Islamorada Rentals
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)VRBO
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)VRBO
From $699 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 $699 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 $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 $244 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 $244 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
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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 ...
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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 $366 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 $366 per night (USD)VRBO
From $213 per night (USD)VRBO
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 $213 per night (USD)VRBO
From $251 per night (USD)Expedia
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 $251 per night (USD)Expedia
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Magnificent Ocean views at Seagulls w\/Heated pool, beach
- 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 ...
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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 ...
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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 $349 per night (USD)Expedia
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)Expedia
From $376 per night (USD)VRBO
Charming 2-bedroom house in gorgeous 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 $376 per night (USD)VRBO
From $361 per night (USD)Expedia
Half-Mi to Boat Ramp: Canal-Front Florida Keys Gem
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
2 Covered Wraparound Balconies w/ Canal Views | BBQ Ready | 2 Mi to Diving & Snorkeling | Pet Friendly w/ Fee | In-Unit ...
From $361 per night (USD)Expedia
From $204 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 $204 per night (USD)VRBO
From $568 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 $568 per night (USD)VRBO
From $1455 per night (USD)VRBO
Luxurious Venetian Shores Pool Paradise - Your Dream Getaway Awaits!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to our beautiful Venetian Shores Canal Home—a luxurious waterfront retreat offering the ultimate Florida Keys ex ...
From $1455 per night (USD)VRBO
From $272 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 $272 per night (USD)VRBO
From $317 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 $317 per night (USD)VRBO
From $3282 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 $3282 per night (USD)VRBO
From $652 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 $652 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 $201 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 $201 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 $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 $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 $238 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 $238 per night (USD)VRBO
From $342 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 $342 per night (USD)VRBO
From $452 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 $452 per night (USD)VRBO
From $1558 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 $1558 per night (USD)VRBO
From $1138 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 $1138 per night (USD)VRBO
From $1865 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 $1865 per night (USD)VRBO
From $1415 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 $1415 per night (USD)VRBO
From $1422 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 $1422 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 $879 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 $879 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 $212 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 $212 per night (USD)VRBO
From $721 per night (USD)VRBO
Tekeze ~ Relaxed Resort Style Home with 5 Bedrooms, Pool & Dockage
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to Tekeze! Short for "Take it Easy,” this oversized 5-bedroom, 4.5-bath home is located on a wide canal in the ...
From $721 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 $518 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 $518 per night (USD)VRBO
From $134 per night (USD)VRBO
Cute Studio in Summer Sea Condominium
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Discounted 2025 season due to a last minute cancellation. This cute apartment is new to the rental market. Modern and cl ...
From $134 per night (USD)VRBO
From $605 per night (USD)Expedia
3 Bedroom Islamorada Condo w\/ 30' Boat Slip & 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 $605 per night (USD)Expedia
From $355 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 $355 per night (USD)VRBO
From $456 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 $456 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 $343 per night (USD)VRBO
Charming Islamorada waterfront home!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
118 Sea Lane - Charming waterfront located on the oceanside 76-mile marker. Sea Lane offers immediate access to the Atla ...
From $343 per night (USD)VRBO
From $280 per night (USD)VRBO
Islamorada's newest vacation rental address is YOURS!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
169 Sebring Drive - Tucked away in a quiet neighborhood with a NEW gorgeous pool and gated homeowners park, this home is ...
From $280 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 $155 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 $155 per night (USD)VRBO
From $535 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 $535 per night (USD)VRBO
From $2757 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 $2757 per night (USD)VRBO
From $630 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 $630 per night (USD)VRBO
From $670 per night (USD)VRBO
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 $670 per night (USD)VRBO
From $517 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 $517 per night (USD)VRBO
From $354 per night (USD)VRBO
A 57-foot trawler in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Located in a friendly marina with a restaurants, gift shop, tiki bar, kayaks, jet skis, and charter fishing boats minute ...
From $354 per night (USD)VRBO
From $504 per night (USD)VRBO
Sale- 20% off April and May: Boat, Fish, Swim from Your Own 70' Dock!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Come Play! Your 70-foot private dock provides instant access to fun – whether boating, fishing, swimming or relaxing und ...
From $504 per night (USD)VRBO
From $755 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 $755 per night (USD)VRBO
From $1049 per night (USD)VRBO
Private Beachfront Paradise
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Village of Islamorada - Vacation Rental License No. 24-0248 This home is remodeled every year in some way or form...We ...
