Islamorada Rentals
From $188 per night (USD)VRBO
Charming 3-bedroom townhome in EXECUTIVE BAY CLUB in delightful Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This EXECUTIVE BAY CLUB townhome in Islamorada boasts 3 inviting bedrooms - 1 king bed, 1 queen bed, and 2 twin beds. Th ...
From $188 per night (USD)VRBO
From $407 per night (USD)Expedia
3-bedroom Waterfront House with Pool & Dock in Tavernier. Relax and unwind
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Unwind in Tavernier at this lovely new waterfront house with a pool and dock. With 3 bedrooms including 1 king bed and 2 ...
From $407 per night (USD)Expedia
From $245 per night (USD)VRBO
Matecumbe Resort: Seaview 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 ...
From $245 per night (USD)VRBO
From $263 per night (USD)Expedia
Cozy 2-bedroom condo with WiFi, fitness room in awesome Islamorada.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to this condo in picturesque Islamorada. This phenomenal Ocean front property features 2 queen beds in 2 bedrooms ...
From $263 per night (USD)Expedia
From $244 per night (USD)VRBO
Matecumbe Resort: Your Home Away From Home in the Florida Keys-1 Bedrm with View
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience Islamorada like a local in this superb 1-bedroom resort. The cozy bedroom features a king bed for a restful n ...
From $244 per night (USD)VRBO
From $345 per night (USD)VRBO
Open Bay View Executive Bay Condo!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Professional photos coming soon! Step into your dream getaway! This beautifully renovated 2-bedroom, 2.5-bath townhome ...
From $345 per night (USD)VRBO
From $509 per night (USD)VRBO
Gorgeous, pool canal front home!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to your own slice of paradise in this stunning canal-front vacation home in Tavernier, Florida. This 3-bedroom, 2 ...
From $509 per night (USD)VRBO
From $664 per night (USD)VRBO
Maison 308 Seaside Cove
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to paradise at Maison Matecumbe in Islamorada! This beautiful 3-bedroom, 3-bathroom townhome offers an unforgett ...
From $664 per night (USD)VRBO
From $984 per night (USD)VRBO
Nautica - Monthly 4 BR home on bay in Islamorada - Upper Matecumbe Key
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Mile Marker 83 – Bayfront Unfortunately all rentals must start on the 1st of the month. Island Villa Rentals and Owner' ...
From $984 per night (USD)VRBO
From $134 per night (USD)VRBO
Stunning Studio Apartment Summer Sea Condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Beautifully remodeled Studio with tropically décor, this 1st floor corner unit (steps required) has a private outdoor en ...
From $134 per night (USD)VRBO
From $114 per night (USD)VRBO
Charming 1 Bedroom Condo on Plantation Key
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Sit back and relax at Port o Palms. Experience the ultimate Florida Keys getaway at this light and bright one-bedroom, ...
From $114 per night (USD)VRBO
From $2352 per night (USD)VRBO
Infinity Bay Islamorada ~ Luxury 9-bed, 10-bath Bayfront Estate in Islamorada
- Bedrooms:
- 10
- Bathrooms:
- 9
- Sleeps:
- 18
Welcome to Infinity Bay Islamorada, an infinite paradise with infinite possibilities in the heart of the Florida Keys. T ...
From $2352 per night (USD)VRBO
From $3276 per night (USD)VRBO
Voted best boutique resort in Islamorada! Beach, dockage, pool + more!
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 22
Located in the heart of Islamorada, Mermaid’s Bay Boutique Estate is a secluded oasis situated directly on the bay. Secu ...
From $3276 per night (USD)VRBO
From $292 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 $292 per night (USD)VRBO
From $1866 per night (USD)VRBO
Your Ultimate Keys Getaway Awaits!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your dream getaway at Coastal Cove Villa! Nestled in the heart of downtown Islamorada, this spacious 4-bedroo ...
From $1866 per night (USD)VRBO
From $2183 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 $2183 per night (USD)VRBO
From $508 per night (USD)VRBO
Best location 3BR house in Islamorada! Pool and beach; walk or bike everywhere.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
AVAILABLE CHRISTMAS & NEW YEARS! Beautiful updated house on dead-end road with pool and private beach access. Launch a k ...
From $508 per night (USD)VRBO
From $287 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 $287 per night (USD)Expedia
From $483 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 $483 per night (USD)VRBO
From $440 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 $440 per night (USD)Expedia
From $690 per night (USD)VRBO
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 $690 per night (USD)VRBO
Click For PricingExpedia
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, ...
Click For PricingExpedia
From $298 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 $298 per night (USD)VRBO
From $592 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 $592 per night (USD)VRBO
From $190 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 $190 per night (USD)VRBO
From $447 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 $447 per night (USD)VRBO
From $136 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 $136 per night (USD)VRBO
From $209 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 $209 per night (USD)VRBO
From $478 per night (USD)VRBO
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 $478 per night (USD)VRBO
From $2357 per night (USD)Expedia
Luxurious PH 5BR 3.5BA Gym\/ Pool & Jacuzzi\/ Sauna
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to your luxurious retreat in Islamorada! Experience the epitome of luxury living at our stunning condo located a ...
