Islamorada Rentals
From $238 per night (USD)VRBO
Gorgeous Beach Bungalow Just Steps from Private Sandy Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
You have found a sandy beach paradise in the Florida Keys! Located just 4 houses from a secret, sandy beach, Little Pea ...
From $238 per night (USD)VRBO
From $540 per night (USD)Expedia
Sunset Peninsula—a multi-family, original, Florida Keys waterfront retreat!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to the Sunset Peninsula! This gated, multi-family compound is perfect for those traveling in larger groups with ...
From $540 per night (USD)Expedia
From $694 per night (USD)VRBO
PARADISE SHORES
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
You won't be disappointed once you arrive at Paradise Shores. This completely remodeled Venetian Shores 4 BD / 3 BA cana ...
From $694 per night (USD)VRBO
From $432 per night (USD)VRBO
Islamorada's Premier Boating Neighborhood; Venetian Shores. A boaters paradise.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled within the serene surroundings of Islamorada, Florida, awaits a charming oasis at 116 Stromboli Drive. This sing ...
From $432 per night (USD)VRBO
From $376 per night (USD)VRBO
Isla Honeydew: 3 En-Suite Bedrooms! FREE boat dockage Sept-Oct only
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $376 per night (USD)VRBO
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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 PricingExpedia
Click For PricingVRBO
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 PricingVRBO
From $1865 per night (USD)VRBO
\"Luxurious Open Bay Retreat: Expansive Dockage & Private Pool Oasis!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Discover your dream vacation at Pirate's Chateau, nestled in the pristine Venetian Shores on the open bay. This luxuriou ...
From $1865 per night (USD)VRBO
From $1057 per night (USD)VRBO
Coastal Retreat in the Heart of Islamorada
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Nestled between the Cheeca Lodge and Caribbean Resort, our 4-bedroom oceanside home offers a unique beachfront experienc ...
From $1057 per night (USD)VRBO
From $405 per night (USD)Expedia
4-bedroom airport community house in Tavernier
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
*MORE PHOTOS TO COME AFTER RENOVATIONS* Experience Tavernier like a local in this 4-bedroom house. Step into a wonderful ...
From $405 per night (USD)Expedia
From $1185 per night (USD)VRBO
Maison 402 Island Charm
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Maison 402 Island Charm, your perfect vacation retreat in the heart of Islamorada! This charming 3-bedroom, 3 ...
From $1185 per night (USD)VRBO
From $137 per night (USD)Expedia
Ocean front property
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2 bedroom, 1 and a half two story Condo. Kitchen, living area, private parking, barbecue area, recreational room, in a ...
From $137 per night (USD)Expedia
From $1535 per night (USD)VRBO
Oceanfront Estate in the Heart of Islamorada
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Morada Shores, an exquisite estate where every detail has been carefully crafted for the ultimate vacation ex ...
From $1535 per night (USD)VRBO
From $1422 per night (USD)VRBO
Luxury Oceanfront Oasis With Deep Water Dockage!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Experience the ultimate coastal getaway at this spectacular 5 bedroom, 5.5 bathroom oceanfront home, complete with deep ...
From $1422 per night (USD)VRBO
From $920 per night (USD)VRBO
REST AND RELAXATION @ EXCLUSIVE DISCOUNTED PRICING PLUS MONTHLY RATE W/DISCOUNT
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Remarkable home nestled in the heart of Islamorada where you will find large outdoor spaces with outdoor dining and priv ...
From $920 per night (USD)VRBO
From $342 per night (USD)VRBO
Beachside Topsider Octagon Pad
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
At Topsider Resort, you’ll be staying in our unique octagonal stilted homes nestled in a lush tropical setting facing di ...
From $342 per night (USD)VRBO
From $463 per night (USD)VRBO
The Reef House, Waterfront, Oceanside, 70' Dock, Heated Pool and Spa Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Reef House! This ideal location allows for direct, bridge-free access to the Atlantic Ocean or bayside via Ta ...
From $463 per night (USD)VRBO
From $194 per night (USD)Expedia
Exec Bay 3 Bedroom townhouse w/heated pool, marina, tennis & more
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come and experience the beauty and tranquility of the Florida Keys at Executive Bay Club! Enjoy gorgeous sunsets from th ...
From $194 per night (USD)Expedia
From $696 per night (USD)VRBO
Islamorada waterfront gem: Total reno ‘24: 3/3.5, pool, spa & deep water dock.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Lower Matecumbe generally, and Sapodilla Drive specifically, is an idyllic location in Islamorada. Only five miles to ev ...
