Islamorada Rentals
From $303 per night (USD)VRBO
Tavernier Creek - Plantation Key Home - 60' Dockage May & September Available!
- Bedrooms:
- 3
- 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 $303 per night (USD)VRBO
From $446 per night (USD)VRBO
Updated 3/2 condo Futura Yacht Club-Spacious Open Floor Plan, Sunset VIEWS!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Gorgeous completely remodeled spacious condo in the highly sought after Futura Yacht Club overlooking Florida Bay with s ...
From $446 per night (USD)VRBO
From $189 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 $189 per night (USD)VRBO
From $253 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 $253 per night (USD)VRBO
From $201 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 $201 per night (USD)VRBO
From $1800 per night (USD)VRBO
Oceanfront Cottage With Stunning Pool & Dockage in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The recently renovated Oceanside Cottage is located directly on the ocean with amazing morning sunrises over the ocean. ...
From $1800 per night (USD)VRBO
From $574 per night (USD)VRBO
Water front home. 50' Dock w/ Pool & Hot Tub. Just S. of Tavernier Creek
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful Conch style home was completed in 2019. The house is a 2000 sq ft. 3 bedroom 2 bath home, each of it's 3 ...
From $574 per night (USD)VRBO
From $625 per night (USD)VRBO
NEW Luxury Modern Coastal Home in Islamorada
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This New construction has all the bells and whistles to make your stay unforgettable. Located in the heart of Islamorada ...
From $625 per night (USD)VRBO
From $134 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 $134 per night (USD)VRBO
From $408 per night (USD)VRBO
Discover comfort at 139 Venetian Way, a spacious 4BR getaway in Islamorada.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy this quiet, peaceful retreat in the desirable Venetian Shores neighborhood of Islamorada. Located on a quiet plugg ...
From $408 per night (USD)VRBO
From $214 per night (USD)VRBO
Florida Keys Chic
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy breathtaking sunsets from your very own private beach in this Florida Keys Chic townhome!!! Beautiful 3 bedroom 2 ...
From $214 per night (USD)VRBO
From $567 per night (USD)VRBO
Experience comfort at Mini Ray's of Sunshine in Islamorada, perfect for families!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Mini Ray's of Sunshine - Beautiful New Pool Home located in a gated community in the Heart of Islamorada. This home, des ...
From $567 per night (USD)VRBO
From $905 per night (USD)VRBO
Sleeps 8 | Sunset + Boat Basin | Islamorada
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Unique property in the heart of Islamorada, ideal for groups and families traveling together. Enjoy rare acces ...
From $905 per night (USD)VRBO
From $147 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 $147 per night (USD)VRBO
From $1161 per night (USD)VRBO
Large Oceanfront 5 Bedroom Estate, Private Pier and 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 $1161 per night (USD)VRBO
From $492 per night (USD)VRBO
Boat, Fish, Swim from Your Own 70' Dock!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come Play! Your 70-foot private dock provides instant access to fun – whether boating, fishing, swimming or relaxing und ...
From $492 per night (USD)VRBO
From $202 per night (USD)VRBO
Ocean Side Condo In Paradise Mm 76.5-Islamorada, Fl (28 day minimum required)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is a quaint, ocean side condo with full amenities and easy access for fishing, diving, snorkeling and much more.The ...
From $202 per night (USD)VRBO
From $684 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 $684 per night (USD)VRBO
From $1008 per night (USD)VRBO
Private Beachfront Paradise
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Village of Islamorada - Vacation Rental License No. 24-0248 This home is remodeled every year in some way or form...We ...
From $1008 per night (USD)VRBO
From $212 per night (USD)VRBO
Bayside Condo with Beach, Pool, Marina & Dockage, Pickle ball and Tennis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your escape to our tropical paradise begins as you enter through the private gates of our community at Futura Yacht Club ...
From $212 per night (USD)VRBO
From $1438 per night (USD)VRBO
Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
OSPREY BAY VILLA – Your private bayfront escape in the heart of Islamorada, Florida Keys! Relax and enjoy incredible p ...
From $1438 per night (USD)VRBO
From $250 per night (USD)Expedia
Beautiful Ocean Access Islamorada Condo. MM 76.5 Bring your Boat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Discounted 3 to 6 months rentals. Plan your perfect getaways to paradise. 1/1 Fully Renovated Beautifully Designed Condo ...
From $250 per night (USD)Expedia
From $659 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 $659 per night (USD)VRBO
From $791 per night (USD)Expedia
Beach Dream House, relax and enjoy the clear waters of Islamorada FL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our Dream Beach House where you can enjoy the most panoramic views in Islamorada, Florida. Enjoy the sun risi ...
