Islamorada Rentals
From $661 per night (USD)VRBO
Waterfront home with private pool, bar/grill, screened patio, & boat access
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Key Largo Islamorado Oasis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $661 per night (USD)VRBO
From $279 per night (USD)VRBO
Enjoy the sunrise from the deck of this 2 bedroom, 2 bath home.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Thi sbeautiful home has stunning views of the Atlantic Ocean and has its own boat slip that will accommodate a 21’ boat ...
From $279 per night (USD)VRBO
From $277 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 $277 per night (USD)VRBO
From $272 per night (USD)VRBO
Amazing 2 bedroom waterfront home in a resort!
- 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 $272 per night (USD)VRBO
From $204 per night (USD)VRBO
Capt Craig's 1 Bedroom /1 Bath Apartment in Islamorada, Florida Keys
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Capt. Craig’s Guest Quarters -The Seahorse is a luxurious retreat located in Islamorada. Only 1 ½ hours from Miami Inter ...
From $204 per night (USD)VRBO
From $148 per night (USD)Expedia
Islamorada Condo with ocean access, monthly rentals only
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Month rentals only, no short term. $3,700 per month plus 12.5% tax and $100 cleaning fee. 2 bedroom 1 bathroom condo w ...
From $148 per night (USD)Expedia
From $203 per night (USD)VRBO
Gorgeous Canal front home with a pool and Tiki hut
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Newly furnished 3 BR / 2 Bath . Minutes from Bay & Ocean Make yourself at home in a newly furnished 3 bedroom, 2 bath ho ...
From $203 per night (USD)VRBO
From $571 per night (USD)VRBO
Turquoise Escape - Newly renovated Canal home with heated pool and dockage.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Boater’s Paradise – Pet-Friendly Bayside Pool Home in Tavernier! Enjoy the ultimate Keys lifestyle in this beautifully ...
From $571 per night (USD)VRBO
From $170 per night (USD)VRBO
Condo on Islamorada on the beautiful Atlantic Ocean.\nCome enjoy and relax!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Wake up and enjoy sunrise on the pier over the Atlantic and walk across the street at night and watch sunset on the Gulf ...
From $170 per night (USD)VRBO
From $217 per night (USD)Expedia
Superb Keys home w/heated pool, jacuzzi, fast wifi & more!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come, relax and enjoy yourself in the heated pool or jacuzzi at our home located on mm90 near shops & restaurants. This ...
From $217 per night (USD)Expedia
From $250 per night (USD)VRBO
Oceanview 2 bedroom 2 bath with draw-dropping views!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This home is in a resort. This is a 2bedroom 2bath home, Home has stunning views of the Atlantic Ocean. Home sleeps 6 a ...
From $250 per night (USD)VRBO
From $279 per night (USD)VRBO
Oceanview 2 bedroom, 2 bath home in a pet friendly resort!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Home is located in an ocean front resortt. This 2 bedroom 2 bath home is pet friendly. Home has amazing views of the Atl ...
From $279 per night (USD)VRBO
From $382 per night (USD)VRBO
Best location 3BR house in Islamorada! Pool and beach; walk or bike everywhere.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
AVAILABLE CHRISTMAS & NEW YEARS! Beautiful updated house on dead-end road with pool and private beach access. Launch a k ...
From $382 per night (USD)VRBO
From $2266 per night (USD)Expedia
Pineapple Beach : 5 BR, 4.5 BA in Islamorada, Sleeps 10
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Pineapple Beach – Private Oceanfront Estate in Islamorada Pineapple Beach is situated on more than 3 acres in the centr ...
From $2266 per night (USD)Expedia
From $399 per night (USD)VRBO
House in Islamorada, in exclusive Venetian Shores.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The moment you step inside this calming retreat in exclusive Venetian Shores you feel on vacation with permanently assig ...
