Islamorada Rentals
From $1529 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 $1529 per night (USD)VRBO
From $926 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 $926 per night (USD)Expedia
From $798 per night (USD)VRBO
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 $798 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 $781 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 $781 per night (USD)VRBO
From $1191 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 $1191 per night (USD)Expedia
From $537 per night (USD)VRBO
NewBeautifulCanal 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 $537 per night (USD)VRBO
From $797 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 $797 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 $317 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 $317 per night (USD)Expedia
From $410 per night (USD)VRBO
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 $410 per night (USD)VRBO
From $231 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 $231 per night (USD)Expedia
From $603 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 $603 per night (USD)VRBO
From $326 per night (USD)Expedia
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 $326 per night (USD)Expedia
From $282 per night (USD)VRBO
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 Kitche ...
From $282 per night (USD)VRBO
From $2213 per night (USD)Expedia
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 $2213 per night (USD)Expedia
From $574 per night (USD)VRBO
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 $574 per night (USD)VRBO
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 $742 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 $742 per night (USD)VRBO
From $688 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 $688 per night (USD)VRBO
From $693 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 $693 per night (USD)VRBO
From $682 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 $682 per night (USD)VRBO
From $277 per night (USD)VRBO
Best sunrises in all of Islamorada!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Isla life starts now! This is more than just another day in paradise. Sun Outdoors Islamorada in the Florida Keys is ...
From $277 per night (USD)VRBO
From $1338 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 $1338 per night (USD)VRBO
From $998 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 $998 per night (USD)VRBO
From $1274 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 $1274 per night (USD)VRBO
From $572 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 $572 per night (USD)VRBO
From $1653 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 $1653 per night (USD)VRBO
From $963 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 $963 per night (USD)VRBO
From $483 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 $483 per night (USD)VRBO
From $1087 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 $1087 per night (USD)VRBO
From $1114 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 $1114 per night (USD)VRBO
From $1446 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 $1446 per night (USD)VRBO
From $862 per night (USD)Expedia
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)Expedia
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 $650 per night (USD)Expedia
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 $650 per night (USD)Expedia
From $256 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 $256 per night (USD)VRBO
From $114 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 $114 per night (USD)VRBO
From $142 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 $142 per night (USD)VRBO
From $207 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 $207 per night (USD)VRBO
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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 ...
Click For PricingVRBO
From $1134 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 $1134 per night (USD)VRBO
From $1260 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 $1260 per night (USD)VRBO
From $230 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 $230 per night (USD)VRBO
From $1422 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 $1422 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
From $490 per night (USD)VRBO
Oversized Islamorada Villa 110 in Gated Anglers Reef: Pool, Kayaks, Bikes, Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Villa #110, your perfect getaway! Nestled in the heart of Islamorada, this spacious 2-bedroom villa - one of ...
From $490 per night (USD)VRBO
From $450 per night (USD)VRBO
Spectacular Keys home-corner canal, hot tub, tiki
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Come experience breathtaking beauty right from your backyard! Relax on the tranquil canal with stunning water views, oft ...
From $450 per night (USD)VRBO
From $270 per night (USD)VRBO
Charming 2-bedroom waterfront home\n in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to this charming canal front house located on the bay side in Islamorada. This wonderful property features 2 coz ...
From $270 per night (USD)VRBO
From $1725 per night (USD)VRBO
BRAND NEW Bayfront Home - Pool/Sandy Beach - private and elegant - Islamorada
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Discover the beauty of Islamorada from this 6-bedroom/6 bath Bayfront house. Beautiful new home on Florida Bay with sand ...
From $1725 per night (USD)VRBO
From $102 per night (USD)Expedia
OCEAN VIEW Islamorada 1/1 newly refreshed concrete house, & tiki in Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
OCEAN VIEW tiki covered rooftop deck, with concrete stairway.Escape to beautiful ocean views, sunrisees/ sunsets, in a c ...
From $102 per night (USD)Expedia
From $941 per night (USD)VRBO
Open Bay 5 bedroom stunning home!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Lobster Tales, a stunning bayfront home in the heart of Islamorada’s Plantation Key Colony. This spacious 5-b ...
From $941 per night (USD)VRBO
From $315 per night (USD)Expedia
Comfortable, spacious 3-bedroom, 2-bath-1 level home --dock on canal, Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Your cozy getaway awaits in quiet Venetian Shores at this bright and airy house. With 3 bedrooms including 2 queen beds ...
From $315 per night (USD)Expedia