Islamorada Rentals
From $595 per night (USD)VRBO
Cozy canal in the Keys - leads directly into crystal blue ocean! 🌊
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
A 75' bulkhead on the main exit channel 3 houses from the bay. Private boat slip in the neighborhood you can put your ow ...
From $595 per night (USD)VRBO
From $651 per night (USD)Expedia
Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome Back!! I temporarily took the property off the market during COVID and for renovations. I am looking forward t ...
From $651 per night (USD)Expedia
From $333 per night (USD)VRBO
Tranquility Cove \nBeautiful Remodeled home in the heart of Islamorada.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
About this space This beautiful newly remodeled (99%) Completed , modern home sits in the middle of great restaurants, t ...
From $333 per night (USD)VRBO
From $248 per night (USD)VRBO
“ The Ultimate redneck” boat experience
- Bedrooms:
- 0
- Bathrooms:
- 1
- Sleeps:
- 2
Are you ready for modern day pirate life ? Wonder how the locals live ? Well then we can show you ! Redneck paradise, Pr ...
From $248 per night (USD)VRBO
From $305 per night (USD)VRBO
Ocean View Delight | Sea Gulls 310 ~ Monthly Rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Best View in the Keys - You will feel right at home in this beautifully renovated condo with FULL OCEAN VIEW. T ...
From $305 per night (USD)VRBO
From $287 per night (USD)Expedia
Islamorada Hidden Treasure
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy luxury in the Florida Keys in this private oasis at Coral Harbour. The property is equipped with a marina, fuel, ...
From $287 per night (USD)Expedia
From $1316 per night (USD)VRBO
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 $1316 per night (USD)VRBO
From $657 per night (USD)Expedia
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 $657 per night (USD)Expedia
From $1968 per night (USD)VRBO
Entire Compound on Gated Bayfront Property
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 18
PROPERTY NAME: Little Bay Compound 82246 Overseas Highway, Islamorada, Florida LOCATION: Cottage and Two Story Duplex ...
From $1968 per night (USD)VRBO
From $658 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 $658 per night (USD)Expedia
From $1270 per night (USD)VRBO
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 $1270 per night (USD)VRBO
From $191 per night (USD)Expedia
Radiant waterfront retreat with remarkable views, patio, tennis court, & grill
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tollgate Tides Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $191 per night (USD)Expedia
From $412 per night (USD)VRBO
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 ...
From $412 per night (USD)VRBO
From $419 per night (USD)Expedia
Port Antigua NEW Luxury one bedroom/2 bath apt with pool/spa/steam in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Be our guest at a one of a kind, brand new, boutique style accommodations in one of the most beautiful areas of the Flor ...
From $419 per night (USD)Expedia
From $767 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 $767 per night (USD)VRBO
From $1053 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 $1053 per night (USD)Expedia
From $351 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 $351 per night (USD)VRBO
From $261 per night (USD)Expedia
3 Bedroom Home in Islamorada with Private Dock, Boat Ramp & private beach access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Visiting a house in Islamorada is a dream come true for those in search of the ultimate tropical paradise. Nestled in th ...
From $261 per night (USD)Expedia
From $472 per night (USD)VRBO
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 $472 per night (USD)VRBO
From $279 per night (USD)VRBO
Classic canal home with vintage charm!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your perfect home away from home! In the heart of Islamorada, this Venetian Shores house is ideally located, ...
From $279 per night (USD)VRBO
From $339 per night (USD)VRBO
Yolo \" You only live once\" - Fishing Paradise in Islamorada with a 70ft Dock!!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
1440 sf - 2 Bedrooms king size bed in master bedroom with 2 queen beds in guest room (also includes xtra bed in guest ro ...
From $339 per night (USD)VRBO
From $285 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 $285 per night (USD)VRBO
From $287 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 $287 per night (USD)VRBO
From $288 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 $288 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
Click For PricingExpedia
Relaxing home with pool - 3/3, 6 miles to Islamorada and 3 miles to Key Largo
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Now available for Feb, March and April! Set on a quiet street, located between Islamorada and Key Largo, you will find ...
Click For PricingExpedia
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)Expedia
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)Expedia
From $221 per night (USD)VRBO
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 $221 per night (USD)VRBO
From $291 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 $291 per night (USD)VRBO
From $326 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 $326 per night (USD)VRBO
From $1289 per night (USD)Expedia
5 bed/4 bath Ocean side, right outside of Tavernier Creek Mile Marker 91
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy a newly built luxurious central waterfront home, offering easy ocean access and a stunning sandbar just 5 minutes ...
