Islamorada Rentals
From $940 per night (USD)VRBO
Making The Best Memories Along The Way! 4 Comfortable Units, FREE Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $940 per night (USD)VRBO
From $408 per night (USD)VRBO
Vacation At its Finest! 2 Convenient Units, Free Parking, Breakfast, Onsite Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $408 per night (USD)VRBO
From $619 per night (USD)VRBO
Best Place to Stay in Florida! 3 Pet-Friendly Units, Free Breakfast, Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $619 per night (USD)VRBO
From $411 per night (USD)VRBO
Get Ready for Blissful Getaway! 2 Relaxing Units, Onsite Pool, Free Breakfast
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $411 per night (USD)VRBO
From $705 per night (USD)VRBO
3 Relaxing Units! FREE Breakfast, FREE Parking, Onsite Pool, Pets Allowed!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $705 per night (USD)VRBO
From $813 per night (USD)VRBO
Snorkeling & Kayaking Beach Resort! Seaside Villa w/Patio! Marina, Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $813 per night (USD)VRBO
From $937 per night (USD)VRBO
Your Home Away From Home! 4 Relaxing Units, FREE Parking, Onsite Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $937 per night (USD)VRBO
From $322 per night (USD)VRBO
Family Escape in Islamorada! Seaside Unit w/ Balcony! Water Sports Equipment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $322 per night (USD)VRBO
From $339 per night (USD)VRBO
Premium Units w/ Ocean Views & Balcony! Marina, Pets Allowed, Beach Access!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $339 per night (USD)VRBO
From $208 per night (USD)VRBO
Sportfishing in Florida Keys! FREE Parking, Pets Allowed, Pool, Bike Rentals!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $208 per night (USD)VRBO
From $288 per night (USD)VRBO
Spacious Villa! Private Beach Access, Pets Allowed, Bike Rentals!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $288 per night (USD)VRBO
From $296 per night (USD)VRBO
Classic Villa w/ Ocean View & Balcony! Beach Access, FREE Parking & Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $296 per night (USD)VRBO
From $296 per night (USD)VRBO
Family Fun at Islamorada! Large Villa, FREE Parking & Breakfast, Heated Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $296 per night (USD)VRBO
From $288 per night (USD)VRBO
Sportfishing in Florida Keys! Large Unit w/ Private Beach Access! Pool, Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $288 per night (USD)VRBO
From $296 per night (USD)VRBO
Relax and Unwind Near Robbie's of Islamorada! FREE Parking & Breakfast, Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $296 per night (USD)VRBO
From $315 per night (USD)VRBO
Sportfishing in Florida Keys! Elegant Villa w/ Beach Access and Pool! Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $315 per night (USD)VRBO
From $208 per night (USD)VRBO
Kayak in Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Kayak
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $208 per night (USD)VRBO
From $339 per night (USD)VRBO
Spacious Unit w/ Kitchenette & Balcony! Marina, Pets Allowed, Bike Rentals!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $339 per night (USD)VRBO
From $288 per night (USD)VRBO
Snorkeling in Islamorada! Premium Villa, Bike Rentals & Water Sports Equipment!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $288 per night (USD)VRBO
From $323 per night (USD)VRBO
Steps to Windley Key! Pet-friendly Villa! Marina, FREE Parking, Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $323 per night (USD)VRBO
From $234 per night (USD)VRBO
Beach View Unit in Islamorada! Pets Allowed, Parking, Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $234 per night (USD)VRBO
From $234 per night (USD)VRBO
Snorkeling & Kayaking Beach Resort! Seaside Villa w/Patio! Marina, Pool, Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $234 per night (USD)VRBO
From $208 per night (USD)VRBO
Discover Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Parking, Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $208 per night (USD)VRBO
From $234 per night (USD)VRBO
