Islamorada Rentals
From $1445 per night (USD)VRBO
OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
82754 Overseas Highway - OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Ke ...
From $1445 per night (USD)VRBO
From $531 per night (USD)VRBO
Brand New \/ Totally Renovated Luxurious Home with POOL
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
***POOL Built in July 2019; Tropical landscaping installed 2020/2021 with great privacy*** Located in Islamorada the pr ...
From $531 per night (USD)VRBO
From $743 per night (USD)VRBO
Charming Beach Front Home in Lower Matecumbe
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
113 Sunset Drive - Come and stay in this adorable "beachy backyard" home located on the crystal-clear Atlantic Ocean! Th ...
From $743 per night (USD)VRBO
From $626 per night (USD)Expedia
Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
COVID-19 Update: Sunrise Haven is professionally cleaned including all linens and towels. The owners or property manag ...
From $626 per night (USD)Expedia
From $393 per night (USD)VRBO
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
WATER FRONT CANAL HOME. BRING YOUR BOAT, LOTS OF PROTECTED DOCKAGE. FULLY UPDATED HOME. All Systems, fully functional, ...
From $393 per night (USD)VRBO
From $312 per night (USD)VRBO
Beautiful Cottage in Islamorada on canal front! Wifi, Smart TVs and No Stairs!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Beautifully renovated and decorated CBS home on bay side with charming details throughout. Wifi, smart TV and no stairs! ...
From $312 per night (USD)VRBO
From $705 per night (USD)VRBO
THE premier gated oceanfront complex in the heart of Islamorada.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
May and June 2024 Special $3400 weekly!!....Oceanfront Maison Matecumbe #303 - Maison Matecumbe is a premier gated ocean ...
From $705 per night (USD)VRBO
From $581 per night (USD)VRBO
Paradise Found - Three Story Beach House w\/ private beach, dock and Ocean Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
28 Day Minimum Stay. However, please contact us for specific dates of availability. 3 story bayside home with its own ...
From $581 per night (USD)VRBO
From $224 per night (USD)VRBO
Beautifully Renovated 2 Bedroom Condo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Futura Yacht Club #205 - This charming condo is located in the Futura Yacht Club community, located at mile marker 88.5 ...
From $224 per night (USD)VRBO
From $1912 per night (USD)Expedia
4 bedroom, Ocean front,Top tier Condo in Islamorada, Florida Keys
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Introducing Maison Residences Unit 204, Poolside... — UP TO 32’ BOAT SLIP MAY BE AVAILABLE, CALL FOR DETAILS — A world- ...
From $1912 per night (USD)Expedia
From $286 per night (USD)VRBO
Florida Keys Plantation Key Colony on Canal with Boat lift, 7K month + Taxes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Canal side Retreat in the Colony 28 day minimum no pets! You won't believe your eyes! It looks like a cozy conch cottag ...
From $286 per night (USD)VRBO
From $415 per night (USD)VRBO
Ocean Views for DAYS!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
132 Columbus Drive - Beautifully renovated home sits right on the ocean. With panoramic ocean views from every room in t ...
From $415 per night (USD)VRBO
From $610 per night (USD)VRBO
Venetian Shores Pool Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Desirable Venetian Shores neighborhood. Newly renovated home with open concept kitchen, dining and living room. Convenie ...
From $610 per night (USD)VRBO
From $527 per night (USD)VRBO
San Remo Canal Front
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
San Remo Canalfront - Venetian Shores five bedroom and four bath home with 70 ft. dock just minutes to Snake Creek for i ...
From $527 per night (USD)VRBO
From $288 per night (USD)VRBO
OPEN -Endless Bay Views... Sues Promise private villas, beach, dock, Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Centrally located at MM 75.5 in beautiful Islamorad, you are only minutes from boat ramps , great restaurants, beaches ...
From $288 per night (USD)VRBO
From $217 per night (USD)VRBO
Executive Bay Club Condo (2 bds + loft & 3 full baths)
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Come stay and watch the sunsets at our beautifully updated Keys townhouse at Executive Bay Club located in Islamorada on ...
From $217 per night (USD)VRBO
From $177 per night (USD)VRBO
Pineapple Point pet friendly paradise Islamorada\n\n
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Pineapple Point, where the quiet peaceful setting will entice you to relax and enjoy Keys living. Our 2 bedro ...
From $177 per night (USD)VRBO
From $336 per night (USD)VRBO
Islamorada 3\/2 condo. Futura Yacht Club Dockage, swimming pool, sunsets
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your own tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada. Futura Yacht Club is a 70 unit c ...