From $399 per night (USD)VRBO
From $892 per night (USD)VRBO
Breathtaking Bayfront Villa w/ Private Patio & Living Area, Perfect For Couple
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $892 per night (USD)VRBO
From $686 per night (USD)VRBO
Stunning Bay View Villa in Florida Keys | Beach Getaway w/ Scenic Outdoor Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $686 per night (USD)VRBO
From $553 per night (USD)VRBO
Picture-Perfect Villas Offering Pool Relaxation & Ocean Adventures Nearby
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $553 per night (USD)VRBO
From $506 per night (USD)VRBO
Waterfront Escape: Bayfront Accommodation w/ Kitchen, Onsite Pool, Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $506 per night (USD)VRBO
From $1154 per night (USD)VRBO
4-Bedroom Oceanfront Home in the Heart of Islamorada
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Immerse yourself in the luxury and beauty of Oceanside Resort, a brand-new gated community with 9 beachfront homes nestl ...
From $1154 per night (USD)VRBO
From $177 per night (USD)VRBO
Starfish -1 bedroom 1 bath apartment with full kitchen in Islamorada, Florida.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Starfish is a luxurious retreat located in Islamorada. Only 1 ½ hours from Miami International Airport, we are loca ...
From $177 per night (USD)VRBO
From $322 per night (USD)VRBO
Coastal Island Retreat with Private Beach Access!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Time Well Wasted, an ideal retreat located in the highly sought-after neighborhood of Port Antiqua on Lower M ...
From $322 per night (USD)VRBO
From $1767 per night (USD)VRBO
2 Relaxing Bayfront Villa w/ Private Patio | Scenic Bayside Resort
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $1767 per night (USD)VRBO
From $1115 per night (USD)VRBO
Bayside Tranquility: 2 Spacious Villa w/ Private Patio | Onsite Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $1115 per night (USD)VRBO
From $1684 per night (USD)VRBO
Bayside Tranquility: 3 Relaxing Villa w/ Spacious Living Area & Kitchen
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 18
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $1684 per night (USD)VRBO
From $351 per night (USD)VRBO
Caribbean style home Islamorada - Oceanfront resort privileges.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Indulge in the allure of the Florida Keys with our Caribbean retreat nestled in the heart of Islamorada. Immerse yoursel ...
From $351 per night (USD)VRBO
From $250 per night (USD)VRBO
Ocean front 2 bedroom home, with breathtaking ocean views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This 2 bed 2 bath home is warm and inviting, The home is fully furnished, Just bring your bathing suit and tooth brush, ...
From $250 per night (USD)VRBO
From $3185 per night (USD)VRBO
Private 150 Ft Oceanfront 2.5 Acre Estate with Saltwater Pool, Spa, Dock
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Completely renovated and expanded to over 3,700 square feet. San Roc is a private ocean front home with spectacular vie ...
From $3185 per night (USD)VRBO
From $1173 per night (USD)VRBO
Beautiful bayfront house, private pool and dock, right in Downtown Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Relaxing is made easy at Coral Cove 8, moving from open, airy living spaces to your own private pool. Bright modern fin ...
From $1173 per night (USD)VRBO
From $319 per night (USD)Expedia
Beachfront Cottage - Islamorada!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Immerse yourself in the tranquil beauty of this fully updated beachfront cottage in the heart of Islamorada. Enjoy the c ...
From $319 per night (USD)Expedia
From $289 per night (USD)VRBO
Salty Suites, simply put, it's paradise 365 days a year.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Salty Suites is simply paradise 365 days a year. Located in the fishing capital of the Florida keys, Islamorada. This pe ...
From $289 per night (USD)VRBO
From $242 per night (USD)Expedia
Waterfront paradise with fire pit, Washer/Dryer, and central AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Angler's Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $242 per night (USD)Expedia
From $278 per night (USD)VRBO
Updated Canal Front Home in Indian Waterways
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Perfectly located and fully updated waterfront home with a private dock. Bring your boat and you’re five minutes from th ...
