Sugarloaf Key vacation rentals

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Top-rated vacation rentals in Sugarloaf Key

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Key West

5 out of 5 average rating, 11 reviews

Key Lime Retreat

Weekly Treat! Downtown vacation experience for entire family. Located in the hearth of Historic Seaport location in Key West. Conveniently walking distance to Duval St shopping, offices, entertainment, restaurants, bars, and everything Key West has to offer. There is not much to say about this condo, The location talks for itself! It’s a must have Key West experience on a quite gated community just steps away from Duval St. It’s a true Gem to experience the Key West living to the fullest extend.

Top guest favorite

Apartment in Marathon

5 out of 5 average rating, 5 reviews

Ocean Side Paradise Awaits!

This gated oceanfront property spans over 7 acres and boasts an Olympic size pool overlooking the mesmerizing Atlantic Ocean. Take advantage of the many tiki huts, fishing dock, air-conditioned clubhouse, and grilling station to cook up your fresh catch. Our turnkey townhouse is perfect for a short vacation or a longer-term stay. Everything in the complex, from the facilities to the furnishings, is brand new. Don't miss the opportunity to experience paradise at its finest. Book your stay now!

Top guest favorite

Cottage in Marathon

4.97 out of 5 average rating, 32 reviews

Catch n' Relax Canalfront Cottage in Marathon

Enjoy our cottage right on a deep canal with 50' dock. Step right into your boat to fish the Atlantic Ocean & Gulf or just relax & enjoy the view! Enjoy an outdoor kitchen space for fish fry & Happy Hour drinks. Tan on our loungers or enjoy dinner under the stars. Kayaks/Bikes for you too. A Perfect location Minutes from Airport, 7Mile Bridge, Sombrero Beach & other Attractions. Close to shops & restaurants. Easily launch your boat from a free public marina nearby. Rental License #VACA-22-85

Guest favorite

Home in Marathon

5 out of 5 average rating, 34 reviews

Waterfront Escape -VACA-23-408

Come stay at this brand new home construction on a deep and wide canal leading to the ocean with pool and exotic decor. 75 foot dock with water and electric. Top of the line appliances with a fully stocked kitchen. Spa style showers with high end decor. Luxury at its best. Heated pool with sundeck and lots of seating around the edges. (Pool heater is an additional $100 per stay). Ground level cooking and dining for those beautiful days after boating or while laying around in the pool.

Guest favorite

Home in Marathon

4.89 out of 5 average rating, 73 reviews

Dream Vacation KCB Marathon with private pool !

Dream Vacation Duplex in Key Colony Beach. Private pool Brand New state of the art house with all commodities and amenities, 3 bicycles 2 kayaks near to restaurants, fast WIFI, washer ,dryer, blue tooth speakers, night mood lights. A modern lift for boat up to 18000 lb Main canal Use of electric golf car Gem and jet sky and boat can be arrange Electric Gem-4 car offered for a minimum extra charge Options of private boat or jet sky (ask) Heated pool on demand (extra cost)

Guest favorite

Home in Cudjoe Key

4.83 out of 5 average rating, 30 reviews

Yellow Home Free Pontoon Rental! See details

If you book your stay for the days shown below May 10th - May 23rd, 2025 May 26th - June 7th, 2025 July 5th - July 26th, 2025 Receive a free 2 day boat rental for a week reservation, 1 day for a 3 days or more reservation. Please reach out before booking for boat availability. Beautiful 3 bedroom 2 bath home nestled off of US 1. Kayaks included with the rental. Private heated pool and deck with a view of the Atlantic Ocean. Boat dockage available with parking.

Superhost

Cottage in Cudjoe Key

4.64 out of 5 average rating, 111 reviews

VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck

This mid-rise home is fully furnished with high ceilings throughout! The living room offers a flat screen television with sleeper sofa. Master bedroom features a queen bed with full bathroom and flat screen television. Guest bedroom features a full size bed and half bath. Additional amenities include large open porch with table and chairs, gas grill and central air conditioning and heat. Free WiFi offered in unit and in Community Recreation Center.

Guest favorite

Home in Cudjoe Key

4.9 out of 5 average rating, 105 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

Superhost

Home in Marathon

5 out of 5 average rating, 5 reviews

Gated w/Bayside Marina- Marlin Bay Resort & Marina

Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort featuring 13 luxury vacation homes, 74 private marina slips and a centrally located pool deck and clubhouse. We provide unparalleled service in an intimate setting allowing you to relax and unwind. We are located in Marathon in The Middle Keys, so you can easily explore all that The Keys have to offer.

Guest favorite

Townhouse in Key West

5 out of 5 average rating, 8 reviews

Exceptional Water View With Boat Dock!

This is the best kept secret. 10 miles from Duval St. for the night life, but a total private oasis if you are looking for a true get away. This is an end unit with a water view from every window in a gated community with a salt water pool. Wake up to an ocean view and have cocktails on the patio. This is a brand unit that has recently been completely renovated.

Top guest favorite

Home in Islamorada

4.92 out of 5 average rating, 118 reviews

SUPERHOST WATERFRONT PARADISE HOME- DOCK32 FT BOAT

(URL HIDDEN)Dream vacation home. TOTALLY REMODELED two bedroom, one bath. Picturesque water views from our balcony. Waterfront with dock, absolutely beautiful sunsets! Lush landscaping and great tiki hut. Tiki hut is a shared space. There is a fee for the dock.