From $336 per night (USD)VRBO
From $491 per night (USD)VRBO
Family\/Pet Friendly Venetian Shores Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful Venetian Shores pool home with plenty of space to relax and play. Situated on a deep water canal with qui ...
From $491 per night (USD)VRBO
From $355 per night (USD)VRBO
Just a Few Friends - Ocean View and Bring your Boat!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Experience all the Florida Keys has to offer in this stunning 2 bed/ 2 ½ bath condominium with an Ocean View, located in ...
From $355 per night (USD)VRBO
From $1052 per night (USD)VRBO
Waterfront Oasis Legal weekly rental*Mins2Beach*Tons of dockage
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
I am a legal weekly rental in Islamorada!!! Commercial Ice Machine, bait freezer, and fish cleaning station!! SUPER PRI ...
From $1052 per night (USD)VRBO
From $1125 per night (USD)Expedia
BAYSIDE PARADISE ~ Heart of Islamorada ~ Private Boat Dockage
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the coastal home of your dreams in the relaxed residential retreat of Coral Cove. As soon as you pull into ou ...
From $1125 per night (USD)Expedia
From $205 per night (USD)VRBO
Indian Mound - Islamorada Keys Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Indian Mound is the ultimate family getaway! Relax in this three bedroom / two bathroom home that has recently been fur ...
From $205 per night (USD)VRBO
From $317 per night (USD)VRBO
Discover the Charm of Island Living
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Privately owned condominium unit at the Futura Yacht Club in the Village of Islamorada. Futura is located on the Gulf o ...
From $317 per night (USD)VRBO
From $639 per night (USD)VRBO
Private Pool, Completely Renovated Lovely Cottage Home in Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful 4 bedroom, 3 bathroom pool home in lovely White Marlin beach, Islamorada, FL. Home has been completely renova ...
From $639 per night (USD)VRBO
From $482 per night (USD)VRBO
Super Penthouse - Futura Yacht Club #603
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Top Floor Penthouse Condo. -Air Conditioning -Stainless Steel appliances. -Granite countertops throughout. -2 Samsung ...
From $482 per night (USD)VRBO
From $502 per night (USD)VRBO
Keys Paradise with Private Beach and Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
NOTE: --PLEASE SEND AN INQUIRY TO BE SURE YOUR DATES ARE AVAILABLE. --DOCKAGE AVAILABLE AT FOUNDERS PARK MARINA RIGHT N ...
From $502 per night (USD)VRBO
From $858 per night (USD)VRBO
Beautiful Bayfront Home with Amazing Sunsets
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This Property has a large kitchen and living area open to amazing views of the bay with 4 bedrooms and 3 full baths. Yo ...
From $858 per night (USD)VRBO
From $406 per night (USD)VRBO
Beautiful 'Keysey' Condo in Bay Harbour Gated Community 24-0169
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
Enjoy the spirit of the Florida Keys in this 'keysey' furnished condo with everything provided. All you have to do is s ...
From $406 per night (USD)VRBO
From $426 per night (USD)Expedia
Islamorada Luxury Waterfront Condo with Boat Slip
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in ...
From $426 per night (USD)Expedia
From $378 per night (USD)VRBO
Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
“Ocean Breeze” – This Beautiful Condominium Features an Ocean view, Protected Boat Slip, Tennis, Gym, and much, much mor ...
From $378 per night (USD)VRBO
From $443 per night (USD)VRBO
Unique 2 Bedroom Bay Front Home with Roof Top Terrace
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
75130 Overseas Highway - Great house in Lower Matecumbe (south side of Islamorada) at the 75-mile marker on the bayside. ...
From $443 per night (USD)VRBO
From $317 per night (USD)VRBO
Amazing Sunsets+Sandy Beach+Pier+Heated Pool+Bikes+Kayak+2 Offices Quiet Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Time to change your latitude, attitude and immerse your body and mind in the calming, soothing waters that surround our ...
From $317 per night (USD)VRBO
From $1072 per night (USD)VRBO
Canal home in Islamorada. Views from 2nd fl pool, partial 65' of dock.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Location, location, location! A tropical palmy dream and playground for ocean lovers. Minutes on boat from the best san ...
From $1072 per night (USD)VRBO
From $743 per night (USD)VRBO
Beautiful New Island Home for 2 Small Families
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Plan your vacation getaway in paradise at this amazing new canal-front home with all the comforts of home in a quiet nei ...