From $278 per night (USD)VRBO
From $596 per night (USD)VRBO
Breathtaking Ocean Views At This Penthouse Suite!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our penthouse condo, a stunning vacation rental with breathtaking ocean views. This modern and tastefully fur ...
From $596 per night (USD)VRBO
From $554 per night (USD)VRBO
5 Bedroom / 4 Bath Relaxed Plantation Key Resort Style Home with Pool & Dockage
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Greetings from Captain's Quarters! Located on Plantation Key (Mile Marker 90), this beautifully updated five bedroom and ...
From $554 per night (USD)VRBO
From $285 per night (USD)Expedia
Capt Craig's 2 Bedroom/1 bath Apartment in Tavernier, Florida Keys
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Capt. Craig’s Guest Quarters The Dolphin Suite is a luxurious retreat located in Islamorada. Only 1 ½ hours from Miami ...
From $285 per night (USD)Expedia
From $258 per night (USD)VRBO
Ocean front home has 2 bedrooms, 2 baths and amazing ocean views.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This home has an upscale decor package and is fully furnished - just bring your suitcase. While here, you will have f ...
From $258 per night (USD)VRBO
From $1688 per night (USD)VRBO
Scenic Resort w/ Private Beach Access | Near History of Diving Museum, 3 Villas
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 18
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $1688 per night (USD)VRBO
From $506 per night (USD)VRBO
Ultimate Vacation in Islamorada! Short Drive to Marathon International Airport
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $506 per night (USD)VRBO
From $1765 per night (USD)VRBO
Islamorada Getaway | 2 Family Ready Bayfront Villa w/ Spacious Living Area
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $1765 per night (USD)VRBO
From $895 per night (USD)VRBO
Relaxing Bay Front Villa Ideal For Romantic Couple Beach Getaway | Free Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $895 per night (USD)VRBO
From $553 per night (USD)VRBO
Enjoy Sunset Views from Your Villa with Pool & Beach Access in FL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $553 per night (USD)VRBO
From $169 per night (USD)VRBO
Islamorada Condo in Highly Sought After Futura Yacht Club
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Futura Yacht Club is located at Mile Marker 88 bayside in the most desired part of the Florida Keys...Islamorada. Futur ...
From $169 per night (USD)VRBO
From $241 per night (USD)VRBO
Futura Yacht Club Condo 403
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Warm up your cold weather blues with some Islamorada sunshine! This updated fourth floor condo can help you do just that ...
From $241 per night (USD)VRBO
From $1952 per night (USD)VRBO
Oceanfront Estate on Islamorada, Florida Keys - Ocean Oasis of Islamorada
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
It's an Ocean Oasis here on this beautiful estate in Islamorada! Over one acre right in front of your PRIVATE beach on t ...
From $1952 per night (USD)VRBO
From $2221 per night (USD)VRBO
Blue Ocean Estate, 3 bedroom ocean front in Islamorada, rented by Island Villa
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Mile Marker 81 - Oceanfront Welcome to your exclusive oceanfront oasis in Islamorada, in the Florida Keys! This 3-bedro ...
From $2221 per night (USD)VRBO
From $1390 per night (USD)VRBO
Beautiful Ocean Front Beach House in Islamorada.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
Beautiful Ocean Front Beach House in the sport fishing capitol of the world Islamorada. Beach with a 200 foot fishing pi ...
From $1390 per night (USD)VRBO
From $795 per night (USD)Expedia
Beautiful Islamorada Home in he heart of the keys, boat-slip, pool, and gated.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to paradise in the heart of Islamorada, the fishing capital of the world! This stunning 4 bedroom home sleeps 8 ...
From $795 per night (USD)Expedia
From $808 per night (USD)VRBO
15% to 20% OFF LUXURY HOUSE CLOSE TO THE OCEAN IN PORT ANTIGUA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Perfect vacation home for those who want to experience privacy and paradise in the Florida Keys! The house features plen ...
