Islamorada Rentals
From $629 per night (USD)VRBO
Newly built 4-bedroom house in Tavernier with ample dock space and Kayak ramp.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This Tavernier house boasts 4 inviting bedrooms - 2 king beds, 2 queen beds, and 1 bunk bed. With 3 bathrooms featuring ...
From $629 per night (USD)VRBO
From $569 per night (USD)VRBO
Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $569 per night (USD)VRBO
From $867 per night (USD)VRBO
Relax and Recharge in Islamorada! 2 Relaxing Units, Pets Allowed, Outdoor Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $867 per night (USD)VRBO
From $1193 per night (USD)VRBO
Relax and Unwind in Islamorada! Swimming Pool, Pet-friendly Property!
- 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 $1193 per night (USD)VRBO
From $1855 per night (USD)VRBO
A Place You'll Surely Enjoy! 3 Comfortable Units, Onsite Pool, Free Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $1855 per night (USD)VRBO
From $1234 per night (USD)VRBO
High Tides and Good Vibes! 2 Relaxing Units, Pet-friendly Property, Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $1234 per night (USD)VRBO
From $2469 per night (USD)VRBO
Make Your Trip More Enjoyable! 4 Family-friendly Units, Pets Allowed, Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $2469 per night (USD)VRBO
From $517 per night (USD)VRBO
Best Place to Unwind! Free Parking, Pet-friendly Property, 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 $517 per night (USD)VRBO
From $524 per night (USD)VRBO
2 Queen Beds Room w/ Balcony, Outdoor Pool, Free Parking & Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located oceanfront in Islamorada, Amara Cay Resort features stylish rooms and suites with balconies in a boutique island ...
From $524 per night (USD)VRBO
From $517 per night (USD)VRBO
Comfort and Relaxation! Free Parking, Minutes to History of Diving Museum
- 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 $517 per night (USD)VRBO
From $540 per night (USD)VRBO
Enjoy a Hassle-Free Stay! 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 $540 per night (USD)VRBO
From $569 per night (USD)VRBO
Best Place to Unwind! Free Parking, Onsite Pool, Short Drive to Anne's Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $569 per night (USD)VRBO
From $618 per night (USD)VRBO
Home Away from Home in Islamorada! Pets Allowed, Free Parking, Outdoor 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 $618 per night (USD)VRBO
From $1855 per night (USD)VRBO
Short Distance From The Well Known Sites! 3 Family-friendly Units, Free Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $1855 per night (USD)VRBO
From $678 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 $678 per night (USD)VRBO
From $619 per night (USD)VRBO
Relaxation at Its Finest in Islamorada! Free Parking, Swimming 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 $619 per night (USD)VRBO
From $2474 per night (USD)VRBO
Indulge in Home Like Comfort! 4 Pleasant Units, Free Parking, Onsite Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $2474 per night (USD)VRBO
From $540 per night (USD)VRBO
Always a Great Idea To Unwind! Free Parking, Onsite Pool, Pet-friendly
- 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 $540 per night (USD)VRBO
From $875 per night (USD)VRBO
Ideal Mix of Comfort and Value! Onsite Pool, Free Parking, Pets Allowed
- 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 $875 per night (USD)VRBO
From $879 per night (USD)VRBO
Experience Soothing Moments & Luxury! Free Parking, Onsite Pool, Pet-friendly
- 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 $879 per night (USD)VRBO
From $1185 per night (USD)VRBO
Your Dream Escape in Islamorada! Pet-friendly Property, Swimming 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 $1185 per night (USD)VRBO
From $678 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 $678 per night (USD)VRBO
From $1234 per night (USD)VRBO
Relax and Recharge! 2 Comfortable Units, Free Parking, Onsite Swimming Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $1234 per night (USD)VRBO
From $691 per night (USD)VRBO
Short Distance From The Well Known Sites! 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 $691 per night (USD)VRBO
From $433 per night (USD)VRBO
Make Your Trip More Enjoyable! Onsite Pool, Pets Allowed, Free Parking
- 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 $433 per night (USD)VRBO
From $573 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 $573 per night (USD)VRBO
From $867 per night (USD)VRBO
Charming Escape in Islamorada! 2 Modern Units, Swimming Pool, Pets Allowed!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $867 per night (USD)VRBO
From $573 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 $573 per night (USD)VRBO
From $597 per night (USD)VRBO
Discover Islamorada's Treasures! Pets Allowed, Swimming Pool, Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $597 per night (USD)VRBO
From $904 per night (USD)VRBO
Your Tropical Home in Islamorada! Pets Allowed, Swimming Pool, Beach!