From $791 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 $501 per night (USD)VRBO
Stunning Bayfront Townhouse with Boat Slip/ Marina Access - A Luxurious Retreat!
- Bedrooms:
- 2
- 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 $501 per night (USD)VRBO
From $2451 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 $2451 per night (USD)VRBO
From $659 per night (USD)VRBO
GREAT LOCATION !!! White Marlin Beach House, Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Contact owner for rates and availability (305-431-2006). Relax in Islamorada, Florida Keys... 'Sport Fishing Capital of ...
From $659 per night (USD)VRBO
From $257 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 $257 per night (USD)VRBO
From $227 per night (USD)VRBO
Escape to Paradise in Islamorada!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 11
Welcome to your perfect family-friendly getaway in the heart of Islamorada, Florida! Nestled between the sun-soaked shor ...
From $227 per night (USD)VRBO
From $620 per night (USD)VRBO
ISLAMORADA BEACH HOUSE
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Luxury Waterfront Home in Exclusive Port Antigua – Islamorada, FL Escape to this stunning 4,200 sq. ft. waterfront retr ...
From $620 per night (USD)VRBO
From $667 per night (USD)VRBO
Impressive Resort Like 5 Bedroom / 4.5 Baths with Pool & Dockage in Islamorada!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Located on a cul-de-sac in the charming city of Islamorada, this beautifully- appointed five-bedroom, four and a half-ba ...
From $667 per night (USD)VRBO
From $213 per night (USD)VRBO
Spacious 3 bedroom home in Plantation key with 30 foot dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Make wonderful memories at this unique and family-friendly waterfront townhouse located on a deep-water canal with 30 fo ...
From $213 per night (USD)VRBO
From $411 per night (USD)Expedia
Islamorada retreat \"Bungalow Blue\" w/ heated pool, Bikes, BBQ, amenities galore!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to paradise! Completely remodeled and immaculately maintained... Bungalow Blue is nestled away in the quiet qua ...
From $411 per night (USD)Expedia
From $422 per night (USD)VRBO
Cozy Modern Beach House with Island Charm
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Elegant modern coastal gem with beautiful canal views and incredible views of the surrounding native landscape. This qui ...
From $422 per night (USD)VRBO
From $310 per night (USD)Expedia
Large Keys Home in Heart of Tavernier with 50 ft of deep water dock.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 11
Incredibly comfortable home located in the heart of Tavernier Key Mile Marker 90. Large home featuring incorporated do ...
From $310 per night (USD)Expedia
From $293 per night (USD)VRBO
Enjoy a cozy stay at 169 Sebring Drive, Tavernier, with 3 bedrooms and a private pool.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This charming home is located in a quiet, peaceful neighborhood on Plantation Key, offering the perfect setting for a re ...
From $293 per night (USD)VRBO
From $234 per night (USD)Expedia
Serenity in Tavernier
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Beautiful 3/2 home in centrally located Tavernier! The Space: Escape to the enchanting Florida Keys – your tro ...
From $234 per night (USD)Expedia
From $673 per night (USD)VRBO
Island Time - Plantation Key Home with 4 beds & 3 baths with Pool & Dockage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Island Time! This newly constructed canal front residence located in the heart of Plantation Key is sure to ...
From $673 per night (USD)VRBO
From $317 per night (USD)VRBO
Beautiful, Spacious, Single Story Home - Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This single-story canal front home located in the heart of Islamorada (MM86) in the Florida Keys-fishing capital of the ...
From $317 per night (USD)VRBO
From $303 per night (USD)VRBO
TICKET TO PARADISE !!! PRIVATE POOL, OCEAN SIDE/VIEW COMPLETELY REMODELED
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
New In Ground Heated pool , Just remodeled with new furniture, flat screen tvs throughout ( including the patio) and a d ...
From $303 per night (USD)VRBO
From $473 per night (USD)Expedia
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Tucked away in the vibrant Florida Keys, is our pristine Bungalow paradise. We are located in the heart of Islamorada, w ...
From $473 per night (USD)Expedia
From $217 per night (USD)VRBO
Penthouse Condo with Rooftop Deck & Panoramic Sunset Bay Views – Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy elevated Keys living in this stunning 2-bedroom, 2-bath penthouse condo located in the gated Summer Seas Condomini ...
