Islamorada Rentals
From $614 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 $614 per night (USD)VRBO
From $576 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 $576 per night (USD)VRBO
From $962 per night (USD)VRBO
Your Dream Escape in Islamorada! Pet-friendly Property, 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 $962 per night (USD)VRBO
From $545 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 $545 per night (USD)VRBO
From $546 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 $546 per night (USD)VRBO
From $490 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 $490 per night (USD)VRBO
From $839 per night (USD)VRBO
Best Place to Unwind! 2 Spacious Units, Free Breakfast, Swimming Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $839 per night (USD)VRBO
From $380 per night (USD)VRBO
Newly renovated Port Antigua canal front home with convenient dockage!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Fall Special Rates!! Discounted rates through December, inquire within! Welcome to your dream vacation getaway in the ...
From $380 per night (USD)VRBO
From $655 per night (USD)VRBO
Gated Estate Duplex on the Bay with dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
PROPERTY NAME: Little Bay Lower Duplex 82246 Overseas Highway, Islamorada, Florida LOCATION: Duplex located directly on ...
From $655 per night (USD)VRBO
From $925 per night (USD)VRBO
Beach Adventure! Unit w\/ Kitchenette, Outdoor Pool, Free Parking!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $925 per night (USD)VRBO
From $427 per night (USD)VRBO
Excellent Choice! Pet-friendly Property, Pool, Free Parking Onsite!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $427 per night (USD)VRBO
From $793 per night (USD)Expedia
Sandy Beach Cove🏝️🏖️ Gated Private Beach Home and Cottage Oasis With Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Relax , Enjoy and Indulge yourself with Family and friends on this Over Half Acre Private Ocean Beach Oasis 🏝️🏖️ with ...
From $793 per night (USD)Expedia
From $208 per night (USD)VRBO
Radiant waterfront retreat with remarkable views, patio, tennis court, & grill
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Tollgate Tides Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $208 per night (USD)VRBO
From $347 per night (USD)Expedia
Islamorada waterfront villa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Resort Style Venetian Shores Home with 70 ft Dock on a 100 foot wide canal Completely remodeled. Two Bedrooms with King ...
From $347 per night (USD)Expedia
From $411 per night (USD)VRBO
Islamorada Home on Canal with Private Beach Access\n\/ 4 bedroom 3 bath
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
This luxurious 4 bedroom, 3 bathroom house offers exceptional opportunity to experience the Florida keys in style with i ...
From $411 per night (USD)VRBO
From $307 per night (USD)Expedia
Exec Bay townhouse w\/heated pool, marina, beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come and experience the beauty and tranquility of the Florida Keys at Executive Bay Club! Enjoy gorgeous views from this ...
From $307 per night (USD)Expedia
From $911 per night (USD)VRBO
Islamorada Keys Waterfront .Pool Luxury Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Waterfront Islamorada 4 bedroom 3 bathroom home on the absolute best Waterfront Deep Water Canal w direct ocean access. ...
From $911 per night (USD)VRBO
From $1309 per night (USD)Expedia
Complete Duplex on Gated Bayfront Property
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
PROPERTY NAME: Little Bay Prime 82246 Overseas Highway, Islamorada, Florida LOCATION: Two story Duplex Located Directl ...
From $1309 per night (USD)Expedia
From $654 per night (USD)VRBO
2nd Floor Duplex on Gated Bayfront Property
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PROPERTY NAME: Little Bay Upper Duplex 82246 Overseas Highway, Islamorada, Florida LOCATION: Upper Duplex located direc ...
From $654 per night (USD)VRBO
From $965 per night (USD)Expedia
Waterfront home with private pool, bar\/grill, screened patio, & boat access
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Waypoint One Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $965 per night (USD)Expedia
From $241 per night (USD)VRBO
Capt Craig's 1 Bedroom \/1 Bath Apartment in Islamorada, Florida Keys
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Capt. Craig’s Guest Quarters -The Seahorse is a luxurious retreat located in Islamorada. Only 1 ½ hours from Miami Inter ...
From $241 per night (USD)VRBO
From $237 per night (USD)VRBO
Brand New Home, Resort Location, Pet Friendly, Oceanview
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This brand new home is sitting quietly behind a controlled access gate with a private balcony overlooking the Atlantic O ...
From $237 per night (USD)VRBO
From $1143 per night (USD)VRBO
Spectacular 4 bedroom 4 1\/2 bath villa on Tavernier Creek in Florida Keys.
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Incomparable villa directly on Tavernier Creek with immediate access to ocean and bay. Fully fenced and gated. Manatees ...