From $1289 per night (USD)Expedia
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 $3068 per night (USD)Expedia
Pineapple Beach : 5 BR, 4.5 BA House 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 $3068 per night (USD)Expedia
From $409 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 $409 per night (USD)VRBO
From $1094 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 $1094 per night (USD)VRBO
From $1023 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 $1023 per night (USD)VRBO
From $738 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 $738 per night (USD)VRBO
From $656 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 $656 per night (USD)VRBO
From $1194 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 $1194 per night (USD)VRBO
From $158 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 $158 per night (USD)VRBO
From $2249 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 $2249 per night (USD)VRBO
From $1521 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 $1521 per night (USD)VRBO
From $2377 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 $2377 per night (USD)VRBO
From $254 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 $254 per night (USD)VRBO
From $289 per night (USD)VRBO
Beautiful, renovated 2/2 house, outdoor patios, Ocean views, Upper Keys, FL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2/2, 1,250 sq. ft. home with a huge 3rd floor rooftop patio with Ocean views, grill, sink, and outdoor dining tables and ...
From $289 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 $403 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 $403 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
Click For PricingExpedia
\"Experience Paradise: Your Ultimate Vacation Rental in The Florida Keys!\"
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
"Welcome to your perfect getaway in Islamorada! This fully updated townhouse features 3 bedrooms and 2 baths, a large li ...
Click For PricingExpedia
From $917 per night (USD)VRBO
Ocean Front Villa, 3/4's acre of private beach! Serenity, Retreat, Island Life!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Come enjoy the beautiful Florida Keys in this new build stylish villa located in Islamorada close to shopping & restaura ...
From $917 per night (USD)VRBO
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 $632 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 $632 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
Click For PricingVRBO
The Harbor House with Open Bay Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful unobstructed bay views with two beaches, dock and plenty of space for outdoor activities. Lounge under the chi ...
Click For PricingVRBO
From $1312 per night (USD)VRBO
Scenic Beachside Stroll at Our Breathtaking Resort | 3 Villa w/ 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 $1312 per night (USD)VRBO
From $2377 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 $2377 per night (USD)VRBO
From $656 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 $656 per night (USD)VRBO
From $2249 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 $2249 per night (USD)VRBO
From $1016 per night (USD)VRBO
Minutes to Library Beach Park! Onsite Parking & Outdoor Swimming 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 $1016 per night (USD)VRBO
From $1088 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 $1088 per night (USD)VRBO
From $743 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 $743 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 $795 per night (USD)VRBO
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)VRBO
From $556 per night (USD)VRBO
Pool Front Home with Ocean Views at Anglers Reef in Islamorada and Slip.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Angler’s Reef Villas & Marina, a stunning Islamorada vacation destination. Quaint streets and walking paths w ...
From $556 per night (USD)VRBO
From $348 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 $348 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 $322 per night (USD)VRBO
Oceanfront 2bedroom home with sweeping ocean views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This home is in the Sun Outdoors Islamorada Resort. This is a lovely 2 bedroom 2 bath home. Home has a east facing views ...
From $322 per night (USD)VRBO
From $132 per night (USD)VRBO
Newly Updated Studio Apartment, Summer Sea 303
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summer Sea Condominium Unit 303 is a brilliant, clean and modern efficiency apartment, upgraded in 2023 with tile throug ...
From $132 per night (USD)VRBO
From $234 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 $234 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 $405 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 $405 per night (USD)VRBO
From $867 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 $867 per night (USD)Expedia
From $284 per night (USD)VRBO
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 $284 per night (USD)VRBO
From $1815 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 $1815 per night (USD)VRBO
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 $397 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 $397 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 $1365 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 $1365 per night (USD)VRBO
From $1968 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 $1968 per night (USD)VRBO
From $1968 per night (USD)VRBO
Three Villa w/ Living Area & Private Patio | Close to Theater of the Sea
- 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 $1968 per night (USD)VRBO
From $2156 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 $2156 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:
- 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)Expedia
From $288 per night (USD)VRBO
2Bed 2 bath Home with ocean views, in a pet friendly resort,
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This lovely home has incredible ocean views. The ocean laps against the rocks on 2 sides of this home. You will have fu ...
From $288 per night (USD)VRBO
Click For PricingExpedia
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 PricingExpedia
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 $536 per night (USD)VRBO
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 $536 per night (USD)VRBO
From $570 per night (USD)Expedia
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 $570 per night (USD)Expedia
From $448 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 $448 per night (USD)VRBO
From $746 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 $746 per night (USD)Expedia
From $437 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 $437 per night (USD)VRBO
From $2797 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 $2797 per night (USD)VRBO
From $303 per night (USD)VRBO
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)VRBO
From $460 per night (USD)Expedia
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)Expedia
From $581 per night (USD)VRBO
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 $581 per night (USD)VRBO
From $480 per night (USD)Expedia
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 $480 per night (USD)Expedia
From $1396 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 $1396 per night (USD)VRBO
From $488 per night (USD)Expedia
2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Rare opportunity to rent this 2 bedroom / 2 full bath beach bungalow complete with a living room with a pull out sleeper ...
From $488 per night (USD)Expedia