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Islamorada Rentals

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 $850 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 $850 per night (USD)
VRBO
From $526 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 $526 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 $816 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 $816 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
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VRBO
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 ...
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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 $229 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 $229 per night (USD)
VRBO
From $1398 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 $1398 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 $223 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 $223 per night (USD)
VRBO
From $313 per night (USD)
VRBO
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 $313 per night (USD)
VRBO
From $194 per night (USD)
Expedia
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)
Expedia
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VRBO
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 ...
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VRBO
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Expedia
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 ...
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Expedia
From $632 per night (USD)
VRBO
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 $632 per night (USD)
VRBO
From $508 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 $508 per night (USD)
VRBO
From $573 per night (USD)
VRBO
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 $573 per night (USD)
VRBO
From $486 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 $486 per night (USD)
VRBO
From $1138 per night (USD)
VRBO
Create Memories w/ Fun-filled Adventures at this P
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Relaxing and indulgent stay on the tropical islands of Islamorada! ✦ Your room is 717 sq. ft, equipped with complimenta ...
From $1138 per night (USD)
VRBO
From $593 per night (USD)
VRBO
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 $593 per night (USD)
VRBO
From $251 per night (USD)
VRBO
Captains Quarters is a charming canal front Keys house in delightful Islamorada
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Your cozy getaway awaits in Islamorada at this superb house. With 2 bedrooms including 1 king, 1 queen, and 2 twin beds ...
From $251 per night (USD)
VRBO
From $148 per night (USD)
Expedia
Winterbirds! Charming studio in the Port Antigua Islamorada Florida Keys
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome winter birds to this enchanting studio in Islamorada Florida Keys. This cozy retreat offers TV, AC, WiFi, kitche ...
From $148 per night (USD)
Expedia
From $248 per night (USD)
VRBO
Wake up every day to the sunrise from the deck of this waterfront home 2bed home
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This lovely home has 2 bedrooms and 2 baths. The home is completely furnished, just bring you sunscreen, flip flops and ...
From $248 per night (USD)
VRBO
From $459 per night (USD)
Expedia
Beautiful ocean front private beach 2-bedroom house gorgeous views Isla morada
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in Islamorada, this peaceful 2-bedroom house. Ocean front -Private beach is a welcoming retreat for guests. this ...
From $459 per night (USD)
Expedia
From $1110 per night (USD)
VRBO
Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Located in Islamorada, enjoy what this 3-bedroom villa has to offer. With 2 king beds and 1 queen bed, guests can relax ...
From $1110 per night (USD)
VRBO
From $490 per night (USD)
Expedia
Luxury 2BR Waterfront Futura Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover paradise in this 2-bedroom, 2.5-bath townhouse in the heart of the Florida Keys. Enjoy a private marina 10 feet ...
From $490 per night (USD)
Expedia
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VRBO
3-bedroom condo in charming Tavernier with AC, WiFi. Relax and unwind
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to this charming condo in Tavernier. This delightful property features 3 cozy bedrooms with a mix of a king bed, ...
Click For Pricing
VRBO
From $213 per night (USD)
Expedia
Updated 3-bedroom Townhome at Executive Bay Club resort
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This spacious, fully remodeled 3-bedroom, 2-bathroom loft townhome is located in the heart of Islamorada at the exclusiv ...
From $213 per night (USD)
Expedia
From $235 per night (USD)
VRBO
3-bedroom Townhome with Direct Ocean Views at resort in Islamorada
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Escape to paradise in this gorgeous 3-bedroom, 3-bathroom townhome is located at Executive Bay Club in Islamorada, FL. I ...
From $235 per night (USD)
VRBO
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Expedia
Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Discover the Gumbo Limbo Suite at Casa Morada—where island relaxation meets outdoor adventure. Nestled in a tropical gar ...
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Expedia
Click For Pricing
VRBO
Garden View Suite w/ Balcony & Seating Area @Islamorada - Sweet Mango Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Step into island serenity in the Sweet Mango Suite at Casa Morada. Designed with lush jungle-inspired decor, this garden ...
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VRBO
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Expedia
Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Welcome to the Iguana Suite, the largest and most luxurious accommodation at Casa Morada. This ground-level retreat feat ...
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Expedia
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 $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 $2129 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 $2129 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 $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 $353 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 $353 per night (USD)
VRBO
From $432 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 $432 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 $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 $550 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 $550 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)
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 $595 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 $595 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
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 $555 per night (USD)
VRBO
Island Oasis in Islamorada: Your Private Paradise Awaits!
Bedrooms:
2
Bathrooms:
3
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 $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 $330 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 $330 per night (USD)
VRBO
From $1141 per night (USD)
VRBO
Brand New 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 $1141 per night (USD)
VRBO
From $425 per night (USD)
VRBO
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 $425 per night (USD)
VRBO
From $485 per night (USD)
Expedia
Mojito Breeze Getaway
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Beachy but elegant, close to mainland FL, sleeps 12 comfortably, timeless tropical getaway, plenty of room Nice, quiet ...
From $485 per night (USD)
Expedia
From $324 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 $324 per night (USD)
VRBO
From $462 per night (USD)
Expedia
Cozy Islamorada retreat!