From $743 per night (USD)VRBO
From $528 per night (USD)VRBO
Beautiful 3 Bedroom Condo with Ocean Views Located in Lower Matecumbe
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bay Harbour C-312 - Beautiful three bedroom two and a half bath luxury condo at mile maker 74.5. Complex comes complete ...
From $528 per night (USD)VRBO
From $682 per night (USD)VRBO
☀️Luxury 3 BR Remodeled! Ocean View PoolSpa, MarinaBikes Boat Slip Tennis\/Pickle
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Boat Slip is available for a small weekly fee of $150 Come enjoy relaxing or being active at luxurious Bay Harbour - a ...
From $682 per night (USD)VRBO
From $278 per night (USD)VRBO
Canal front Oasis with Pool and Tiki Hut
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
128 Tequesta Street - The perfect vacation home! This charming three-bedroom two bath home has everything you need for t ...
From $278 per night (USD)VRBO
From $1431 per night (USD)VRBO
Seaside Sanctuary 5 bed, 5 bath pool home
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
This impressive home is located in Islamorada on a private lagoon with quick direct access to the Florida Bay. Featurin ...
From $1431 per night (USD)VRBO
From $587 per night (USD)VRBO
Cute Canal front Venetian Shores Weekly Rental!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
107 San Remo Drive - Comfortable Venetian Shores canal home that has two-bedroom one bath upstairs and a one bedroom one ...
From $587 per night (USD)VRBO
From $239 per night (USD)VRBO
Bay Views from this Charming 3 Bedroom Canal Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
186 Airstream Lane - Located on a quiet street in Islamorada, this home offers you the best of both worlds. Fantastic, p ...
From $239 per night (USD)VRBO
From $537 per night (USD)VRBO
Panoramic Ocean Views from this 3 Bedroom Islamorada Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
137 LeSerra Lane - Beautiful designer appointed Oceanside canal home located at the mile marker 76.5 in Lower Matecumbe ...
From $537 per night (USD)VRBO
Click For PricingExpedia
Island Dreams: Islamorada Studio
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 3
Nestled in the stunning Islamorada, Florida Keys, this modernized oceanfront Studio Suite boasts a queen-size bed, and t ...
Click For PricingExpedia
From $428 per night (USD)Expedia
Studio Sleeps 3, Kitchenette, Balcony, Heart of the Keys
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Designed to accommodate up to three guests, this spacious studio features a cozy queen-size bed and a twin sleeper sofa. ...
From $428 per night (USD)Expedia
From $377 per night (USD)VRBO
Vibrant Islamorada Studio Queen Bed, Balcony, Kitchen
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Experience the charm of the Studio Suite, a spacious single room featuring a comfortable queen-size bed and a twin sleep ...
From $377 per night (USD)VRBO
From $664 per night (USD)Expedia
Large Screened Porch, Professional Cleaning, Wifi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Oceanfront 90 mm Plantation Key , full screened in terrace 6.5 ft by 28.5 ft. Newly decorated white tile & Berber carp ...
From $664 per night (USD)Expedia
From $489 per night (USD)VRBO
Embrace the Sugar Rush Experience! Courtyard View, Free Parking, Onsite Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $489 per night (USD)VRBO
From $325 per night (USD)Expedia
FLORIDA KEYS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
ONLY WEEK AVAILABLE: OCTOBER 5-12, 2024. Caloosa Cove Resort and Marina is located on 10 tropical acres in Islamorada, F ...
From $325 per night (USD)Expedia
From $526 per night (USD)VRBO
SALT HAVEN - BEAUTIFUL & CLEAN 70' WATERFRONT\/CANAL POOL HOME + PRIVATE BEACH
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
The Salt Haven is a beautiful canal front, pool home in Port Antigua ready for your vacation get away. Port Antigua is o ...
From $526 per night (USD)VRBO
From $371 per night (USD)Expedia
Canal-front home with private dock, wraparound deck, & central AC - snowbirds OK
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Plaza Del Sol Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $371 per night (USD)Expedia
From $389 per night (USD)VRBO
Keys Villa--Islamorada private beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Two bedroom "gem" in the Florida Keys!! Enjoy our sand beach, beautiful sunsets, fish from our docks, swim in our pool, ...
From $389 per night (USD)VRBO
From $346 per night (USD)VRBO
Stunning Penthouse 3 bedroom Apartment, New
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This Stunning 3 bedroom Penthouse is absolutely stunning! The photos do not due justice to the amazing ceiling, Livingro ...
From $346 per night (USD)VRBO
From $267 per night (USD)VRBO
Best location in downtown Islamorada. Beach access and boat trailer parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Unbelievable location in Islamorada Florida Keys! You have beach access and boat trailer parking. Close enough to walk a ...
