Islamorada, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Islamorada, Florida on RentalSaver.com!

Islamorada Rentals

$Condo on Islamorada on the beautiful Atlantic Ocean.\nCome enjoy and relax!$
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
$Superb Keys home w\/heated pool, jacuzzi, fast wifi & more!$
From $304 per night (USD)
Expedia
Superb Keys home w\/heated pool, jacuzzi, fast wifi & more!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Come, relax and enjoy yourself in the heated pool or jacuzzi at our home located on mm90 near shops & restaurants. This ...
From $304 per night (USD)
Expedia
From $186 per night (USD)
VRBO
Waterfront oasis with boat dock, amazing views, patio, & hammock - dog-friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Gemstone Isle Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $186 per night (USD)
VRBO
$Oceanview 2b\/2b w\/ Boatslip$
From $291 per night (USD)
VRBO
Oceanview 2b\/2b w\/ Boatslip
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Home sits in the Sun Outdoors Islamorada Resort. New 2b/2b home w/ a boat slip within the private marina . Home has a vi ...
From $291 per night (USD)
VRBO
$Oceanview 2b\/2b w\/ Boatslip$
From $282 per night (USD)
VRBO
Oceanview 2b\/2b w\/ Boatslip
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Home sits in the Sun Outdoors Islamorada Resort. New 2b/2b home w/ a boat slip within the private marina is pet friendly ...
From $282 per night (USD)
VRBO
From $351 per night (USD)
Expedia
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)
Expedia
From $2282 per night (USD)
VRBO
Islamorada Bayfront, sunsets, beautifully remodeled, infinity pool, and dockage.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Located in an enclave of a handful of Bayfront homes. this totally remodeled home is a special way to enjoy the Keys. ...
From $2282 per night (USD)
VRBO
From $209 per night (USD)
Expedia
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 $209 per night (USD)
Expedia
From $398 per night (USD)
VRBO
Brand New Home, Resort Location, Ocean View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This brand new home is sitting quietly behind a controlled access gate with a personal view of the Atlantic Ocean. Full ...
From $398 per night (USD)
VRBO
From $318 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 $318 per night (USD)
Expedia
From $233 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 $233 per night (USD)
VRBO
$Waterfront paradise with fire pit, W\/D, central AC$
From $196 per night (USD)
Expedia
Waterfront paradise with fire pit, W\/D, central AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Angler's Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $196 per night (USD)
Expedia
From $1008 per night (USD)
VRBO
Sunset Views and Serenity! Outdoor Pool, Free Parking, Near Hurricane Monument
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Stay close to Florida Keys Brewing Co. and Bud n' Mary's Dive Center. Explore Indian Key Historic State Park and dive in ...
From $1008 per night (USD)
VRBO
From $1088 per night (USD)
VRBO
Coastal Elegance Near Theater of the Sea! 2 Stylish Villas, Kitchen, Bayfront!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Nestled along the stunning coastline, our newly renovated resort offers a tranquil escape from the everyday hustle and b ...
From $1088 per night (USD)
VRBO
From $403 per night (USD)
VRBO
Beach Getaway! Outdoor Pool, Free Parking, Near Keys History & Discovery Center
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $403 per night (USD)
VRBO
$2 Relaxing Bayfront Villa w\/ Private Patio | Scenic Bayside Resort$
From $2645 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 $2645 per night (USD)
VRBO
$Bayside Tranquility: 2 Spacious Villa w\/ Private Patio | Onsite Pool$
From $1841 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 $1841 per night (USD)
VRBO
From $1285 per night (USD)
VRBO
Oceanfront Paradise Retreat! Outdoor Pool, Pets Allowed, Near Coral Bay Marina
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay close to Florida Keys Brewing Co. and Bud n' Mary's Dive Center. Explore Indian Key Historic State Park and dive in ...
From $1285 per night (USD)
VRBO
$Bayside Tranquility: 3 Relaxing Villa w\/ Spacious Living Area & Kitchen$
From $2962 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 $2962 per night (USD)
VRBO
$Islamorada Getaway | 2 Family Ready Bayfront Villa w\/ Spacious Living Area$
From $2645 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 $2645 per night (USD)
VRBO
$Scenic Resort w\/ Private Beach Access | Near History of Diving Museum, 3 Villas$
From $2962 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 $2962 per night (USD)
VRBO
From $790 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 $790 per night (USD)
VRBO
From $693 per night (USD)
VRBO
Ultimate Vacation in Islamorada! Short Drive to Marathon International Airport
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Nestled along the stunning coastline, our newly renovated resort offers a tranquil escape from the everyday hustle and b ...
From $693 per night (USD)
VRBO
Click For Pricing
Expedia
Topsider Unit 12
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled along the shores of the Florida Straits in between the Atlantic Ocean and the Gulf of Mexico, Topsider Resort is ...
