Islamorada Rentals
- From $1021 per night (USD)
VRBO
Coastal Retreat! Pool, Pets Allowed, Minutes to Indian Key Historic State Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $1021 per night (USD)VRBO
- From $1386 per night (USD)
VRBO
Everything You Need For The Perfect Vacation! 3 Sleek Units, Beachfront, Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $1386 per night (USD)VRBO
- From $996 per night (USD)
VRBO
Beach Bliss, Just Steps to the Ocean! Outdoor Pool, Near Coral Bay Marina
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $996 per night (USD)VRBO
- From $1311 per night (USD)
VRBO
Dip Your Toes In The Sand! Beachfront, Pool, Near History of Diving Museum
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $1311 per night (USD)VRBO
- From $465 per night (USD)
VRBO
Come Create Memories w\/ Fun-filled Adventures at this Paradise! Beachfront, Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $465 per night (USD)VRBO
- From $998 per night (USD)
VRBO
Dive Into Your Dream Vacation! Beachfront, Outdoor Pool, Near Hurricane Monument
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $998 per night (USD)VRBO
- From $410 per night (USD)
VRBO
Steps Away from Coral Bay Marina! Pool, Beachfront, Free Parking, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $410 per night (USD)VRBO
- From $1070 per night (USD)
VRBO
You Don’t Want to Miss This! Beachfront, Onsite Pool, Near Coral Bay Marina
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $1070 per night (USD)VRBO
- From $457 per night (USD)
VRBO
Exciting Water Adventures! Beachfront, Pool, Near Lorelei\/Morada Bay Anchorage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $457 per night (USD)VRBO
- From $462 per night (USD)
VRBO
Escape to Paradise! Beachfront, Outdoor Pool, Near Theater of the Sea
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $462 per night (USD)VRBO
- From $2894 per night (USD)
VRBO
Keys to Relaxation! Pool, Pets Allowed, Short Drive to Florida Keys Airport
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $2894 per night (USD)VRBO
- From $812 per night (USD)
VRBO
Your Islamorada Hideaway! Beachfront Accommodation. Onsite Pool, Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $812 per night (USD)VRBO
- From $678 per night (USD)
VRBO
Coastal Gem! Water Activities Onsite, Pool, Private Patio, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $678 per night (USD)VRBO
- From $1848 per night (USD)
VRBO
High Tides and Good Vibes! 4 Spacious Units, Outdoor Pool, Free Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $1848 per night (USD)VRBO
- From $752 per night (USD)
VRBO
Cozy Coastal Haven for Relaxation! With Pools and Water Sports Onsite!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $752 per night (USD)VRBO
- From $812 per night (USD)
VRBO
Sun, Sand, and Relaxation Awaits! Ocean View Accommodation w\/ Private Patio!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $812 per night (USD)VRBO
- From $1700 per night (USD)
VRBO
Private 150 Ft Oceanfront 2.5 Acre Estate with Saltwater Pool, Spa, Dock
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Completely renovated and expanded to over 3,700 square feet. San Roc is a private ocean front home with spectacular vie ...
From $1700 per night (USD)VRBO
- From $289 per night (USD)
VRBO
Best location 3BR house in Islamorada! Pool and beach; walk or bike everywhere.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Beautiful updated house on dead-end road with pool and private beach access. Launch a kayak or paddleboard from the beac ...
From $289 per night (USD)VRBO
- From $97 per night (USD)
VRBO
1 Bedroom Apartment with Pool on Plantation Key
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Paradise awaits at Port o Palms! Escape the snow! This 1-bedroom, 1-bath apartment is well-equipped with a queen bed, a ...
From $97 per night (USD)VRBO
- From $1558 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 $1558 per night (USD)VRBO
- From $222 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 $222 per night (USD)VRBO
- From $250 per night (USD)
Expedia
Tranquility Cove \nBeautiful Remodeled home in the heart of Islamorada.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
About this space This beautiful newly remodeled (90 %) Completed , modern home sits in the middle of great restaurants, ...
From $250 per night (USD)Expedia
- From $380 per night (USD)
VRBO
Port Antigua Waterfront Home With Private Beach Access
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This Keys Home is Located in Beautiful Port Antigua. 4 Br/ 3 Ba Sleeps 8 Comfortably. All Rooms Have Queen Sized Beds. L ...
From $380 per night (USD)VRBO
- From $235 per night (USD)
VRBO
Islamorada Escape - Executive Bay w\/Pool, Fishing Dock, Beach, Tennis\/Pickleball
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located in Islamorada, mile marker 87 right in the middle of beautiful Florida Key's. This Executive Bay Club Condo prov ...