- 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 $904 per night (USD)VRBO
From $691 per night (USD)VRBO
Indulge in Home Like Comfort! Oceanfront, Free Parking, 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 $691 per night (USD)VRBO
From $867 per night (USD)VRBO
Fun and Sun in Islamorada! Free Parking, Swimming 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 $867 per night (USD)VRBO
From $867 per night (USD)VRBO
Peaceful Retreat in Islamorada! Pet-friendly, Swimming Pool, Free Parking!
- 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 $867 per night (USD)VRBO
From $460 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 $460 per night (USD)VRBO
From $807 per night (USD)VRBO
Your Blissful Haven in Islamorada! Beach, Swimming 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 $807 per night (USD)VRBO
From $807 per night (USD)VRBO
Peaceful Mornings in Islamorada! Swimming Pool, Beach, Pet-friendly!
- 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 $807 per night (USD)VRBO
From $444 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 $444 per night (USD)VRBO
From $904 per night (USD)VRBO
Waterfront Elegance in Islamorada! Beach, Swimming Pool, Pet-friendly!
- 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 $904 per night (USD)VRBO
From $584 per night (USD)VRBO
Ideal Mix of Comfort and Value! Pool, Free Parking, Near Anne's Beach & Sea Oats
- 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 $584 per night (USD)VRBO
From $584 per night (USD)VRBO
Indulge in Home-Like Comfort! Free Parking, Pool, Pet-friendly Property
- 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 $584 per night (USD)VRBO
From $460 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 $460 per night (USD)VRBO
From $456 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 $456 per night (USD)VRBO
From $542 per night (USD)VRBO
Spacious Good-Value Accommodation! Free Parking, Onsite 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 $542 per night (USD)VRBO
From $534 per night (USD)VRBO
Indulge in Home Like Comfort! Free Parking, Onsite 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 $534 per night (USD)VRBO
From $596 per night (USD)VRBO
Your Charming Stay in Islamorada! Beach, Swimming Pool, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $596 per night (USD)VRBO
From $974 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 $974 per night (USD)VRBO
From $152 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 $152 per night (USD)VRBO
From $339 per night (USD)VRBO
SEASONAL WATERFRONT RENTAL in Venetian Shores, Islamorada, Pool & New Dock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
After a few years of construction, Morada Breeze , Venetian Shore's Waterfront Paradise is back and better than ever. ...
From $339 per night (USD)VRBO
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Cozy waterfront home with dock, BBQ, dog friendly, AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Treasure Cove Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
Click For PricingVRBO
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 $393 per night (USD)VRBO
2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience paradise like a local in this superb 2-bedroom 2 bath Villa with private patio and your own on premises boat ...
From $393 per night (USD)VRBO
From $319 per night (USD)Expedia
Deep Water Home located in White Marlin Beach Neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
PROPERTY NAME: Marlin House 156 Venetian Drive, Islamorada, FL 33036 LOCATION: Bayside Canal home located in the popula ...
From $319 per night (USD)Expedia
From $565 per night (USD)VRBO
House with ocean and bay views in Middle Keys with boat launch, ramp and dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your perfect getaway in Islamorada/Lower Matecumbe. This charming rental home offers the best of both worlds ...
