Home Vacation Rentals By Owner In Key Largo, FL

Showing 220 Of 1037 Vacation Rentals
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$300.79

/ Nightly
Private Vacation Home

Key Largo Canalfront Home w/ Boat Lift, Swim Spa, Tiki Hut & Game Room

Key Largo, Florida, United States

Welcome to Your Key Largo Canal-Front Paradise! brbrWelcome to your ultimate Key Largo escape!brTucked along a serene canal with direct access to the Gulf of Mexico and Atlantic Ocean, this waterfront retreat is a paradise for boaters, anglers, and island dreamers alike. With a private 10,000 lb boat lift, a swim spa/hot tub combo, and plenty of space to relax and play, this home delivers the full Florida Keys experience.brbrWaterfront Living at Its BestbrBring your boat and explore open waters in minutes. After a day of fishing or cruising, take advantage of the fish cleaning station, then grill your fresh catch on either the gas or charcoal grill beneath the shady Tiki hut—the perfect spot for al fresco dining and cocktails at sunset.brbrUnwind in StylebrWhether you’re starting your day with coffee in the spa or stargazing under the palms, the swim spa and hot tub combo offers the ideal setting for relaxation and recharge.brbrEndless Fun inside the Outdoor Living RoombrCovered and out of the sun, the good times continue with a game room vibe—complete with a pool table and dart board—so you can challenge your crew to friendly competition after a day on the water.brbrComfortable & Flexible LayoutbrDownstairs: One private bedroom and full bathroom—great for early risers or guests wanting extra privacy.brbrUpstairs: Two spacious bedrooms and an additional full bath, comfortably sleeping up to 6 guests.brbrExplore the Best of Key LargobrLocated just minutes from top-rated restaurants, dive shops, beaches, and unforgettable snorkeling excursions, this home puts you close to everything while offering a peaceful retreat when you're ready to unwind.brbrImportant to Know:br28-day minimum stay required by local ordinance (no exceptions)brbrLicensed & professionally managed by Star Properties Destinations LLCbrLicense #VRE-19-18 | Business Tax #25230-122730
Bed 2

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Bath 1

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Sleep 6

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Exceptional(2)

$245.63

/ Nightly
Private Vacation Home

Charming 3-bedroom home in Key Largo, perfect for a family getaway!

Key Largo, Florida, United States

Located in the highly desirable Jewfish neighborhood at Mile Marker 103.5, this charming ground-level 3-bedroom, 2-bath home is brand new to the rental market and ready for your Florida Keys vacation.brbrThe home features a bright open living, dining, and kitchen layout, creating a comfortable space for relaxing after a day on the water. Step outside to a large, beautifully landscaped backyard, perfect for BBQs, enjoying the island breeze, or unwinding in the warm Keys sunshine.brbrOne of the highlights of this property is access to the Jewfish homeowners park, often considered one of the best private parks in Key Largo. Just a short walk away, guests can enjoy the private beach area, boat ramp, picnic tables, and waterfront spaces—perfect for launching your boat, relaxing by the water, or enjoying happy hour with a sunset view.brbrConveniently located close to grocery stores, local restaurants, marinas, and both ocean and bay boating access, this home offers everything you need for a classic Florida Keys escape.brbrOne pet may be considered (under 20 lbs and crate trained).brbrPlease note: If booking more than one year in advance, pricing may be subject to annual cost-of-living adjustments. Many of our guests return year after year to enjoy this property. Reservations are confirmed after speaking directly with our team.brIf booking more than a year in advance current prices may not reflect the annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.
Bed 3

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Bath 2

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Sleep 6

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$1209.41

/ Nightly
Hotel

2 Waterfront Room In 2 Queen Beds w/ Beach & Pool

Key Largo, Florida, United States

Ideal for families or friends, our Waterfront Room in the Coconut Wing features two queen beds and all the essentials for comfort. Step outside to the bay for paddle-boarding, fishing, or simply soaking in the scenery. With daily housekeeping and amenities like a mini-fridge, this room is your gateway to an unforgettable Key Largo escape.brbrThis listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 1200 sq. ft, equipped with complimentary toiletries, high definition 32-inch TV, available with Premium cable.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Outdoor shared pool available all year, opened from 8:00AM to 9:00PM.brbr✦ Paid parking lot – 1 space(s), available for $23 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $200 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $49.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. Pets allowed for $75 per night up to 100lbsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The current early departure fee is one night charge, subject to change.brbr✦ Bag handling/porterage available for a fee per room, roundtrip.brbr✦ Other available parking options for a fee: Valet, Oversize Vehicles/Boat Trailers & Day Parking/Event Parking
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Bath 2

