Islamorada Rentals
From $545 per night (USD)VRBO
Islamorada-Anglers Reef-LARGE\/updated\/Views DOCKAGE AVAILABLE
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Village of Islamorada license #24-0370 138 Anglers Way and boat slip #1 for 26' max boat length for this slip (extra fee ...
From $545 per night (USD)VRBO
From $457 per night (USD)Expedia
132 Anglers Reef Islamorada- POOL, DOCK, BIKES INCL
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
VR License #24-4011 132 Anglers Way is an Adorable Key West style home in Anglers Reef. Small gated community located a ...
From $457 per night (USD)Expedia
From $722 per night (USD)VRBO
3BR2.5BA OceanFRONT HOME-PanoramicOceanViews-HugeDecks-Quiet Location-Optl Slip
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
THERE ARE SOME HOMES WITH OCEAN PEEKS OR PARTIAL VIEWS THRU THE TREES, BUT FOR PANORAMIC UNOBSTRUCTED OCEAN VIEWS - FROM ...
From $722 per night (USD)VRBO
From $469 per night (USD)Expedia
Relax in this beautiful townhome overlooking the sparkling Atlantic Ocean
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Windy Cove #1 - Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo feat ...
From $469 per night (USD)Expedia
From $511 per night (USD)VRBO
Anglers Reef- Family Friendly Community at a Fraction of the Cost.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
This Property is fully insured for rentals and licensed by the Village of Islamorada, license #24-0318. Welcome to 134 ...
From $511 per night (USD)VRBO
From $462 per night (USD)Expedia
Charming 2 Bedroom House at Angler's Reef
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Angler's Reef #118 - Angler's Reef is a beautiful oceanfront gated community located in Islamorada. This modern updated ...
From $462 per night (USD)Expedia
From $187 per night (USD)VRBO
Spectacular Top Floor Oceanfront View Condo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Do everything or nothing at all - the heart of the Florida Keys on Plantation Key, FL - sport fishing and diving capital ...
From $187 per night (USD)VRBO
From $1292 per night (USD)Expedia
Alligator Reef Conch & Lobster Homes, a special slice of paradise
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Conch & Lobster Homes - Alligator Reef is a truly special slice of paradise with two individual homes nestled on a priva ...
From $1292 per night (USD)Expedia
From $454 per night (USD)VRBO
Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef (Unit # 114) at mile marker 85 in Isl ...
From $454 per night (USD)VRBO
From $106 per night (USD)VRBO
ISLAMORADA AFFORDABLE 2023 2\/2\n Ocean Views\nNeighborhood jetty & tiki -sunsets\n
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Islamorada- Windley Key ,affordable 2 / 2 bath new 2023 Steps away from the gorgeous turquoise ocean. Bayside is also v ...
From $106 per night (USD)VRBO
From $666 per night (USD)VRBO
Front Row, DIRECT Ocean\/Pool Views, Anglers Reef, Islamorada. Boat Dock, Beach
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Paradise is only a click away. Our 2 BR/2.5 BA conch style townhouse is available for weekly and monthly vacation renta ...
From $666 per night (USD)VRBO
From $930 per night (USD)Expedia
Anglers Reef Direct Ocean, 4 bedroom, Dock, Comm Pool & Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Direct OCEANFRONT home with HEATED POOL, BOAT SLIP, & BEACHES in the desirable Anglers Reef Community. This 4 bedroom, 3 ...
From $930 per night (USD)Expedia
From $317 per night (USD)VRBO
Incredible Bayside Home in the Florida Keys!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
**To our guests** Nautilus Getaway has always been proud to utilize a contact-less check in process. We use CDC recommen ...
From $317 per night (USD)VRBO
From $199 per night (USD)Expedia
Charming 2 Bedroom Condo in Wonderful Beacon Reef
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beacon Reef 404 - Beautiful two-bedroom two baths, condo with everything that you need for a perfect relaxing vacation. ...
From $199 per night (USD)Expedia
From $380 per night (USD)VRBO
Waterfront Sunset View Aqua Villa Dolphin @ Mangrove Marina Resort
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
The Dolphin houseboat has 1 Queen bed, 1 Queen sofa sleeper and 2 Twin beds in the loft. Each houseboat has flat-screen ...
From $380 per night (USD)VRBO
From $199 per night (USD)Expedia
Ocean Views from Balcony, Living Room and Bedroom. Islamorada License 24-0380
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
The major reconstruction projects are finally complete. The game room, gym, pool, lobby, elevators and grounds are built ...
From $199 per night (USD)Expedia
From $1025 per night (USD)VRBO
Alligator Reef Conch House, a special slice of paradise
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Alligator Reef - Conch Home - Alligator Reef is a truly special slice of paradise with two individual homes nestled on a ...
