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Islamorada Rentals

From $206 per night (USD)
VRBO
Cozy Family Townhome next to Tennis Courts in FL Keys Gated Community
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to this charming townhome in Islamorada. This pleasant retreat features 2 bedrooms with a cozy king, twin, and q ...
From $206 per night (USD)
VRBO
From $786 per night (USD)
VRBO
Blue Palm Oasis ~ 4 Bedroom Plantation Key Home w/ Pool & 170` of Dockage
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Blue Palm Oasis! Escape to paradise at Blue Palm Oasis, a charming 4-bedroom, 3-bath home located on Plantat ...
From $786 per night (USD)
VRBO
From $116 per night (USD)
VRBO
Open Concept Studio Apartment in Islamorada
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This cute Studio apartment has just been updated to a fully open concept beautiful apartment. Fully furnished, modern a ...
From $116 per night (USD)
VRBO
From $576 per night (USD)
VRBO
Private Beach Access: Islamorada Canal-Front Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Full Access to Private White Marlin Beach | Screened Porch | Outdoor Entertaining Space Immerse yourself in the coastal ...
From $576 per night (USD)
VRBO
From $403 per night (USD)
VRBO
New Bay Hammock Vacation Rental!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Be one of the first guests to experience this brand new vacation rental, perfectly situated in the sought-after, gated c ...
From $403 per night (USD)
VRBO
From $802 per night (USD)
VRBO
Stunning Tropical Escape with Dock, Pool, Hot Tub & Direct Ocean Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This jaw-dropping 3-bedroom, 3-bath Islamorada gem is where luxury meets laid-back island vibes. From the island chic de ...
From $802 per night (USD)
VRBO
From $264 per night (USD)
VRBO
Lovely 2 bdrm home in a resort, have a coffee and watch the sunrise on the deck
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to a unique and serene retreat at a beautiful resort perched on the edge of the Atlantic Ocean. This home feature ...
From $264 per night (USD)
VRBO
From $318 per night (USD)
Expedia
Ocean Resort, Key Largo
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Escape to Paradise in Key Largo: Your Dream Vacation Awaits! Mile Marek 94.8 Welcome to your slice of paradise in Key ...
From $318 per night (USD)
Expedia
From $529 per night (USD)
VRBO
Charming house boat with 2 bedrooms and WiFi, AC in wonderful Islamorada
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This amazing house boat in Islamorada is a unique and pleasant retreat for guests. With 2 cozy bedrooms and a comfortabl ...
From $529 per night (USD)
VRBO
From $296 per night (USD)
Expedia
Beachfront Villa w/ Pier & Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to a tropical paradise at this villa at Topsider Resort in Islamorada. Nestled among lush gardens, this private o ...
From $296 per night (USD)
Expedia
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VRBO
White Marlin Beach Townhome. Seconds to Matecumbe Bight
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Coastal Retreat with Private Beach Access & Boat Dockage Discover the perfect blend of comfort and convenience at this ...
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VRBO
From $670 per night (USD)
Expedia
2 Bedroom Updated Canal Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Your Dream Florida Keys Escape! This charming retreat offers modern upgrades, blending comfort and style, wit ...
From $670 per night (USD)
Expedia
From $518 per night (USD)
VRBO
Coconut Hut Oasis - 3 Bedroom Waterfront home with Pool/Spa, Tiki Hut, and Dock
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Waterfront Escape with Heated Pool, Dockage & Hot Tub – Bayside Beauty in Islamorada Welcome to your perfect Keys getaw ...
From $518 per night (USD)
VRBO
From $1267 per night (USD)
Expedia
Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Escape to paradise in the Jungle Suite, the largest and most luxurious stay at Casa Morada in Islamorada. Unwind in your ...
From $1267 per night (USD)
Expedia
From $1361 per night (USD)
VRBO
Deactivated due to Bad Review and Low Productivity compared to other listings.