From $696 per night (USD)VRBO
From $231 per night (USD)Expedia
Charming 2-bedroom townhome with WiFi, AC in enjoyable Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Your Islamorada adventure begins at this 2-bedroom townhome. Inside, guests will find a delightful mix of comfort and st ...
From $231 per night (USD)Expedia
From $230 per night (USD)VRBO
Charming 2-bedroom house in welcoming Islamorada with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This brilliant house in Islamorada is a wonderful choice for guests seeking a cozy retreat. With 2 bedrooms, 2 bathrooms ...
From $230 per night (USD)VRBO
From $235 per night (USD)VRBO
NEW! Canal-Front with Tropical Charm & Private Guest Apartment on Plantation Key
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Manatee Manor! Nestled in the desirable Indian Waterways neighborhood on Plantation Key, this charming canal- ...
From $235 per night (USD)VRBO
From $210 per night (USD)VRBO
Executive Bay Club R8 ~ 3 Bed / 3 Bath + Loft Townhouse on Plantation Key
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Discover your ideal getaway at this charming seascape in Islamorada! This lovely 3-bedroom, 3-bathroom townhome, complet ...
From $210 per night (USD)VRBO
From $379 per night (USD)Expedia
Escape to beautiful Islamorada!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Located 90 minutes from Miami and 20 minutes to the world-famous Tiki Bar sandbar (dock to anchor) one of the best in ...
From $379 per night (USD)Expedia
From $207 per night (USD)VRBO
Charming 3-bedroom house with private beach access in beautiful Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Bask in the warmth of Islamorada Florida with this 3-bedroom, 2-bath home. 90 minutes from Miami and ½ way down the Flor ...
From $207 per night (USD)VRBO
From $324 per night (USD)VRBO
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
- 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 $324 per night (USD)VRBO
From $223 per night (USD)VRBO
Amazing new 2-bedroom, 2-bathroom apartment in the heart of Islamorada!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Islamorada apartment boasts 2 inviting bedrooms with 2 queen beds. The cozy living room also offers an extra queen ...
From $223 per night (USD)VRBO
From $518 per night (USD)Expedia
Canal front pool home in Florida key's Islamorada! Access to ocean w/boat lift!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Luxury Waterfront Vacation Home in Islamorada Escape to paradise in this stunning waterfront vacation home located in t ...
From $518 per night (USD)Expedia
From $277 per night (USD)VRBO
Coral Harbour Club ~ 2 Bedroom Condo in Islamorada with Pool & Dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Coral Harbour Club! Find your escape, experience relaxing days at this oceanside getaway! Located on Planta ...
From $277 per night (USD)VRBO
From $834 per night (USD)VRBO
Oceanfront Oasis in Angler’s Reef with Private Boat Slip
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this laid-back, oceanfront townhouse in Angler’s Reef, where coastal vibes and easy living come together in th ...
From $834 per night (USD)VRBO
From $254 per night (USD)VRBO
Tavernier Canal front Retreat with Boat Lift – 28-Day Keys Getaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Your Tavernier Canal front Retreat! Escape to the Florida Keys for a serene 28-day stay in our charming 2-bed ...
From $254 per night (USD)VRBO
From $201 per night (USD)Expedia
Beautiful Home located in Downtown Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
PROPERTY NAME: Mango House 81212 Old Highway Islamorada, Florida Location: Ocean side located on the Old Road by Gree ...
From $201 per night (USD)Expedia
From $3208 per night (USD)VRBO
Entire Floor - 8 BR overlooking pool, sandy beach & Ocean! Luxury finishings
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 16
Introducing Maison Residences Full floor for rent – Oceanfront & Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE — ...
From $3208 per night (USD)VRBO
From $620 per night (USD)VRBO
Morada Breeze ~ 6 Bedroom Plantation Key Home with Pool & Dockage
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to Morada Breeze! This 6-bedroom, 4-bath bayside slice of paradise is ready to make your next vacation an enjoya ...
From $620 per night (USD)VRBO
From $659 per night (USD)VRBO
Morada Zen - 4BR/3Bath Waterfront Ocean & Bay Access, Pool, Tiki, Dockage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Islamorada Florida - Fishing Capital of the World!! Beautiful 4 bedroom, 3 bath home available for monthly rental (28 da ...