From $235 per night (USD)VRBO
- From $219 per night (USD)
VRBO
Paradise found !<br>Florida Keys hidden gem …. A retreat for anyone at anytime
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This remodeled townhouse has three floors of living space . Brand new kitchen and appliances. Full stairs to second floo ...
From $219 per night (USD)VRBO
- From $275 per night (USD)
Expedia
Islamorada Hidden Treasure
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy luxury in the Florida Keys in this private oasis at Coral Harbour. The property is equipped with a marina, fuel, ...
From $275 per night (USD)Expedia
- From $450 per night (USD)
VRBO
Feel the breeze of the keys
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
**HOUSE HAS BEEN RENOVATED AND PICTURES TO COME** Perfect Vacation Home in Islamorada, the center of the Keys Island. T ...
From $450 per night (USD)VRBO
- From $308 per night (USD)
Expedia
Bay view villa in Islamorada, palm trees, shade trees and two private porches
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Unwind with a Bay view, approx. 1 hour from Miami airport. Access to mini beach, great sunsets and boat ramp, swimming ...
From $308 per night (USD)Expedia
- From $379 per night (USD)
VRBO
Charming Angler's Reef Home with Pool, Dock, Beach & Ocean View
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Islamorada’s Finest Oceanfront Gated Community Soak up the sun and enjoy the ocean breeze from this charming ...
From $379 per night (USD)VRBO
- From $158 per night (USD)
VRBO
Fabulous 2-Bedroom with a million-dollar View!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This Fantastic Condo is just steps away from the fabulous turquoise waters of Florida Bay! Enjoy spectacular sunsets and ...
From $158 per night (USD)VRBO
- From $99 per night (USD)
VRBO
A 28 Day or More Rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Take it easy at this unique and tranquil getaway. Enjoy this well equipped 2 bedroom, 2 bath home. Enjoy beautiful suns ...
From $99 per night (USD)VRBO
- From $843 per night (USD)
VRBO
A Pet Friendly Tropical Oasis with a Pool and Dockage on Plantation Key
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Introducing Palm Harbor, a tropical oasis in desirable Kahiki Harbor. This luxurious 4 bedroom, 3 bath pool home has ...
From $843 per night (USD)VRBO
- From $166 per night (USD)
VRBO
Zesty Lower Matecumbe Condo with Private Beach & Dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
It's not every day that you come across a rental like this. This delightful and fun 2 bedroom, 1.5 located in Lower Mate ...
From $166 per night (USD)VRBO
- From $400 per night (USD)
Expedia
Bungalow #5 - 2 Bed\/1 Bath & Pool in Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Tucked away in the vibrant Florida Keys, is our pristine Bungalow paradise. We are located in the heart of Islamorada, w ...
From $400 per night (USD)Expedia
- From $2000 per night (USD)
VRBO
Luxurious PH 5BR 3.5BA Gym\/ Pool & Jacuzzi\/ Sauna
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
<p>You'll find a kayak on site at this pet-friendly apartment. There's convenient covered onsite parking, so you can lea ...
From $2000 per night (USD)VRBO
- From $945 per night (USD)
VRBO
Amazing 4 Bedroom Canal Home with Pool and Dockage-Holly's Hideout by Florida Ke
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: This amazing home is centrally located on a clean, clear canal with deep water access to either the bay or ocea ...
From $945 per night (USD)VRBO
- From $192 per night (USD)
VRBO
Mercy’s waterfront piece of paradise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our home is a unique place situated in the best location in the mid/upper keys. A single family property, all refurbishe ...
From $192 per night (USD)VRBO
- From $360 per night (USD)
VRBO
Sit back and relax in this beautiful Islamorada Pool home!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Put your mail on hold, your new Islamorada address is waiting! Sit back and relax in this beautiful Islamorada Pool ho ...
From $360 per night (USD)VRBO
- From $905 per night (USD)
VRBO
The Villa by the Bay, Islamorada FL
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Take your heart, family & fishing gear to the blissful Villa by the Bay! Quaint gated 8 homes; Coral Cove is centrally l ...
From $905 per night (USD)VRBO
- From $265 per night (USD)
VRBO
Waterfront unit breathtaking sunset
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Breathtaking waterfront view 2/2.5 townhouse in desirable Futura Yacht club. Lots of outdoor coveted living space,great ...
From $265 per night (USD)VRBO
- From $325 per night (USD)
VRBO
The Nest Villa & Marina with boat ramp, sun terrace, water views & pet friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The "Nest" villa is one of only seven units nestled on a one acre native tropical hammock directly on Florida Bay with s ...