From $1025 per night (USD)VRBO
From $453 per night (USD)Expedia
Anglers Reef Islamorada Ocean Views DOCK Beach Pool Boat Slip NO ROAD NOISE!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
INTERIOR LOT—-NO ROAD NOISE—-BOAT SLIP AVAILABLE———Interior Painted Jan 2024---New Furniture in Family Room---Beautifull ...
From $453 per night (USD)Expedia
From $433 per night (USD)VRBO
Anglers Reef Islamorada 2\/2.5 DOCK AVAILABLE Bikes, Kayak available, Pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Village of Islamorada Vacation Rental license #24-0372. 113 Anglers Way Call Jennifer for more information 305-240-0592. ...
From $433 per night (USD)VRBO
From $408 per night (USD)Expedia
Anglers Reef Islamorada, Bikes,Kayak,Paddle Boards DOCK available-Pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
112 Anglers Way Islamorada Village vacation rental #24-0371 Call me for more information 305-240-0592. (2 houses side b ...
From $408 per night (USD)Expedia
From $461 per night (USD)VRBO
Anglers Reef Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
2 Bed & 2.5 Bath Villa in Anglers Reef .Upscale gated community with resort living in the Florida Keys. Everything you n ...
From $461 per night (USD)VRBO
From $599 per night (USD)Expedia
Breathtaking Bay Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
76004 Overseas Highway - Enjoy spectacular sunsets while drinking an iced cold beverage on the observation deck of this ...
From $599 per night (USD)Expedia
From $354 per night (USD)VRBO
Waterfront Sunset View in the Aqua Villa Sand Dollar @ Mangrove Resort LLC
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
The Sand Dollar houseboat has 1 Queen bed, 1 Queen sofa sleeper and 2 Twin beds in the loft. Each house boat has flat-sc ...
From $354 per night (USD)VRBO
From $279 per night (USD)Expedia
SPECTACULAR OCEANFRONT VIEWS , FREE WIFI, HD SMART TV'S, SUMMER SPECIAL RATES
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
OCEAN VIEWS EVERYWHERE in this Gorgeous 2 Bedroom/2bath Apartment overlooking the ATLANTIC OCEAN on next to top floor!! ...
From $279 per night (USD)Expedia
From $278 per night (USD)VRBO
Relax in this updated townhome while overlooking the sparkling Atlantic Ocean
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Windy Cove #3 - Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo feat ...
From $278 per night (USD)VRBO
From $381 per night (USD)Expedia
Serenity by the Sea!! Anglers Reef with Boat Slip Available!!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This beautiful villa is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Mark ...
From $381 per night (USD)Expedia
From $194 per night (USD)VRBO
Captain's Quarters Piece of Peace
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy, quaint, and peaceful townhouse with Best Location in Islamorada, Florida. Close enough yet not too far from the To ...
From $194 per night (USD)VRBO
From $391 per night (USD)Expedia
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 $391 per night (USD)Expedia
From $435 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 $435 per night (USD)VRBO
From $295 per night (USD)Expedia
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 $295 per night (USD)Expedia
From $393 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 $393 per night (USD)VRBO
From $385 per night (USD)Expedia
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 $385 per night (USD)Expedia
From $385 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 $385 per night (USD)VRBO
From $393 per night (USD)Expedia
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 $393 per night (USD)Expedia
From $385 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 $385 per night (USD)VRBO
From $391 per night (USD)Expedia
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 $391 per night (USD)Expedia
From $295 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 $295 per night (USD)VRBO
From $435 per night (USD)Expedia
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 $435 per night (USD)Expedia
From $393 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 $393 per night (USD)VRBO
From $391 per night (USD)Expedia
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 $391 per night (USD)Expedia
From $331 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 $331 per night (USD)VRBO
From $331 per night (USD)Expedia
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 $331 per night (USD)Expedia
From $295 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 $295 per night (USD)VRBO
From $331 per night (USD)Expedia
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 $331 per night (USD)Expedia
From $352 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 $352 per night (USD)VRBO
From $352 per night (USD)Expedia
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 $352 per night (USD)Expedia
From $362 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 $362 per night (USD)VRBO
From $362 per night (USD)Expedia
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 $362 per night (USD)Expedia
From $352 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 $352 per night (USD)VRBO
From $362 per night (USD)Expedia
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 $362 per night (USD)Expedia
From $663 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 $663 per night (USD)VRBO
From $584 per night (USD)Expedia
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 $584 per night (USD)Expedia
From $993 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 $993 per night (USD)VRBO
From $663 per night (USD)Expedia
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 $663 per night (USD)Expedia
From $1317 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 $1317 per night (USD)VRBO
From $993 per night (USD)Expedia
Dive Into Your Dream Vacation! 3 Spacious Units, Onsite Pool, FREE Breakfast!
