Islamorada Rentals
- From $586 per night (USD)
VRBO
Tiki Bar,Heated Pool,Pri Spa, kayaks,SUP’s,Bikes,BBQ,Fire ring, outside TV, more
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
We are so proud to say our tropical Bungalow now has 72 Straight 5 STAR REVIEWS on VRBO What sets us apart from "just ...
From $586 per night (USD)VRBO
- From $211 per night (USD)
Expedia
Work remote, or not at all, in paradise at this cozy, beachy condo!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Flexible cancellation policy. Futura Yacht Club is an exclusive private, gated resort community. Not like a hotel, FYC ...
From $211 per night (USD)Expedia
- From $325 per night (USD)
VRBO
Oceanfront! Oceanfront! Oceanfront!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
License # VR-282 - Completely Renovated - 2 Bedroom, 2 Bath, condominium unit. Just steps from the elevator on the 5th f ...
From $325 per night (USD)VRBO
- Click For Pricing
Expedia
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 ...
Click For PricingExpedia
- From $180 per night (USD)
VRBO
Private Tropical Oasis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our Green Turtle! My family and I relocated to the beautiful Florida Keys, from Orlando. The property we pur ...
From $180 per night (USD)VRBO
- From $750 per night (USD)
Expedia
To Paradise \nBook our website fishing & excursions bigdavechartersandtours.com\n
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 14
Forget your worries in this spacious and serene space. Relax while sitting and watching TV or listening. . to music in ...
From $750 per night (USD)Expedia
- From $157 per night (USD)
VRBO
Spring & summer dates available licensed rental vr #24-0235 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 $157 per night (USD)VRBO
- From $818 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 $818 per night (USD)Expedia
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- From $141 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 $141 per night (USD)VRBO
- From $423 per night (USD)
VRBO
Beautiful Venetian Shores, Cozy home, Heated pool, Tiki, Boat Lift, Fish & Dive.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Cozy waterfront villa with heated pool and quick access to Ocean and Gulf fishing and diving. Laid back Tiki Hut great f ...
From $423 per night (USD)VRBO
- From $1542 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 $1542 per night (USD)VRBO
- From $182 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 $182 per night (USD)VRBO
- From $276 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 $276 per night (USD)Expedia
- From $1000 per night (USD)
VRBO
Islamorada Boaters Paradise with 70' Dock and private beach access..
- Bedrooms:
- 5
- Bathrooms:
- 4
- 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 $1000 per night (USD)VRBO
- From $250 per night (USD)
Expedia
Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $250 per night (USD)Expedia
- From $280 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 homeown ...
From $280 per night (USD)VRBO
- From $144 per night (USD)
Expedia
SPECIAL SUMMER SALE RATES MAY-JULY!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
SEE SPECIAL POSTED RATES MAY-JULY! Beacon Reef Condo Oceanfront Islamorada, Florida (Max 4 Persons / **MONTHLY RENTALS ...
From $144 per night (USD)Expedia
- From $250 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 $250 per night (USD)VRBO
- From $500 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 $500 per night (USD)VRBO
- From $325 per night (USD)
VRBO
By The Sea ~ Islamorada Home with Ocean Views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Canal front 2/2 with ocean views and relaxing breezes! The Space: This canal front two bedroom two bathroom ho ...
From $325 per night (USD)VRBO
- From $234 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 $234 per night (USD)Expedia
- From $164 per night (USD)
VRBO
PARADISE FOUND - ISLAMORADA FLORIDA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
BEAUTIFUL THREE BEDROOM, 2 FULL SIZE BATHROOM VACATION RENTAL IS LOCATED IN THE EXECUTIVE BAY CLUB. BREATHTAKING BAY VI ...
From $164 per night (USD)VRBO
- From $293 per night (USD)
Expedia
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 furnishings, newly remodeled with three bedrooms plus oversized lof ...
From $293 per night (USD)Expedia
- From $372 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 $372 per night (USD)VRBO
- From $77 per night (USD)
Expedia
Beautiful, sunlit home with pool, tennis court & beach access - near the marina
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Executive Bay Club Condo M-1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $77 per night (USD)Expedia
- From $139 per night (USD)
VRBO
Keys Life Cottage ~ Downtown Islamorada Cottage with Pool Access!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to the "Keys Life Cottage!" This beautifully updated and spacious two bedroom, one bath home is tucked away on ...