Swim with Dolphins in the Florida Keys! FREE Breakfast & Parking, Marina, Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $234 per night (USD)VRBO
From $247 per night (USD)VRBO
Seaside Villas w/ Ocean Views & Front Porch! Marina, Pets Allowed, Bike Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $247 per night (USD)VRBO
From $247 per night (USD)VRBO
Steps to Windley Key! 3 Pet-friendly Units w/ Balcony! Beach Access & Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $247 per night (USD)VRBO
From $259 per night (USD)VRBO
Swim with Dolphins in the Florida Keys! FREE Breakfast & Parking, Marina, Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $259 per night (USD)VRBO
From $259 per night (USD)VRBO
Snorkel and Kayak in Islamorada! Unit w/ Balcony! Pets Allowed, FREE Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $259 per night (USD)VRBO
From $247 per night (USD)VRBO
Exquisite Unit w/ Balcony and Kitchenette! Pool Pets Allowed, Bike Rental!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $247 per night (USD)VRBO
From $259 per night (USD)VRBO
Florida Keys Tour! Private Beach Access with Marina! Pets Allowed, FREE Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $259 per night (USD)VRBO
From $468 per night (USD)VRBO
Make Your Trip More Enjoyable! 2 Convenient Units, Pets Allowed, Onsite Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $468 per night (USD)VRBO
From $408 per night (USD)VRBO
Better Choice for your Vacation! 2 Pet-Friendly Units, Free Breakfast, Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $408 per night (USD)VRBO
From $703 per night (USD)VRBO
Everything You Need For The Perfect Vacation! 3 Convenient Units, FREE Parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $703 per night (USD)VRBO
From $469 per night (USD)VRBO
Escape The Hustle and Bustle! 2 Classy Units, Free Parking, Onsite Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $469 per night (USD)VRBO
From $940 per night (USD)VRBO
Vacation Day Is Always A Great Idea! 4 Classy Units, FREE Parking, Pets Allowed!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $940 per night (USD)VRBO
From $350 per night (USD)Expedia
Beautiful Water Views from every room in the House
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
PROPERTY NAME: Harbor House 101 San Juan Dr., Islamorada, FL LOCATION: Bayside Canal home located in the Upscale Veneti ...
From $350 per night (USD)Expedia
From $385 per night (USD)VRBO
2BR/2.5BA Angler's Reef Cottage 116 With Private Beach and Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Check out our video tour! All NEW Anglers Reef Villa 116, a modern beach retreat offering relaxation at its finest. Our ...
From $385 per night (USD)VRBO
From $388 per night (USD)Expedia
2BR/2.5BA Angler's Reef Conch Villa 103 With Private Beach and Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
In the heart of the Florida Keys - Islamorada - an ancient reef awaits your arrival, where its waters brim with earth's ...
From $388 per night (USD)Expedia
From $1430 per night (USD)VRBO
Beautiful Ocean Front Beach House in Islamorada.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
Beautiful Ocean Front Beach House in the sport fishing capitol of the world Islamorada. Beach with a 200 foot fishing pi ...
From $1430 per night (USD)VRBO
From $248 per night (USD)VRBO
“ The Ultimate redneck” boat experience
- Bedrooms:
- 0
- Bathrooms:
- 1
- Sleeps:
- 2
Are you ready for modern day pirate life ? Wonder how the locals live ? Well then we can show you ! Redneck paradise, Pr ...
From $248 per night (USD)VRBO
From $353 per night (USD)VRBO
Isla Honeydew: 3 En-Suite Bedrooms! FREE boat dockage Sept-Oct only
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $353 per night (USD)VRBO
From $476 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 $476 per night (USD)Expedia
From $922 per night (USD)VRBO
SPECTACULAR MONTH RENTAL DISCOUNT & ON ADDITIONAL WEEK FOR WEEKLY RENTAL.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Remarkable home nestled in the heart of Islamorada where you will find large outdoor spaces with outdoor dining and priv ...
