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Islamorada Rentals

From $1396 per night (USD)
VRBO
Waterfront, dock, private oasis in the heart of Islamorada! Pool & Sunsets!
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
You don’t want to miss this! Old Florida charm in the heart of Islamorada on a half-acre private oasis. The Butterfly Ho ...
From $1396 per night (USD)
VRBO
From $3276 per night (USD)
VRBO
Voted best boutique resort in Islamorada! Beach, dockage, pool + more!
Bedrooms:
7
Bathrooms:
8
Sleeps:
22
Located in the heart of Islamorada, Mermaid’s Bay Boutique Estate is a secluded oasis situated directly on the bay. Secu ...
From $3276 per night (USD)
VRBO
From $116 per night (USD)
VRBO
Charming 1 Bedroom Condo on Plantation Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Sit back and relax at Port o Palms. Experience the ultimate Florida Keys getaway at this light and bright one-bedroom, ...
From $116 per night (USD)
VRBO
From $2378 per night (USD)
VRBO
Infinity Bay Islamorada ~ Luxury 9-bed, 10-bath Bayfront Estate in Islamorada
Bedrooms:
9
Bathrooms:
9
Sleeps:
18
Welcome to Infinity Bay Islamorada – an infinite paradise with endless possibilities in the heart of the Florida Keys. T ...
From $2378 per night (USD)
VRBO
From $462 per night (USD)
VRBO
Port Antigua Home in a Private Beach & Golf Cart Community
Bedrooms:
3
Bathrooms:
4
Sleeps:
15
Our relaxing 3 STORY, 4 bedroom, 3.5 bathroom home is located in Islamorada, Florida within the Private Beach community ...
From $462 per night (USD)
VRBO
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 $570 per night (USD)
VRBO
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 $570 per night (USD)
VRBO
From $468 per night (USD)
Expedia
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 $468 per night (USD)
Expedia
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VRBO
Luxury One Bedroom Condo #2
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
One Bedroom, One Bathroom Condo, Separate Living Space and Fully Equipped Kitchen. Outdoor Fire pit under palm trees w ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Luxury One Bedroom Condo #3
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
One Bedroom, One Bathroom Condo, Separate Living Space and Fully Equipped Kitchen. Outdoor Fire pit under palm trees w ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Luxury One Bedroom Condo #4
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
One Bedroom 700 Square Feet Condo One Bedroom, One Bathroom Condo, Separate Living Space and Fully Equipped Kitchen. ...
Click For Pricing
VRBO
From $2716 per night (USD)
Expedia
Oceanfront Oasis / Pool • Kayaks • Rooftop Terrace sleeps 12,
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Welcome to Wander Islamorada Beach, a luxurious three-story, six-bedroom beachfront property. Enjoy three living rooms, ...
From $2716 per night (USD)
Expedia
From $137 per night (USD)
VRBO
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)
VRBO
From $1736 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 $1736 per night (USD)
VRBO
From $948 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 $948 per night (USD)
VRBO
From $431 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 $431 per night (USD)
VRBO
From $185 per night (USD)
VRBO
Exec Bay T8 - 3 bedrooms
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 $185 per night (USD)
VRBO
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 $415 per night (USD)
VRBO
Bring the Whole Family [sleeps 11] 4/3 w Dock & Pool - Make Memories Here!
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Relax with the whole family at "Casalbelo," your peaceful home away from home. Unique canal front home in the coveted Ve ...
From $415 per night (USD)
VRBO
From $214 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 $214 per night (USD)
VRBO
From $379 per night (USD)
VRBO
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)
VRBO
From $227 per night (USD)
Expedia
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 $227 per night (USD)
Expedia
From $534 per night (USD)
VRBO
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 $534 per night (USD)
VRBO
From $278 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 $278 per night (USD)
VRBO
From $875 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 $875 per night (USD)
VRBO
From $253 per night (USD)
Expedia
Tavernier Canal front Retreat with Boat Lift & Fish Station 28+ Day Keys Escape
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Tavernier Canalfront Retreat: Your 28-Day Keys Sanctuary Awaits!Picture this: A tranquil morning on your private dock, c ...