- 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 $993 per night (USD)Expedia
From $897 per night (USD)VRBO
Comfort & Convenience, 3 Classy Units, Free Breakfast, Free Parking, Pool
- 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 $897 per night (USD)VRBO
From $1317 per night (USD)Expedia
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 $1317 per night (USD)Expedia
From $584 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 $584 per night (USD)VRBO
From $897 per night (USD)Expedia
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 $897 per night (USD)Expedia
From $584 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 $584 per night (USD)VRBO
From $993 per night (USD)Expedia
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 $993 per night (USD)Expedia
From $1259 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 $1259 per night (USD)VRBO
From $1317 per night (USD)Expedia
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 $1317 per night (USD)Expedia
From $422 per night (USD)VRBO
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)VRBO
From $517 per night (USD)Expedia
Isla Honeydew: 3 En-Suite Bedrooms! FREE boat dockage Sept-Oct only
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $517 per night (USD)Expedia
From $136 per night (USD)VRBO
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)VRBO
From $749 per night (USD)Expedia
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)Expedia
From $331 per night (USD)VRBO
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)VRBO
From $1100 per night (USD)Expedia
DISCOUNTED MONTHLY RENTAL + 10% OFF ON ADDITIONAL WEEK FOR WEEKLY RENTALS
- 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 $1100 per night (USD)Expedia
From $434 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 $434 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 $753 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 $753 per night (USD)VRBO
From $248 per night (USD)Expedia
“ The Ultimate redneck” boat experience
- Bedrooms:
- 1
- 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)Expedia
From $351 per night (USD)VRBO
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 $351 per night (USD)VRBO
From $1430 per night (USD)Expedia
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)Expedia
From $471 per night (USD)VRBO
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 $471 per night (USD)VRBO
From $441 per night (USD)Expedia
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 $441 per night (USD)Expedia
From $983 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 $983 per night (USD)VRBO
From $560 per night (USD)Expedia
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)Expedia
From $415 per night (USD)VRBO
3-bedroom cozy pool home in exclusive Venetian Shores, Islamorada .
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Discover tranquility at our Venetian Shores Escape, Islamorada. Nestled in a serene neighborhood, this property boasts ...
From $415 per night (USD)VRBO
From $320 per night (USD)Expedia
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 $320 per night (USD)Expedia
From $226 per night (USD)VRBO
3-bedroom townhome in charming Islamorada with AC, WiFi
- Bedrooms:
- 3
- 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)VRBO
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Matecumbe Resort: King Studio Suite. Your Home Away From Home In The FL Keys.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Matecumbe Resort offers well-appointed, air-conditioned accommodations in Islamorada, renowned as the fishing capital of ...
Click For PricingExpedia
Click For PricingVRBO
Matecumbe Resort: Large One Bedroom. Your Home Away From Home In The FL Keys.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Matecumbe Resort offers well-appointed, air-conditioned accommodations in Islamorada, renowned as the fishing capital of ...
Click For PricingVRBO
From $278 per night (USD)Expedia
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 $278 per night (USD)Expedia
From $654 per night (USD)VRBO
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 $654 per night (USD)VRBO
From $660 per night (USD)Expedia
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 $660 per night (USD)Expedia
From $1731 per night (USD)VRBO
BeachFront Paradise\/By The Glam Homes
- Bedrooms:
- 4
- Bathrooms:
- 5
- 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 $1731 per night (USD)VRBO
From $470 per night (USD)Expedia
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 $470 per night (USD)Expedia
From $996 per night (USD)VRBO
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 $996 per night (USD)VRBO
From $428 per night (USD)Expedia
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 $428 per night (USD)Expedia
From $1506 per night (USD)VRBO
Family Beach Getaway | 3 Relaxing Rooms w\/ Balcony
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $1506 per night (USD)VRBO
From $1998 per night (USD)Expedia
4 Scenic Marina View Rooms w\/ Balcony | Refreshing Outdoor Pool & Free Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 4
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $1998 per night (USD)Expedia
From $1760 per night (USD)VRBO
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 $1760 per night (USD)VRBO
From $878 per night (USD)Expedia
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 $878 per night (USD)Expedia
From $1325 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 $1325 per night (USD)VRBO
From $1325 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 $1325 per night (USD)Expedia
From $638 per night (USD)VRBO
Beachfront Stay Perfect for Island Couple Retreat | Suite w\/ Balcony
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $638 per night (USD)VRBO
From $494 per night (USD)Expedia
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 $494 per night (USD)Expedia