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 $1361 per night (USD)
VRBO
From $655 per night (USD)
Expedia
NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Experience waterfront FL Keys living at its finest at The Seascape, a modern, newly constructed retreat nestled directly ...
From $655 per night (USD)
Expedia
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VRBO
Islamorada Suite With Kayaks •Patio & Garden Views - Wildflower Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Stay in the Wildflower Suite at Casa Morada, where relaxation meets island adventure. Enjoy a king-size bed, garden-view ...
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VRBO
From $1148 per night (USD)
Expedia
Cozy Islamorada Stay- Garden, Patio & Living Room - Barefoot Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Unwind in the Barefoot Suite at Casa Morada, your private garden escape in Islamorada. This bright, airy suite features ...
From $1148 per night (USD)
Expedia
From $2250 per night (USD)
VRBO
Relaxing Garden Suite With Pool @Islamorada- Sea Turtle Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This phenomenal hotel suite in Islamorada offers a cozy retreat with a gorgeous king bed, AC, and WiFi. The bathroom fea ...
From $2250 per night (USD)
VRBO
From $1894 per night (USD)
Expedia
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Treat yourself to island luxury in the Moon Suite at Casa Morada. Perched on the high floor with garden views, this eleg ...
From $1894 per night (USD)
Expedia
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VRBO
Jacuzzi Retreat W/ Garden View @Islamorada - Wild Water Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Unwind in the Wild Water Suite, where garden serenity meets indulgent comfort. This king-bed suite features an indoor ja ...
Click For Pricing
VRBO
From $2250 per night (USD)
Expedia
Charming Suite @Islamorada With Pool Access - Twilight Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Perched on the upper floor, the Twilight Suite at Casa Morada offers stunning garden views and a peaceful terrace perfec ...
From $2250 per night (USD)
Expedia
From $1267 per night (USD)
VRBO
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 ...
From $1267 per night (USD)
VRBO
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Expedia
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 ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Treat yourself to island luxury in the Moon Suite at Casa Morada. Perched on the high floor with garden views, this eleg ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Oceanview Sun Suite W/ Private Terrace Bliss @Islamorada - Sun Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Soak in sweeping bay views from the Sun Suite, a romantic retreat at Casa Morada in Islamorada. With large picture windo ...
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Expedia
From $2248 per night (USD)
VRBO
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 ...
From $2248 per night (USD)
VRBO
From $3780 per night (USD)
Expedia
Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Discover the Coconut Palm Suite—a relaxing island retreat at Casa Morada in the Florida Keys. Unwind in a spacious suite ...
From $3780 per night (USD)
Expedia
From $2044 per night (USD)
VRBO
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Escape to the Jungles Suite at Casa Morada, where tropical vibes meet modern comfort. Featuring a king-size bed, private ...
From $2044 per night (USD)
VRBO
Click For Pricing
Expedia
Terrace & Sea View Suite @Islamorada W/ Pool - Starfish Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Relax in the Starfish Suite at Casa Morada—your peaceful, ground-level escape with direct sea views. This charming suite ...
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Expedia
From $1832 per night (USD)
VRBO
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The Shangri La Suite offers a peaceful getaway with spectacular views of Florida Bay. This second-level suite includes a ...
From $1832 per night (USD)
VRBO
From $684 per night (USD)
Expedia
Waterfront / Ocean Access Canal / Kamp Key / Homes
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
This quaint Keys-style home offers timeless charm in a premier waterfront setting on an ocean-access canal. The open-con ...
From $684 per night (USD)
Expedia
From $673 per night (USD)
VRBO
Fun Under the Sun! Beachfront, w/ Pool Onsite, Free Parking, Pets Allowed!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 370 sq. ft, equipped with complimentary toiletries, TV. ✦ Da ...
From $673 per night (USD)
VRBO
From $755 per night (USD)
VRBO
Your Key to Unforgettable Island Moments! 2 Relaxing Units with Balcony!
Bedrooms:
2
Bathrooms:
4
Sleeps:
16
✦ Each room is 1350 sq. ft, equipped with complimentary toiletries, TV. ✦ Daily cleaning services included in the night ...