From $808 per night (USD)VRBO
From $350 per night (USD)VRBO
Fabulous Futura Yacht Club Townhome with boat slip!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Your own tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada. Futura Yacht Club is a 70 unit c ...
From $350 per night (USD)VRBO
From $361 per night (USD)VRBO
Oceanfront, Private Pool Oasis!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Indulge in a retreat to paradise at this exquisite 3-bedroom, 3-bathroom oceanfront home on the captivating shores of Is ...
From $361 per night (USD)VRBO
From $285 per night (USD)Expedia
Flakey's B&B in the heart of Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
VR-284 A well established, extremely well maintained and family owned and operated vacation rental in the heart of Islam ...
From $285 per night (USD)Expedia
From $230 per night (USD)VRBO
Beautiful Waterfront Pool Home in the Best Location for Your Best Vacation!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Best Home to Share with Family and Friends! This Beautiful Home consists of two levels. The ground level has a 3bedrooms ...
From $230 per night (USD)VRBO
Click For PricingExpedia
2BR/2.5BA Angler's Reef Cottage 116 With Private Beach and Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Check out our video tour! All NEW Anglers Reef Villa 116, a modern beach retreat offering relaxation at its finest. Our ...
Click For PricingExpedia
From $346 per night (USD)VRBO
2BR/2.5BA Angler's Reef Conch Villa 103 With Private Beach and Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
In the heart of the Florida Keys - Islamorada - an ancient reef awaits your arrival, where its waters brim with earth's ...
From $346 per night (USD)VRBO
From $827 per night (USD)Expedia
Unmatched Panoramic Oceanside Luxury, Game Room, & Boat Dockage: Paradise Palms
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Your Ultimate Oceanfront Escape Unmatched Panoramic Views | Crown Jewel of the Neighborhood | Closest Home to the Water ...
From $827 per night (USD)Expedia
From $346 per night (USD)VRBO
Newly Renovated - 2-bedroom state of the art condo Islamorada. Perfect Location!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Palms - Islamorada Brand New - Ripped down to the studs and just completed a $150k remodel with state of the art eve ...
From $346 per night (USD)VRBO
From $277 per night (USD)Expedia
Charming Islamorada house with waterfront, private dock and beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in Islamorada, this delightful house offers a peaceful and serene retreat for guests. With 2 bedrooms, including ...
From $277 per night (USD)Expedia
From $1637 per night (USD)VRBO
Your Ultimate Keys Getaway Awaits!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your dream getaway at Coastal Cove Villa! Nestled in the heart of downtown Islamorada, this spacious 4-bedroo ...
From $1637 per night (USD)VRBO
From $315 per night (USD)Expedia
FULLY RENOVATED piece of paradise. 2 bdrs, 2 king beds, 1 Queen bed 2 full baths
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FULLY RENOVATED piece of paradise. 2 bdrs, 2 king beds, 1 Queen bed 2 full bathrooms and a loft for gaming etc. freshly ...
From $315 per night (USD)Expedia
From $295 per night (USD)VRBO
Bayside Home Dock/Lift quick to ocean perfect spot to enjoy the best of the Keys
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Waterfront home with dock & lift (6k dry weight max) small ramp for your kayaks & paddle boards has direct access to bay ...
From $295 per night (USD)VRBO
From $460 per night (USD)VRBO
Spacious 5-bedroom house with AC and WiFi in welcoming Tavernier
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy a peaceful stay at this 5-bedroom house in Tavernier. This superb property offers a beautiful blend of comfort and ...
From $460 per night (USD)VRBO
From $227 per night (USD)VRBO
Cozy Oceanfront Studio in the Heart of Islamorada.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This property sits directly behind the main oceanfront house on the same property, Your Islamorada adventure begins at t ...
From $227 per night (USD)VRBO
From $321 per night (USD)Expedia
Manatee Manor ~ 3 Bedroom Island Home on Plantation Key with Pool & Dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Swim. Sleep. Repeat., at Manatee Manor. This 3-bedroom, 2.5-bath home on Plantation Key has something for everyone. Enjo ...
