Islamorada Rentals
From $450 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 $450 per night (USD)VRBO
From $441 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 $441 per night (USD)VRBO
From $417 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 $417 per night (USD)VRBO
From $404 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 $404 per night (USD)VRBO
From $541 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 $541 per night (USD)VRBO
From $1624 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 $1624 per night (USD)VRBO
From $562 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 $562 per night (USD)VRBO
From $541 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 $541 per night (USD)VRBO
From $2166 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 $2166 per night (USD)VRBO
From $418 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 $418 per night (USD)VRBO
From $821 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 $821 per night (USD)VRBO
From $819 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 $819 per night (USD)VRBO
From $1035 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 $1035 per night (USD)VRBO
From $562 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 $562 per night (USD)VRBO
From $1082 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 $1082 per night (USD)VRBO
From $624 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 $624 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 $474 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 $474 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 $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 $525 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 $525 per night (USD)VRBO
From $771 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 $771 per night (USD)VRBO
From $624 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 $624 per night (USD)VRBO
From $588 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 $588 per night (USD)VRBO
From $588 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 $588 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 $686 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 $686 per night (USD)VRBO
From $686 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 $686 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 $772 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 $772 per night (USD)VRBO
From $514 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 $514 per night (USD)VRBO
From $510 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 $510 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 $495 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 $495 per night (USD)VRBO
From $484 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 $484 per night (USD)VRBO
From $525 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 $525 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 $153 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 $153 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
From $311 per night (USD)VRBO
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 ...
From $311 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 $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 $583 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 $583 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 $221 per night (USD)VRBO
Gone Coastal! 3 bedroom 2 Bath house in Treasure Harbor! Minutes to the Sandbar!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
2 bed 1 bath upstairs with a 1 bed 1 bath separate entrance downstairs. Located in the Treasure Harbor neighborhood of I ...
From $221 per night (USD)VRBO
From $274 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 $274 per night (USD)VRBO
From $263 per night (USD)VRBO
Winter Escape, Modern 3-bedroom plus Loft, Heated Pool, Beach, Fishing Pier
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy a warm winter in the Florida Keys at this beautifully furnished 3-bedroom, 2.5 bathroom townhouse with bonus loft ...
From $263 per night (USD)VRBO
From $680 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 $680 per night (USD)VRBO
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 $3453 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 $3453 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 $1252 per night (USD)VRBO
Luxurious Venetian Shores Pool Paradise - Your Dream Getaway Awaits!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to our beautiful Venetian Shores Canal Home—a luxurious waterfront retreat offering the ultimate Florida Keys ex ...
From $1252 per night (USD)VRBO
From $1474 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 $1474 per night (USD)VRBO
From $295 per night (USD)Expedia
Charming 3-bedroom condo with WiFi and AC in delightful Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience Islamorada like a local in this 3-bedroom condo. This superb property features 2 queen beds and 2 bunk beds, ...
From $295 per night (USD)Expedia
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 $316 per night (USD)Expedia
BAY UNIT! 3-bedroom townhome in beautiful Islamorada with full amenities
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stunning Bay-View Townhome in Executive Bay Club – Newly Renovated! Don't miss out on this rare gem! Perfectly located ...
From $316 per night (USD)Expedia
From $663 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 $663 per night (USD)VRBO
From $305 per night (USD)VRBO
Charming 3-bedroom townhome in fabulous Islamorada seconds from the bay!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your home away from home in Islamorada with 3 bedrooms plus a loft. This cool townhome features a king bed, queen bed, 2 ...
From $305 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 $459 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 $459 per night (USD)Expedia
From $315 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 $315 per night (USD)VRBO
From $246 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 $246 per night (USD)Expedia
From $290 per night (USD)VRBO
Charming 2/2 in Islamorada - Private Access to White Marlin Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This Islamorada house boasts 2 inviting bedrooms with 1 king bed and 2 queen beds. The spacious living room features a c ...
From $290 per night (USD)VRBO
From $241 per night (USD)Expedia
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)Expedia
From $375 per night (USD)VRBO
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 $375 per night (USD)VRBO
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 $148 per night (USD)VRBO
Winterbirds! Charming studio in the Port Antigua Islamorada Florida Keys
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome winter birds to this enchanting studio in Islamorada Florida Keys. This cozy retreat offers TV, AC, WiFi, kitche ...
From $148 per night (USD)VRBO
From $224 per night (USD)Expedia
3-bedroom House in tranquil Islamorada with Modern Amenities
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Make yourself at home in this 3-bedroom Islamorada retreat. This charming house features 2 queen beds and 2 full beds, p ...
From $224 per night (USD)Expedia
From $423 per night (USD)VRBO
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 $423 per night (USD)VRBO
From $1082 per night (USD)Expedia
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 $1082 per night (USD)Expedia
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 $594 per night (USD)VRBO
Islamorada's Newest Luxury Address
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Vacation Rental License #25-0283 Welcome to Peaceful Palms, your little slice of paradise in the heart of Islamorada! S ...
From $594 per night (USD)VRBO
From $192 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 $192 per night (USD)VRBO
From $363 per night (USD)VRBO
Experience Waterfront Bliss at Futura Yacht Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your slice of paradise at Futura Yacht Club! This beautifully renovated 2-bedroom, 2-bathroom townhome offers ...
From $363 per night (USD)VRBO
From $630 per night (USD)VRBO
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 $630 per night (USD)VRBO
From $287 per night (USD)Expedia
FALL SPECIALS! Islamorada Anglers Reef Oceanview: 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 $287 per night (USD)Expedia
From $349 per night (USD)VRBO
Charming 3-bedroom estate with WiFi, AC in enchanting Tavernier
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
237 Bougainville Street Tavernier FL Welcome to your enchanting estate in Tavernier, where coastal charm meets modern c ...
From $349 per night (USD)VRBO
From $279 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 $279 per night (USD)Expedia
From $379 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 $379 per night (USD)VRBO
From $2025 per night (USD)Expedia
Stunning 2-acre Oceanfront Estate with Private Pool ~ Beach. Very private
- 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 $577 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 $577 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 $227 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 $227 per night (USD)VRBO
From $605 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 $605 per night (USD)Expedia
From $908 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 $908 per night (USD)VRBO
From $1401 per night (USD)Expedia
Beach Residence / 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 $1401 per night (USD)Expedia
From $451 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 $451 per night (USD)VRBO
From $733 per night (USD)Expedia
Beautiful Beach House directly ON the beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Islamorada Oceanfront home located directly on a private beach; enjoy swimming snorkeling, and ideal for kitesurfing! ...
From $733 per night (USD)Expedia
From $179 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 $179 per night (USD)VRBO
From $394 per night (USD)Expedia
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 $394 per night (USD)Expedia
From $939 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 $939 per night (USD)VRBO
From $1375 per night (USD)Expedia
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 $1375 per night (USD)Expedia
From $1398 per night (USD)VRBO
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 $1398 per night (USD)VRBO
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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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 $534 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 $534 per night (USD)VRBO
From $376 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 $376 per night (USD)VRBO