Click For Pricing
Expedia
$Capt Craig's 2 Bedroom\/1 bath Apartment in Tavernier, Florida Keys$
From $328 per night (USD)
VRBO
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 $328 per night (USD)
VRBO
From $232 per night (USD)
VRBO
Brand New Home, Resort Location, Ocean View
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 $232 per night (USD)
VRBO
From $315 per night (USD)
VRBO
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)
VRBO
$Keys home on water w\/ access to beach *monthly*$
Click For Pricing
Expedia
Keys home on water w\/ access to beach *monthly*
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Canal front house in the white marlin beach neighborhood of Lower Matecumbe (Islamorada) The space Three bedroom two bat ...
Click For Pricing
Expedia
From $249 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 $249 per night (USD)
VRBO
From $1372 per night (USD)
VRBO
2 Spacious Units, Beachfront Property, Onsite Pool, Free Parking, Pet-friendly!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Stay close to Florida Keys Brewing Co. and Bud n' Mary's Dive Center. Explore Indian Key Historic State Park and dive in ...
From $1372 per night (USD)
VRBO
$Oceanfront Property w\/ Outdoor Pools, Pets Allowed, Free Parking Onsite$
From $1218 per night (USD)
VRBO
Oceanfront Property w\/ Outdoor Pools, Pets Allowed, Free Parking Onsite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay close to Florida Keys Brewing Co. and Bud n' Mary's Dive Center. Explore Indian Key Historic State Park and dive in ...
From $1218 per night (USD)
VRBO
From $2744 per night (USD)
VRBO
4 Units Perfect for Big Groups! Beachfront Property with Outdoor Pools!
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Stay close to Florida Keys Brewing Co. and Bud n' Mary's Dive Center. Explore Indian Key Historic State Park and dive in ...
From $2744 per night (USD)
VRBO
From $2058 per night (USD)
VRBO
Family Getaway! 3 Tropical View Units, Outdoor Pools, Pet-friendly!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Stay close to Florida Keys Brewing Co. and Bud n' Mary's Dive Center. Explore Indian Key Historic State Park and dive in ...
From $2058 per night (USD)
VRBO
From $732 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 $732 per night (USD)
VRBO
From $281 per night (USD)
VRBO
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 $281 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:
4
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 $1292 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 $1292 per night (USD)
VRBO
From $886 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 $886 per night (USD)
VRBO
$Minutes to Library Beach Park! 2 Villa w\/ Living Area | Free Onsite Parking$
From $1841 per night (USD)
VRBO
Minutes to Library Beach Park! 2 Villa w\/ Living Area | Free Onsite Parking
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 $1841 per night (USD)
VRBO
From $2293 per night (USD)
VRBO
Have Fun at this Beachfront Paradise with Outdoor Pools, Free Parking!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Stay close to Florida Keys Brewing Co. and Bud n' Mary's Dive Center. Explore Indian Key Historic State Park and dive in ...
From $2293 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 $1992 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 $1992 per night (USD)
VRBO
From $262 per night (USD)
Expedia
Delightful 3-bedroom townhome in Islamorada, Florida Keys with many amenities!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Located in Islamorada, this townhome is a dream. With 3 bedrooms, including 1 king bed, 2 queen beds, and 2 full beds( l ...
From $262 per night (USD)
Expedia
From $195 per night (USD)
VRBO
Tropical Oasis Anchor located on the bay side. Community private boat ramp.
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 $195 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 $207 per night (USD)
VRBO
Cozy Oceanfront Studio in the Heart of Islamorada.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Your Islamorada adventure begins at this lovely studio with oceanfront beach access. Enjoy three levels of living. Nestl ...
From $207 per night (USD)
VRBO
From $334 per night (USD)
Expedia
Manatee Manor ~ 3 Bedroom Island Home on Plantation Key with Pool & Dockage
Bedrooms:
3
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 $334 per night (USD)
Expedia
$Three Villa w\/ Living Area & Private Patio | Close to Theater of the Sea$
From $2312 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 $2312 per night (USD)
VRBO
From $208 per night (USD)
Expedia
THIS is the ONE!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Perfect for the whole family! Enjoy this spacious and newly remodeled unit in a private community. Beach and pool access ...
From $208 per night (USD)
Expedia
Click For Pricing
VRBO
Luxury One Bedroom Condo #3
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
One Bedroom, One Bathroom Condo, Separate Living Space and Fully Equipped Kitchen. Outdoor Fire pit under palm trees w ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Luxury One Bedroom Condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
One Bedroom, One Bathroom Condo, Separate Living Space and Fully Equipped Kitchen. Outdoor Fire pit under palm trees w ...
