Islamorada Rentals
From $1159 per night (USD)VRBO
TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
We are proud to announce- Castaway Island has been named for 2024’s KW people’s choice awards as a FINALIST for Best Va ...
From $1159 per night (USD)VRBO
From $260 per night (USD)Expedia
Work remote, or not at all, in paradise at this cozy, beachy condo!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Flexible cancellation policy. Futura Yacht Club is an exclusive private, gated resort community. Not like a hotel, FYC ...
From $260 per night (USD)Expedia
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A great place to relax, fish, or even work from. 2\/2 , 66 ft
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
2 Master suites with great screened in porch overlooking Bayside canal. 66 dock, fully furnished. Large family room with ...
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From $394 per night (USD)Expedia
Oceanfront! Oceanfront! Oceanfront!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
License # 25-0123 - Completely Renovated - 2 Bedroom, 2 Bath, condominium unit. Just steps from the elevator on the 5th ...
From $394 per night (USD)Expedia
From $1093 per night (USD)VRBO
To Paradise \nBook our website fishing & excursions bigdavechartersandtours.com\n
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Forget your worries in this spacious and serene space. Relax while sitting and watching TV or listening. . to music in ...
From $1093 per night (USD)VRBO
From $1074 per night (USD)Expedia
Egret House @ Tarpon Point
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Indulge in breathtaking ocean vistas from every living level, complemented by an inviting waterfront pool! The ...
From $1074 per night (USD)Expedia
From $225 per night (USD)VRBO
Spring & summer dates available licensed rental vr #25-0235 NO BOATS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This is a legally licensed rental in the Village of Islamorada license # vr 131 The entire condo has been updated ...
From $225 per night (USD)VRBO
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Beautiful 2\/2 Florida keys home rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful 2/2 fully equipped Islamorda premier private neighborhood florida keys home . Private community with privat ...
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From $159 per night (USD)VRBO
Beautiful home in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come and enjoy all that Islamorada has to offer! Live the Keys life in this beautiful deep water canal front home. Lo ...
From $159 per night (USD)VRBO
From $488 per night (USD)Expedia
Beautiful Venetian Shores, Cozy home, Heated pool, Tiki, Boat Lift, Fish & Dive.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Cozy waterfront villa with heated pool and quick access to Ocean and Gulf fishing and diving. Laid back Tiki Hut great f ...
From $488 per night (USD)Expedia
From $1863 per night (USD)VRBO
Lush Garden Estate in Islamorada FL, W\/ Pool, Dockage, Ocean Front & great views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Island Villa Rental Properties offers this 3 bedroom home with a one bedroom guest house, rents all as one. Located on t ...
From $1863 per night (USD)VRBO
From $354 per night (USD)Expedia
Bayside: 1st Floor Apartment in Native Hammock on Florida Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a nat ...
From $354 per night (USD)Expedia
From $210 per night (USD)VRBO
Paradise in Plantation Key\/Deep Water Canal House\/Boat Dock\/MM 89
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Paradise in Plantation Key. If you are looking to relax and learn about “Keys Time” you are looking in the right area! ...
From $210 per night (USD)VRBO
From $1274 per night (USD)Expedia
Islamorada Boaters Paradise with 70' Dock and private beach access..
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Calling all boaters and anglers! You will love our home. Nestled on a canal only 3 minutes to the bay and 10 minutes to ...
From $1274 per night (USD)Expedia
From $358 per night (USD)VRBO
Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Kottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on ...
From $358 per night (USD)VRBO
From $287 per night (USD)VRBO
Executive Bay Club Bayfront\/Beachfront paradise
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Watch the sunset from your private balcony from this bay front , beach front townhouse/condo. Recently remodeled and ful ...
From $287 per night (USD)VRBO
From $366 per night (USD)VRBO
Beautiful vacation home in the heart of Islamorada , Florida Keys
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A perfect Keys home located in the heart of Islamorada in the sought-after Port Antigua community with access to the hom ...
