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Villa 4204 on Duck Key - Boat Slip available

Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. Ask for availability. This apartment boasts breathtaking sunsets, close to water sports, charter fishing, restaurants while being surrounded by one of the most exclusive island neighborhoods with lush landscaping. Duck Key is family-friendly, or it can be a serene couples retreat. Dine with Sunsets on the rear deck, or explore the world-class restaurants of the middle keys. Please NO Smoking indoors NO pets

Sombrero Beach Tropical Paradise

Spacious 1 Bedroom Condo at Skip Jacks Resort in the heart of Marathon, located at Mile Marker 50 Positions you in the perfect spot to explore all that the Florida Keys has to offer, Just 1 hour to Key West or Key Largo Spend your day,Boating,Snorkeling, Fishing, Lounging by the Pool or spend the Day at Sombrero Beach. The Condo has TV's with Wifi and a Fully Stocked Kitchen if you just want to Stay in sit on the Balcony and Enjoy the Music coming from the Live band at the Tiki bar VACA-24-205

Hidden Gem Islamorada | 1st Floor

This newly renovated unit is truly is a Hidden Gem in the heart of Islamorada! This duplex is nestled in the trees just a few steps from one of the most amazing sunsets in the Upper Keys. Walking distance to all the wonderful shops, restaurants and breweries that Islamorada has to offer. Bikes and Kayaks can be rented steps away from the front door of this unit. Want to find a place that you'll want to return year after year? Look no further! 🌅🌴😎💎 This unique property was originally built

Dock POOL Kayaks Bikes Beach2mi WalkToStores

Come enjoy tranquil Atlantic breezes at our DUPLEX. Enjoy all the keys islands & adventure in three (3) bedrooms & two (2) bathrooms with full tubs. Enjoy cooking & baking for family & friends On-site gated parking and dock space for ocean toys/ boat (35 ft max) on the 75 ft waterfront concrete seawall & wood dock complete with fish cleaning station and outdoor kitchen & grill to prepare your daily catches. Enjoy the multiple spacious outdoor spaces (shared) for playing, relaxing & dining.

2 Bdrm Oceanfront Complex Private Beach & Pool

Ground floor 2 bdrm/1 bath condo in Key Colony Beach. Oceanfront complex with heated pool and private white sandy beach. New renovation with new beds, furnishings and new bathroom! Condo has kitchen stocked with everything you'll need to cook & serve complete meals. You will be a 20 second walk to our private beach and enjoy glorious sunrises every morning. Lounge chairs, patio tables, tiki huts & BBQ grills available for guest use. Sorry no boats or trailers allowed in our parking lot

*NEW* Coral Sands Oceanfront-Beach & Pool

Welcome to Coral Sand Oceanfront, your private slice of paradise in Key Colony Beach. This beautifully appointed 2-bedroom, 2-bath condo offers breathtaking ocean views, a private beach, and resort-style pool—perfect for a relaxing Florida Keys escape. Step outside and feel the ocean breeze, unwind by the pool, or stroll along your private beach. Whether you’re planning a romantic getaway or a family vacation, Coral Sand Oceanfront delivers comfort, views, and true Keys tranquility.

Steps to the Ocean & Heated Pool

Escape to paradise in a new 1 bed/2 bath centrally located in Marathon. Our condo is steps away from open ocean views, where you can fish off the docks, lounge under one of the many Tiki huts, or cool off in the vast elevated swimming pool that overlooks the Atlantic. Fully air conditioned clubhouse on property is equipped with a commercial ice machine. Convenient grilling stations located next to the clubhouse, to cook your fresh catch. Come enjoy paradise. VACA-23-312

#1 Island Hideaway 89 - OCEAN FRONT

Enjoy the BEST VIEW from your living room window, 1st floor balcony and 2nd floor balcony directly overlook the Atlantic, marina and clubhouse. This 1 bedroom 1.5 bathroom is luxury and peaceful. Enjoy coffee in the captain's chairs on the balcony as the sun goes up or cocktails as the sun goes down. Custom kitchen bigger than most any other in this property, designer upgrades, professionally decorated. Enjoy the sitting area on the third floor overlooking the ocean.

Ocean View Duplex Penthouse | Pool | Vista Two

Indulge in the epitome of coastal living in this expansive duplex penthouse boasting ocean views in Islamorada. Relish captivating tranquility with an open-concept layout seamlessly blending living, dining, and a chef’s kitchen, all framed by panoramic seascapes and access to top-tier amenities. Just a short walk from the beach and world-class waterfront dining, this private haven is where serenity meets sophistication. Enhanced cleaning practices implemented.

The Sandcastle Suite! NEW 2BD! Oceanfront Complex!

SPECIAL DISCOUNTED PRICING FOR OUR FIRST GUESTS! Experience the ultimate Florida Keys vacation getaway at our BRAND NEW beach home in the breathtaking community of Ocean Isles! We are the ONLY 2 Bedroom/2 Bathroom in the community that offers complete, comfortable accommodations for up to 6 guests at competitive 1Bed/1Bath pricing! Unit 38 is the larger style, 2-story design. Walk in the front door to this gorgeously furnished, cozy home! See more...

Cozy Keys Efficiency 8a

Efficiency has a queen size bed, a 3-seat sofa and a small dining table with 2 chairs. Private bathroom. AC will keep you cool. Kitchen is fully equipped with 4 burner stove, microwave, medium size refrigerator with freezer. Enjoy the breezes on your patio, each unit has a gas BBQ grill and a picnic bench outside. Enjoy a swim in our shared pool. Optional boat slip can be rented for $25/night Efficiency has a 2 person maximum occupancy - no exceptions.

Sitting at the Dock on the Bay Waterfront Pool Hom

Welcome to Sittin at the Dock on the Bay, a waterfront pool home in the quiet Coco Plum area of Marathon. Enjoy canal views, a private pool, covered outdoor dining, and kayaks for exploring the water. The home offers a comfortable ground level living space designed for a relaxed Keys getaway. The upstairs level is not part of the rental and remains closed during guest stays. Close to restaurants, boating, beaches, and everything Marathon has to offer.