From $1049 per night (USD)VRBO
From $1447 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 $1447 per night (USD)VRBO
From $323 per night (USD)VRBO
Your Islamorada Vacation dream just became a reality!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
139 Venetian Way - Your Islamorada Winter Vacation dream just became a reality! Brand new to the market, this Venetian S ...
From $323 per night (USD)VRBO
From $888 per night (USD)Expedia
Hidden Gem Duplex in Heart of Islamorada! Sleeps 8
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: This truly is a Hidden Gem in the heart of Islamorada. Nestled in the trees just a few steps from one of the mo ...
From $888 per night (USD)Expedia
From $158 per night (USD)VRBO
Beautiful 1 bedroom apartment with stunning open water view Apt 317
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Premier 1 bedroom unit with both that stunning direct open water bay view and a view of the pool off the balcony. Beauti ...
From $158 per night (USD)VRBO
From $1215 per night (USD)VRBO
Blue Dolphin Oceanfront Estate, Millionaire's Row, Private Saltwater Pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Beautiful Oceanfront 1.8 Acre Estate located in Islamorada featuring amazing ocean views. 5 Bedrooms, 4 Baths, Winding ...
From $1215 per night (USD)VRBO
From $286 per night (USD)VRBO
Idyllic Tropical Paradise Overlooking the Fabulous Florida Bay.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This condo is located in your tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada in Futura Yac ...
From $286 per night (USD)VRBO
From $2472 per night (USD)VRBO
Oceanfront Estate with 4 Cozy Cottages
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 16
Turtle Cove - Turtle Cove is a true hidden treasure in Islamorada. This oceanfront gated estate consists of an enclave o ...
From $2472 per night (USD)VRBO
From $948 per night (USD)VRBO
Charming cottage on the Florida Bay in the heart of Islamorada with pool, dockage, beach + more
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The Bay View Cottage is one of three private homes located at Mermaid's Bay Boutique Estate. Located in the heart of Isl ...
From $948 per night (USD)VRBO
From $171 per night (USD)VRBO
Modern one bedroom apartment with beautiful garden view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This beautiful, modern updated unit is absolutely beautiful with a private balcony with a wonderful garden view. Homey t ...
From $171 per night (USD)VRBO
From $410 per night (USD)VRBO
5 Star Modern Oceanfront Islamorada Townhome on the Beach!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Lazy Daze Beach House is a piece of paradise literally on the Beach! Gorgeous and all new! One King plus set of Full/Tw ...
From $410 per night (USD)VRBO
From $642 per night (USD)Expedia
Relaxing waterfront retreat with boat dock & amazing ocean views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Paradise Beach Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $642 per night (USD)Expedia
From $415 per night (USD)VRBO
Canal Front Beautifully Renovated Home w\/ Great Deck, Private Boat Ramp + WI-FI
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This comfortable house, located in the quiet neighborhood of Plantation Key Colony, Offers three inviting bedrooms and 2 ...
From $415 per night (USD)VRBO
From $707 per night (USD)VRBO
Private Cottage on Bayfront Estate – Pool, Beach, and Boating Paradise
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the Garden View Cottage at Mermaid's Bay Boutique Estate, a serene hideaway located in the heart of Islamorad ...
From $707 per night (USD)VRBO
From $212 per night (USD)VRBO
Beautiful water front home, private dock in Islamorada, World Fishing Capital
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 9
This two-story house is located on an ocean access canal that is literally minutes from the Atlantic Ocean. Guest can do ...
From $212 per night (USD)VRBO
From $220 per night (USD)VRBO
Oceanfront condo in Islamorada, amazing sunrise views, renovated in 2019!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Watch the sunrise from your private balconies in both bedrooms overlooking the Atlantic ocean, and walk across the stree ...
From $220 per night (USD)VRBO
From $205 per night (USD)VRBO
Off the beaten path in one of Islamorada’s hidden gem of a community!.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Vacation like a local! This charming 2 bedroom, 2 bath home is located in one of Islamorada’s quaintest and quietest nei ...
From $205 per night (USD)VRBO
From $2873 per night (USD)VRBO
Open Ocean Views - 2 separate properties -House & Cottage With Dockage & Pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
We privately own a total of 5 boutique vacation rentals in Islamorada: VRBO listing #1576833 (5 bedroom) VRBO listing #1 ...
From $2873 per night (USD)VRBO
From $167 per night (USD)VRBO
Beautiful 2 bedroom Summer Sea Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This beautiful, modern, upgraded 2-bedroom, 1.5 bath apartment at Summer Sea has everything you would want for your fabu ...