Click For Pricing
Expedia
$Create Memories w\/ Fun-filled Adventures at this P$
Click For Pricing
VRBO
Create Memories w\/ Fun-filled Adventures at this P
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
Click For Pricing
VRBO
From $479 per night (USD)
Expedia
Modern ground-floor apartment with pool, water views, patio, grill, & central AC
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Treasure Harbor Hideaway - Lower Our calendar is updated in real-time & our nightly rates are accurately displayed. Sim ...
From $479 per night (USD)
Expedia
From $465 per night (USD)
VRBO
Deluxe upper apartment with pool, canal-view balcony, water access, grill, & AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Treasure Harbor Hideaway - Upper Our calendar is updated in real-time & our nightly rates are accurately displayed. Sim ...
From $465 per night (USD)
VRBO
From $389 per night (USD)
Expedia
Your Blissful Haven in Islamorada! Beach, Swimming Pool, Pets Allowed!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $389 per night (USD)
Expedia
From $354 per night (USD)
VRBO
Indulge in Home Like Comfort! Oceanfront, Free Parking, Pet-friendly Property
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $354 per night (USD)
VRBO
From $373 per night (USD)
Expedia
Fun and Sun in Islamorada! Free Parking, Swimming Pool, Pet-friendly Property!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $373 per night (USD)
Expedia
From $332 per night (USD)
VRBO
Enjoy a Hassle-Free and Suiting Stay! Pets Allowed, Free Parking, Onsite Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $332 per night (USD)
VRBO
Click For Pricing
Expedia
Tropical 6BR Beach House in a Resort right on the Beach - Ideal for Groups
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
Click For Pricing
Expedia
From $334 per night (USD)
VRBO
Matecumbe Resort: 2 Bedroom Oceanview. Your Home Away From Home in the FL Keys.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Matecumbe Resort offers well-appointed, air-conditioned accommodations in Islamorada, renowned as the fishing capital of ...
From $334 per night (USD)
VRBO
From $1457 per night (USD)
VRBO
Luxury Oceanfront Estate in Islamorada - Your Tropical Paradise Awaits!
Bedrooms:
5
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 $554 per night (USD)
VRBO
Islamorada Cay ~ Resort Style 4 Bed Plantation Key Home with Pool & 100' Dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Chill out in style at Islamorada Cay! This resort style, 4-bedroom, 3-bathroom canal-front property is nestled in the id ...
From $554 per night (USD)
VRBO
From $633 per night (USD)
VRBO
Southern Comfort - Charming oceanfront private oasis!
Bedrooms:
4
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
$Peninsula Villa \/ Heated Pool \/ Sunset Point$
From $2228 per night (USD)
VRBO
Peninsula Villa \/ Heated Pool \/ Sunset Point
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
This grand peninsula retreat is embraced by the Ocean and lush mangroves, offering privacy to the heated pool with its t ...
From $2228 per night (USD)
VRBO
$Bayside Home Dock\/Lift quick to ocean perfect spot to enjoy the best of the Keys$
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 $2294 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 $2294 per night (USD)
VRBO
From $1623 per night (USD)
VRBO
Islamorada | Maison Residences
Bedrooms:
8
Bathrooms:
4
Sleeps:
10
Welcome to Maison Residences 203, your exclusive 4-bedroom, 4.5-bathroom haven for the perfect oceanside holiday retreat ...
From $1623 per night (USD)
VRBO
From $380 per night (USD)
VRBO
Fabulous Futura Yacht Club Townhome with boat slip!
Bedrooms:
3
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 $380 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 $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 $633 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 $633 per night (USD)
VRBO
$5 Bedroom \/ 4 Bath Relaxed Plantation Key Resort Style Home with Pool & Dockage$
From $607 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 $607 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 $1173 per night (USD)
VRBO
Beautiful bayfront house, private pool and dock, right in Downtown Islamorada
Bedrooms:
4
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 $555 per night (USD)
VRBO
Island Oasis in Islamorada: Your Private Paradise Awaits!
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Welcome to your ultimate Florida Keys dream getaway! This secluded home is perfectly located in the desired gated neighb ...
From $555 per night (USD)
VRBO
From $330 per night (USD)
VRBO
Coastal Island Retreat with Private Beach Access!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to Time Well Wasted, an ideal retreat located in the highly sought-after neighborhood of Port Antiqua on Lower M ...
From $330 per night (USD)
VRBO
From $1032 per night (USD)
VRBO
Tropical Haven in the Heart of Islamorada
Bedrooms:
5
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 $1032 per night (USD)
VRBO
From $169 per night (USD)
VRBO
Cute Canal Front Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Two Bedroom one bath, one sleeper sofa canal front cottage. Enjoy the 50 foot dock on a deep water canal. Fully equippe ...