From $565 per night (USD)VRBO
Click For PricingExpedia
Wander Islamorada Shores w/ Ocean View – 4 Bedrooms, Sleeps 8
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Wander Islamorada Shores is a stunning coastal escape with 180-degree Atlantic views. This home features four-bedroom en ...
Click For PricingExpedia
From $277 per night (USD)VRBO
Charming Bayside 2 bed, 2 bath Condo at Futura in Islamorada WiFi, Pool, Dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This charming and beautifully renovated 2 bedroom condo is located in the Futura Yacht Club community at mile marker 88. ...
From $277 per night (USD)VRBO
From $1326 per night (USD)Expedia
Isla Cove Collection: Sleeps 12, All Ensuite Bedrooms, Waterfront
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $1326 per night (USD)Expedia
From $396 per night (USD)VRBO
Pool Home in Venetian Shores
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 16
Spacious, open layout designed for ultimate comfort and convenience. The fully equipped kitchen flows seamlessly into th ...
From $396 per night (USD)VRBO
From $3147 per night (USD)VRBO
PRIVATE BEACH, Pickleball Court and Tiki Bar/ Heated Pool / Designated Paradise Key
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
Hidden in the heart of Islamorada, this oceanfront villa offers an unmatched privilege of a secluded private beach—an ex ...
From $3147 per night (USD)VRBO
From $251 per night (USD)VRBO
Captains Quarters is a charming canal front Keys house in delightful Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Your cozy getaway awaits in Islamorada at this superb house. With 2 bedrooms including 1 king, 1 queen, and 2 twin beds ...
From $251 per night (USD)VRBO
From $1473 per night (USD)VRBO
Stunning Bayfront Home with Pool & Dockage in Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Grab a margarita and unwind at Marchettiville! This stunning 5-bedroom, 3-bathroom oceanfront property offers private b ...
From $1473 per night (USD)VRBO
From $688 per night (USD)VRBO
Spacious & Remodeled condo w/ sunset views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
LIVE AND LOVE THE FLORIDA KEYS LIFESTYLE! Welcome to this stunning, fully remodeled condo in the highly sought-after Fu ...
From $688 per night (USD)VRBO
From $618 per night (USD)VRBO
Ultimate Islamorada Oasis with Pool, Dock, & More
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 4
Welcome to your own island oasis! This beautiful 4-bedroom, 3-bathroom canal-front home blends luxurious coastal modern ...
From $618 per night (USD)VRBO
From $226 per night (USD)VRBO
3-bedroom townhome in charming Islamorada with AC, WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to your dream getaway! This stunning fully renovated 3-bedroom, 2.5-bathroom townhouse in a gated marina commun ...
From $226 per night (USD)VRBO
From $518 per night (USD)Expedia
Beautiful ocean front private beach 2-bedroom house gorgeous views Isla morada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located in Islamorada, this peaceful 2-bedroom house. Ocean front -Private beach is a welcoming retreat for guests. this ...
From $518 per night (USD)Expedia
From $392 per night (USD)VRBO
Studio, Second Floor Partial Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Perched on the second floor with partial side views, this charming studio is perfect for a cozy getaway in the heart of ...
From $392 per night (USD)VRBO
From $250 per night (USD)Expedia
Wake up every day to the sunrise from the deck of this waterfront home 2bed home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This lovely home has 2 bedrooms and 2 baths. The home is completely furnished, just bring you sunscreen, flip flops and ...
From $250 per night (USD)Expedia
From $241 per night (USD)VRBO
Charming 2-bedroom water-front home in Islamorada in the Florida Keys
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Florida Keys are waiting for you at this 2-bedroom water-front home. Nestled in a tranquil setting, this quaint prop ...
From $241 per night (USD)VRBO
From $317 per night (USD)Expedia
3-bedroom cozy pool home in exclusive Venetian Shores, Islamorada .
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover tranquility at our Venetian Shores Escape, Islamorada. Nestled in a serene neighborhood, this property boasts ...