From $325 per night (USD)VRBO
- From $786 per night (USD)
VRBO
Light + Bright Islamorada Pool Home with Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to Islamorada Reef Home, a light and bright Islamorada pool home with dockage. You’ll feel right at home in th ...
From $786 per night (USD)VRBO
- From $625 per night (USD)
VRBO
Luxury Home with 60' Deep Water Dock, Waterfall Pool, HotTub, A\/C and WiFi
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Minimum 28 day stay. Dreaming of a FL Keys vacation where you can boat, fish, dive, snorkel or stay home and swim in yo ...
From $625 per night (USD)VRBO
- From $675 per night (USD)
VRBO
Islamorada paradise vacation home in sought after Venation shores
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Location, location! Venetian Shores is the premier luxury private community with deep water access to Snake creek, which ...
From $675 per night (USD)VRBO
- Click For Pricing
VRBO
Pristine canal-front home with heated pool and access to open water
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 9
Beautifully appointed getaway perfectly situated to allow exploration of the mangroves or the open water, since Tavernie ...
Click For PricingVRBO
- From $998 per night (USD)
VRBO
The Sailfish House ~ 4 Bed \/ 4 Bath Luxury Oceanfront Home in Islamorada!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the “Sailfish House” at Tarpon Point! Soak up the sun and take in the spectacular views at this opulent 4 be ...
From $998 per night (USD)VRBO
- From $427 per night (USD)
VRBO
4BR waterfront home with POOL, boat slip with straight shot to Alligator Reef!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Island Villa Rental Properties offers Seas The Day in Islamorada, Florida Keys. Seas the Day is a fun, 4 bedroom house ...
From $427 per night (USD)VRBO
- From $725 per night (USD)
VRBO
Spectacular Coastal Paradise with outstanding outdoor living spaces
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 10
Escape to the islands in your own private resort. This Florida Keys home feels like your own private tropical oasis loc ...
From $725 per night (USD)VRBO
- From $550 per night (USD)
VRBO
ISLAMORADA DREAM HOUSE
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
ONE-OF-A-KIND VACATION EXPERIENCE. You will never want to leave. Large open space, dining, kitchen and living room. Priv ...
From $550 per night (USD)VRBO
- From $500 per night (USD)
Expedia
A place in paradise!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This unique home gives you the quintessential keys experience. Nestled in a small, quaint gated, private community with ...
From $500 per night (USD)Expedia
- From $380 per night (USD)
VRBO
Beautiful Keys Style Retreat - with bonus room, private pool and private dock.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Experience paradise in our stunning 2-story, 2-bedroom, 3-bathroom rental property located in a peaceful residential nei ...
From $380 per night (USD)VRBO
- From $463 per night (USD)
VRBO
Venetian Shores 20K boat lift 28 day Minimum, ..August Cancellation now open....
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Venetian shores 4 bedroom 3 bath, pool, hotub, 300lbs ice machine with 20K boat lift, Master has a double walk-in shower ...
From $463 per night (USD)VRBO
- From $180 per night (USD)
VRBO
Beautiful 2 Bedroom 2 Bath Condo Coral Harbour Islamorada - Marina, Pool, Gated
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This special place is close to everything, making it easy to plan your visit. Beautiful updated 2 bedroom 2 bath watervi ...
From $180 per night (USD)VRBO
- From $174 per night (USD)
Expedia
Reduced for Late Summer\/Fall - Marina, Pool, Tennis and More!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
REDUCED BY 20% FOR LATE SUMMER/EARLY FALL.....Enjoy this stylishly remodeled townhome in the Heart of Islamorada at Exec ...
From $174 per night (USD)Expedia
- From $200 per night (USD)
VRBO
PARADISE FOUND! 3 BD townhome in BEACHFRONT Executive Bay Club in Islamorada, FL
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Paradise Found! Enjoy fantastic sunsets in an updated 1400 sq. ft. townhouse in beautiful Executive Bay Club, on mile ma ...
From $200 per night (USD)VRBO
- From $746 per night (USD)
VRBO
Maison Matecumbe.... the heart of Islamorada!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Maison Matecumbe #301 - Maison Matecumbe is an exclusive gated and private boutique complex comprised of 9 units. Centra ...
From $746 per night (USD)VRBO
- From $2200 per night (USD)
VRBO
New luxury 6 bedroom - truly spectacular beachfront property
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Spectacular, brand new property - three stories of true luxury in a relaxed beachfront setting. Our newest addition to ...