From $217 per night (USD)VRBO
From $429 per night (USD)VRBO
Relax at 134 Tequesta Street, a 3BR canal home in Tavernier with a private pool.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stunning 3-bedroom heated pool home located on Plantation Key, designed for relaxing and enjoying the Florida Keys lifes ...
From $429 per night (USD)VRBO
From $310 per night (USD)VRBO
Eclectic Easeful Stay At The Keys!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Come and enjoy this spacious, airy, and recently renovated condo at Summer Sea in beautiful Tavernier, Florida. The buil ...
From $310 per night (USD)VRBO
From $572 per night (USD)VRBO
Ocean Access - Pool + Tiki Hut - Boat Friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Bring your boat! Stay just 5 homes from ocean access in this spacious 2-story coastal home—perfect for families. ✨ High ...
From $572 per night (USD)VRBO
From $259 per night (USD)VRBO
Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Take a break and experience the laid-back lifestyle in the beautiful Islamorada! This listing is for a room within a ho ...
From $259 per night (USD)VRBO
From $217 per night (USD)Expedia
Reel Paradise at Sea Gulls
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Stunning ocean views and beautiful island sunrises! The Space: Welcome to Reel Paradise! This beautiful condo ...
From $217 per night (USD)Expedia
From $706 per night (USD)VRBO
Venetian Shores with Deep Water Dock, Waterfall Pool, A/C, Hot Tub, and Wi-Fi
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Minimum 28 day stay. Dreaming of a FL Keys vacation where you can boat, fish, dive, snorkel or stay home and swim in yo ...
From $706 per night (USD)VRBO
From $483 per night (USD)VRBO
Light + Bright Islamorada Pool Home with Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to Islamorada Reef Home, a light and bright Islamorada pool home with dockage. You’ll feel right at home in th ...
From $483 per night (USD)VRBO
From $565 per night (USD)VRBO
Feel the breeze of the keys
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
**HOUSE HAS BEEN RENOVATED AND PICTURES TO COME** Perfect Vacation Home in Islamorada, the center of the Keys Island. T ...
From $565 per night (USD)VRBO
From $611 per night (USD)VRBO
The \"Nest\" Villa & Marina in the heart of beautiful Islamorada. Pet Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
If you are looking for peace and tranquility and a relaxing escape or maybe somewhere to launch and dock your boat for t ...
From $611 per night (USD)VRBO
From $493 per night (USD)VRBO
Islamorada Oasis, Luxurious 4 bedroom 3 bath home. Heated pool! Boat Lift option
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Islamorada Oasis is designed for families and outdoor lovers! Inside and out, its ready for entertaining and keys styl ...
From $493 per night (USD)VRBO
From $1197 per night (USD)Expedia
Islamorada Florida Bay Villa Plunge Pool, Boat Dock, Amazing Sunset Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Villa by the Bay – Your Islamorada Escape for Sunsets, Fishing & Island Living Bring your heart, your family, and your ...
From $1197 per night (USD)Expedia
From $290 per night (USD)VRBO
Fall in the Keys Special Heated Pool, Beach, Kayaks, Bikes & Sunsets on the Dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Your Florida Keys Getaway – A Slice of Paradise in Islamorada Welcome to our beautiful 2-bedroom, 2-bathroom t ...
From $290 per night (USD)VRBO
From $684 per night (USD)VRBO
Immaculate Islamorada Home with 100' of Dockage, Pool & More!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This tropical oasis has everything you need and more for the perfect summer vacation! Nestled in the highly sought-aft ...
From $684 per night (USD)VRBO
From $398 per night (USD)VRBO
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Take a break and experience the laid-back lifestyle in the beautiful Islamorada! This listing is for a room within a ho ...
From $398 per night (USD)VRBO
From $281 per night (USD)VRBO
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Take a break and experience the laid-back lifestyle in the beautiful Islamorada! This listing is for a room within a ho ...
From $281 per night (USD)VRBO
From $398 per night (USD)VRBO
Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Take a break and experience the laid-back lifestyle in the beautiful Islamorada! This listing is for a room within a ho ...
From $398 per night (USD)VRBO
From $475 per night (USD)VRBO
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 $475 per night (USD)VRBO
From $514 per night (USD)VRBO
Best location in downtown Islamorada. 2 Houses with Beach access!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 18
Unbelievable location in Islamorada Florida Keys! You have beach access and boat trailer parking. This listing is for 2 ...
From $514 per night (USD)VRBO
From $630 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 $630 per night (USD)VRBO
From $3657 per night (USD)VRBO
10 Bedroom Private Ocean Front Estate
- Bedrooms:
- 10
- 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 $3657 per night (USD)VRBO
From $496 per night (USD)VRBO
Pet Friendly 3 Bedroom in Venetian Shores Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Salty B is located in the popular neighborhood of Venetian Shores! Canal front home on Snake Creek gives you fast ac ...