From $253 per night (USD)
Expedia
From $340 per night (USD)
VRBO
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 $340 per night (USD)
VRBO
From $621 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 $621 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 $1076 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 $1076 per night (USD)
VRBO
From $968 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 $968 per night (USD)
VRBO
From $734 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 $734 per night (USD)
VRBO
From $543 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 $543 per night (USD)
VRBO
From $574 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 $574 per night (USD)
VRBO
From $1060 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 $1060 per night (USD)
VRBO
From $439 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 $439 per night (USD)
VRBO
From $1281 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 $1281 per night (USD)
VRBO
From $539 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 $539 per night (USD)
VRBO
From $340 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 $340 per night (USD)
VRBO
From $569 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 $569 per night (USD)
VRBO
From $540 per night (USD)
VRBO
Always a Great Idea To Unwind! Free Parking, Onsite Pool, Pet-friendly
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 $540 per night (USD)
VRBO
From $867 per night (USD)
VRBO
Peaceful Retreat in Islamorada! Pet-friendly, Swimming Pool, Free Parking!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $867 per night (USD)
VRBO
From $974 per night (USD)
VRBO
Nautica - Monthly 4 BR home on bay in Islamorada - Upper Matecumbe Key
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Mile Marker 83 – Bayfront Unfortunately all rentals must start on the 1st of the month. Island Villa Rentals and Owner' ...
From $974 per night (USD)
VRBO
From $152 per night (USD)
VRBO
Stunning Studio Apartment Summer Sea Condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Beautifully remodeled Studio with tropically décor, this 1st floor corner unit (steps required) has a private outdoor en ...
From $152 per night (USD)
VRBO
From $339 per night (USD)
VRBO
SEASONAL WATERFRONT RENTAL in Venetian Shores, Islamorada, Pool & New Dock
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
After a few years of construction, Morada Breeze , Venetian Shore's Waterfront Paradise is back and better than ever. ...
From $339 per night (USD)
VRBO
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Expedia
Cozy waterfront home with dock, BBQ, dog friendly, AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Treasure Cove Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
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Expedia
From $319 per night (USD)
VRBO
Deep Water Home located in White Marlin Beach Neighborhood
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
PROPERTY NAME: Marlin House 156 Venetian Drive, Islamorada, FL 33036 LOCATION: Bayside Canal home located in the popula ...
From $319 per night (USD)
VRBO
From $565 per night (USD)
VRBO
House with ocean and bay views in Middle Keys with boat launch, ramp and dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to your perfect getaway in Islamorada/Lower Matecumbe. This charming rental home offers the best of both worlds ...
From $565 per night (USD)
VRBO
Click For Pricing
VRBO
Wander Islamorada Shores w/ Ocean View – 4 Bedrooms, Sleeps 8
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Wander Islamorada Shores is a stunning coastal escape with 180-degree Atlantic views. This home features four-bedroom en ...
Click For Pricing
VRBO
From $277 per night (USD)
VRBO
Charming Bayside 2 bed, 2 bath Condo at Futura in Islamorada WiFi, Pool, Dockage
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This charming and beautifully renovated 2 bedroom condo is located in the Futura Yacht Club community at mile marker 88. ...
From $277 per night (USD)
VRBO
From $396 per night (USD)
VRBO
Pool Home in Venetian Shores
Bedrooms:
3
Bathrooms:
4
Sleeps:
16
Spacious, open layout designed for ultimate comfort and convenience. The fully equipped kitchen flows seamlessly into th ...
From $396 per night (USD)
VRBO
From $3147 per night (USD)
VRBO
PRIVATE BEACH, Pickleball Court and Tiki Bar/ Heated Pool / Designated Paradise Key
Bedrooms:
4
Bathrooms:
6
Sleeps:
16
Hidden in the heart of Islamorada, this oceanfront villa offers an unmatched privilege of a secluded private beach—an ex ...
From $3147 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 $1473 per night (USD)
VRBO
Stunning Bayfront Home with Pool & Dockage in Islamorada
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Grab a margarita and unwind at Marchettiville! This stunning 5-bedroom, 3-bathroom oceanfront property offers private b ...
From $1473 per night (USD)
VRBO
From $618 per night (USD)
VRBO
Ultimate Islamorada Oasis with Pool, Dock, & More
Bedrooms:
3
Bathrooms:
4
Sleeps:
4
Welcome to your own island oasis! This beautiful 4-bedroom, 3-bathroom canal-front home blends luxurious coastal modern ...
From $618 per night (USD)
VRBO
From $226 per night (USD)
Expedia
3-bedroom townhome in charming Islamorada with AC, WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Welcome to your dream getaway! This stunning fully renovated 3-bedroom, 2.5-bathroom townhouse in a gated marina commun ...