From $2357 per night (USD)Expedia
From $221 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 $221 per night (USD)VRBO
From $424 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 $424 per night (USD)VRBO
From $1074 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 $1074 per night (USD)VRBO
From $408 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 $408 per night (USD)VRBO
From $613 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 $613 per night (USD)VRBO
From $212 per night (USD)VRBO
OCEAN FRONT TOWN HOUSE with breath taking views from all 3 balconies.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
We are delighted to offer this 2 bedroom, 1 1/2 bathrooms OCEANFRONT TOWNHOUSE!!! Breathtaking views off of all 3 balco ...
From $212 per night (USD)VRBO
From $438 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 $438 per night (USD)VRBO
From $2704 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 $2704 per night (USD)VRBO
From $441 per night (USD)VRBO
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 $441 per night (USD)VRBO
From $901 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 $901 per night (USD)VRBO
From $433 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 $433 per night (USD)VRBO
From $614 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 $614 per night (USD)VRBO
From $206 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 $206 per night (USD)VRBO
From $206 per night (USD)Expedia
Comfy Townhome at Executive Bay Club - Marina, Pool, and Tennis!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
Enjoy this stylishly remodeled townhome in the Heart of Islamorada at Executive Bay Club. This 7-guest retreat features ...
From $206 per night (USD)Expedia
From $236 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 $236 per night (USD)VRBO
From $1315 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 $1315 per night (USD)VRBO
From $512 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 $512 per night (USD)VRBO
From $843 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 $843 per night (USD)VRBO
From $619 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 $619 per night (USD)VRBO
From $444 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 $444 per night (USD)VRBO
Click For PricingVRBO
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 $607 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 $607 per night (USD)VRBO
From $775 per night (USD)VRBO
Islamorada paradise vacation home in sought after Venation shores
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Location, location! Venetian Shores is the premier luxury private community with deep water access to Snake creek, which ...
From $775 per night (USD)VRBO
From $407 per night (USD)Expedia
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 $407 per night (USD)Expedia
From $295 per night (USD)VRBO
Embrace the Sugar Rush Experience! Onsite Pool, Free Parking, Near Anne's Beach
- 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 $295 per night (USD)VRBO
From $402 per night (USD)VRBO
Indulge in Home Like Comfort! Free Parking, Onsite Pool, Pet-friendly Property
- 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 $402 per night (USD)VRBO
From $489 per night (USD)VRBO
Indulge in Home-Like Comfort! Free Parking, Onsite Pool, Pet-friendly Property
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
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 $496 per night (USD)VRBO
Make Your Trip More Enjoyable! Free Parking, Pets Allowed, Onsite Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $496 per night (USD)VRBO
From $378 per night (USD)VRBO
Indulge in Home Like Comfort! Courtyard View, Free Parking, Pool, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $378 per night (USD)VRBO
From $381 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 $381 per night (USD)VRBO
From $477 per night (USD)VRBO
Short Distance From The Well Known Sites! Pool, Free Parking, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $477 per night (USD)VRBO
From $398 per night (USD)VRBO
Enjoy a Hassle-Free and Suiting Stay! Pets Allowed, Free Parking, Onsite Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $398 per night (USD)VRBO
From $475 per night (USD)VRBO
Come Create Memories w\/ Fun-filled Adventures at this Paradise! Free Parking
- 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 $475 per night (USD)VRBO
From $472 per night (USD)VRBO
Relax and Unwind! Courtyard View, Free Parking, Onsite Pool, Near Anne's Beach
- 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 $472 per night (USD)VRBO
From $371 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 $371 per night (USD)VRBO
From $371 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 $371 per night (USD)VRBO
From $264 per night (USD)VRBO
Canal-Front Florida Keys Home w\/ Dock!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Ocean breezes and beautiful water views are in store at this 2-bedroom, 2-bathroom home. This Florida Keys vacation rent ...
From $264 per night (USD)VRBO
From $411 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 $411 per night (USD)VRBO
From $411 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 $411 per night (USD)VRBO
From $389 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 $389 per night (USD)VRBO
From $389 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 $389 per night (USD)VRBO
From $389 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 $389 per night (USD)VRBO
From $219 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 $219 per night (USD)VRBO
From $532 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 $532 per night (USD)VRBO
From $210 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 $210 per night (USD)VRBO
From $345 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 $345 per night (USD)VRBO
From $1033 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 $1033 per night (USD)VRBO
From $175 per night (USD)VRBO
Escape to Paradise in Islamorada!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
Welcome to your perfect family-friendly getaway in the heart of Islamorada, Florida! Nestled between the sun-soaked shor ...