From $2200 per night (USD)VRBO
- From $325 per night (USD)
Expedia
Tropical Paradise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful bayside villa in Islamorada. Sandy beach, fishing dock, pool, tennis court and boat slip for up to 25 ft boat ...
From $325 per night (USD)Expedia
- From $605 per night (USD)
VRBO
Pet Friendly 2 Bedroom in Venetian Shores Sleeps 10
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
The Salty B is located in the popular neighborhood of Venetian Shores! Canal front home on Snake Creek gives you fast ac ...
From $605 per night (USD)VRBO
- From $180 per night (USD)
VRBO
OCEAN FRONT TOWN HOUSE with breath taking views from all 3 balconies.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
We are delighted to offer this 2 bedroom, 1 1/2 bathrooms OCEANFRONT TOWNHOUSE!!! Breathtaking views off of all 3 balco ...
From $180 per night (USD)VRBO
- From $400 per night (USD)
VRBO
New home with 95' of dock, pool with breathtaking Atlantic Ocean Views.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
New 4br/3bth home off Tavernier Creek, Ocean side with 95' of dock and lowered dock area for boarding kayaks and paddle ...
From $400 per night (USD)VRBO
- From $140 per night (USD)
VRBO
Executive Bay Club unit V4 Islamorada,FL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
SERVICE ANIMALS are OK, otherwise NO PETS ALLOWED 30 Day Minimum Stays 2 Bedroom, 1.5 Bathroom townhome located in Isl ...
From $140 per night (USD)VRBO
- From $530 per night (USD)
VRBO
ENDLESS SUMMER- Ocean side, private pool, pet friendly!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Pet friendly! Bring your boat and enjoy this large, 2-story house right on the ocean side. Private extra-large pool, Tik ...
From $530 per night (USD)VRBO
- From $291 per night (USD)
VRBO
Relax and Unwind! Pet-Friendly Property, Onsite Pool, 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 $291 per night (USD)VRBO
- From $291 per night (USD)
VRBO
Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed
- 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 $291 per night (USD)VRBO
- From $217 per night (USD)
Expedia
Canal-Front Florida Keys Home w\/ Dock!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Ocean breezes and beautiful water views are in store at this 2-bedroom, 2-bathroom home. This Florida Keys vacation rent ...
From $217 per night (USD)Expedia
- From $328 per night (USD)
VRBO
Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking
- 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 $328 per night (USD)VRBO
- From $328 per night (USD)
VRBO
Prime Location! Pet-Friendly Property, Free Parking, 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 $328 per night (USD)VRBO
- From $280 per night (USD)
VRBO
Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed
- 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 $280 per night (USD)VRBO
- From $280 per night (USD)
VRBO
Relax and Unwind! Pet-Friendly Property, Onsite Pool, 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 $280 per night (USD)VRBO
- From $328 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 $328 per night (USD)VRBO
- From $280 per night (USD)
VRBO
Ideal Location! Onsite Pool, Free Breakfast, Free Parking
- 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 $280 per night (USD)VRBO
- From $156 per night (USD)
VRBO
Charming canal-front home with dock, full kitchen, central AC, & washer\/dryer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Salt House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $156 per night (USD)VRBO
- From $527 per night (USD)
VRBO
Enjoy the good life in the perfect Islamorada Home!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
133 Stromboli Drive - If ever you have imagined yourself vacationing in Islamorada, this home was in your head! Beautif ...
From $527 per night (USD)VRBO
- From $172 per night (USD)
VRBO
Reel Paradise at Sea Gulls
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Stunning ocean views and beautiful island sunrises! The Space: Welcome to Reel Paradise! This beautiful condo ...
From $172 per night (USD)VRBO
- From $360 per night (USD)
VRBO
Get ready to dive into your Islamorada Retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
134 Tequesta Street - Get ready to dive into your Islamorada Winter Retreat! Move in ready today! This beautiful three-b ...