From $659 per night (USD)VRBO
From $1175 per night (USD)Expedia
Oceanfront 3 bedroom with dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Behold this exquisite oceanfront pool residence, which has been flawlessly renovated. Nestled in a remarkable location w ...
From $1175 per night (USD)Expedia
From $753 per night (USD)VRBO
Coastal Retreat! Pool, Pets Allowed, Minutes to Indian Key Historic State Park
- 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 $753 per night (USD)VRBO
From $1127 per night (USD)VRBO
Oceanfront Property w/ Outdoor Pools, Pets Allowed, Free Parking Onsite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $1127 per night (USD)VRBO
From $790 per night (USD)VRBO
Cozy Coastal Haven for Relaxation! With Pools and Water Sports Onsite!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $790 per night (USD)VRBO
From $1671 per night (USD)VRBO
High Tides and Good Vibes! 4 Spacious Units, Outdoor Pool, Free Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located on a private beach and close to Indian Key Historic State Park. This listing is for 4 separate rooms within a h ...
From $1671 per night (USD)VRBO
From $1671 per night (USD)VRBO
4 Units Perfect for Big Groups! Beachfront Property with Outdoor Pools!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located on a private beach and close to Indian Key Historic State Park. This listing is for 4 separate rooms within a h ...
From $1671 per night (USD)VRBO
From $792 per night (USD)VRBO
Oceanfront Paradise Retreat! Outdoor Pool, Pets Allowed, Near Coral Bay Marina
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $792 per night (USD)VRBO
From $554 per night (USD)VRBO
Beach Getaway! Outdoor Pool, Free Parking, Near Keys History & Discovery Center
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $554 per night (USD)VRBO
From $444 per night (USD)VRBO
Escape to Paradise! Beachfront, Outdoor Pool, Near Theater of the Sea
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Escape to oceanfront tranquility at Islander Resort in Islamorada. Enjoy beach access, oceanfront pools, on-site dining, ...
From $444 per night (USD)VRBO
From $364 per night (USD)VRBO
Fun Under the Sun! Beachfront, w/ Pool Onsite, Free Parking, Pets Allowed!
- 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 $364 per night (USD)VRBO
From $1127 per night (USD)VRBO
You Don’t Want to Miss This! Beachfront, Onsite Pool, 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 $1127 per night (USD)VRBO
From $926 per night (USD)VRBO
Your Islamorada Hideaway! Beachfront Accommodation - Onsite Pool, Parking
- 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 $926 per night (USD)VRBO
From $1138 per night (USD)VRBO
Prime Location! Beachfront Property with Outdoor Pool, Pets are Welcome!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $1138 per night (USD)VRBO
From $926 per night (USD)VRBO
Sun, Sand, and Relaxation Awaits! Ocean View Accommodation w/ Private Patio!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $926 per night (USD)VRBO
From $1326 per night (USD)VRBO
Family Getaway! 3 Tropical View Units, Outdoor Pools, Pet-friendly!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Located on a private beach and close to Indian Key Historic State Park. This listing is for 3 separate rooms within a h ...
From $1326 per night (USD)VRBO
From $922 per night (USD)VRBO
2 Spacious Units, Beachfront Property, Onsite Pool, Free Parking, Pet-friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located on a private beach and close to Indian Key Historic State Park. This listing is for 2 separate rooms within a h ...
From $922 per night (USD)VRBO
From $444 per night (USD)VRBO
Best Location! Beachfront Property with Outdoor Pool, Pets are Welcome!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $444 per night (USD)VRBO
From $454 per night (USD)VRBO
Steps Away from Coral Bay Marina! Pool, Beachfront, Free Parking, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Escape to oceanfront tranquility at Islander Resort in Islamorada. Enjoy beach access, oceanfront pools, on-site dining, ...
From $454 per night (USD)VRBO
From $922 per night (USD)VRBO
Better Choice for your Vacation! 2 Comfortable Units, Beachfront, Outdoor Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located on a private beach and close to Indian Key Historic State Park. This listing is for 2 separate rooms within a h ...
From $922 per night (USD)VRBO
From $1326 per night (USD)VRBO
Everything You Need For The Perfect Vacation! 3 Sleek Units, Beachfront, Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Located on a private beach and close to Indian Key Historic State Park. This listing is for 3 separate rooms within a h ...