Bedrooms:
2
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 $1679 per night (USD)
VRBO
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 $1679 per night (USD)
VRBO
From $383 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 $383 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 $369 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 $369 per night (USD)
VRBO
From $402 per night (USD)
VRBO
Beautiful Venetian Shores canal home with dockage!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
130 Stromboli Drive - Beautiful Venetian Shores canal home that has two-bedroom two bath upstairs and a one-bedroom one ...
From $402 per night (USD)
VRBO
From $615 per night (USD)
VRBO
Island Time - Plantation Key Home with 4 beds & 3 baths with Pool & Dockage
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Island Time! This newly constructed canal front residence located in the heart of Plantation Key is sure to ...
From $615 per night (USD)
VRBO
From $345 per night (USD)
VRBO
Beautiful, Spacious, Single Story Home - Islamorada
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This single-story canal front home located in the heart of Islamorada (MM86) in the Florida Keys-fishing capital of the ...
From $345 per night (USD)
VRBO
From $326 per night (USD)
VRBO
TICKET TO PARADISE !!! PRIVATE POOL, OCEAN SIDE/VIEW COMPLETELY REMODELED
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
New In Ground Heated pool , Just remodeled with new furniture, flat screen tvs throughout ( including the patio) and a d ...
From $326 per night (USD)
VRBO
From $47073 per night (USD)
VRBO
Ultra-Luxury Exclusive Private Oceanfront Estate - White Glove Service Available
Bedrooms:
10
Bathrooms:
7
Sleeps:
14
* Exquisite White Glove Service is Available for an additional fee. See below. We proudly present the first of its col ...
From $47073 per night (USD)
VRBO
$Open February 2024! \Paradise South\ ~ Chic Island Home with Pool & Dockage$
From $568 per night (USD)
VRBO
Open February 2024! \"Paradise South\" ~ Chic Island Home with Pool & Dockage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Paradise South! This delightful 3 bedroom, 2 bath home in the heart of Plantation Key welcomes you for your ...
From $568 per night (USD)
VRBO
From $731 per night (USD)
VRBO
Canary Island Palm North Poolside,1 King Bed, 2 QueenBeds, 1 Pull Out
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Poolside,1 King Bed, 2 QueenBeds, 1 Pull Out Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoga ...
From $731 per night (USD)
VRBO
From $731 per night (USD)
Expedia
Coconut Palm South,1 King Bed, 2 Full Beds, 1 Pull Out
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
1 King Bed, 2 Full Beds, 1 Pull Out Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, tea ...
From $731 per night (USD)
Expedia
From $900 per night (USD)
VRBO
Harbor house 2 Bedrooms, 2 Baths, Partial Ocean View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Partial Ocean View 1 King Bed, 1 Queen Bed, 1 Pull Out Resort guests stay in warm and inviting Caribbean-style homes. R ...
From $900 per night (USD)
VRBO
From $731 per night (USD)
Expedia
Canary Island Palm South 2 Bedrooms, 2 Baths, Poolside
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Poolside,1 King Bed, 2 Queen Beds, 1 Pull Out Resort guests stay in warm and inviting Caribbean-style homes. Rich mahog ...
From $731 per night (USD)
Expedia
From $1153 per night (USD)
VRBO
Jamaican Palm House 3 Bedrooms, 2 Bath, Poolside
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Poolside,3 Queen Beds,1 Pull Out Welcome to the Jamaican Palm. Our most recently renovated home is a sight to behold. E ...
From $1153 per night (USD)
VRBO
From $203 per night (USD)
VRBO
Ocean Side Condo In Paradise Mm 76.5-Islamorada, Fl (28 day minimum required)
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This is a quaint, ocean side condo with full amenities and easy access for fishing, diving, snorkeling and much more.The ...
From $203 per night (USD)
VRBO
From $232 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 $232 per night (USD)
VRBO
From $274 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 $274 per night (USD)
VRBO
From $436 per night (USD)
VRBO
Updated 3/2 condo Futura Yacht Club-Spacious Open Floor Plan, Sunset VIEWS!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Gorgeous completely remodeled spacious condo in the highly sought after Futura Yacht Club overlooking Florida Bay with s ...
From $436 per night (USD)
VRBO
From $494 per night (USD)
VRBO
Beautiful New Pool Home located in a gated community in the Heart of Islamorada.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
29 Flamingo Hammock Road - This Beautiful Ground-Level Vacation Retreat awaits your arrival. Walk into this home and you ...
From $494 per night (USD)
VRBO
From $494 per night (USD)
VRBO
NEW Luxury Modern Coastal Home in Islamorada
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This New construction has all the bells and whistles to make your stay unforgettable. Located in the heart of Islamorada ...
From $494 per night (USD)
VRBO
From $426 per night (USD)
VRBO
Mini Ray's of Sunshine
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Mini Ray's of Sunshine - Beautiful New Pool Home located in a gated community in the Heart of Islamorada. This home, des ...