From $496 per night (USD)VRBO
From $417 per night (USD)VRBO
Fabulous Island Getaway! Easy access to Florida Bay, Private Beach, Elevator
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy watching the ospreys and manatees from the dock at this beautiful Port Antigua home on Biscayne Blvd. You have acc ...
From $417 per night (USD)VRBO
From $2815 per night (USD)Expedia
Luxury 6 bedroom - truly spectacular beachfront property
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Spectacular, oceanfront, Keys property - three stories of true luxury in a relaxed beachfront setting, the property has ...
From $2815 per night (USD)Expedia
From $676 per night (USD)VRBO
Best Location in the Keys Waterfront 3/3 Home, Boat Dock, Great layout!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
BEST Location in the Florida Keys! Waterfront 3bed/3bath home in the Village of Islamorada with 60ft canal frontage. Pe ...
From $676 per night (USD)VRBO
From $756 per night (USD)Expedia
ISLAMORADA DREAM
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
ONE-OF-A-KIND VACATION HOME. Elegant living at its finest. You will never want to visit any other place. Large open spa ...
From $756 per night (USD)Expedia
From $205 per night (USD)VRBO
New to the Market: Summer Sea 207
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summer Sea Condo #207: Modern and spectacularly updated 2nd floor unit with private balcony just steps away from the sta ...
From $205 per night (USD)VRBO
From $248 per night (USD)Expedia
This condo is located in one of Islamorada's most prestigious condo complexes.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
PROPERTY NAME: Beacon Reef #307 83201 Old Highway, Islamorada, Florida LOCATION: Ocean side Condo MINIMUM STAY: 28 Day ...
From $248 per night (USD)Expedia
From $412 per night (USD)VRBO
Beautifully remodeled roomy single family stilt home,
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
PROPERTY NAME: West Plaza 63 West Plaza Del Lago, Islamorada, FL LOCATION: Bayside House MINIMUM STAY: 28 Days, All s ...
From $412 per night (USD)VRBO
From $428 per night (USD)VRBO
Charming Angler's Reef Home with Pool, Dock, Beach & Ocean View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Islamorada’s Finest Oceanfront Gated Community Soak up the sun and enjoy the ocean breeze from this charming ...
From $428 per night (USD)VRBO
From $609 per night (USD)VRBO
Boaters Paradise - Luxury Islamorada waterfront home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Stunning waterfront Islamorada house on a corner lot with direct access to the Bay and 5 minutes from the Atlantic Ocean ...
From $609 per night (USD)VRBO
From $494 per night (USD)VRBO
\"Our Happy Place\" Paradise in Islamorada with Heated Pool and 90 ft Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Located in the desirable Islamorada which is know as the “Sportfishing Capital of the World” and where you will find the ...
From $494 per night (USD)VRBO
From $313 per night (USD)VRBO
Bayside Boater's Paradise-great for Snowbirds-60 d min stay- add 1:1private unit
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
This 2 bedroom- 2 bath, fully-equipped kitchen waterfront home on a deep canal offers a 75 ft-wide frontage dock with 38 ...
From $313 per night (USD)VRBO
From $145 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 $145 per night (USD)VRBO
From $570 per night (USD)VRBO
3 Bedroom Islamorada Condo w/ 30' Boat Slip & Ocean Views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Mother Ocean! This stunning ocean view condo boasts three bedrooms and two full bathrooms, making it perfec ...
From $570 per night (USD)VRBO
From $754 per night (USD)VRBO
Canalfront 4-Bedroom Mangrove Sunset in Islamorada with dockage and 2 boat lifts
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This stunning pool home is nestled along a private canal with convenient dockage and quick access to the bay! This lu ...
From $754 per night (USD)VRBO
From $730 per night (USD)VRBO
Lush tropical plantings in a gated compound located directly on the Florida Bay
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
PROPERTY NAME: Little Bay Cottage 82246 Overseas Highway, Islamorada, Florida LOCATION: Cottage located directly on th ...
From $730 per night (USD)VRBO
From $443 per night (USD)VRBO
Port Antigua Waterfront Home With Private Beach Access
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This Keys Home is Located in Beautiful Port Antigua. 4 Br/ 3 Ba Sleeps 8 Comfortably. All Rooms Have Queen Sized Beds. L ...