From $1326 per night (USD)VRBO
From $1256 per night (USD)VRBO
Enjoy a Hassle-free Stay! Unit w/ Full Kitchen, Beachfront, Outdoor Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $1256 per night (USD)VRBO
From $1261 per night (USD)VRBO
Dip Your Toes In The Sand! Beachfront, Pool, Near History of Diving Museum
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $1261 per night (USD)VRBO
From $2103 per night (USD)VRBO
Keys to Relaxation! Pool, Pets Allowed, Short Drive to Florida Keys Airport
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $2103 per night (USD)VRBO
From $489 per night (USD)VRBO
Sunset Views and Serenity! Outdoor Pool, Free Parking, Near Hurricane Monument
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $489 per night (USD)VRBO
From $489 per night (USD)VRBO
Dream Paradise! Beachfront Property with Pool, Free Parking, Partial Ocean View
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $489 per night (USD)VRBO
From $771 per night (USD)VRBO
Coastal Gem! Water Activities Onsite, Pool, Private Patio, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $771 per night (USD)VRBO
From $771 per night (USD)VRBO
Spacious Ocean View Accommodation w/ Patio! Beachfront Property w/ Outdoor Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $771 per night (USD)VRBO
From $757 per night (USD)VRBO
Excellent Choice! Beachfront Location, Outdoor Pool, Free Parking, Pet-friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $757 per night (USD)VRBO
From $1078 per night (USD)VRBO
Dive Into Your Dream Vacation! Beachfront, Outdoor Pool, 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 $1078 per night (USD)VRBO
From $1135 per night (USD)VRBO
Beach Bliss, Just Steps to the Ocean! Outdoor Pool, Near Coral Bay Marina
- 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 $1135 per night (USD)VRBO
From $549 per night (USD)VRBO
Summer Escapade! Onsite Pool, Steps from the Beach, Pets Allowed, Free Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $549 per night (USD)VRBO
From $1078 per night (USD)VRBO
Best Vacation Choice! Outdoor Pool, Beachfront Location, Pets are Welcome!
- 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 $1078 per night (USD)VRBO
From $2108 per night (USD)VRBO
Have Fun at this Beachfront Paradise with Outdoor Pools, Free Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $2108 per night (USD)VRBO
From $1523 per night (USD)VRBO
Isla Sunset Collection: Sleeps 18, All Ensuite Bedrooms, Waterfront
- Bedrooms:
- 10
- Bathrooms:
- 9
- Sleeps:
- 18
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $1523 per night (USD)VRBO
From $2083 per night (USD)Expedia
Isla Sands Collection: Sleeps 24, All Ensuite Bedrooms, Waterfront
- Bedrooms:
- 14
- Bathrooms:
- 12
- Sleeps:
- 24
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $2083 per night (USD)Expedia
From $466 per night (USD)VRBO
Ensuring a Very Comfortable & Memorable Stay, Near History of Diving Museum
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Relaxing and indulgent stay on the tropical islands of Islamorada! ✦ Your room is 450 sq. ft, equipped with complimenta ...
From $466 per night (USD)VRBO
From $327 per night (USD)VRBO
Studio w/ King Bed, Kitchenette, Outdoor Pool, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Set along a private beach in Islamorada, La Siesta Resort & Villas features studios with premium amenities. Guests enjoy ...
From $327 per night (USD)VRBO
From $385 per night (USD)VRBO
1 Bedroom Suite w/Kitchenette, Pool View, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Set along a private beach in Islamorada, La Siesta Resort & Villas features suites with premium amenities. Guests enjoy ...
From $385 per night (USD)VRBO
From $396 per night (USD)VRBO
2 Bedroom Suite w/ Kitchenette, Outdoor Pool, Free Parking & Pet Friendly!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Set along a private beach in Islamorada, La Siesta Resort & Villas features suites with premium amenities. Guests enjoy ...
From $396 per night (USD)VRBO
From $542 per night (USD)VRBO
Ocean Front Unit In Islamorada | Enjoy Scenic Walks on Private Beach
- 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 $542 per night (USD)VRBO
From $720 per night (USD)VRBO
Two Spacious 1BR Suites w/ Scenic Pool View | Breathtaking Resort | Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 12
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $720 per night (USD)VRBO
From $1073 per night (USD)VRBO
Scenic Beachfront Suite w/ Gorgeous Views & Family-Friendly Pool | Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This listing is for a room within a hotel. ✦ Your room is 850 sq. ft, equipped with complimentary toiletries, TV. ✦ Da ...
From $1073 per night (USD)VRBO
From $975 per night (USD)VRBO
2 Bedroom Suite in Islamorada! Swimming Pool, Kitchenette, Pets Allowed!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront suites with premium amenities. Gu ...