From $366 per night (USD)VRBO
From $250 per night (USD)Expedia
BOOK YOUR DREAM VACATION TODAY - Limited dates available after May 1, 2025
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
World Famous Beacon Reef Condo Oceanfront Islamorada, Florida (Max 4 Persons / **MONTHLY RENTALS ONLY!!) Come and enjoy ...
From $250 per night (USD)Expedia
From $446 per night (USD)VRBO
By The Sea ~ Islamorada Home with Ocean Views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Canal front 2/2 with ocean views and relaxing breezes! The Space: This canal front two bedroom two bathroom ho ...
From $446 per night (USD)VRBO
From $287 per night (USD)Expedia
Ocean View Condo is a Fisherman's Paradise in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This spacious two bedroom, two bath condominium overlooking the ocean is located on a quiet 12 acre private gated commun ...
From $287 per night (USD)Expedia
From $687 per night (USD)VRBO
Latitude Adjustment FLKeys
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Latitude Adjustment, Islamorada, Florida This home is our families' paradise in the Florida Keys and we want to share it ...
From $687 per night (USD)VRBO
From $343 per night (USD)VRBO
Gorgeous 3\/2 plus loft Islamorada next to Marina, Pool, Dock & Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Townhome with all extras. Keys style with beautiful new furnishings, newly remodeled with three bedrooms plus oversized ...
From $343 per night (USD)VRBO
From $386 per night (USD)VRBO
Sunsets on the bay at Villa Mia
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come and enjoy sunsets on the bay at Villa Mia! We created a peaceful retreat for our family and friends to enjoy. It is ...
From $386 per night (USD)VRBO
From $216 per night (USD)Expedia
Keys Life Cottage ~ Downtown Islamorada Cottage with Pool Access!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to the "Keys Life Cottage!" This beautifully updated and spacious two bedroom, one bath home is tucked away on ...
From $216 per night (USD)Expedia
From $262 per night (USD)VRBO
Beautiful, sunlit home with pool, tennis court & beach access - near the marina
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Executive Bay Club Condo M-1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $262 per night (USD)VRBO
From $782 per night (USD)Expedia
Venetian Tropics weekly Pvt home w\/heated Pool, 3 bedroom \/70ft dock w\/canal
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Vacation Rental License No VR-001 WEEKLY RENTAL Located on the peaceful upper Keys, in Islamorada, this home is situat ...
From $782 per night (USD)Expedia
From $210 per night (USD)VRBO
Remodeled Townhome at EBC w\/ Beach, Pool and more - 20% OFF FOR THE SUMMER!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Newly renovated and remodeled 1,359sf townhome at EXECUTIVE BAY CLUB in the heart of Islamorada REDUCED 20% MAY-AUGUST 2 ...
From $210 per night (USD)VRBO
From $258 per night (USD)Expedia
Winter Special - Beautiful Waterfront Pool Home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
“A Little Slice of Heaven”- completely renovated and updated in December 2020 waterfront pool home in paradise. This is ...
From $258 per night (USD)Expedia
From $369 per night (USD)VRBO
2BR\/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a unique and secluded vacation experience in the heart of Islamorada at Shady Palms! Our charming cottage features ...
From $369 per night (USD)VRBO
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Studio in the heart of the Florida Keys, snowbird community
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
400 sq ft fully equipped studio,full bathroom & kitchenette. Chase sofa with sleeper. On wide private canal to the Ocea ...
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From $637 per night (USD)VRBO
Waterfront Vacation Home w\/Stunning Bay\/Canal Views, Private Dock, Private Beach
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Casa Koto Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $637 per night (USD)VRBO
From $648 per night (USD)Expedia
A Pirates Great Escape ~ 3bed\/2baths Ocean View Boat Slip included
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Oceanfront Penthouse Condo with a Private Boat slip. Small Gated Community on the southern tip of Islamorada. The condo ...
