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Waterfront vacation rentals in Sugarloaf Key

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Top-rated waterfront rentals in Sugarloaf Key

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Townhouse in Marathon

4.92 out of 5 average rating, 13 reviews

Waterfront luxury Villa (42) with sunset views and boat slip

Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse yourself in long leisurely days of boating, lounging by the pool and watching spectacular sunsets from your back porch. Located just 90 miles south of Miami and 45 miles from Key West, the resort overlooks the Gulf of Mexico with full access to the Atlantic Ocean through Vaca Cut which is right around the corner from Indigo Reef. You’ll have your own private boat dock just steps from your back porch. The Florida Keys are known for the best fishing, diving and tropical reefs in the world. (Note: Minimum weekly rental. All bedrooms and full baths are located on the second floor of the Villa and involve stairs). This spacious three bedroom, two and a half bath Villa will make you feel right at home. Each bedroom has it’s own television, with a 75" 4k, ultra HD flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony. Just steps from your back porch is your own private boat dock for boats up to 31'. The kitchen is fully stocked with all you’ll need to dine in and you can easily grill your daily catch on one of several charcoal grills located throughout the resort grounds. This home is does not allow pets and smoking is not permitted in the Villa or on the porches. It is a completely pet-free, smoke-free home. The villa is fully appointed for everything you will need for your stay. Just pack and relax! License: PLR2019-00481

Townhouse in Marathon

4.98 out of 5 average rating, 164 reviews

Marathon Keys Coral Lagoon Unit 2 Waterfront Villa

*Currently the seawall repair is not affecting our side of the property, our view is unobstructed and not affected. Also, our marina is 100% open and operational should you need to rent a slip during your stay Welcome to paradise! We are proud to offer you one of the nicest waterfront units in Coral Lagoon! Please Note: For your safety, the entire house is sanitized prior to your arrival. Along with our standard cleaning practices we have a local company that comes in and fogs the entire house

Villa in Marathon

5 out of 5 average rating, 10 reviews

Waterfront Home w/Dock, Pool, Bikes & SO MUCH MORE

Looking for the perfect home for your next Florida Keys vacation? Our Waterfront home with over 30 feet of dock space is Just a short boat ride out to open water for a day of fishing, snorkeling, or cruising around. Our home features your own private dock & private pool... complete with chaise lounges, outdoor dining, gas grill, Adirondack chairs, fish cleaning station, bait freezer & so much more! Lastly, everyone is sure to enjoy water views & sunsets from our balcony that never disappoint.

Cottage in Cudjoe Key

4.86 out of 5 average rating, 35 reviews

Tidewater Views at Venture Out

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ** Last Key Realty requires a credit card on file for all reservations. ** TIDEWATER VIEWS is a cozy 800 square foot cottage that has everything you want for the perfect tropical vacation: open water views from a covered porch, a private 35-foot boat slip, kayaks, bikes and access to the wonderful amenities at Venture Out Resort: a heated 80-foot pool with large Jacuzzi and Kiddie Pool,

Home in Marathon

5 out of 5 average rating, 22 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.

Cottage in Little Torch Key

4.9 out of 5 average rating, 163 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

Home in Key Colony Beach

4.94 out of 5 average rating, 106 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

Condo in Key West

4.88 out of 5 average rating, 146 reviews

Aruba - Downtown Waterfront 2/2 Dock, Pool, Pet

Time to relax! Bring your family & friends to this 1200 sqft Waterfront home. Boat slips available on site with commercial ice machine, fish cleaning station and BBQ grills. Located in historic Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Historic Seaport, Hemingway House, etc. On-site amenities: heated pool, boat slip, tiki bar & grills, parking, secure keyless entry, & private elevator. Large Park adjacent with tennis courts. 10min from airport (EYW).

Home in Marathon

4.69 out of 5 average rating, 16 reviews

#7 Waterfront 4Bed 3Bath Pool Home

🌸Home #7 "BEACHY🏖KEEN" Full WATERFRONT View over the docks and beach and Ocean!🌸 Totally Private😉- Turn-Key and fully Stocked- Single Family Home 4BR/3BA with your own Heated-Cooled Private Swimming Pool 🤿and BBQ Patio. Includes Private Guest Beach🏖 with Kayaks and Paddle boards and Private powered ⛵Boat Dock right on the Gulf of Mexico! 🌅🥂 Kick back and completely🍷 relax in our Beautiful and 🍹comfortable home! Perfect for 🍻Adults and kids of all Ages!

