expedia
From $3282 per night (USD)
VRBO
Entire Floor - 8 BR overlooking pool, sandy beach & Ocean! Luxury finishings
Bedrooms:
9
Bathrooms:
8
Sleeps:
16
Introducing Maison Residences Full floor for rent – Oceanfront & Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE — ...
From $3282 per night (USD)
VRBO
From $652 per night (USD)
VRBO
Morada Breeze ~ 6 Bedroom Plantation Key Home with Pool & Dockage
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Welcome to Morada Breeze! This 6-bedroom, 4-bath bayside slice of paradise is ready to make your next vacation an enjoya ...
From $652 per night (USD)
VRBO
$Morada Zen - 4BR\/3Bath Waterfront Ocean & Bay Access, Pool, Tiki, Dockage$
From $659 per night (USD)
VRBO
Morada Zen - 4BR\/3Bath Waterfront Ocean & Bay Access, Pool, Tiki, Dockage
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Islamorada Florida - Fishing Capital of the World!! Beautiful 4 bedroom, 3 bath home available for monthly rental (28 da ...
From $659 per night (USD)
VRBO
From $1175 per night (USD)
Expedia
Oceanfront 3 bedroom with dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Behold this exquisite oceanfront pool residence, which has been flawlessly renovated. Nestled in a remarkable location w ...
From $1175 per night (USD)
Expedia
From $823 per night (USD)
VRBO
Coastal Retreat! Pool, Pets Allowed, Minutes to Indian Key Historic State Park
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Stay close to Florida Keys Brewing Co. and Bud n' Mary's Dive Center. Explore Indian Key Historic State Park and dive in ...
From $823 per night (USD)
VRBO
$Oceanfront Property w\/ Outdoor Pools, Pets Allowed, Free Parking Onsite$
From $1185 per night (USD)
VRBO
Oceanfront Property w\/ Outdoor Pools, Pets Allowed, Free Parking Onsite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay close to Florida Keys Brewing Co. and Bud n' Mary's Dive Center. Explore Indian Key Historic State Park and dive in ...
From $1185 per night (USD)
VRBO

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