From $648 per night (USD)Expedia
From $420 per night (USD)VRBO
Breezy Beach Waterfront home in Port Antigua
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Relax in this beautiful and comfortably updated bayside home in Port Antigua. Port Antigua is the Lower Keys best kept ...
From $420 per night (USD)VRBO
From $779 per night (USD)Expedia
Luxury waterfront Islamorada Retreat w\/private pool, hot tub, lanai bar& firepit
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to "Casa de Karma", your own private, resort style paradise! Enjoy your large heated pool (with sun shelf and s ...
From $779 per night (USD)Expedia
From $595 per night (USD)VRBO
Waterfront beautifully renovated 6 Bedrooms 4 Bath , Gated Private Home
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
This Beautifully renovated Compound / Property Comes With A recently completed and Magnificent Landscape Oasis , That Be ...
From $595 per night (USD)VRBO
From $404 per night (USD)VRBO
Boater's Paradise
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
This incredible property in Islamorada is the ultimate getaway, offering a spacious and flexible layout with 9 beds—per ...
From $404 per night (USD)VRBO
From $235 per night (USD)VRBO
RESERVE QUICKLY! YOU’LL LOVE IT! EVERYONE DOES!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Huge terrace- accessible from every room! Spacious and clean. Peaceful and away from the highway, yet near everything! S ...
From $235 per night (USD)VRBO
From $132 per night (USD)VRBO
Oceanfront Luxury Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Seagulls Condominiums Islamorada Tavernier Key Largo New Lazy Boy recliner added to our open concept living room. Uppe ...
From $132 per night (USD)VRBO
From $602 per night (USD)VRBO
Islamorada Waterfront Paradise with 5 Bedrooms, Pool and Dock
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Escape to your tropical island paradise in the heart of the Florida Keys! Nestled in cross keys location, to Tavernier C ...
From $602 per night (USD)VRBO
From $453 per night (USD)Expedia
Beautiful Harbor Front Oceanside Home on the Atlantic Ocean
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Oceanside 3/3 located on beautiful 10 acre harbor. Amazing natural surroundings, harbor & ocean views. New furnishings, ...
From $453 per night (USD)Expedia
From $1269 per night (USD)VRBO
Opulent waterfront estate with dock, pool, hot tub & rooftop view - dog-friendly
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Waterfront Wonder Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1269 per night (USD)VRBO
From $388 per night (USD)Expedia
Keys Villa - Secluded tropical paradise located on the water!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Private, secluded villa faces Florida Bay in view of the fabulous Everglades. Located in a lush tropical hammock in a q ...
From $388 per night (USD)Expedia
From $1011 per night (USD)VRBO
Marlin House @ Tarpon Point
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Stunning ocean views from all living levels & a waterfront pool! The Space: Welcome to the captivating Marlin ...
From $1011 per night (USD)VRBO
From $420 per night (USD)Expedia
Bayview Villa- Pet-Friendly Waterfront Paradise. A fisherman's dream!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
We have recently completed an inside and outside renovation. The Bayview Villa is a private, secluded villa facing Flori ...
From $420 per night (USD)Expedia
From $525 per night (USD)VRBO
Waterfront with a pool & private beach access.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Waterfront with pool. Private beach access within a mile. All amenities needed to enjoy a fun and relaxing vacation. A f ...
From $525 per night (USD)VRBO
From $257 per night (USD)Expedia
Beautiful centrally located home in the Florida keys<br>
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Centrally located in the Florida keys close to Islamorada where there are great restaraunts and shops.Park your boat in ...
From $257 per night (USD)Expedia
Click For PricingVRBO
Dog-friendly escape with private dock, porch, balcony, water view, & central AC
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Sun-kissed Bliss Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
Click For PricingVRBO
From $821 per night (USD)Expedia
Bay Front Home With Magnificent Views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 6
Located in Islamorada, the fishing capital of the world, this house is tucked away in a quite neighborhood on the bay si ...