From $443 per night (USD)VRBO
From $363 per night (USD)VRBO
Relax and Recharge! Pets Allowed, Outdoor Swimming Pool, Free Parking+Breakfast!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Take a break and experience the laid-back lifestyle in the beautiful Islamorada! This listing is for a room within a ho ...
From $363 per night (USD)VRBO
From $117 per night (USD)VRBO
Pool, Beach and Tennis Court! Fishing, swimming and relaxation!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Take it easy at this unique and tranquil getaway. Enjoy this well equipped 2 bedroom, 2 bath home. Enjoy beautiful suns ...
From $117 per night (USD)VRBO
From $387 per night (USD)VRBO
Canal front home in Venetian Shores. Perfect for families . A boater's paradise!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 14
This canal front home is located in the prestigious Venetian Shores neighborhood. The perfect location right off of Snak ...
From $387 per night (USD)VRBO
From $560 per night (USD)VRBO
Discover La Casita White Marlin, a spacious 5-bedroom escape in sunny Islamorada.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to this stunningly renovated 5-bedroom, 3-bathroom home situated on a picturesque canal, offering a seamless ble ...
From $560 per night (USD)VRBO
From $316 per night (USD)VRBO
Islamorada Escape - Executive Bay w/Pool, Fishing Dock, Beach, Tennis/Pickleball
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located in Islamorada, mile marker 87 right in the middle of beautiful Florida Key's. This Executive Bay Club Condo prov ...
From $316 per night (USD)VRBO
From $1482 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 $1482 per night (USD)Expedia
From $738 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 $738 per night (USD)VRBO
From $739 per night (USD)Expedia
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 $739 per night (USD)Expedia
From $833 per night (USD)VRBO
Sandy Beach Cove🏝️🏖️ Gated Private Beach Home Plus Cottage Oasis , With Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
😊**(Now For Limited Time!. Listed nightly rate includes a 40% Discount On All Stays of 28 days min.!!)**. ...
From $833 per night (USD)VRBO
Click For PricingExpedia
Port Antigua Retreat on Canal with Boat Lift and Private Beach Access
- 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 ...
Click For PricingExpedia
From $807 per night (USD)VRBO
Tekeze ~ Relaxed Resort Style Home with 5 Bedrooms, Pool & Dockage
- Bedrooms:
- 4
- 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 $807 per night (USD)VRBO
From $1072 per night (USD)Expedia
Best Canal in the Keys! 4/3 Waterfront,Heated Pool, Ocean access, Dock, 5⭐ Rated
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Waterfront Islamorada 4/3 Deep Water Canal w direct easy access to ocean and bay with Amazing heated Pool and Hottub. ...
From $1072 per night (USD)Expedia
From $405 per night (USD)VRBO
Experience luxury at Salty B in Islamorada with private pool and canal views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled within the prestigious Venetian Shores community, this captivating canal front duplex offers a remarkable blend ...
From $405 per night (USD)VRBO
From $372 per night (USD)VRBO
Newly Renovated Waterfront Home located in beautiful Islamorada with dockage.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Ready for your dream vacation? Newly remodeled and gated waterfront home located in the fishing capital of the world. T ...
From $372 per night (USD)VRBO
From $622 per night (USD)VRBO
Charming 3BR retreat in Islamorada, perfect for family getaways!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your ultimate Florida Keys dream getaway! This secluded home is perfectly located in the extremely desired ga ...
From $622 per night (USD)VRBO
From $779 per night (USD)Expedia
Gorgeous Keys Vacation Home in Prestigious Neighborhood of Port Antigua
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Beautiful Port Antigua waterfront home with a 60 foot concrete dock on a wide, clear-water canal. Access to Port Antigu ...
From $779 per night (USD)Expedia
From $268 per night (USD)VRBO
Enjoy the Ocean from the deck of this 2BR. Minimum 28-Day Reservation Required
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This beautiful home has stunning views of the Atlantic Ocean. This home has 2 full two bedroom, two baths and is fully ...
From $268 per night (USD)VRBO
From $266 per night (USD)VRBO
2-bedroom home with stunning ocean views in a resort!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Prime location for a relaxing stay, take in the views of the Atlantic from your private balcony. This 2 bedroom,2 bath, ...
From $266 per night (USD)VRBO
From $261 per night (USD)VRBO
Amazing 2-bedroom waterfront resort home! Minimum 28-Day Reservation Required
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sun Outdoors resort offers first class amenities, in the heart of Islamorada, near many restaurants, and across the stre ...
From $261 per night (USD)VRBO
From $198 per night (USD)Expedia
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 $198 per night (USD)Expedia