From $321 per night (USD)Expedia
From $194 per night (USD)VRBO
Tropical Oasis Anchor located on the bayside. Upcoming Pool ready by Oct 2025.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Tropical Oasis Anchor a Beautiful Place To Stay conveniently located just two blocks away from private community boat r ...
From $194 per night (USD)VRBO
From $1081 per night (USD)VRBO
Seaside Sanctuary in the Heart of Islamorada
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Nestled between the Cheeca Lodge and Caribbean Resort, discover our exclusive 4-bedroom oceanside sanctuary, delivering ...
From $1081 per night (USD)VRBO
From $1550 per night (USD)VRBO
Your Idyllic Getaway Awaits! Breathtaking Beachfront, Outdoor Pool | 3 Units
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 18
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $1550 per night (USD)VRBO
From $1550 per night (USD)VRBO
Three Villa w/ Living Area & Private Patio | Close to Theater of the Sea
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 18
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $1550 per night (USD)VRBO
From $633 per night (USD)VRBO
Southern Comfort - Charming oceanfront private oasis!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Southern Comfort, your home away from home! Your ideal oceanfront getaway boasting 3 bedrooms and 4 baths an ...
From $633 per night (USD)VRBO
From $1984 per night (USD)VRBO
Peninsula Villa | Boat Dock | Heated Pool | Sunset Point
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
This grand peninsula retreat is embraced by the Ocean and lush mangroves, offering privacy to the heated pool with its t ...
From $1984 per night (USD)VRBO
From $1125 per night (USD)VRBO
Spectacular 4 bedroom 4 1/2 bath villa on Tavernier Creek in Florida Keys.
- Bedrooms:
- 4
- 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)VRBO
From $249 per night (USD)VRBO
2Bed 2 bath Home with ocean views, in a pet friendly resort,
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This lovely home has incredible ocean views. The ocean laps against the rocks on 2 sides of this home. You will have fu ...
From $249 per night (USD)VRBO
From $191 per night (USD)VRBO
BEAUTIFUL PLACE TO STAY!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
ONE OF "THE BEST" vacation value getaways in the Florida Keys. Packed with amenities, access to gulf side dockage, a g ...
From $191 per night (USD)VRBO
From $351 per night (USD)Expedia
Ocean Harbor Paradise in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Talk about an Atlantic Ocean View; you've found it! You will fall in love as soon as you enter the gates at Ocean Harbor ...
From $351 per night (USD)Expedia
Click For PricingVRBO
THIS is the ONE!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Perfect for the whole family! Enjoy this spacious and newly remodeled unit in a private community. Beach and pool access ...
Click For PricingVRBO
From $856 per night (USD)Expedia
Keys home overlooking the ocean and beautiful sunrises!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful oceanfront residence with pool, and modern renovations. Located in desirable Islamorada with access to a priva ...
From $856 per night (USD)Expedia
From $1425 per night (USD)VRBO
Bayfront paradise in Islamorada, FL.
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
This stunning residence in Islamorada offers breathtaking views and luxurious amenities, ideal for serene living. Each b ...
From $1425 per night (USD)VRBO
From $619 per night (USD)Expedia
Bayfront Townhome with Boat Slip, Pool and Beach
- Bedrooms:
- 2
- 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 $428 per night (USD)VRBO
Ultimate Keys Oasis! 4 Bedroom, Poolside Retreat!