Home in Marathon

4.88 out of 5 average rating, 16 reviews

Boaters delight! 1 min to open water, Dock & Beach

Inquire for monthly discounts. Quaint and charming home nestled in the Florida Keys. Secluded single family property with open water access. Private Dock, Beach, kayak launch area with kayaks and bikes available to use. Very private tranquil location. See manatees/fish swimming by. Enjoy endless sunsets from the front porch. Fantastic views from every room in the house. Beds: 1 King bed, 2 twins, 2 trundle Marathon Vacation Rental License#. VACA-22-375

Home in Marathon

5 out of 5 average rating, 9 reviews

Boaters Dream- 40FT Deep Dock Home- M#13

Deep 40Ft Dock Waterfront home on a large lot with seaside porch. Easy quick access to the Ocean, Bay or 7 mile bridge. Enjoy the Tiki & BBQ. The bedrooms and 2 baths sleep 6 . The home is located in a Island community that is one the most unique places in the world. Living area also has sofa sleeper. In minutes you can fish the Bay, Ocean or 7 Mile Bridge, Best boat access in Marathon. You a short drive to sandy Sombrero Beach & local plazas.

Home in Marathon

4.91 out of 5 average rating, 151 reviews

Waterfront Cozy Modern Retreat w/Deep Canal

Welcome to our beautiful waterfront home in Marathon! Our smoke-free property is modern, clean and features a 37ft long concrete dock, perfect for boating and fishing enthusiasts. With easy access to the movie theater, Sombrero Beach, Turtle Hospital, Publix, Walgreens, and delicious restaurants, you'll have everything you need right at your fingertips. We can't wait for you to experience the peacefulness and convenience of our lovely home.

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Popular amenities for Sugarloaf Key waterfront rentals

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Air conditioning

Waterfront apartment rentals

Apartment in Marathon

5 out of 5 average rating, 11 reviews

"O" Fish Ally Paradise @Ocean Isle Fishing Village

Apartment in Marathon

5 out of 5 average rating, 4 reviews

*NEW* Sea La Vie-Pool & Beach

Apartment in Key Colony Beach

4.84 out of 5 average rating, 104 reviews

Beachside Unit 22 - Private Beach on Atlantic

Apartment in Key West

5 out of 5 average rating, 3 reviews

Key West at Hyatt Beach House

Apartment in Marathon

5 out of 5 average rating, 12 reviews

#1 Island Hideaway 89 - OCEAN FRONT

Apartment in Marathon

5 out of 5 average rating, 7 reviews

Best Catch on Grouper LN at Ocean Isles

Apartment in Marathon

4.83 out of 5 average rating, 41 reviews

Little Venice in Marathon (in the Beautiful Keys)

Apartment in Marathon

4.96 out of 5 average rating, 52 reviews

Dock POOL Kayaks Bikes Beach2mi WalkToStores

Waterfront house rentals

Home in Key Colony Beach

5 out of 5 average rating, 69 reviews

Dock, Beach Club, January avail., tennis, golf

Home in Key West

5 out of 5 average rating, 19 reviews

Nautical Wheeler: Waterfront Home with private Poo

Home in Cudjoe Key

5 out of 5 average rating, 27 reviews

Paradise in Cudjoe! Perfect Family Home!

Home in Marathon

4.81 out of 5 average rating, 31 reviews

Luxury Waterfront Retreat with Dockage & Pool

Home in Key Colony Beach

4.92 out of 5 average rating, 131 reviews

The Snapper House 3/2.5 45' dock sleeps 8+ pets OK

Home in Key Colony Beach

5 out of 5 average rating, 25 reviews

Easy Ocean Access 30' Dock House Pool Cabana Club

Home in Key Colony Beach

4.98 out of 5 average rating, 98 reviews

Waterfront House with 37 ft Dock & Cabana Club

Home in Marathon

4.95 out of 5 average rating, 66 reviews

Ocean View with Dock and Jacuzzi

Waterfront condo rentals

Condo in Key West

4.94 out of 5 average rating, 35 reviews

Condo de Paradise/Salt Water Pool/Boat Dock

Condo in Key West

4.98 out of 5 average rating, 63 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

Condo in Duck Key

5 out of 5 average rating, 27 reviews

Oceanfront and Sunrise Views!

Condo in Marathon

5 out of 5 average rating, 9 reviews

P80 - Coral Lagoon 3bd/2.5ba townhome with large c

Condo in Key West

4.84 out of 5 average rating, 153 reviews

Anchor Drop modern elegance upgrades throughout vi

Condo in Key West

4.87 out of 5 average rating, 95 reviews

Key Wes't Best- Upgraded condo 5 mins to Smathers

Condo in Marathon

4.88 out of 5 average rating, 24 reviews

Paradise @ MM61 - Waterfront 1 BR / 1 Bath Condo

Condo in Key West

4.73 out of 5 average rating, 26 reviews

Ocean Front Suite | Beachside Resort

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