From $175 per night (USD)VRBO
From $130 per night (USD)VRBO
Beautiful Efficiency Apartment - Bayfront, Islamorada Apt 232
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summer Sea Condominium Unit 232 is a brilliant, clean and modern efficiency apartment, newly upgraded in 2023 with tile ...
From $130 per night (USD)VRBO
From $136 per night (USD)VRBO
This studio makes the best of the space
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $136 per night (USD)VRBO
From $141 per night (USD)VRBO
Beautifully Updated Studio Apartment, Summer Sea Condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This beautifully updated apartment is new to the rental market. Modern and clean with all the comforts of home, tropical ...
From $141 per night (USD)VRBO
From $133 per night (USD)VRBO
Beautiful Modern Studio, recently remodeled, new to the market, Summer Sea 405
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This beautiful modern Studio apartment has just been completely remodeled and new to the rental market. Every detail has ...
From $133 per night (USD)VRBO
From $112 per night (USD)VRBO
Beautiful Studio Apartment - Summer Sea Condo #230
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summer Sea Condominium Unit 230 is a brilliant, clean and modern efficiency apartment, upgraded with tile throughout and ...
From $112 per night (USD)VRBO
From $169 per night (USD)Expedia
New 2\/1 Remodeled Cozy Home in Tavernier Key
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Relax at this peaceful and centrally-located 2/1 remodeled private home in Tavernier Key. Located near Tavernier Creek M ...
From $169 per night (USD)Expedia
From $183 per night (USD)VRBO
Charming 2 bed, 2 bath cottage 100 feet from private sandy ocean beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Charming fully furnished 2 bedrooms each with a king bed, 2 bath cottage just 100 feet from shared private sandy beach o ...
From $183 per night (USD)VRBO
From $858 per night (USD)VRBO
Large Canal Front Family home in the heart of Islamorada
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Make yourself at home at this beautiful stay in Islamorada. Minutes away from the open ocean and the bay, this home is o ...
From $858 per night (USD)VRBO
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Beautiful oceanfront resort located at mile marker 73.8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
We are committed to providing outstanding service and a great vacation experience to all of our guests. While Caloosa Co ...
Click For PricingVRBO
From $396 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 $396 per night (USD)Expedia
From $402 per night (USD)VRBO
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 $402 per night (USD)VRBO
From $310 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 $310 per night (USD)VRBO
From $3975 per night (USD)VRBO
Stunning Oceanfront Villa, Luxe Resort Perks at the Islands of Islamorada Resort
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Islands of Islamorada Resort: Your Luxury Oceanfront Retreat Awaits! Indulge in the epitome of coastal e ...
From $3975 per night (USD)VRBO
From $1215 per night (USD)Expedia
Romantic Oceanview Retreat with Beach Access at The Islands of Islamorada Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience Coastal Luxury at The Islands of Islamorada Resort Welcome to Your Perfect Oceanview Suite! Immerse yoursel ...
From $1215 per night (USD)Expedia
From $1189 per night (USD)VRBO
Accessible Ocean View Suite, Luxe Resort Amenities at The Islands of Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience Coastal Luxury at The Islands of Islamorada Resort Welcome to Your Perfect Oceanview Suite! Immerse yoursel ...
From $1189 per night (USD)VRBO
From $3487 per night (USD)Expedia
Stunning Accessible Oceanfront Villa, Luxe Perks at The Islands of Islamorada
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Islands of Islamorada Resort: Your Tropical Paradise Awaits! Experience the perfect blend of coastal cha ...
From $3487 per night (USD)Expedia
From $242 per night (USD)VRBO
Beautiful Townhouse in the heart of the Florida Keys
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
SNOW BIRD.. COME TO PARADISE. 2/2 with a Loft (can be a 3rd bedroom) beautifully located in the heart of the Florida Key ...
From $242 per night (USD)VRBO
From $432 per night (USD)Expedia
Paradise Retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful tranquil private beach is just the beginning of what awaits you in our completely renovated beach house. Port ...
From $432 per night (USD)Expedia
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Little Piece of Paradise (AVAIL Oct-Dec)
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Our Little Piece of Paradise is a relaxing place to enjoy with family and friends. We look forward to making it your hom ...
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From $504 per night (USD)Expedia
Private Bayside Waterfront Home 2 acres, Beach, Deep Water Boat Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Private 2acre Single Family Home awaits! Just another day in Paradise. Located at 75.7MM! Cozy, quiet, 3 bedroom (1 K ...
From $504 per night (USD)Expedia
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Islamorada Gem
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
A completely renovated oceanfront townhome in beautiful Islamorada in the Florida Keys. 3 Story spacious 2 bedroom 2. ...
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From $523 per night (USD)Expedia
Beautiful Waterfront Port Antigua Home, Pool, Private Beach
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Stunning two-story, 3-bedroom resort-style, professionally decorated home. Inside, you'll find a modern and welcoming ho ...
From $523 per night (USD)Expedia