- Bedrooms:
- 3
- 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 $416 per night (USD)Expedia
Isla Mamey: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $416 per night (USD)Expedia
From $464 per night (USD)VRBO
Isla Key Acaí: Waterfront Boutique Resort, FREE Boat Dockage Sep-Oct Only!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $464 per night (USD)VRBO
From $402 per night (USD)Expedia
Isla Lychee: Boutique Resort, FREE Boat Dockage Sep-Oct Only!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $402 per night (USD)Expedia
From $392 per night (USD)VRBO
Isla Kiwi: Waterfront Boutique Resort, FREE Boat Dockage Sept-Oct Only
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $392 per night (USD)VRBO
From $473 per night (USD)Expedia
Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $473 per night (USD)Expedia
From $420 per night (USD)VRBO
Isla Key Lime: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $420 per night (USD)VRBO
From $736 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 $736 per night (USD)VRBO
From $2668 per night (USD)VRBO
A Premier Oceanfront Estate in Islamorada
- Bedrooms:
- 8
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to Ocean’s Edge, a premier oceanfront estate in Islamorada. Nestled along the pristine shores of the Atlantic Oc ...
From $2668 per night (USD)VRBO
From $303 per night (USD)Expedia
Leisure Inn Islamorada - 3/2 canal home on a double lot, bring all of the toys!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This charming Florida home is situated on a double lot with a full sea basin on an ocean side, deep water canal...second ...
From $303 per night (USD)Expedia
From $460 per night (USD)VRBO
Cosy Cottage in Islamorada with private garden & pool - 6 pers.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Flamingo Cottage! The pretty cottage is located in Islamorada, the heart of the Keys. A part of the interior ...
From $460 per night (USD)VRBO
From $526 per night (USD)Expedia
Bayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $526 per night (USD)Expedia
From $435 per night (USD)VRBO
Isla Mirabelle: Boutique Resort, FREE Boat Dockage Sep-Oct Only!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $435 per night (USD)VRBO
From $1389 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 $1389 per night (USD)VRBO
From $3276 per night (USD)VRBO
Voted best boutique resort in Islamorada! Beach, dockage, pool + more!
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 22
Located in the heart of Islamorada, Mermaid’s Bay Boutique Estate is a secluded oasis situated directly on the bay. Secu ...
From $3276 per night (USD)VRBO
From $422 per night (USD)Expedia
1.5 Bedroom, 1 bath with back deck. Pet friendly with 2 Queen and 2 twin beds.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Quaint Aqua Lodge located in Mangrove Marina. 1.5 bedroom, 1 bath with a back deck. With 4 beds, 2 Queens and 2 twins, ...
From $422 per night (USD)Expedia
From $109 per night (USD)VRBO
Charming 1 Bedroom Condo on Plantation Key
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Sit back and relax at Port o Palms. Experience the ultimate Florida Keys getaway at this light and bright one-bedroom, ...
From $109 per night (USD)VRBO
From $2378 per night (USD)VRBO
Infinity Bay Islamorada ~ Luxury 9-bed, 10-bath Bayfront Estate in Islamorada
- Bedrooms:
- 9
- Bathrooms:
- 9
- Sleeps:
- 18
Welcome to Infinity Bay Islamorada, an infinite paradise with infinite possibilities in the heart of the Florida Keys. T ...
From $2378 per night (USD)VRBO
From $1457 per night (USD)VRBO
Luxury Oceanfront Estate in Islamorada - Your Tropical Paradise Awaits!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Orchid Beach, your ultimate oceanside escape! Nestled directly on the beach, this gated estate greets you wit ...
From $1457 per night (USD)VRBO
From $437 per night (USD)VRBO
Welcome to Our Beautiful Spacious 2 BR Home in the Heart of Islamorada, Florida
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Experience the perfect getaway in our stunning 2-bedroom home located in the vibrant heart of Islamorada, Florida. Nestl ...
From $437 per night (USD)VRBO
From $466 per night (USD)VRBO
Tut's Cay: 4 BR, 5.5 BA House in Tavernier, Sleeps 10
- Bedrooms:
- 5
- 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 $466 per night (USD)VRBO
From $437 per night (USD)VRBO
Port Antigua Home in a Private Beach & Golf Cart Community
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 15
Our relaxing 3 STORY, 4 bedroom, 3.5 bathroom home is located in Islamorada, Florida within the Private Beach community ...
From $437 per night (USD)VRBO