From $167 per night (USD)VRBO
From $376 per night (USD)VRBO
Breezy Happy Hours in Port Antigua Beach Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This 2,500sf home has been completely renovated. With 4/3.5 this comfortable home is located in one of the most desirabl ...
From $376 per night (USD)VRBO
From $283 per night (USD)VRBO
Tavernier Creek - Plantation Key Home - 60' Dockage May & September Available!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to "Port of Call." The only thing missing is You and Your Boat! And You are in the premier location, just off Ta ...
From $283 per night (USD)VRBO
From $918 per night (USD)Expedia
Bayfront Home In Florida Keys
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy your stay at your own private oasis! You will approach this stunning home down a secluded road that leads into pa ...
From $918 per night (USD)Expedia
From $728 per night (USD)VRBO
Lg Waterfront lot off Tavernier Crk. 26' dock space, 3\/3-two living areas, Grill
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
The property has a huge corner lot with a double sliding gate ample room to keep your trailer and/or trailers as well a ...
From $728 per night (USD)VRBO
From $1238 per night (USD)Expedia
4 Bedroom Private Oceanfront House - Bahia
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Nestled in the tropical setting of La Jolla Resort in Islamorada, Florida, this 4 bedroom private oceanfront house overl ...
From $1238 per night (USD)Expedia
From $325 per night (USD)VRBO
Water Front 3\/3 Family and Boat Friendly Home, Great Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful well-kept and spacious two story bay-side waterfront home is a perfect rental home for you and your famil ...
From $325 per night (USD)VRBO
From $2338 per night (USD)VRBO
Stunning Oceanfront Home located in Islamorada Florida
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 10
This stunning, completely renovated 5 bedroom, 6.5 bathroom home, sleeps 14 guests. Southwind sits on 1 acre of beachfr ...
From $2338 per night (USD)VRBO
From $679 per night (USD)VRBO
\" Endless Summer\" Awaits!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Stay in a beautiful home in one of the best communities in the Florida Keys, Venetian Shores. You can watch from your v ...
From $679 per night (USD)VRBO
From $439 per night (USD)VRBO
Clean, Fully Remodeled, completely stocked Houseboat, Luxury on the Water
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Very spacious, Comfortable and "super clean" Houseboat. “Baycation” is a 44'x15' triple level upper deck ...
From $439 per night (USD)VRBO
From $1739 per night (USD)VRBO
Luxury home, Heated pool, Hot tub, Chefs kitchen, Sundeck, 100 ft of dockage.
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 12
*** MINIMUM 28 NIGHT STAY *** Once you check-in, you’ll never want to leave 216 Johnny Road With quick ocean access, a ...
From $1739 per night (USD)VRBO
From $291 per night (USD)VRBO
Islamorada beach house - PRIVATE BEACH - KAYAKS - DOCK SPACE
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy the Florida Keys from our newly renovated home in a quaint neighborhood located in Islamorada. This 2 bedroom, 2 ...
From $291 per night (USD)VRBO
From $1474 per night (USD)VRBO
Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed\/5 bath-Next avail 5.17.25
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Islamorada Rental License: VR - 065 *** SATURDAY TO SATURDAY RENTALS ONLY! *** Please note: VRBO is having some AI up ...
From $1474 per night (USD)VRBO
From $261 per night (USD)VRBO
3 Bed Beautiful Keys Home, Quick walk to private beach.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
If you are looking for the perfect home base for your family gathering or friend getaway look no further than this quai ...
From $261 per night (USD)VRBO
From $253 per night (USD)VRBO
Canalfront, Dog-Friendly Home with High-Speed WiFi, Private Boat Ramp, and Kayak
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Islamorada Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $253 per night (USD)VRBO
From $1114 per night (USD)Expedia
3 Bedroom Private Oceanfront House - Sol
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Nestled in the tropical setting of La Jolla Resort in Islamorada, Florida, this 3 bedroom private oceanfront house overl ...
From $1114 per night (USD)Expedia
From $920 per night (USD)VRBO
Islamorada Happy Tarpon House: Heated Pool - Deep Water Boat Dock- Family Fun!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Happy Tarpon - The best of the Florida Keys. The best of Islamorada! Enjoy privacy in our beautifully renovated home in ...
From $920 per night (USD)VRBO
From $606 per night (USD)VRBO
Waterfront, Heated Pool, Spa & 15k lb Boat Lift: Express access to Ocean & Bay!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Fisherman's paradise! 70 feet of Canalfront with immediate access to ocean or bay and 15k pound boat lift. MINIMUM 28 N ...
From $606 per night (USD)VRBO