From $922 per night (USD)VRBO
From $424 per night (USD)VRBO
Sunset Views and Serenity! Outdoor Pool, Free Parking, Near Hurricane Monument
- 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 $424 per night (USD)VRBO
From $1651 per night (USD)VRBO
Isla Sunset Collection: Sleeps 18, All Ensuite Bedrooms, Waterfront
- Bedrooms:
- 10
- Bathrooms:
- 9
- Sleeps:
- 18
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $1651 per night (USD)VRBO
From $2109 per night (USD)Expedia
Isla Sands Collection: Sleeps 24, All Ensuite Bedrooms, Waterfront
- Bedrooms:
- 14
- Bathrooms:
- 12
- Sleeps:
- 24
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $2109 per night (USD)Expedia
From $1175 per night (USD)VRBO
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)VRBO
From $730 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 $730 per night (USD)VRBO
From $529 per night (USD)VRBO
Charming house boat with 2 bedrooms and WiFi, AC in wonderful Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This amazing house boat in Islamorada is a unique and pleasant retreat for guests. With 2 cozy bedrooms and a comfortabl ...
From $529 per night (USD)VRBO
From $560 per night (USD)VRBO
Green Coconut, Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Mile Marker 80 – Heart of Islamorada Located on scenic Old Highway, this inviting Islamorada retreat offers the perfect ...
From $560 per night (USD)VRBO
From $1347 per night (USD)VRBO
BeachFront Paradise/By The Glam Homes
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 15
Summary: This is a truly unique and spectacular Villa thanks to its breathtaking view of the sea and its warm sandy beac ...
From $1347 per night (USD)VRBO
From $383 per night (USD)Expedia
3-bedroom cozy pool home in exclusive Venetian Shores, Islamorada .
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover tranquility at our Venetian Shores Escape, Islamorada. Nestled in a serene neighborhood, this property boasts ...
From $383 per night (USD)Expedia
From $313 per night (USD)VRBO
Studio, Second Floor Partial Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Perched on the second floor with partial side views, this charming studio is perfect for a cozy getaway in the heart of ...
From $313 per night (USD)VRBO
From $226 per night (USD)Expedia
3-bedroom townhome in charming Islamorada with AC, WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to your dream getaway! This stunning fully renovated 3-bedroom, 2.5-bathroom townhouse in a gated marina commun ...
From $226 per night (USD)Expedia
From $626 per night (USD)VRBO
Oceanfront Islamorada Townhome- Private Dock, Pool & Pet-Friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to your oceanfront Florida Keys vacation rental in the heart of Islamorada! This luxury 3-bedroom, 3-bath townho ...
From $626 per night (USD)VRBO
From $830 per night (USD)VRBO
Come Create Memories w/ Fun-filled Adventures at this Paradise! Outdoor Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $830 per night (USD)VRBO
From $227 per night (USD)VRBO
Beautiful Home in a Great Neighborhood with Ocean Access and Boat Ramp on Property
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
PROPERTY NAME: Fisherman's Gem 113 Iroquois Drive Islamorada, Florida LOCATION: Oceanside Canal home with Boat dock a ...
From $227 per night (USD)VRBO
From $526 per night (USD)Expedia
Ocean View Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key Two
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Indulge in the epitome of coastal living in this expansive duplex penthouse boasting ocean views in Islamorada. Relish c ...