From $755 per night (USD)
VRBO
From $692 per night (USD)
VRBO
Island Living! Pool, Spa, 100’ Dock + Paddleboards – Islamorada Gem
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Tucked away on a quiet street in Lower Matecumbe, this beautifully furnished canalfront home is everything you imagine w ...
From $692 per night (USD)
VRBO
From $100 per night (USD)
Expedia
Turnkey Modern Studio in the Upper Keys – Stylish, Bright & Fully Equipped!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Gorgeous Turnkey Studio with Modern Finishes and Full Kitchen! Step into this beautifully updated, open-concept studio t ...
From $100 per night (USD)
Expedia
From $614 per night (USD)
VRBO
Off The Charts-Waterfront Tiki Bar & Private Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to a one-of-a-kind Florida Keys escape! This unique home, originally used as the Islamorada Courthouse, has been ...
From $614 per night (USD)
VRBO
From $901 per night (USD)
Expedia
Waterfront / Covered alfresco lounge / Heated Pool / Anchor Key
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
This waterfront retreat, crafted for the ultimate outdoor lifestyle, features an expansive covered alfresco lounge with ...
From $901 per night (USD)
Expedia
From $592 per night (USD)
VRBO
New Listing Canal Home Snake Creek with Bay&Ocean Access Tiki&Pool 100ft Dockage
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
⭐️5 bedroom 4 bathrooms (One bathroom by pool) ⭐️Canal home in Venetian Shores with access to bay and ocean ⭐️100 foot o ...
From $592 per night (USD)
VRBO
From $761 per night (USD)
Expedia
*Charming Beach House directly ON the beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Islamorada Oceanfront home located directly on a private beach; enjoy swimming snorkeling, and ideal for kitesurfing! ...
From $761 per night (USD)
Expedia
From $826 per night (USD)
VRBO
Beautiful Pool Home located in Port Antigua
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
PROPERTY NAME: Casa Mar 115 Ponce de Leon Blvd, Islamorada, Florida LOCATION: Bayside Canal home located in the popular ...
From $826 per night (USD)
VRBO
From $316 per night (USD)
Expedia
Beautiful Pool home in Islamorada
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
PROPERTY NAME: The Bungalow House 32 Park Rd Islamorada, Florida Location: Bayside Very close to the Publix Shopping ...
From $316 per night (USD)
Expedia
From $220 per night (USD)
VRBO
Paradise in the Heart of Islamorada.Come relax and have the time of your life!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your stunning 2 bed/2 bath “Keys Vibe” condo in the heart of Islamorada—also known worldwide as the Sport‑Fis ...
From $220 per night (USD)
VRBO
From $409 per night (USD)
Expedia
NEW! Waterfront, 3 Bedroom, 3 Bath. Keys Living, Peaceful Retreat
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This home is the definition of 'Keys' living. Situated on an oversized lot this 3 bedroom, 3 bath home offers 68 feet of ...
From $409 per night (USD)
Expedia
From $435 per night (USD)
VRBO
Oceanfront Islamorada Home with Epic Views from Every Room!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to 137 Ocean Lane in beautiful Islamorada—your private slice of paradise in the Florida Keys. This charming 3-be ...
From $435 per night (USD)
VRBO
From $1034 per night (USD)
VRBO
Bay Views, Spa, Pool, Tiki Hut, The Perfect Islamorada Getaway!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This stunning, fully renovated retreat checks every box for the perfect Keys escape—sweeping bay views, a private pool a ...
From $1034 per night (USD)
VRBO
From $238 per night (USD)
VRBO
Cozy Keys Hideaway on the water
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Your Tropical Getaway Experience the ultimate Florida Keys lifestyle in this beautifully renovated 2-bedroom, ...
From $238 per night (USD)
VRBO
From $230 per night (USD)
Expedia
Spacious Exec Bay Townhouse w/heated pool marina+
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Come and relax in Paradise at our updated Executive Bay Club (EBC) townhouse. EBC is located in Islamorada, mile marker ...