From $821 per night (USD)Expedia
From $458 per night (USD)VRBO
Tavernier Keys Home w\/ 70’ Dock & 20k Boat Lift on Bayside! 3\/2.5 Plus Game Room
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Gorgeous and Spacious Bayside Tavernier Keys Home with a 70’ foot Dock for your Boat and 20,000 lb Boat Lift. Be in the ...
From $458 per night (USD)VRBO
From $917 per night (USD)Expedia
Estate Home with Private Beach, Dock & Bay\/Ocean Access
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Three story traditional Keys home located directly on a channel with one of the best Atlantic Ocean/Bay access points in ...
From $917 per night (USD)Expedia
From $217 per night (USD)VRBO
SPECTACULAR SUNSETS AND FRESH OCEAN BREEZE AWAIT YOU IN ISLAMORADA, FLORIDA!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Just under 1.5 hours from Miami International Airport, you will find the beautiful gated community of Executive Bay Club ...
From $217 per night (USD)VRBO
From $716 per night (USD)Expedia
Island pool home awaits in Islamorada's Port Antigua
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Your island pool home awaits in Islamorada's Port Antigua! 3,500 square foot, 3 bedroom, additional 2nd floor loft that ...
From $716 per night (USD)Expedia
From $1753 per night (USD)VRBO
100'Private Sandy Beach,Pool,Bikes,Kayaks,EV chrgr
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
See why we have ALL 5-star reviews. It's named The Oasis for good reason! Located in the HEART of Islamorada on Upper M ...
From $1753 per night (USD)VRBO
From $379 per night (USD)Expedia
Florida Keys Spacious 1 BR with 2 Balconies Pool view
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Immerse yourself in the serenity of island life with this spacious second-floor pool-view suite thoughtfully designed to ...
From $379 per night (USD)Expedia
From $384 per night (USD)VRBO
1BR with Den, Living Room, Kitchen: Marina and Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your island retreat! This spacious ground-floor Den Suite offers the perfect blend of relaxation and fun, com ...
From $384 per night (USD)VRBO
From $340 per night (USD)Expedia
Ground Floor 1BR with Den and Two Balconies
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This spacious suite offers comfort and convenience and is located on the ground floor with a pool and partial ocean view ...
From $340 per night (USD)Expedia
From $427 per night (USD)VRBO
Relax and Recharge in Islamorada – Ground Floor Suite
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Start your day with coffee on your private patio, soaking in the fresh sea breeze as you plan your Florida Keys adventur ...
From $427 per night (USD)VRBO
From $384 per night (USD)Expedia
1 BR Condo Oceanfront Resort and Marina
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Immerse yourself in the tranquility of island living with this spacious first-floor pool-view suite, perfectly designed ...
From $384 per night (USD)Expedia
From $355 per night (USD)VRBO
Keys Dreams: 1 BR Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover the spacious comfort of our 1-bedroom, 2-bathroom suite, offering a tranquil haven for guests to unwind. Relax ...
From $355 per night (USD)VRBO
From $394 per night (USD)Expedia
Casa Del Pirata | 3 bed \/ 2 ba Canal Home in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Casa Del Pirata! Located in the heart of Port Antigua, this canal front home boasts tropical vibes and can ...
From $394 per night (USD)Expedia
From $332 per night (USD)VRBO
Oceanfront 5th Floor Corner Condo, Panoramic Ocean Views! Pool, WiFi, Gym\n\n
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FOR VIEW LOVERS! Breathtaking panoramic ocean views from this rare 5th floor direct oceanfront corner condo in Islamor ...
From $332 per night (USD)VRBO
From $212 per night (USD)Expedia
Beautiful Beach Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to our beach house located in the heart of Islamorada. Just a short drive from the best restaurants, bars, state ...
From $212 per night (USD)Expedia
From $253 per night (USD)VRBO
Waterfront Community Townhome with Marina, Beach and a Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
SPRING SPECIAL: SAVE 20% When You Book Between April-June! Take your dream Keys vacation in this spacious 3bd/2bth wate ...