From $526 per night (USD)Expedia
From $395 per night (USD)VRBO
Waterfront Retreat Perfect Romantic Couple Getaway | Free Parking and Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $395 per night (USD)VRBO
From $1084 per night (USD)Expedia
Breathtaking Marina View Room w/ Balcony | 2 Family Ready Rooms w/ Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $1084 per night (USD)Expedia
From $338 per night (USD)VRBO
Ultimate Beach Relaxation: Resort w/ Marina and Outdoor Pool | Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $338 per night (USD)VRBO
From $1274 per night (USD)Expedia
Family Beach Getaway | 3 Relaxing Rooms w/ Balcony
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $1274 per night (USD)Expedia
From $2159 per night (USD)VRBO
4 Scenic Marina View Rooms w/ Balcony | Refreshing Outdoor Pool & Free Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $2159 per night (USD)VRBO
From $1465 per night (USD)Expedia
4 Family-friendly Rooms w/ Balcony | Refreshing Outdoor Pool & Free Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $1465 per night (USD)Expedia
From $961 per night (USD)VRBO
Beach Getaway: Room with Access to Pristine Sands | 2 Relaxing Rooms
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $961 per night (USD)VRBO
From $1099 per night (USD)Expedia
Beachside Solace: Room for Your Perfect Vacation |
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $1099 per night (USD)Expedia
From $1099 per night (USD)VRBO
Beachside Solace: Room for Your Perfect Vacation |
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $1099 per night (USD)VRBO
From $682 per night (USD)Expedia
Beachfront Stay Perfect for Island Couple Retreat | Suite w/ Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $682 per night (USD)Expedia
From $397 per night (USD)VRBO
Beachfront Room with Private Access & Breathtaking Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $397 per night (USD)VRBO
From $501 per night (USD)Expedia
Beachfront Retreat in the Heart of Islamorado | Spacious Room w/ Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $501 per night (USD)Expedia
From $425 per night (USD)VRBO
Marina Room with Direct Beach Access | Islamorado Ultimate Retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $425 per night (USD)VRBO
From $480 per night (USD)Expedia
Island Getaway: Relaxing Room w/ Balcony Steps to Sandy Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $480 per night (USD)Expedia
From $732 per night (USD)VRBO
Beach Getaway: Room with Access to Pristine Sands | 2 Relaxing Rooms
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $732 per night (USD)VRBO
From $705 per night (USD)VRBO
Ultimate Islamorada Oasis with Pool, Dock, & More
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 4
Welcome to your own island oasis! This beautiful 4-bedroom, 3-bathroom canal-front home blends luxurious coastal modern ...
From $705 per night (USD)VRBO
From $1474 per night (USD)VRBO
Stunning Bayfront Home with Pool & Dockage in Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Grab a margarita and unwind at Marchettiville! This stunning 5-bedroom, 3-bathroom oceanfront property offers private b ...
From $1474 per night (USD)VRBO
From $1455 per night (USD)VRBO
Bayfront Bliss in Lower Matecumbe – 4BR/3.5BA with Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to paradise at this stunning bayfront home in Lower Matecumbe, Islamorada. With breathtaking open bay views, a pr ...
From $1455 per night (USD)VRBO
From $180 per night (USD)VRBO
Classic 2 bedroom, 2 Bath Islamorada Home with Dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
** 60 day minimum in peak season (January- March) Enjoy the timeless charm of Old Salt Retreat. This cozy and classic ...
From $180 per night (USD)VRBO
From $625 per night (USD)VRBO
Galleon Cove, Islamorada
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
This stunning 5-bedroom, 4-bath canal-front getaway has everything you need for the perfect Florida Keys escape—private ...
From $625 per night (USD)VRBO
From $339 per night (USD)VRBO
SEASONAL WATERFRONT RENTAL in Venetian Shores, Islamorada, Pool & New Dock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
After a few years of construction, Morada Breeze , Venetian Shore's Waterfront Paradise is back and better than ever. ...
From $339 per night (USD)VRBO
From $317 per night (USD)VRBO
Oceanfront Condo with Amenities Galore & Perfect Islamorada Location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ocean Harbour Awaits – Your Perfect Islamorada Escape This beautiful 3-bedroom, 2-bath oceanfront condo boasts a luxu ...
From $317 per night (USD)VRBO
From $345 per night (USD)VRBO
Island Sanctuary Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Stay aboard the eco-friendly two-story 63 ft River Queen with a 360 degree view with beautiful sunrises and sets, mored ...