From $230 per night (USD)
Expedia
From $702 per night (USD)
VRBO
Beautiful two- story beach house
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Your cozy getaway awaits in Islamorada at this superb house. With 4 bedrooms including a king, queen, bunk, and twin bed ...
From $702 per night (USD)
VRBO
From $2136 per night (USD)
Expedia
Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Stay comfortably in Islamorada at this 1-bedroom hotel suites. The room features a cozy king bed, AC, WiFi, and a conven ...
From $2136 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Modern 2BR Getaway | Full Kitchen + Bunks + AC
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
🌟 HIGHLIGHTS 🌟 🛏 2 Bedrooms: 1 King Bed, 1 Full-over-Full Bunk Bed 🛋️ Stylish Living Area w/ Smart TV & Sofa 🍽️ ...
From $203 per night (USD)
VRBO
From $185 per night (USD)
Expedia
Cozy Keys Stay | King Bed + Luxe Bath
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
🌟 HIGHLIGHTS 🌟 🛌🏻 1 Bedroom: 1x King Bed 🚿 1 Full Bathroom w/ Complimentary Toiletries 🍽️ Fully Equipped Kitchen � ...
From $185 per night (USD)
Expedia
From $1984 per night (USD)
VRBO
Palm Escape- Beachside Bliss w/ Private Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
🌴 First Time Ever Available – A True Keys Treasure! After 8 years searching, we found paradise. At the heart of the est ...
From $1984 per night (USD)
VRBO
From $567 per night (USD)
Expedia
Waterfront Florida Keys Home with Boat Dock and Hot Tub!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Discover the beauty of Islamorada and the surrounding Florida Keys from this spacious canal-side townhome! You will slid ...
From $567 per night (USD)
Expedia
From $180 per night (USD)
VRBO
Modern remodeled 2 bedroom Apt - Summer Sea 434
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This beautiful, modern, upgraded 2-bedroom, 1.5 bath apartment at Summer Sea has everything you would want for your fabu ...
From $180 per night (USD)
VRBO
From $376 per night (USD)
Expedia
See the sunrises in Islamorada!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Get ready to relax in this 2-bedroom house in Islamorada. This adorable property features AC and a hair dryer for your c ...
From $376 per night (USD)
Expedia
From $668 per night (USD)
VRBO
Oceanfront Cottage in Islamorada! Swimming Pool, Pets Allowed, Free Parking!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Set along a private beach in Islamorada, La Siesta Resort & Villas features colorful cottages with premium amenities. Gu ...
From $668 per night (USD)
VRBO
From $646 per night (USD)
VRBO
Ocean view Studio w/kitchenette, Pool, Free Parking & Pet Friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront studios with premium amenities. G ...
From $646 per night (USD)
VRBO
From $623 per night (USD)
VRBO
Oceanfront Studio Queen w/Kitchenette, Pool, Free Parking & Pet Friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront studios with premium amenities. G ...
From $623 per night (USD)
VRBO
From $668 per night (USD)
VRBO
Ocean Front Studio w/Kitchenette, Pool, Free Parking & Pet Friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront studios with premium amenities. G ...
From $668 per night (USD)
VRBO
From $247 per night (USD)
VRBO
Best sunrises in all of Islamorada!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Come see the sunrise from your second-floor patio! This charming 2-bedroom, 2-bath home is ready for you to create unfor ...
From $247 per night (USD)
VRBO
From $1288 per night (USD)
VRBO
Two Bedroom Ocean Front Suite w/Kitchenette, Pool, Free Parking & Pet Friendly
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront suites with premium amenities. Gu ...
From $1288 per night (USD)
VRBO
From $956 per night (USD)
VRBO
One Bedroom Suite w/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
12
Set along a private beach in Islamorada, La Siesta Resort & Villas features suites with premium amenities. Guests enjoy ...