From $169 per night (USD)
VRBO
From $299 per night (USD)
VRBO
Classic canal home with vintage charm!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Welcome to your perfect home away from home! In the heart of Islamorada, this Venetian Shores house is ideally located, ...
From $299 per night (USD)
VRBO
From $360 per night (USD)
VRBO
Canal Front Oasis with Private Pool: Your Perfect Waterfront Getaway!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Nestled within the prestigious Venetian Shores community, this captivating canal front duplex offers a remarkable blend ...
From $360 per night (USD)
VRBO
From $684 per night (USD)
Expedia
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 $684 per night (USD)
Expedia
From $287 per night (USD)
VRBO
Waterfront property with a pool and great spot for fishing Islamorada FL
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Follow your dream vacation keys home to 124 Gardenia St.. A water direct view offering an open dock and a pool area. The ...
From $287 per night (USD)
VRBO
Click For Pricing
Expedia
Holiday house Islamorada for 1 - 6 persons with 2 bedrooms - Holiday home
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
ED Refnr. 3158286 Executive Bay Club (EBC) is located at MM87 in the heart of Islamorada. Located next door to Founder' ...
Click For Pricing
Expedia
From $319 per night (USD)
VRBO
Sunshine Villa | Bayfront apartment with pool, dockage, and sunsets!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Sunshine Villa! This home is a 1 bedroom, 1 bath downstairs apartment and is conveniently located in Tavern ...
From $319 per night (USD)
VRBO
From $2159 per night (USD)
Expedia
Ocean & Pool Front Maison Residences, on sandy beach, heated pool in Islamorada
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
FLORIDA KEYS BEACHFRONT VACATION RENTALS AT MAISON RESIDENCES While staying at the Maison Residences, you’ll have the c ...
From $2159 per night (USD)
Expedia
From $416 per night (USD)
VRBO
Comfort and Convenience! Swimming Pool, Free Parking, Pets Allowed!
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 $416 per night (USD)
VRBO
From $462 per night (USD)
Expedia
Cozy Islamorada retreat!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Our Islamorada home is your home away from home! Our home is in a private and quiet, gated community on the bay side, w ...
From $462 per night (USD)
Expedia
From $319 per night (USD)
VRBO
Cozy Islamorada home! Pet-Friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to this beautiful and Newley renovated cozy Islamorada home! This home is a couple blocks away from the famous A ...
From $319 per night (USD)
VRBO
From $449 per night (USD)
VRBO
Relax and Unwind! Pet-Friendly Property, Onsite Pool, 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 $449 per night (USD)
VRBO
From $462 per night (USD)
VRBO
Beachy but elegant, close to mainland FL, sleeps 12 comfortably
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
The house itself looks like a classic New Orleans or Key West home, straight out of the 20th century. But it has all the ...
From $462 per night (USD)
VRBO
$Islamorada Key Waterfront House w\/ Private Boat Dock$
From $440 per night (USD)
Expedia
Islamorada Key Waterfront House w\/ Private Boat Dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Cozy 2/2 Waterfront home located in the Best Location. Two King beds . High speed Wifi, Smart TVs, BBQ, Great living r ...
From $440 per night (USD)
Expedia
From $184 per night (USD)
VRBO
Charming Condo in Paradise!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Take a break & unwind at this charming Islamorada gem! Let this 1/1 bright & homey condo be your needed getaway to parad ...
From $184 per night (USD)
VRBO
From $379 per night (USD)
Expedia
Fabulous Island Getaway! Easy access to Florida Bay, Private Beach, Elevator
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Enjoy watching the ospreys and manatees from the dock at this beautiful Port Antigua home on Biscayne Blvd. You have acc ...
From $379 per night (USD)
Expedia
From $318 per night (USD)
VRBO
A Place You'll Surely Enjoy! Courtyard View, Free Parking, Onsite Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $318 per night (USD)
VRBO
From $326 per night (USD)
VRBO
Best Place to Unwind! Free Parking, Onsite Pool, Short Drive to Anne's Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $326 per night (USD)
VRBO
From $354 per night (USD)
VRBO
Make Your Trip More Enjoyable! Onsite Pool, Pets Allowed, Free Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $354 per night (USD)
VRBO
From $443 per night (USD)
VRBO
Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $443 per night (USD)
VRBO
From $371 per night (USD)
VRBO
Just What You Were Looking For! Free Breakfast, Onsite Pool, Free Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $371 per night (USD)
VRBO
$Spectacular Penthouse w\/Panoramic Open Water Views-New rental$
From $226 per night (USD)
VRBO
Spectacular Penthouse w\/Panoramic Open Water Views-New rental
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Fantastic Penthouse Apartment is just steps away from the fabulous turquoise waters of Florida Bay! Enjoy spectacul ...
From $226 per night (USD)
VRBO

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