From $360 per night (USD)VRBO
- From $371 per night (USD)
VRBO
Short Distance From The Well Known Sites! Pool, Free Parking, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $371 per night (USD)VRBO
- From $417 per night (USD)
VRBO
Enjoy a Hassle-Free and Suiting Stay! Pets Allowed, Free Parking, Onsite Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $417 per night (USD)VRBO
- From $341 per night (USD)
VRBO
Come Create Memories w\/ Fun-filled Adventures at this Paradise! Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $341 per night (USD)VRBO
- From $341 per night (USD)
VRBO
Relax and Unwind! Courtyard View, Free Parking, Onsite Pool, Near Anne's Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $341 per night (USD)VRBO
- From $341 per night (USD)
VRBO
Best Value, Quality Stay! Onsite Pool, Free Parking, Short Drive to Anne's Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $341 per night (USD)VRBO
- From $364 per night (USD)
VRBO
Indulge in Home Like Comfort! Free Parking, Onsite Pool, Pet-friendly Property
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $364 per night (USD)VRBO
- From $417 per night (USD)
VRBO
Indulge in Home-Like Comfort! Free Parking, Onsite Pool, Pet-friendly Property
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $417 per night (USD)VRBO
- From $377 per night (USD)
VRBO
Make Your Trip More Enjoyable! Free Parking, Pets Allowed, Onsite Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $377 per night (USD)VRBO
- From $377 per night (USD)
VRBO
Indulge in Home Like Comfort! Courtyard View, Free Parking, Pool, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $377 per night (USD)VRBO
- From $341 per night (USD)
VRBO
Embrace the Sugar Rush Experience! Onsite Pool, Free Parking, Near Anne's Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $341 per night (USD)VRBO
- Click For Pricing
Expedia
Eclectic Easeful Stay At The Keys!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come and enjoy this spacious, airy, and recently renovated condo at Summer Sea in beautiful Tavernier, Florida. The buil ...
Click For PricingExpedia
- From $300 per night (USD)
VRBO
Oceanside Oasis in Private Gated Marina Community
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Ocean Harbour (a gated community) contemporary 2 bedroom 2 bath condo with breathtaking views of the Atlantic Ocean and ...
From $300 per night (USD)VRBO
- From $117 per night (USD)
VRBO
Beautiful Efficiency Apartment - Bayfront, Islamorada Apt 232
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Summer Sea Condominium Unit 232 is a brilliant, clean and modern efficiency apartment, newly upgraded in 2023 with tile ...
From $117 per night (USD)VRBO
- From $108 per night (USD)
VRBO
This studio makes the best of the space
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This studio makes the best of the space. Living room by day bedroom by night with the convenient Murphy bed. All newly u ...
From $108 per night (USD)VRBO
- From $106 per night (USD)
VRBO
Beautifully Updated Studio Apartment, Summer Sea Condo
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
This beautifully updated apartment is new to the rental market. Modern and clean with all the comforts of home, tropical ...
From $106 per night (USD)VRBO
- From $117 per night (USD)
VRBO
Beautiful Modern Studio, recently remodeled, new to the market, Summer Sea 405
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
This beautiful modern Studio apartment has just been completely remodeled and new to the rental market. Every detail has ...
From $117 per night (USD)VRBO
- From $83 per night (USD)
VRBO
Beautiful Studio Apartment - Summer Sea Condo #230
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Summer Sea Condominium Unit 230 is a brilliant, clean and modern efficiency apartment, upgraded with tile throughout and ...
From $83 per night (USD)VRBO
- From $140 per night (USD)
Expedia
New 2\/1 Remodeled Cozy Home in Tavernier Key
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Relax at this peaceful and centrally-located 2/1 remodeled private home in Tavernier Key. Located near Tavernier Creek M ...
From $140 per night (USD)Expedia
- From $242 per night (USD)
VRBO
Keys Cozy Townhouse
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy breathtaking sunset from your own private beach. Cottage nautical townhouse with your outside terrace. Best r ...
From $242 per night (USD)VRBO
- From $338 per night (USD)
Expedia
Large Waterfront Home with 80 ft Dockage and Boat Lift with Pool In Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
80ft Dock and Boat Lift very close to Islamorada Sandbar and Alligator Reef. Great fishing, diving, snorkeling and boat ...
From $338 per night (USD)Expedia
- From $200 per night (USD)
VRBO
Mullet's End
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 8
Welcome to Islamorada, known as the Sport Fishing Capital of the World, where you can find big game fish, like Tarpon, s ...
From $200 per night (USD)VRBO
- From $357 per night (USD)
Expedia
Gulf View Retreat @ Bay Harbor
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: 2/2 Bay harbor condo with stunning Marina and Ocean views! The Space: Escape to the breathtaking Gulf View Ret ...
From $357 per night (USD)Expedia
- From $2317 per night (USD)
VRBO
Luxury Oceanfront Villa with Resort Amenities
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
WELCOME TO THE ISLANDS OF ISLAMORADA Designed for those who love the bounty and beauty of the ocean, The Islands of Isla ...
From $2317 per night (USD)VRBO
- From $650 per night (USD)
Expedia
Radiant Suite with Ocean View and Resort Amenities
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
WELCOME TO THE ISLANDS OF ISLAMORADA Designed for those who love the bounty and beauty of the ocean, The Islands of Isla ...
From $650 per night (USD)Expedia