From $956 per night (USD)
VRBO
From $849 per night (USD)
VRBO
2 Separate Unites w/ 2 Bedrooms, Kitchenette, Pool, Free Parking & Pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
16
Set along a private beach in Islamorada, La Siesta Resort & Villas features suites with premium amenities. Guests enjoy ...
From $849 per night (USD)
VRBO
From $399 per night (USD)
VRBO
Courtyard View Room w/Patio, Outdoor Pool, Free Parking & Pet Friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located oceanfront in Islamorada, Amara Cay Resort features stylish rooms and suites with balconies in a boutique island ...
From $399 per night (USD)
VRBO
From $650 per night (USD)
VRBO
2 Queen Beds Room w/Patio, Outdoor Pool, Free Parking & Pet Friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located oceanfront in Islamorada, Amara Cay Resort features stylish rooms and suites with balconies in a boutique island ...
From $650 per night (USD)
VRBO
From $571 per night (USD)
VRBO
1 King Room w/ Balcony, 3 Outdoor Pools & Free Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Set on 15 oceanfront acres in Islamorada, Three Waters Resort & Marina features island-inspired rooms. Guests enjoy thre ...
From $571 per night (USD)
VRBO
From $1650 per night (USD)
VRBO
4 Rooms w/ Queen Beds, Balcony, 3 Outdoor Pools, Free Parking & Pet Friendly
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Set on 15 oceanfront acres in Islamorada, Three Waters Resort & Marina features island-inspired rooms. Guests enjoy thre ...
From $1650 per night (USD)
VRBO
From $962 per night (USD)
VRBO
2 Rooms w/ Queen Beds, Balcony, 3 Outdoor Pools, Free Parking & Pet Friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Set on 15 oceanfront acres in Islamorada, Three Waters Resort & Marina features island-inspired rooms. Guests enjoy thre ...
From $962 per night (USD)
VRBO
From $482 per night (USD)
VRBO
2 Queen Bed Rooms w/ Balcony, 3 Outdoor Pools, Free Parking & Pet Friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Set on 15 oceanfront acres in Islamorada, Three Waters Resort & Marina features island-inspired rooms. Guests enjoy thre ...
From $482 per night (USD)
VRBO
From $1097 per night (USD)
VRBO
Two Bedrooms Suite w/Ocean View, Pool, Free Parking & Pet Friendly
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront suites with premium amenities. Gu ...
From $1097 per night (USD)
VRBO
From $632 per night (USD)
VRBO
2 Suites w/Queen Beds, Kitchenette, Outdoor Pool, Free Parking & Pet Friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
12
Set along a private beach in Islamorada, La Siesta Resort & Villas features suites with premium amenities. Guests enjoy ...
From $632 per night (USD)
VRBO
From $571 per night (USD)
VRBO
Courtyard View King Room w/ Balcony, Outdoor Pool & Free Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Located oceanfront in Islamorada, Amara Cay Resort features stylish rooms and suites with balconies in a boutique island ...
From $571 per night (USD)
VRBO
From $1204 per night (USD)
VRBO
2 Rooms w/ Balcony, Courtyard View, Outdoor Pool, Free Parking & Pet Friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Located oceanfront in Islamorada, Amara Cay Resort features stylish rooms and suites with balconies in a boutique island ...
From $1204 per night (USD)
VRBO
From $1925 per night (USD)
VRBO
4 Rooms w/ Queen Beds, Balcony, 3 Outdoor Pools, Free Parking & Pet Friendly
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Set on 15 oceanfront acres in Islamorada, Three Waters Resort & Marina features island-inspired rooms. Guests enjoy thre ...
From $1925 per night (USD)
VRBO
From $1443 per night (USD)
VRBO
3 Rooms w/ Queen Beds, Balcony, 3 Outdoor Pools, Free Parking & Pet Friendly
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Set on 15 oceanfront acres in Islamorada, Three Waters Resort & Marina features island-inspired rooms. Guests enjoy thre ...