From $975 per night (USD)VRBO
From $314 per night (USD)VRBO
Studio w/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Set along a private beach in Islamorada, La Siesta Resort & Villas features studios with premium amenities. Guests enjoy ...
From $314 per night (USD)VRBO
From $1160 per night (USD)VRBO
3 Bedroom Suite w/Kitchenette, Pool, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Set along a private beach in Islamorada, La Siesta Resort & Villas features suites with premium amenities. Guests enjoy ...
From $1160 per night (USD)VRBO
From $476 per night (USD)VRBO
Better Choice For Your Vacation, Near History of Diving Museum, Pets are Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Relaxing and indulgent stay on the tropical islands of Islamorada! ✦ Your room is 450 sq. ft, equipped with complimenta ...
From $476 per night (USD)VRBO
From $1141 per night (USD)VRBO
Best Value, Quality Stay with Free Parking, Near Islamorada Brewery & Distillery
- 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. ...
From $1141 per night (USD)VRBO
From $476 per night (USD)VRBO
Sunny Escape! Spacious Oceanfront Suite with Balcony! Beachfront Resort w/ Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $476 per night (USD)VRBO
From $715 per night (USD)Expedia
Your Key to Unforgettable Island Moments! 2 Relaxing Units with Balcony!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 16
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $715 per night (USD)Expedia
From $900 per night (USD)VRBO
Relaxation at its Finest in Islamorada! Swimming Pool, Beach, Pet-friendly!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Relaxing and indulgent stay on the tropical islands of Islamorada! This listing is for a room within a hotel. ✦ Your r ...
From $900 per night (USD)VRBO
From $500 per night (USD)VRBO
Ideal Mix of Comfort & Value! Studio 2 Queen beds w/ Pool & Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront studios with premium amenities. G ...
From $500 per night (USD)VRBO
From $648 per night (USD)VRBO
2 Spacious Garden Suite w/ Kitchenette | Outdoor Pool + Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 12
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $648 per night (USD)VRBO
From $569 per night (USD)VRBO
Relax, Play, and Soak in Islamorada! Swimming Pool, Pets Allowed, Free Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Relaxing and indulgent stay on the tropical islands of Islamorada! ✦ Your room is 450 sq. ft, equipped with complimenta ...
From $569 per night (USD)VRBO
From $342 per night (USD)VRBO
Oceanfront Condo with Amenities Galore & Perfect Islamorada Location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ocean Harbour Awaits – Your Perfect Islamorada Escape This beautiful 3-bedroom, 2-bath oceanfront condo boasts a luxu ...
From $342 per night (USD)VRBO
From $423 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 $423 per night (USD)VRBO
From $324 per night (USD)VRBO
Spacious 1BR Suite w/Kitchenette, Outdoor Pool, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Set along a private beach in Islamorada, La Siesta Resort & Villas features suites with premium amenities. Guests enjoy ...
From $324 per night (USD)VRBO
From $423 per night (USD)VRBO
Relax and Unwind! Courtyard View, Free Parking, Onsite Pool, Near Anne's Beach
- 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 $423 per night (USD)VRBO
From $629 per night (USD)VRBO
Newly built 4-bedroom house in Tavernier with ample dock space and Kayak ramp.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This Tavernier house boasts 4 inviting bedrooms - 2 king beds, 2 queen beds, and 1 bunk bed. With 3 bathrooms featuring ...
From $629 per night (USD)VRBO
From $404 per night (USD)VRBO
Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $404 per night (USD)VRBO
From $867 per night (USD)VRBO
Relax and Recharge in Islamorada! 2 Relaxing Units, Pets Allowed, Outdoor Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $867 per night (USD)VRBO
From $1035 per night (USD)VRBO
Relax and Unwind in Islamorada! Swimming Pool, Pet-friendly Property!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $1035 per night (USD)VRBO
From $1620 per night (USD)VRBO
A Place You'll Surely Enjoy! 3 Comfortable Units, Onsite Pool, Free Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $1620 per night (USD)VRBO
From $1082 per night (USD)VRBO
High Tides and Good Vibes! 2 Relaxing Units, Pet-friendly Property, Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $1082 per night (USD)VRBO
From $2166 per night (USD)VRBO
Make Your Trip More Enjoyable! 4 Family-friendly Units, Pets Allowed, Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $2166 per night (USD)VRBO
From $441 per night (USD)VRBO
Best Place to Unwind! Free Parking, Pet-friendly Property, 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 $441 per night (USD)VRBO