From $226 per night (USD)
Expedia
From $518 per night (USD)
VRBO
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 $518 per night (USD)
VRBO
From $250 per night (USD)
Expedia
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 $250 per night (USD)
Expedia
From $317 per night (USD)
VRBO
3-bedroom cozy pool home in exclusive Venetian Shores, Islamorada .
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover tranquility at our Venetian Shores Escape, Islamorada. Nestled in a serene neighborhood, this property boasts ...
From $317 per night (USD)
VRBO
From $1033 per night (USD)
VRBO
Bayfront Home with Pool in Islamorada
Bedrooms:
4
Bathrooms:
5
Sleeps:
9
This home includes 5 bedrooms, 4.5 baths, elevator, spacious living room and kitchen. Guests can enjoy the open water a ...
From $1033 per night (USD)
VRBO
From $663 per night (USD)
VRBO
At The Sandbar: Oceanfront, Htd Pool, Free Dockage, GameRoom, EV Charger
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Short Description 🏡 Amenities: Free Boat dockage, htd pool, BBQ grill, EV charger 🏓 Game room 📍 Mins to the famous ...
From $663 per night (USD)
VRBO
From $903 per night (USD)
Expedia
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 $903 per night (USD)
Expedia
From $490 per night (USD)
VRBO
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)
VRBO
From $195 per night (USD)
VRBO
Quaint Islamorada Cottage with Unbeatable Location
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to this quaint 2-bedroom, 1-bathroom conch-style cottage in the heart of Islamorada. The fully equipped kitchen a ...
From $195 per night (USD)
VRBO
From $798 per night (USD)
VRBO
Oceanfront Islamorada Townhome- Private Dock, Pool & Pet-Friendly
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Welcome to your oceanfront Florida Keys vacation rental in the heart of Islamorada! This luxury 3-bedroom, 3-bath townho ...
From $798 per night (USD)
VRBO
From $470 per night (USD)
Expedia
PRIME LOCATION Islamorada Anglers Reef Oceanview w/ Private Beach, Pool, Marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to REELaxation! Everything you need for your vacation is here, gorgeous private beach, heated resort style pool, ...
From $470 per night (USD)
Expedia
From $326 per night (USD)
VRBO
This 2 bedroom pet friendly ocean front home has the best views in the resort!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This amazing 2 bedroom 2 bath home is fully furnished, with calming and welcoming decor just bring your flip flops, sun ...
From $326 per night (USD)
VRBO
From $386 per night (USD)
Expedia
Lovely 2-bedroom house in ocean front resort.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Islamorada house boasts 2 inviting bedrooms with 1 full bed and 1 king bed. The serene atmosphere and lovely decor ...
From $386 per night (USD)
Expedia
From $2025 per night (USD)
VRBO
Stunning Oceanfront Estate with Private Pool ~ Beach.
Bedrooms:
6
Bathrooms:
6
Sleeps:
14
License # 204. | ** 3 payment schedule available** | No Pet Charges | No security deposit | SATURDAY TO SATURDAY ONLY ...
From $2025 per night (USD)
VRBO
From $277 per night (USD)
Expedia
Beautiful Home in a Great Neighborhood with Ocean Access and Boat Ramp on Property
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
PROPERTY NAME: Fisherman's Gem 113 Iroquois Drive Islamorada, Florida LOCATION: Oceanside Canal home with Boat dock a ...
From $277 per night (USD)
Expedia
From $670 per night (USD)
VRBO
Ocean View Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key Two
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Indulge in the epitome of coastal living in this expansive duplex penthouse boasting ocean views in Islamorada. Relish c ...
From $670 per night (USD)
VRBO
From $890 per night (USD)
Expedia
Ocean View Duplex Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key One
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Indulge in the epitome of coastal living in this expansive duplex penthouse boasting ocean views in Islamorada. Relish c ...
From $890 per night (USD)
Expedia
From $1842 per night (USD)
VRBO
Private Beach / Private overwater dock / Heated Pool / Mahi Key
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Relish ocean serenity in this residence set directly on a secluded beach, where an open-concept design seamlessly merges ...
From $1842 per night (USD)
VRBO
From $397 per night (USD)
VRBO
Half-Mi to Boat Ramp: Canal-Front Florida Keys Gem
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
2 Covered Wraparound Balconies w/ Canal Views | BBQ Ready | 2 Mi to Diving & Snorkeling | Pet Friendly w/ Fee | In-Unit ...