From $267 per night (USD)VRBO
From $259 per night (USD)VRBO
Escape the cold Work from Home Beach, Pool, Fishing Pier & 2 Kayaks & 2 Bikes\n
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Getaway to the Florida Keys in our slice of paradise. Unwind in our 2-bedroom, 2-bathroom townhome. You will enjoy rela ...
From $259 per night (USD)VRBO
From $547 per night (USD)VRBO
Villa Morada ~ Relaxed Luxury 4 Bedroom Islamorada Home with Pool & Dockage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This beautifully updated 4 bedroom and 2.5 bath resort-like home is nestled in one of Plantation Keys most desirable nei ...
From $547 per night (USD)VRBO
From $295 per night (USD)Expedia
Best Location in Islamorada!! Beach access - Boat trailer parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Gorgeous and highly appointed luxury Island villa with beach access. You are right in the middle of it all with this per ...
From $295 per night (USD)Expedia
From $690 per night (USD)VRBO
Islamorada Oasis, Luxury open concept 4 bedroom 3 bath private home, heated pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Islamorada Oasis is designed for families and outdoor lovers! Inside and out, its ready for entertaining and keys styl ...
From $690 per night (USD)VRBO
From $437 per night (USD)VRBO
Fantastic Bayside Townhouse
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Fantastic gated Bayside townhouse with all the bells and whistles. Excellant location with everything you need to have a ...
From $437 per night (USD)VRBO
From $455 per night (USD)VRBO
Ocean Breeze. Oceanfront Resort Style Condo in the Florida Keys (Islamorada)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Oceanfront resort style condo in the Florida Keys (waterfront) Over1,700 square feet with screened in porch for amazing ...
From $455 per night (USD)VRBO
From $392 per night (USD)Expedia
Beautiful Lower Unit with Dockage, Pool and Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
PROPERTY NAME: Parrot Eyes 130 Plantation Ave. Tavernier, Florida 33070 LOCATION: Bayside Canal home located in Taverni ...
From $392 per night (USD)Expedia
From $10620 per night (USD)VRBO
Island Beach House Oasis Your Memory Maker awaits
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
There is luxury, luxury and unrivaled, and then there is the Bay front Island Beach House Oasis that offers that and mor ...
From $10620 per night (USD)VRBO
From $516 per night (USD)Expedia
Islamorada Home with Private Beach Freshly updated Waterfront and Swimming Pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Relax in Islamorada, Enjoy the day deep sea fishing, and watch the sunset at our private beach. Our 5/3 House is freshl ...
From $516 per night (USD)Expedia
From $621 per night (USD)VRBO
Remodeled Stilt home with Ocean Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
PROPERTY NAME: Blue Water Retreat 137 Ocean Lane, Islamorada, Florida LOCATION: Oceanside Canal home located in Lower M ...
From $621 per night (USD)VRBO
From $3592 per night (USD)VRBO
Keys to Relaxation! Pool, Pets Allowed, Short Drive to Florida Keys Airport
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stay close to Florida Keys Brewing Co. and Bud n' Mary's Dive Center. Explore Indian Key Historic State Park and dive in ...
From $3592 per night (USD)VRBO
From $942 per night (USD)VRBO
Your Islamorada Hideaway! Beachfront Accommodation. Onsite Pool, Parking
- 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 $942 per night (USD)VRBO
From $1172 per night (USD)VRBO
Coastal Gem! Water Activities Onsite, Pool, Private Patio, Pets Allowed!
- 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 $1172 per night (USD)VRBO
From $2744 per night (USD)VRBO
High Tides and Good Vibes! 4 Spacious Units, Outdoor Pool, Free Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Stay close to Florida Keys Brewing Co. and Bud n' Mary's Dive Center. Explore Indian Key Historic State Park and dive in ...
From $2744 per night (USD)VRBO
From $1625 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 $1625 per night (USD)VRBO
From $2058 per night (USD)VRBO
Everything You Need For The Perfect Vacation! 3 Sleek Units, Beachfront, Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Stay close to Florida Keys Brewing Co. and Bud n' Mary's Dive Center. Explore Indian Key Historic State Park and dive in ...