From $1143 per night (USD)VRBO
From $416 per night (USD)VRBO
Brand New Home, Resort Location, Oceanview
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This brand new home is sitting quietly behind a controlled access gate with a personal view of the Atlantic Ocean. Full ...
From $416 per night (USD)VRBO
From $209 per night (USD)VRBO
BEAUTIFUL PLACE TO STAY!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
ONE OF "THE BEST" vacation value getaways in the Florida Keys. Packed with amenities, access to gulf side dockage, a g ...
From $209 per night (USD)VRBO
From $351 per night (USD)Expedia
Ocean Harbor Paradise in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Talk about an Atlantic Ocean View; you've found it! You will fall in love as soon as you enter the gates at Ocean Harbor ...
From $351 per night (USD)Expedia
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Welcome to Villa Hodali
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Experience a luxurious stay in our newly renovated 3-bedroom, 2.5-bathroom townhome at Executive Bay Club. Centrally loc ...
Click For PricingExpedia
From $619 per night (USD)Expedia
Bayfront Townhome with Boat Slip, Pool and Beach
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
PROPERTY NAME: Seas The Day 88540 Overseas Highway TH#701, Plantation Key, Florida LOCATION: End unit townhouse on the ...
From $619 per night (USD)Expedia
From $498 per night (USD)VRBO
Isla Mamey: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $498 per night (USD)VRBO
From $978 per night (USD)Expedia
Isla Lychee: Little Basin Villas, Waterfront Boutique Resort, Walkable
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $978 per night (USD)Expedia
From $530 per night (USD)VRBO
Isla Key Lime: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $530 per night (USD)VRBO
From $929 per night (USD)Expedia
Isla Mirabelle: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $929 per night (USD)Expedia
From $241 per night (USD)VRBO
Islamorada Slice of Paradise with private beach and glorious sunsets!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautifully decorated townhome community located right next door to Founder’s Park in Islamorada. This community offer ...
From $241 per night (USD)VRBO
From $520 per night (USD)Expedia
Sunset Peninsula—a multi-family, original, Florida Keys waterfront retreat!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to the Sunset Peninsula! This gated, multi-family compound is perfect for those traveling in larger groups with ...
From $520 per night (USD)Expedia
From $694 per night (USD)VRBO
PARADISE SHORES
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
You won't be disappointed once you arrive at Paradise Shores. This completely remodeled Venetian Shores 4 BD / 3 BA cana ...
From $694 per night (USD)VRBO
From $432 per night (USD)Expedia
Islamorada's Premier Boating Neighborhood; Venetian Shores. A boaters paradise.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled within the serene surroundings of Islamorada, Florida, awaits a charming oasis at 116 Stromboli Drive. This sing ...
From $432 per night (USD)Expedia
From $880 per night (USD)VRBO
Tut's Cay: 4 BR, 5.5 BA House in Tavernier, Sleeps 10
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Tut’s Cay, an opulent 4-bedroom, 5.5-bathroom sanctuary nestled in the heart of Islamorada within the captiva ...
From $880 per night (USD)VRBO
From $405 per night (USD)Expedia
4-bedroom airport community house in Tavernier
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
*MORE PHOTOS TO COME AFTER RENOVATIONS* Experience Tavernier like a local in this 4-bedroom house. Step into a wonderful ...
From $405 per night (USD)Expedia
From $279 per night (USD)VRBO
Charming 3-bedroom house in Islamorada with Marina access.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This Islamorada house boasts 3 inviting bedrooms. Bedrooms are furnished with 1 king bed and 2 full beds, ensuring a com ...
From $279 per night (USD)VRBO
From $379 per night (USD)Expedia
Casa Margarita Islamorada, Paradise awaits!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Experience Islamorada like a local in this 3-bedroom 3-bath pool home. This beautiful recently remodeled 3 bed 3 bath po ...
From $379 per night (USD)Expedia
From $694 per night (USD)VRBO
4-bedroom house in Islamorada, The Sportfishing Capital of the World
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
You won't be disappointed once you arrive at Paradise Shores. This completely remodeled Venetian Shores 4 BD / 3 BA cana ...
From $694 per night (USD)VRBO
From $212 per night (USD)Expedia
Exec Bay 3 Bedroom townhouse w\/heated pool, marina, tennis & more
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Come and experience the beauty and tranquility of the Florida Keys at Executive Bay Club! Enjoy gorgeous sunsets from th ...
From $212 per night (USD)Expedia
From $230 per night (USD)VRBO
Charming 2-bedroom house in welcoming Islamorada with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This brilliant house in Islamorada is a wonderful choice for guests seeking a cozy retreat. With 2 bedrooms, 2 bathrooms ...