From $139 per night (USD)VRBO
- Click For Pricing
Expedia
Remodeled Townhome with Beach, Pool, Tennis and Marina!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Newly renovated and remodeled 1,359sf townhome at EXECUTIVE BAY CLUB in the heart of Islamorada REDUCED 20% APRIL-JUNE!! ...
Click For PricingExpedia
- From $695 per night (USD)
VRBO
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 $695 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingExpedia
- From $335 per night (USD)
VRBO
2BR\/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
Enjoy a unique and secluded vacation experience in the heart of Islamorada at Shady Palms! Our charming cottage home fea ...
From $335 per night (USD)VRBO
- Click For Pricing
Expedia
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 ...
Click For PricingExpedia
- From $485 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 $485 per night (USD)VRBO
- From $345 per night (USD)
Expedia
A Pirates Great Escape ~ 3bed\/2baths Ocean View Boat Slip included
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront Penthouse Condo with a Private Boat slip. Small Gated Community on the southern tip of Islamorada. The condo ...
From $345 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Breezy Beach Waterfront home in Antigua Harbor
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Relax in this beautiful and comfortably updated bayside home in Port Antigua. Relax in this designer waterfront cul de ...
From $313 per night (USD)VRBO
- From $675 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 $675 per night (USD)Expedia
- From $528 per night (USD)
VRBO
Waterfront beautifully renovated 6 Bedrooms 4 Bath , Gated Family Compound.
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
This Beautifully renovated Compound / Property Comes With A recently completed Magnificent Landscape Oasis , That Begins ...
From $528 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Boater's Paradise
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Huge 9 bed home perfect for Family Reunions -2,000 SqFt under air- with an extra secured lot for RV's, Jet Ski's, Boats, ...
From $350 per night (USD)VRBO
- From $239 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 $239 per night (USD)VRBO
- From $119 per night (USD)
VRBO
Florida Keys! Seagulls condominiums Luxury 2 bedroom condo direct oceanfront
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Seagulls Condominiums Condo, 2 Bedrooms, 2 Baths, (Sleeps 4) This is one of the nicest condos in the Florida Keys Islamo ...
From $119 per night (USD)VRBO
- From $525 per night (USD)
VRBO
Islamorada Waterfront Paradise | 5br | Dock | Pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to the fabulous Florida Keys, where the good times await! As you drive south, the world you leave behind fades i ...
From $525 per night (USD)VRBO
- From $374 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 $374 per night (USD)Expedia
- From $1003 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 $1003 per night (USD)VRBO
- Click For Pricing
Expedia
Mitchells Keys Villa - private, secluded bayfront home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Private, secluded villa faces Florida Bay in view of the fabulous Everglades. Located in a lush tropical hammock in a q ...
Click For PricingExpedia
- From $809 per night (USD)
VRBO
Marlin House @ Tarpon Point ~ Luxury Oceanfront 4\/4
- 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 $809 per night (USD)VRBO
- Click For Pricing
Expedia
See Special Fall Rates
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Special Fall Rates for these weeks: 11-07-20 to 11-14-20, 11-14- to 11-21.., and 12-05 to 12-12-20. We have recently c ...
Click For PricingExpedia
- From $300 per night (USD)
VRBO
Coral Harbour Condo 3\/2 Oceanside with 33' Boat Slip Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ground level 3/2 Flat with wrap around screened in lanai in gated community. 3/2 Split Floor Plan: Master Suite with 2 ...
From $300 per night (USD)VRBO
- Click For Pricing
Expedia
Your Keys Getaway - B
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A beautiful home on the bay, in sunny Islamorada, Florida. You have access to one of the only beaches in Islamorada, whi ...
Click For PricingExpedia
- From $298 per night (USD)
VRBO
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 $298 per night (USD)VRBO
- From $203 per night (USD)
Expedia
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 ...
From $203 per night (USD)Expedia
- From $702 per night (USD)
VRBO
Bay Front Home With Magnificent Views
- Bedrooms:
- 4
- Bathrooms:
- 3
- 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 $702 per night (USD)VRBO
- From $165 per night (USD)
VRBO
Florida Keys Peaceful Paradise in Executive Bay Club, Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This gorgeous 3 bedroom/2 bath townhouse has all the comforts of home in paradise. Everywhere you look, reminds you to ...