From $253 per night (USD)VRBO
From $188 per night (USD)Expedia
Waterfront Townhome w\/ Private Beach in the Florida Keys!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
20% OFF FROM APR-JUN!! Take your dream Keys vacation in this spacious 2bd/3bth waterfront town home in the heart of Isl ...
From $188 per night (USD)Expedia
From $404 per night (USD)VRBO
Peacock Shores Islamorada - Vacation On The Beach!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
The ocean is your front yard at this modern, luxurious townhome hidden away in a small, private seaside community. Enjoy ...
From $404 per night (USD)VRBO
From $513 per night (USD)Expedia
NEW POOL ** Waterfront Paradise with Amazing Sunsets on Beach**
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
The house is perfect for those traveling with different age groups, in-laws, teenagers or 2 families. The house is extra ...
From $513 per night (USD)Expedia
From $462 per night (USD)VRBO
New Construction 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 $462 per night (USD)VRBO
From $226 per night (USD)Expedia
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 $226 per night (USD)Expedia
From $937 per night (USD)VRBO
Venetian Shores Islamorada New Home w\/dock & pool
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
Located in Venetian Shores, Islamorada Luxurious bayside waterfront home on a wide canal with easy access to the ocean ...
From $937 per night (USD)VRBO
From $239 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 $239 per night (USD)Expedia
From $749 per night (USD)VRBO
Beach Dream House, relax and enjoy the clear waters of Islamorada FL
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our Dream Beach House where you can enjoy the most panoramic views in Islamorada, Florida. Enjoy the sun risi ...
From $749 per night (USD)VRBO
From $686 per night (USD)VRBO
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $686 per night (USD)VRBO
From $502 per night (USD)VRBO
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $502 per night (USD)VRBO
From $686 per night (USD)VRBO
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $686 per night (USD)VRBO
From $502 per night (USD)VRBO
Prime Location! Onsite Pool, Free Breakfast, Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $502 per night (USD)VRBO
From $686 per night (USD)VRBO
Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $686 per night (USD)VRBO
From $692 per night (USD)VRBO
Why watch the Sunrise when you have a Mangrove Sunset
- 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 $692 per night (USD)VRBO
From $892 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 $892 per night (USD)VRBO
From $381 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 $381 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 $756 per night (USD)Expedia
Sandy Beach Cove🏝️🏖️ Gated Private Beach Home Plus 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 $756 per night (USD)Expedia
From $315 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 $315 per night (USD)VRBO
From $353 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 $353 per night (USD)Expedia
From $411 per night (USD)VRBO
Port Antigua Retreat on Canal with Boat Lift and Private Beach Access 4BR\/ 3BA
- 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 $655 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 $655 per night (USD)Expedia
From $145 per night (USD)VRBO
Disc Apr-Jun2025-Exec Bay w\/heated pool, marina, beach, tennis\/pickleball
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Disc Apr-Jun2025 due to pool renovation Come and experience the beauty and tranquility of the Florida Keys at Executive ...
From $145 per night (USD)VRBO
From $985 per night (USD)Expedia
Islamorada Keys Waterfront Heated Pool Hottub Luxury Canal Home w Private Dock
- 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 $985 per night (USD)Expedia
From $812 per night (USD)VRBO
Waterfront home with private pool, bar\/grill, screened patio, & boat access
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Key Largo Islamorado Oasis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $812 per night (USD)VRBO
From $458 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 $458 per night (USD)Expedia
From $263 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 $263 per night (USD)VRBO
From $1125 per night (USD)Expedia
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 $1125 per night (USD)Expedia
From $364 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 $364 per night (USD)VRBO
From $151 per night (USD)Expedia
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 $151 per night (USD)Expedia
From $351 per night (USD)VRBO
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)VRBO
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 $733 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 $733 per night (USD)VRBO
From $736 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 $736 per night (USD)Expedia
From $750 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 $750 per night (USD)VRBO
From $659 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 $659 per night (USD)Expedia