From $230 per night (USD)VRBO
From $307 per night (USD)Expedia
Ocean View Beautifully Remodeled 2\/2 at Seagulls
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful ocean views, spacious interior, and recent renovations of the condo make it the perfect place for Florida Keys ...
From $307 per night (USD)Expedia
From $231 per night (USD)VRBO
Charming 2-bedroom townhome with WiFi, AC in enjoyable Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Your Islamorada adventure begins at this 2-bedroom townhome. Inside, guests will find a delightful mix of comfort and st ...
From $231 per night (USD)VRBO
From $274 per night (USD)Expedia
Charming 2-bedroom apartment with WiFi, AC in serene Islamorada. 75' dock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Islamorada is waiting for you at this superb 2-bedroom apartment. With a king bed, a queen bed, and a cozy living room w ...
From $274 per night (USD)Expedia
From $1151 per night (USD)VRBO
Beach Getaway! Outdoor Pool, Free Parking, Near Keys History & Discovery Center
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay close to Florida Keys Brewing Co. and Bud n' Mary's Dive Center. Explore Indian Key Historic State Park and dive in ...
From $1151 per night (USD)VRBO
From $1900 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 $1900 per night (USD)VRBO
From $480 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 $480 per night (USD)VRBO
From $227 per night (USD)Expedia
Amazing new 2-bedroom, 2-bathroom apartment in the heart of Islamorada!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Islamorada apartment boasts 2 inviting bedrooms with 2 queen beds. The cozy living room also offers an extra queen ...
From $227 per night (USD)Expedia
From $250 per night (USD)VRBO
Beautiful Home located in Downtown Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
PROPERTY NAME: Mango House 81212 Old Highway Islamorada, Florida Location: Ocean side located on the Old Road by Gree ...
From $250 per night (USD)VRBO
From $1021 per night (USD)VRBO
2 Spacious Garden Suite w\/ Kitchenette | Outdoor Pool + Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 12
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $1021 per night (USD)VRBO
From $511 per night (USD)VRBO
Steps Away from the Beach | Spacious 1BR Suite w\/
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $511 per night (USD)VRBO
From $535 per night (USD)VRBO
Beachside Retreat in Islamorada - Suite w\/ Pool View Queen | Family Ready
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $535 per night (USD)VRBO
From $1540 per night (USD)VRBO
Scenic Beachfront Suite w\/ Gorgeous Views & Family-Friendly Pool | Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $1540 per night (USD)VRBO
From $1070 per night (USD)VRBO
Two Spacious 1BR Suite w\/ Scenic Pool View | Breathtaking Resort | Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 12
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $1070 per night (USD)VRBO
From $194 per night (USD)VRBO
Magnificent Seagulls Ocean View 1B Condo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful ocean views, spacious interior, and recent renovations of the condo make it the perfect place for a Florida Ke ...
From $194 per night (USD)VRBO
From $968 per night (USD)Expedia
Wander Islamorada Shores
- 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 ...
From $968 per night (USD)Expedia
From $234 per night (USD)VRBO
Winter Escape, Modern 3-bedroom plus Loft, Heated Pool, Beach, Fishing Pier
- Bedrooms:
- 3
- 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 $234 per night (USD)VRBO
From $478 per night (USD)Expedia
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 $478 per night (USD)Expedia
From $240 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 $240 per night (USD)VRBO
From $296 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 $296 per night (USD)VRBO
From $687 per night (USD)VRBO
Gorgeous newly constructed home in the exclusive neighborhood of Venetian Shores
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Escape to this delightful coastal home in picturesque Islamorada. With 4 spacious bedrooms, including 2 king beds and 3 ...
From $687 per night (USD)VRBO
From $4029 per night (USD)VRBO
Entire Floor - 8 BR overlooking pool, sandy beach & Ocean! Luxury finishings
- Bedrooms:
- 9
- Bathrooms:
- 8
- Sleeps:
- 16
Introducing Maison Residences Full floor for rent – Oceanfront & Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE — ...
From $4029 per night (USD)VRBO
From $646 per night (USD)VRBO
Morada Breeze ~ 6 Bedroom Plantation Key Home with Pool & Dockage
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to Morada Breeze! This 6-bedroom, 4-bath bayside slice of paradise is ready to make your next vacation an enjoya ...
From $646 per night (USD)VRBO
From $659 per night (USD)VRBO
Morada Zen - 4BR\/3Bath Waterfront Ocean & Bay Access, Pool, Tiki, Dockage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Islamorada Florida - Fishing Capital of the World!! Beautiful 4 bedroom, 3 bath home available for monthly rental (28 da ...