From $397 per night (USD)
VRBO
From $1290 per night (USD)
VRBO
Ocean View Two Duplex Penthouses / Retreat amenities: tennis court, heated Pool | Vista Key
Bedrooms:
6
Bathrooms:
8
Sleeps:
24
Indulge in the epitome of coastal living in these two connected expansive duplex penthouses boasting ocean views in Isla ...
From $1290 per night (USD)
VRBO
From $1712 per night (USD)
Expedia
BeachFront Paradise/By The Glam Homes
Bedrooms:
4
Bathrooms:
4
Sleeps:
15
Summary: This is a truly unique and spectacular Villa thanks to its breathtaking view of the sea and its warm sandy beac ...
From $1712 per night (USD)
Expedia
From $1455 per night (USD)
VRBO
Bayfront Bliss in Lower Matecumbe – 4BR/3.5BA with Heated Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Escape to paradise at this stunning bayfront home in Lower Matecumbe, Islamorada. With breathtaking open bay views, a pr ...
From $1455 per night (USD)
VRBO
Click For Pricing
Expedia
Come relax in this oceanside 2 bedroom home, in a pet friendly resort!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This home has amazing views of the Atlantic, and has 2 two bedroom, two baths. The vibe is tasteful and relaxing - jus ...
Click For Pricing
Expedia
From $235 per night (USD)
VRBO
Charming 2-bedroom home in brilliant Tavernier near Marinas and Founders Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Unwind in Tavernier at this delightful home. This charming property features 2 bedrooms - one with a king bed and the ot ...
From $235 per night (USD)
VRBO
From $566 per night (USD)
VRBO
Bay Harbour 209C ~ Chic 3 Bed / 2.5 Bath Condo with Ocean Views in Islamorada
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Pressure Drop! This beautiful ocean-view condo features three bedrooms and two full bathrooms, making it an ...
From $566 per night (USD)
VRBO
From $318 per night (USD)
VRBO
King Room: Resort w/ Marina and 3 Outdoor Pool | 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 $318 per night (USD)
VRBO
From $692 per night (USD)
VRBO
2 Relaxing Rooms w/ Balcony, Free Parking, 3 Pools & 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 $692 per night (USD)
VRBO
From $1038 per night (USD)
VRBO
3 Rooms w/ 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 $1038 per night (USD)
VRBO
From $373 per night (USD)
VRBO
King Room w/Ocean View, 3 Outdoor Pools, Free Parking & Pet Friendly
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 $373 per night (USD)
VRBO
From $186 per night (USD)
VRBO
Classic 2 bedroom, 2 Bath Islamorada Home with Dockage
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
** 60 day minimum in peak season (January- March) Enjoy the timeless charm of Old Salt Retreat. This cozy and classic ...
From $186 per night (USD)
VRBO
From $224 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 $224 per night (USD)
Expedia
From $257 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 $257 per night (USD)
VRBO
From $890 per night (USD)
VRBO
Escape in this 2 Sun-Kissed Studios w/Gulf views! Perfect place for relaxation!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $890 per night (USD)
VRBO
From $504 per night (USD)
VRBO
Ideal Family Haven w/Kitchen, Grill facilities near Breathtaking Ocean access
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This listing is for a room within a hotel. ✦ Your room is 1500 sq. ft, equipped with complimentary toiletries, kitchen ...
From $504 per night (USD)
VRBO
From $601 per night (USD)
VRBO
Perfect Island Getaway! 2 Studio w/Kitchen & Resort amenities - Onsite Parking!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $601 per night (USD)
VRBO
From $403 per night (USD)
VRBO
Breathtaking Island Oasis! Relaxing Studio w/Resort amenities & Gulf views!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 331 sq. ft, equipped with complimentary toiletries, kitchen w ...
From $403 per night (USD)
VRBO
From $257 per night (USD)
VRBO
Waterfront Florida Keys Cottage!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your perfect slice of Old Florida paradise! Tucked away on a spacious waterfront lot, this classic Keys cotta ...
From $257 per night (USD)
VRBO
From $211 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 $211 per night (USD)
VRBO
From $798 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 $798 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 $423 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 $423 per night (USD)
VRBO
From $802 per night (USD)
VRBO
Stunning Islamorada Escape with Dock, Pool, Hot Tub & Direct Ocean Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to O'fish'ally Paradise! This jaw-dropping 3-bedroom, 3-bath Islamorada gem is where luxury meets laid-back isla ...
From $802 per night (USD)
VRBO
From $262 per night (USD)
Expedia
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 $262 per night (USD)
Expedia
From $305 per night (USD)
VRBO
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 $305 per night (USD)
VRBO
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

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