From $165 per night (USD)VRBO
- From $85 per night (USD)
VRBO
Beautiful\/tropical decorated one bed room Condo over looking Bay side
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful/Tropical decorated one bedroom condo in Summer Seas Condominiums Located at mile marker 88.5 Bayside Islamorad ...
From $85 per night (USD)VRBO
- From $303 per night (USD)
Expedia
Tavernier Keys Home w\/ 70’ Dock & 20k Boat Lift on Bayside! 3\/2.5 Plus Game Room
- Bedrooms:
- 4
- Bathrooms:
- 3
- 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 $303 per night (USD)Expedia
- From $800 per night (USD)
VRBO
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 $800 per night (USD)VRBO
- From $157 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 $157 per night (USD)VRBO
- From $694 per night (USD)
VRBO
Island pool home awaits in Islamorada's Port Antigua
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 12
Your island pool home awaits in Islamorada's Port Antigua! 3 bedroom, additional 2nd floor loft that serves as 4th bedr ...
From $694 per night (USD)VRBO
- From $1250 per night (USD)
VRBO
Private walk-in beach,Amazing pool,kayaks,bikes~EV
- 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 $1250 per night (USD)VRBO
- From $105 per night (USD)
VRBO
Very Nice 3 Bedroom Home With Large Lot! Basketball Court!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
This is a beautiful property that offers a home like atmosphere as well as complete privacy. The property is in the comm ...
From $105 per night (USD)VRBO
- From $316 per night (USD)
VRBO
Unity & Autonomy 2 sides a Beach Duplex & 70' DOCK
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: This is for BOTH upstairs sides of the duplex the whole upstairs of the house can be rented through here so tha ...
From $316 per night (USD)VRBO
- From $540 per night (USD)
VRBO
Experience Life in Islamorada: 1BR Condo
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Immerse yourself in our spacious 1-bedroom, 2-bathroom suite, offering a delightful haven for guests. Relax in the bedro ...
From $540 per night (USD)VRBO
- From $540 per night (USD)
Expedia
Florida Keys Spacious 1 BR with 2 Balconies
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
This generously spacious 1-bedroom, 2-bathroom suite presents a delightful retreat. In the bedroom, guests are treated t ...
From $540 per night (USD)Expedia
- From $399 per night (USD)
VRBO
Islamorada Escape: 1 BR with Den: 2 Balconies
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to your spacious retreat in Islamorada, Florida Keys! This suite offers ample privacy and relaxation. Enjoy the ...
From $399 per night (USD)VRBO
- From $399 per night (USD)
Expedia
Island Time: 1BR with Den and Two Balconies
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to your serene sanctuary in Islamorada, Florida Keys! This spacious 1-bedroom, 2-bathroom suite with a den offer ...
From $399 per night (USD)Expedia
- From $400 per night (USD)
VRBO
Gateway to Island Living: One Bedroom Condo
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Start your day with a delightful cup of coffee on your secluded balcony, embracing the refreshing sea breeze as you plan ...
From $400 per night (USD)VRBO
- From $378 per night (USD)
Expedia
Discover the Florida Keys: 1BR Condo
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Experience the inviting comfort of our 1-bedroom, 2-bathroom suite, designed as a serene sanctuary for guests. Relax in ...
From $378 per night (USD)Expedia
- From $389 per night (USD)
VRBO
Keys Dreams: 1 BR Condo
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Discover the spacious comfort of our 1-bedroom, 2-bathroom suite, offering a tranquil haven for guests to unwind. Relax ...
From $389 per night (USD)VRBO
- From $350 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 $350 per night (USD)Expedia
- From $275 per night (USD)
VRBO
Islamorada End Unit, PANORAMIC Ocean Views, Oceanfront, WiFi, Pool, Gym, Breezes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discount April 13 week, normally $280 Escape to this Keys Oceanfront Corner condo, in an art-deco inspired community wi ...
From $275 per night (USD)VRBO
- From $180 per night (USD)
Expedia
Beautiful Beach Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our beach house located in the heart of Islamorada. Just a short drive from the best restaurants, bars, state ...
From $180 per night (USD)Expedia
- From $224 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 $224 per night (USD)VRBO
- From $182 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 $182 per night (USD)Expedia
- From $307 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 $307 per night (USD)VRBO
- From $450 per night (USD)
Expedia
NEW POOL ** Waterfront Paradise with Amazing Sunsets on Beach**
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
The house is perfect for those traveling with different age groups, in-laws, teenagers or 2 families. The house is extra ...