From $659 per night (USD)VRBO
From $276 per night (USD)VRBO
Coral Harbour Club ~ 2 Bedroom Condo in Islamorada with Pool & Dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Coral Harbour Club! Find your escape, experience relaxing days at this oceanside getaway! Located on Planta ...
From $276 per night (USD)VRBO
From $207 per night (USD)VRBO
Charming 3-bedroom house with private beach access in beautiful Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Bask in the warmth of Islamorada Florida with this 3-bedroom, 2-bath home. 90 minutes from Miami and ½ way down the Flor ...
From $207 per night (USD)VRBO
From $304 per night (USD)VRBO
NEW! Boater's Paradise with Boat Lift, Ice Machine, and Screened Porch
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This cozy haven is perfect for a laid-back Keys getaway centered around boating and fishing. Nestled in the heart of Tav ...
From $304 per night (USD)VRBO
From $286 per night (USD)VRBO
NEW! Canal-Front with Tropical Charm & Private Guest Apartment on Plantation Key
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Manatee Manor! Nestled in the desirable Indian Waterways neighborhood on Plantation Key, this charming canal- ...
From $286 per night (USD)VRBO
From $237 per night (USD)VRBO
Executive Bay Club R8 ~ 3 Bed \/ 3 Bath + Loft Townhouse on Plantation Key
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Discover your ideal getaway at this charming seascape in Islamorada! This lovely 3-bedroom, 3-bathroom townhome, complet ...
From $237 per night (USD)VRBO
From $308 per night (USD)VRBO
Beachside Topsider Octagon Pad
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
At Topsider Resort, you’ll be staying in our unique octagonal stilted homes nestled in a lush tropical setting facing di ...
From $308 per night (USD)VRBO
From $488 per night (USD)VRBO
The Reef House, Waterfront, Oceanside, 70' Dock, Heated Pool and Spa Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Reef House! This ideal location allows for direct, bridge-free access to the Atlantic Ocean or bayside via Ta ...
From $488 per night (USD)VRBO
From $2560 per night (USD)VRBO
Oceanfront Estate in the Heart of Islamorada
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Morada Shores, an exquisite estate where every detail has been carefully crafted for the ultimate vacation ex ...
From $2560 per night (USD)VRBO
From $1185 per night (USD)VRBO
Maison 402 Island Charm
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Maison 402 Island Charm, your perfect vacation retreat in the heart of Islamorada! This charming 3-bedroom, 3 ...
From $1185 per night (USD)VRBO
From $2280 per night (USD)VRBO
\"Luxurious Open Bay Retreat: Expansive Dockage & Private Pool Oasis!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Discover your dream vacation at Pirate's Chateau, nestled in the pristine Venetian Shores on the open bay. This luxuriou ...
From $2280 per night (USD)VRBO
From $1419 per night (USD)VRBO
Coastal Retreat in the Heart of Islamorada
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Nestled between the Cheeca Lodge and Caribbean Resort, our 4-bedroom oceanside home offers a unique beachfront experienc ...
From $1419 per night (USD)VRBO
From $1406 per night (USD)VRBO
Waterfront, dock, private oasis in the heart of Islamorada! Pool & Sunsets!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
You don’t want to miss this! Old Florida charm in the heart of Islamorada on a half-acre private oasis. The Butterfly Ho ...
From $1406 per night (USD)VRBO
From $428 per night (USD)VRBO
Ultimate Keys Oasis! 4 Bedroom, Poolside Retreat!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Indulge in the ultimate waterfront getaway at this 4-bedroom canal front, pool side oasis, conveniently located at mile ...
From $428 per night (USD)VRBO
From $921 per night (USD)VRBO
Heart of Islamorada Dream Getaway Awaits!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Get ready to experience an incredible Islamorada vacation at Maison 305, located in the heart of Islamorada, FL. This wa ...
From $921 per night (USD)VRBO
From $197 per night (USD)VRBO
NEW! Delightful 2 Bedroom Townhouse with Pool, Beach, Tennis Courts & More
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to paradise in this delightful 2-bedroom townhouse, nestled in the peaceful compound of Executive Bay Club. Ste ...
From $197 per night (USD)VRBO
From $319 per night (USD)VRBO
Canal-Front Oasis in the Florida Keys
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to paradise in this stunning 3-bedroom, 2-bathroom vacation home in the heart of the Florida Keys. Situated on a ...
From $319 per night (USD)VRBO
From $406 per night (USD)VRBO
Spectacular Keys home on corner canal, hot tub, tiki hut + much more!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come experience the breathtaking beauty of nature right from your backyard! Relax on the tranquil canal with stunning wa ...