From $345 per night (USD)VRBO
From $805 per night (USD)Expedia
NEW! 🏆 Panoramic Oceanfront Bliss 🌊, Gameroom 🏓, Boat Dockage 🚤: 🌴Paradise Palms
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
🌊 Your Ultimate Oceanfront Escapes – Unmatched Panoramic Views. 🌊 ✅ NEW TO THE MARKET! ✅ Indulge at Paradise Palms, ...
From $805 per night (USD)Expedia
From $356 per night (USD)VRBO
108 Anglers Reef Islamorada 31' BOAT SLIP AVAILABLE
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful Key West Style home 2 BR 2 BA (en suites) + 1 HF BA Sleeps 6 Islamorada Vacation rental #24-3018 108 Anglers ...
From $356 per night (USD)VRBO
From $817 per night (USD)VRBO
Snorkeling & Kayaking Beach Resort! Seaside Villa w/Patio! Marina, Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $817 per night (USD)VRBO
From $206 per night (USD)VRBO
Coconut Palm Inn Beachfront Hideway's Harborview House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 3 bedroom, 2 bathroom Key Largo vacation rental's layout is a perfect setting to enjoy the Florida Keys on your ter ...
From $206 per night (USD)VRBO
From $813 per night (USD)VRBO
Snorkeling & Kayaking Beach Resort! Seaside Villa w/Patio! Marina, Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $813 per night (USD)VRBO
From $619 per night (USD)VRBO
Convenient Location! 3 Convenient Units, Pool, Pet-Friendly, Free Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $619 per night (USD)VRBO
From $469 per night (USD)VRBO
Pets are Allowed Here! 2 Comfortable Units, Free Breakfast, Parking, Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $469 per night (USD)VRBO
From $746 per night (USD)VRBO
4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful 4-bedroom, 3.5 bath home in Angler's Reef. Located at MM85, this tastefully decorated, open floor plan feature ...
From $746 per night (USD)VRBO
From $379 per night (USD)VRBO
Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $379 per night (USD)VRBO
From $380 per night (USD)VRBO
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $380 per night (USD)VRBO
From $227 per night (USD)VRBO
Just What You Were Looking For! Free Breakfast, Onsite Pool, Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $227 per night (USD)VRBO
From $228 per night (USD)VRBO
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $228 per night (USD)VRBO
From $228 per night (USD)VRBO
Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $228 per night (USD)VRBO
From $414 per night (USD)VRBO
Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to island time at beautiful Anglers Reef, the perfect way to experience and relax in the Florida Keys. Our hom ...
From $414 per night (USD)VRBO
From $1384 per night (USD)VRBO
Islamorada Oceanfront Estate, Pool, Beach Cottages-- Sea Ranch -- Florida Keys
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Island Villa Rental Properties offers this two adorable, private cottages right on the Atlantic Ocean. Located in the he ...
From $1384 per night (USD)VRBO
From $335 per night (USD)VRBO
Ocean View with protected dock on lagoon with private boat ramp
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Large 3/2 with ground level carport. Lagoon side screened porch 50' x 10'. Terrace on Ocean side is open. Boat acces ...
From $335 per night (USD)VRBO
From $512 per night (USD)Expedia
Oceanfront Penthouse w with Gigantic Ocean Views! Like a private resort!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3/2 2100+ sf penthouse with ocean views from all main rooms and bedrooms! This is it! Newly available. Forget your wo ...
From $512 per night (USD)Expedia
From $829 per night (USD)VRBO
Paradise Awaits!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Beautiful canal front Tavernier, FL home with minutes to the bay and easy ocean access through Tavernier Creek. Newly re ...
From $829 per night (USD)VRBO
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Safety harbor seasonal fishing getaway with room for 12
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 15
Private fortress-like vacation home in coveted Safety Harbor Lower Matecumbe Key of the Village of Islamorada. 100 ft o ...
Click For PricingExpedia