From $1443 per night (USD)
VRBO
From $862 per night (USD)
VRBO
Luxury vacation home. This is Paradise. Perfect for all family occasions.
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Enjoy a peaceful stay at this 3-bedroom house in Islamorada. The bedrooms feature a queen bed, bunk bed, and king bed, e ...
From $862 per night (USD)
VRBO
From $669 per night (USD)
VRBO
Turtles Nest Islamorada Getaway 28 day rental
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
This beautiful home is nestled in the quiet neighborhood of Venetian Shores. It sits right on a deep water canal minutes ...
From $669 per night (USD)
VRBO
From $560 per night (USD)
VRBO
Anglers Reef Islamorada Oceanfront 3BR Pool Front Home Private Beach & Boat Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Oceanfront Paradise in Anglers Reef, Islamorada – Florida Keys Vacation Rental Experience the ultimate Florida Keys vac ...
From $560 per night (USD)
VRBO
From $239 per night (USD)
VRBO
Las Maravillas ~ 2 Bed / 2.5 Bath Townhouse on Lower Matecumbe Key
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Welcome to Las Maravillas, your ideal Florida Keys retreat! This charming 2-bedroom, 2.5-bath townhome on Lower Matecum ...
From $239 per night (USD)
VRBO
From $113 per night (USD)
VRBO
Walk to Beach: Tavernier Apartment w/ Patio!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Bicycles Provided | Quiet Location | Day Trip to Everglades National Park Seaside days and starlit nights are yours at ...
From $113 per night (USD)
VRBO
From $140 per night (USD)
VRBO
Steps to Gulf: Sleek Top-Floor Apt in Tavernier!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Al Fresco Dining | Day Trip to Everglades National Park Adventure starts here — discover the best of Tavernier at this ...
From $140 per night (USD)
VRBO
From $201 per night (USD)
VRBO
OCEANIQUE 1 - Luxury 3/2 Condo & Boat Slip - Oceanside in Islamorada
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Coral Harbour Club, a Gated Oceanfront Community in Islamorada, Florida Keys 3 Bedrooms | 2 Bathrooms | 30’ Boat Slip ( ...
From $201 per night (USD)
VRBO
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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 o ...
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Expedia
From $1138 per night (USD)
VRBO
Breathtaking Bayfront Retreat in Venetian Shores
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to 116 Gulfside Drive — a breathtaking waterfront retreat in one of Islamorada’s most desirable neighborhoods. F ...
From $1138 per night (USD)
VRBO
From $1296 per night (USD)
VRBO
Flamingo Bay – Private Waterfront Paradise with Pool, Tiki Hut & Kayaks
Bedrooms:
8
Bathrooms:
6
Sleeps:
12
Welcome to Flamingo Bay, where luxury, space, and jaw-dropping beauty come together on the sparkling open waters of Flor ...
From $1296 per night (USD)
VRBO
From $197 per night (USD)
VRBO
Beautiful Penthouse Apartment with Direct Open Water Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This Beautiful Penthouse Apartment overlooks the fabulous turquoise waters of Florida Bay! Arranged for family enjoyment ...
From $197 per night (USD)
VRBO
From $1720 per night (USD)
VRBO
Stay at the Pirate House conveniently located on Snake Creek in Venetian Shores
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This unique home is located directly on Snake Creek which is ideal for experiencing the amazing sunsets and convenient f ...
From $1720 per night (USD)
VRBO
From $341 per night (USD)
VRBO
Venetian Shores Retreat with Boat Lift, Tiki Hut & Hot Tub
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Tucked away in the sought-after community of Venetian Shores, this 3-bedroom, 2-bath canal-front home is designed for ea ...
From $341 per night (USD)
VRBO
From $759 per night (USD)
VRBO
Irish Ayes | Venetian Shores Canalfront with Pool, Hot Tub, Dock & Elevator
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Irish Ayes, a stunning 4-bedroom canalfront retreat in the prestigious neighborhood of Venetian Shores, Islam ...
From $759 per night (USD)
VRBO

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