From $450 per night (USD)Expedia
- From $400 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 $400 per night (USD)VRBO
- From $195 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 $195 per night (USD)Expedia
- From $999 per night (USD)
VRBO
Venetian Shores Islamorada New Home w\/dock & pool
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Located in Venetian Shores, Islamorada Luxurious bayside waterfront home on a wide canal with easy access to the ocean ...
From $999 per night (USD)VRBO
- From $194 per night (USD)
Expedia
Beautiful Islamorada <br> Renovated Condo MM 76.5
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Location, Location, Location! Plan your perfect getaway to paradise. 1/1 Fully Renovated Beautifully Designed Condo. Mm7 ...
From $194 per night (USD)Expedia
- From $607 per night (USD)
VRBO
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 $607 per night (USD)VRBO
- From $695 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 $695 per night (USD)VRBO
- From $513 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 $513 per night (USD)VRBO
- From $695 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 $695 per night (USD)VRBO
- From $513 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 $513 per night (USD)VRBO
- From $695 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 $695 per night (USD)VRBO
- Click For Pricing
Expedia
3 Bedroom Single_family 441701 by Houzlet
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come Enjoy Beautiful Sunsets in this perfect piece of paradise known as Villa Mia. The owners of this breathtaking home ...
Click For PricingExpedia
- From $437 per night (USD)
VRBO
Enjoy a Hassle-Free and Suiting Stay! Free Parking, Onsite Pool, Pet-friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $437 per night (USD)VRBO
- From $437 per night (USD)
VRBO
Indulge in Home-Like Comfort! Free Parking, Pool, Pet-friendly Property
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $437 per night (USD)VRBO
- From $553 per night (USD)
VRBO
Experience Soothing Moments & Luxury! Free Parking, Onsite Pool, Pet-friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Inspired by the lush tropical surroundings of Islamorada, our fully equipped resort rooms feature premium bedding and ge ...
From $553 per night (USD)VRBO
- From $707 per night (USD)
VRBO
Best Value, Quality Stay! Onsite Pool, Free Parking, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Inspired by the lush tropical surroundings of Islamorada, our fully equipped resort rooms feature premium bedding and ge ...
From $707 per night (USD)VRBO
- From $420 per night (USD)
VRBO
Indulge in Home Like Comfort! Free Parking, Onsite Pool, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $420 per night (USD)VRBO
- From $458 per night (USD)
VRBO
Indulge in Home Like Comfort! Oceanfront, Free Parking, Pet-friendly Property
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $458 per night (USD)VRBO
- From $637 per night (USD)
VRBO
Always a Great Idea To Unwind! Free Parking, Onsite Pool, Pet-friendly Property
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $637 per night (USD)VRBO
- From $383 per night (USD)
VRBO
Always a Great Idea To Unwind! Free Parking, Onsite Pool, Pet-friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $383 per night (USD)VRBO
- From $420 per night (USD)
VRBO
Spacious Good-Value Accommodation! Free Parking, Onsite Pool, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $420 per night (USD)VRBO
- From $458 per night (USD)
VRBO
Experience Soothing Moments & Luxury! Free Parking, Pet-friendly Property, Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $458 per night (USD)VRBO
- From $458 per night (USD)
VRBO
Short Distance From The Well Known Sites! Free Parking, Onsite Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $458 per night (USD)VRBO
- From $606 per night (USD)
VRBO
Best Value, Quality Stay! Free Parking, Onsite Pool, Pet-friendly Property
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $606 per night (USD)VRBO
- From $553 per night (USD)
VRBO
Ideal Mix of Comfort and Value! Onsite Pool, Free Parking, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Inspired by the lush tropical surroundings of Islamorada, our fully equipped resort rooms feature premium bedding and ge ...
From $553 per night (USD)VRBO
- From $437 per night (USD)
VRBO
Ideal Mix of Comfort and Value! Pool, Free Parking, Near Anne's Beach & Sea Oats
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $437 per night (USD)VRBO
- From $383 per night (USD)
VRBO
Enjoy a Hassle-Free Stay! Free Parking, Onsite Pool, Near Anne's Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $383 per night (USD)VRBO