From $426 per night (USD)
VRBO
From $173 per night (USD)
VRBO
Home in Paradise- Tavernier Cottage,p Pool & Dockage
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Totally remodeled, canal front home, quiet and in the nicest neighborhoods (Plantation Key Colony). Situated on the bays ...
From $173 per night (USD)
VRBO
From $588 per night (USD)
VRBO
Impressive Resort Like 5 Bedroom / 4.5 Baths with Pool & Dockage in Islamorada!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Located on a cul-de-sac in the charming city of Islamorada, this beautifully- appointed five-bedroom, four and a half-ba ...
From $588 per night (USD)
VRBO
From $719 per night (USD)
VRBO
Beautiful 7 BR estate in Islamorada, FL keys, with pool, dockage, & sandy beach!
Bedrooms:
4
Bathrooms:
7
Sleeps:
14
Island Villa Rental Properties offers fantastic panoramic views of the Atlantic Ocean from this 7 BR, oceanfront home in ...
From $719 per night (USD)
VRBO
From $233 per night (USD)
VRBO
Bayside Condo with Marina, Boat Slips, Pool, Beach and awesome Sunsets
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your escape to our tropical paradise begins as you enter through the private gates of our community at Futura Yacht Club ...
From $233 per night (USD)
VRBO
From $438 per night (USD)
VRBO
Venetian Shores Home -DOCK remodeled 3/3 POOL/Hot Tub! Deep water Dockage
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
126 Palermo Drive Check out this new to the Vacation Rental Market home in Venetian Shores on canal with 70' dock, pool, ...
From $438 per night (USD)
VRBO
From $425 per night (USD)
VRBO
Futura Yacht Club Bayfront Townhome with Endless Sunsets!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Endless Sunsets!! This is a beautiful Bayfront Townhome in Islamorada's popular Futura Yacht Club. 3 level townhome w ...
From $425 per night (USD)
VRBO
From $576 per night (USD)
VRBO
ULTIMATE outdoor living area at this 4/4 canal home with pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This beautifully remodeled home in desirable Plantation Key Colony has the sought-after amenities of a large resort, in ...
From $576 per night (USD)
VRBO
From $451 per night (USD)
VRBO
Keys Waterfront House with large pool 30' Dock w/ 50 Amp power 10% off Nov-Feb
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
NOW OFFERING A SPECIAL RATE OF 10% OFF FOR BOOKINGS FROM DECEMBER 2024 THROUGH FEBUARY 2025 ONLY, Fishermans parad ...
From $451 per night (USD)
VRBO
From $1122 per night (USD)
VRBO
Tropical retreat where location meets quintessential Keys vacation home.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Heart of Morada - This unique townhome is located bay front at Mile Marker 81.5 on U.S. Highway 1 in the heart of downto ...
From $1122 per night (USD)
VRBO
From $229 per night (USD)
Expedia
Best Location for Your best vacation!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Best Home to Share with Family and Friends! This Beautiful Home consists of 2 levels with 2 separate units. The 1st leve ...
From $229 per night (USD)
Expedia
From $293 per night (USD)
VRBO
New saltwater pool, pet friendly, waterfront house with dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Lower Matecumbe waterfront home, pet friendly for 1 dog. New concrete saltwater pool (heated/cooled) in 2022. New 20,0 ...
From $293 per night (USD)
VRBO
From $1559 per night (USD)
VRBO
Large bay-front home with dockage, pool and beach in the heart of Islamorada
Bedrooms:
7
Bathrooms:
4
Sleeps:
10
The Dock View House is one of three private homes located at Mermaid's Bay Boutique Estate. Located in the heart of Isla ...
From $1559 per night (USD)
VRBO
From $2126 per night (USD)
VRBO
Luxury Waterfront Home with Sandy Beach, Hot Tub and Theater
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Enjoy all the beauty of Islamorada's clear blue waters from your private beachfront estate. Turtle Nest Estate features ...
From $2126 per night (USD)
VRBO
From $2110 per night (USD)
VRBO
Charming Ocean Front Pool Home with dockage & pool
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Step out the door to your private oceanfront beach with pool and dock at Midnight Runner. The property features two livi ...
From $2110 per night (USD)
VRBO
From $347 per night (USD)
VRBO
Home in Islamorada Florida
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Water Front modern home perfectly situated on the Bay side. Located on a deep-water canal that offers all sorts of enjoy ...
From $347 per night (USD)
VRBO
From $324 per night (USD)
VRBO
Waterfront Pool Home with great dockage!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Adorable waterfront pool home in Tavernier! Great dockage close to Tavernier Creek for easy bay and ocean access. Cozy c ...
From $324 per night (USD)
VRBO
From $144 per night (USD)
VRBO
Charming and Cozy Townhouse in the Fl Keys with Pool and Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Drive down south to enjoy the tranquil and beautiful Florida Keys. Enjoy a cozy and spacious townhome in the heart of I ...
From $144 per night (USD)
VRBO
From $520 per night (USD)
VRBO
Luxury Islamorada Oasis: Pool, Dock, Fire Pit, King Beds & Canal Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover Your Slice of Islamorada Paradise! Contact Us Directly for Availability Welcome to our newly remodeled, canal ...
From $520 per night (USD)
VRBO

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