From $317 per night (USD)Expedia
From $1033 per night (USD)VRBO
Bayfront Home with Pool in Islamorada
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 9
This home includes 5 bedrooms, 4.5 baths, elevator, spacious living room and kitchen. Guests can enjoy the open water a ...
From $1033 per night (USD)VRBO
From $663 per night (USD)Expedia
At The Sandbar: Oceanfront, Htd Pool, Free Dockage, GameRoom, EV Charger
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Amenities: Free Boat dockage, htd pool, BBQ grill, EV charger 🏓 Game room 📍 Mins to the famous ...
From $663 per night (USD)Expedia
From $903 per night (USD)VRBO
Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Located in Islamorada, enjoy what this 3-bedroom villa has to offer. With 2 king beds and 1 queen bed, guests can relax ...
From $903 per night (USD)VRBO
From $490 per night (USD)VRBO
Luxury 2BR Waterfront Futura Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover paradise in this 2-bedroom, 2.5-bath townhouse in the heart of the Florida Keys. Enjoy a private marina 10 feet ...
From $490 per night (USD)VRBO
From $195 per night (USD)VRBO
Quaint Islamorada Cottage with Unbeatable Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to this quaint 2-bedroom, 1-bathroom conch-style cottage in the heart of Islamorada. The fully equipped kitchen a ...
From $195 per night (USD)VRBO
From $798 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 $798 per night (USD)Expedia
From $470 per night (USD)VRBO
PRIME LOCATION Islamorada Anglers Reef Oceanview w/ Private Beach, Pool, Marina
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to REELaxation! Everything you need for your vacation is here, gorgeous private beach, heated resort style pool, ...
From $470 per night (USD)VRBO
From $326 per night (USD)Expedia
This 2 bedroom pet friendly ocean front home has the best views in the resort!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This amazing 2 bedroom 2 bath home is fully furnished, with calming and welcoming decor just bring your flip flops, sun ...
From $326 per night (USD)Expedia
From $386 per night (USD)VRBO
Lovely 2-bedroom house in ocean front resort.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Islamorada house boasts 2 inviting bedrooms with 1 full bed and 1 king bed. The serene atmosphere and lovely decor ...
From $386 per night (USD)VRBO
From $2025 per night (USD)Expedia
Stunning Oceanfront Estate with Private Pool ~ Beach.
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
License # 204. | ** 3 payment schedule available** | No Pet Charges | No security deposit | SATURDAY TO SATURDAY ONLY ...
From $2025 per night (USD)Expedia
From $610 per night (USD)VRBO
Relax & Unwind at Peaceful Palms – A Luxury Islamorada Escape
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Peaceful Palms, a 3-bedroom, 3-bathroom townhome that’s all about easy, laid-back island living. Tucked away ...
From $610 per night (USD)VRBO
From $728 per night (USD)VRBO
Luxury Waterfront Escape- Brand New Home In Venetian Shores
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to 104 Leoni Drive, a stunning new home in the highly sought-after Venetian Shores neighborhood of Islamorada. T ...
From $728 per night (USD)VRBO
From $277 per night (USD)VRBO
Beautiful Home in a Great Neighborhood with Ocean Access and Boat Ramp on Property
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
PROPERTY NAME: Fisherman's Gem 113 Iroquois Drive Islamorada, Florida LOCATION: Oceanside Canal home with Boat dock a ...
From $277 per night (USD)VRBO
From $670 per night (USD)Expedia
Ocean View Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key Two
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Indulge in the epitome of coastal living in this expansive duplex penthouse boasting ocean views in Islamorada. Relish c ...
From $670 per night (USD)Expedia
From $890 per night (USD)VRBO
Ocean View Duplex Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key One
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Indulge in the epitome of coastal living in this expansive duplex penthouse boasting ocean views in Islamorada. Relish c ...