From $406 per night (USD)VRBO
From $626 per night (USD)VRBO
Canal front home in Venetian Shores. Perfect for families . A boater's paradise!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 16
This canal front home is located in the prestigious Venetian Shores neighborhood. The perfect location right off of Snak ...
From $626 per night (USD)VRBO
From $140 per night (USD)VRBO
Cute Studio in Summer Sea Condominium
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This cute apartment is new to the rental market. Modern and clean with all the comforts of home with tropical décor, lig ...
From $140 per night (USD)VRBO
From $617 per night (USD)Expedia
MOTHER OCEAN! Islamorada Condo w\/ Dockage & Ocean Views!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Mother Ocean! This stunning ocean view condo boasts three bedrooms and two full bathrooms, making it perfec ...
From $617 per night (USD)Expedia
From $348 per night (USD)VRBO
Upscale Waterfront Home with Private Beach & Dockage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The perfect upscale Islamorada getaway awaits. Sandy Pointe 113 is a newly renovate home that offers panoramic water vi ...
From $348 per night (USD)VRBO
From $458 per night (USD)Expedia
Keys waterfront paradise
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful keys oceanfront home fully equipped . great for entertainment. fishing paradise just a short distance from wor ...
From $458 per night (USD)Expedia
From $568 per night (USD)VRBO
Amazing 4 Bedroom Canal Home with Pool and Dockage-Holly's Hideout by FKLR
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Canal Front......Pool......Dockage......Pet friendly......It’s all here at Holly's Hideout! Located in beautiful Tave ...
From $568 per night (USD)VRBO
From $3453 per night (USD)VRBO
10 Bedroom Private Ocean Front Estate
- Bedrooms:
- 11
- Bathrooms:
- 10
- Sleeps:
- 22
The Island Palm Estates is a newly constructed estate that includes 2 separate, luxurious homes with all the modern conv ...
From $3453 per night (USD)VRBO
From $612 per night (USD)VRBO
GREAT LOCATION !!! White Marlin Beach House, Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Contact owner for rates and availability (305-431-2006). Relax in Islamorada, Florida Keys... 'Sport Fishing Capital of ...
From $612 per night (USD)VRBO
From $648 per night (USD)Expedia
Harbor Hideaway | Island style beach house with pool, dockage & bay views!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Introducing “Harbor Hideaway!” This charming, island style beach house on Lower Matecumbe Key is the perfect spot for y ...
From $648 per night (USD)Expedia
From $147 per night (USD)VRBO
NEW-Summer Sea - Sweet updated 1B Apartment w\/ Garden View Apt 125
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
1 bedroom apartment new to the rental market! Modern and updated, this first floor unit has a gorgeous kitchen with stai ...
From $147 per night (USD)VRBO
From $445 per night (USD)VRBO
Stunning Bayfront Townhouse with Boat Slip\/ Marina Access - A Luxurious Retreat!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Our Cozy Townhouse at Futura Yacht Club! Nestled right by the ocean, our townhouse offers a peaceful escape ...
From $445 per night (USD)VRBO
From $2829 per night (USD)VRBO
Caribee Beach House ~ Private Islamorada Beach Estate W\/ Heated Pool & Dockage
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to Caribee Beach House! Discover the enchanting charm of Caribee Beach House, where the timeless allure of old- ...
From $2829 per night (USD)VRBO
From $422 per night (USD)VRBO
Spacious Home in Islamorada with boat dock, private beach, & Fast
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
**Please contact owner directly via email if dates do not appear on calendar** There is also an in-laws quarter 1/1 avai ...
From $422 per night (USD)VRBO
From $172 per night (USD)VRBO
Gorgeous Atlantic Ocean Views from 2BR\/2BA Condo in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sorry, no smoking, no pets. Sweeping views of the Atlantic Ocean from this updated and fully furnished Sea Gulls 2 bedr ...
From $172 per night (USD)VRBO
From $630 per night (USD)VRBO
GREAT LOCATION !!! ** White Marlin Beach House, Islamorada FLORIDA KEYS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Contact owner for rates and availability at (305-431-2006). Relax in Islamorada, Florida Keys... 'Sport Fishing Capital ...
From $630 per night (USD)VRBO
From $1366 per night (USD)VRBO
Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
OSPREY BAY VILLA! Wonderful Bay front Home in the heart of Islamorada in the fabulous Florida Keys for rent by the week, ...
From $1366 per night (USD)VRBO
From $723 per night (USD)VRBO
The Perfect Getaway with Swimming Pool, Jacuzzi and Boatslip
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital o ...
From $723 per night (USD)VRBO