From $2058 per night (USD)VRBO
From $1203 per night (USD)VRBO
Beach Bliss, Just Steps to the Ocean! Outdoor Pool, Near Coral Bay Marina
- 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 $1203 per night (USD)VRBO
From $1954 per night (USD)VRBO
Dip Your Toes In The Sand! Beachfront, Pool, Near History of Diving Museum
- 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 $1954 per night (USD)VRBO
From $466 per night (USD)VRBO
Come Create Memories w\/ Fun-filled Adventures at this Paradise! Beachfront, Pool
- 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 $466 per night (USD)VRBO
From $1163 per night (USD)VRBO
Dive Into Your Dream Vacation! Beachfront, Outdoor Pool, 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 $1163 per night (USD)VRBO
From $597 per night (USD)VRBO
Steps Away from Coral Bay Marina! Pool, Beachfront, Free Parking, Pets Allowed
- 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 $597 per night (USD)VRBO
From $1218 per night (USD)VRBO
You Don’t Want to Miss This! Beachfront, Onsite Pool, Near Coral Bay Marina
- 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 $1218 per night (USD)VRBO
From $528 per night (USD)VRBO
Exciting Water Adventures! Beachfront, Pool, Near Lorelei\/Morada Bay Anchorage
- 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 $528 per night (USD)VRBO
From $796 per night (USD)VRBO
Escape to Paradise! Beachfront, Outdoor Pool, Near Theater of the Sea
- 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 $796 per night (USD)VRBO
From $1285 per night (USD)VRBO
Cozy Coastal Haven for Relaxation! With Pools and Water Sports 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 $1285 per night (USD)VRBO
From $942 per night (USD)VRBO
Sun, Sand, and Relaxation Awaits! Ocean View Accommodation w\/ Private Patio!
- 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 $942 per night (USD)VRBO
From $1009 per night (USD)VRBO
Dream Paradise! Beachfront Property with Pool, Free Parking, Partial Ocean View
- 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 $1009 per night (USD)VRBO
From $1159 per night (USD)VRBO
Best Vacation Choice! Outdoor Pool, Beachfront Location, Pets are Welcome!
- 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 $1159 per night (USD)VRBO
From $1954 per night (USD)VRBO
Enjoy a Hassle-free Stay! Unit w\/ Full Kitchen, Beachfront, Outdoor Pool
- 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 $1954 per night (USD)VRBO
From $796 per night (USD)VRBO
Best Location! Beachfront Property with Outdoor Pool, Pets are Welcome!
- 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 $796 per night (USD)VRBO
From $597 per night (USD)VRBO
Fun Under the Sun! Beachfront, w\/ Pool Onsite, Free Parking, Pets Allowed!
- 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 $597 per night (USD)VRBO
From $528 per night (USD)VRBO
Dive Into Your Dream Vacation! With Pool, Beachfront Location, Pet-friendly
- 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 $528 per night (USD)VRBO
From $466 per night (USD)VRBO
Steps Away from the Beach! Enjoy Your Own Patio, Outdoor Pool, Free Parking
- 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 $466 per night (USD)VRBO
From $982 per night (USD)VRBO
Summer Escapade! Onsite Pool, Steps from the Beach, Pets Allowed, Free Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $982 per night (USD)VRBO
From $402 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 $402 per night (USD)Expedia
From $1442 per night (USD)VRBO
Bayfront paradise in Islamorada, FL.
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 14
This stunning residence in Islamorada offers breathtaking views and luxurious amenities, ideal for serene living. Each b ...
From $1442 per night (USD)VRBO
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 $620 per night (USD)VRBO
Sunny Escape! Spacious Oceanfront Suite with Balcony! Beachfront Resort w\/ Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $620 per night (USD)VRBO
From $2312 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 $2312 per night (USD)VRBO
From $1198 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 $1198 per night (USD)VRBO
From $544 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 $544 per night (USD)VRBO
From $138 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 $138 per night (USD)VRBO
From $798 per night (USD)Expedia
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 $798 per night (USD)Expedia
From $1487 per night (USD)VRBO
Turtle Beach is an Oasis on the Atlantic Ocean
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Spacious private beach front home located on the Atlantic Ocean in beautiful Islamorada, Florida - the sport fishing cap ...
From $1487 per night (USD)VRBO
From $1052 per night (USD)Expedia
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 $1052 per night (USD)Expedia
From $728 per night (USD)VRBO
Cozy Coastal Haven for Relaxation! With Pools and Water Sports 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 $728 per night (USD)VRBO
From $1612 per night (USD)Expedia
High Tides and Good Vibes! 4 Spacious Units, Outdoor Pool, Free Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Stay close to Florida Keys Brewing Co. and Bud n' Mary's Dive Center. Explore Indian Key Historic State Park and dive in ...
From $1612 per night (USD)Expedia