From $890 per night (USD)VRBO
From $1842 per night (USD)Expedia
Private Beach / Private overwater dock / Heated Pool / Mahi Key
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Relish ocean serenity in this residence set directly on a secluded beach, where an open-concept design seamlessly merges ...
From $1842 per night (USD)Expedia
From $481 per night (USD)VRBO
Bayfront Bliss in Islamorada, Private Dock & Stunning Sunset Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your front-row seat to breathtaking bayfront sunsets in the Indian Waterways neighborhood of Plantation Key! ...
From $481 per night (USD)VRBO
From $190 per night (USD)VRBO
Coastal Getaway at Plantation by the Sea
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to Islamorada and enjoy the laid-back lifestyle of the Florida Keys in this 2-bedroom, 2-bathroom condo at Planta ...
From $190 per night (USD)VRBO
From $397 per night (USD)VRBO
Half-Mi to Boat Ramp: Canal-Front Florida Keys Gem
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
2 Covered Wraparound Balconies w/ Canal Views | BBQ Ready | 2 Mi to Diving & Snorkeling | Pet Friendly w/ Fee | In-Unit ...
From $397 per night (USD)VRBO
From $993 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 $993 per night (USD)VRBO
From $1290 per night (USD)VRBO
Ocean View Two Duplex Penthouses / Retreat amenities: tennis court, heated Pool | Vista Key
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 24
Indulge in the epitome of coastal living in these two connected expansive duplex penthouses boasting ocean views in Isla ...
From $1290 per night (USD)VRBO
From $1712 per night (USD)Expedia
BeachFront Paradise/By The Glam Homes
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 15
Summary: This is a truly unique and spectacular Villa thanks to its breathtaking view of the sea and its warm sandy beac ...
From $1712 per night (USD)Expedia
From $1455 per night (USD)VRBO
Bayfront Bliss in Lower Matecumbe – 4BR/3.5BA with Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to paradise at this stunning bayfront home in Lower Matecumbe, Islamorada. With breathtaking open bay views, a pr ...
From $1455 per night (USD)VRBO
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4-bedroom villa in amazing Islamorada with AC, WiFi, fitness room and more!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
In the row of residences, this tri-level home is the third closest to the beach. The ground level of the house has a two ...
Click For PricingExpedia
Click For PricingVRBO
Come relax in this oceanside 2 bedroom home, in a pet friendly resort!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This home has amazing views of the Atlantic, and has 2 two bedroom, two baths. The vibe is tasteful and relaxing - jus ...
Click For PricingVRBO
From $235 per night (USD)Expedia
Charming 2-bedroom home in brilliant Tavernier near Marinas and Founders Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Unwind in Tavernier at this delightful home. This charming property features 2 bedrooms - one with a king bed and the ot ...
From $235 per night (USD)Expedia
From $566 per night (USD)VRBO
Bay Harbour 209C ~ Chic 3 Bed / 2.5 Bath Condo with Ocean Views in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Pressure Drop! This beautiful ocean-view condo features three bedrooms and two full bathrooms, making it an ...
From $566 per night (USD)VRBO
From $373 per night (USD)VRBO
2 Queen Beds Room w/ Ocean View | Free Parking & 3 Outdoor Pools
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Set on 15 oceanfront acres in Islamorada, Three Waters Resort & Marina features island-inspired rooms. Guests enjoy thre ...
From $373 per night (USD)VRBO
From $813 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 $813 per night (USD)VRBO
From $318 per night (USD)VRBO
King Room: Resort w/ Marina and 3 Outdoor Pool | Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Set on 15 oceanfront acres in Islamorada, Three Waters Resort & Marina features island-inspired rooms. Guests enjoy thre ...
From $318 per night (USD)VRBO
From $1221 per night (USD)VRBO
Family Beach Getaway | 3 Relaxing Rooms w/ Balcony
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $1221 per night (USD)VRBO
From $1627 per night (USD)VRBO
4 Scenic Marina View Rooms w/ Balcony | Refreshing Outdoor Pool & Free Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $1627 per night (USD)VRBO