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Sleep 8

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$605.22

/ Nightly
Hotel

Coconut Wing 2 Queen Waterfront Room Near Beach

Key Largo, Florida, United States

Ideal for families or friends, our Waterfront Room in the Coconut Wing features two queen beds and all the essentials for comfort. Step outside to the bay for paddleboarding, fishing, or simply soaking in the scenery. With daily housekeeping and amenities like a mini-fridge, this room is your gateway to an unforgettable Key Largo escape.brbrThis listing is for a room within a hotel.brbr✦ Your room is 1200 sq. ft, equipped with complimentary toiletries, high definition 32-inch TV, available with Premium cable.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Outdoor shared pool available all year, opened from 8:00AM to 9:00PM.brbr✦ Paid parking lot – 1 space(s), available for $23 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $49.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. Pets allowed for $75 per night up to 100lbsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The current early departure fee is one night charge, subject to change.brbr✦ Bag handling/porterage available for a fee per room, roundtrip.brbr✦ Other available parking options for a fee: Valet, Oversize Vehicles/Boat Trailers & Day Parking/Event Parking
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Bath 1

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Sleep 4

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$2065.46

/ Nightly
Hotel

4 Rooms w/ 2 Queen Partial Waterfront & Balcony

Key Largo, Florida, United States

Experience Key Largo’s charm in our Partial Waterfront Room in the Hammock Wing, featuring two queen beds, a mini-fridge, daily housekeeping, and all essentials for comfort. After paddle-boarding, snorkeling, or savoring bayside views, unwind in this cozy retreat where adventure and relaxation meet at your doorstep.brbrThis listing is for 4 separate rooms within a hotel. The price shown in the listing covers all 4 rooms.brbr✦ Each room is 1050 sq. ft, equipped with complimentary toiletries, high definition 32-inch TV, available with Premium cable.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Outdoor shared pool available all year, opened from 8:00AM to 9:00PM.brbr✦ Paid parking lot – 1 space(s), available for $23 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $400 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $49.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. Pets allowed for $75 per night up to 100lbsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The current early departure fee is one night charge, subject to change.brbr✦ Bag handling/porterage available for a fee per room, roundtrip.brbr✦ Other available parking options for a fee: Valet, Oversize Vehicles/Boat Trailers & Day Parking/Event Parking
Bed 4

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Bath 4

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Sleep 16

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$2418.78

/ Nightly
Hotel

4 Waterfront Room w/ 2 Queen Beds in Coconut Wing

Key Largo, Florida, United States

Ideal for families or friends, our Waterfront Room in the Coconut Wing features two queen beds and all the essentials for comfort. Step outside to the bay for paddle-boarding, fishing, or simply soaking in the scenery. With daily housekeeping and amenities like a mini-fridge, this room is your gateway to an unforgettable Key Largo escape.brbrThis listing is for 4 separate rooms within a hotel. The price shown in the listing covers all 4 rooms.brbr✦ Each room is 1200 sq. ft, equipped with complimentary toiletries, high definition 32-inch TV, available with Premium cable.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Outdoor shared pool available all year, opened from 8:00AM to 9:00PM.brbr✦ Paid parking lot – 1 space(s), available for $23 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $400 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $49.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. Pets allowed for $75 per night up to 100lbsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The current early departure fee is one night charge, subject to change.brbr✦ Bag handling/porterage available for a fee per room, roundtrip.brbr✦ Other available parking options for a fee: Valet, Oversize Vehicles/Boat Trailers & Day Parking/Event Parking
Bed 4

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Bath 4

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Sleep 16

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$1032.74

/ Nightly
Hotel

Unwind Here! 2 Pet-friendly Units, Near Beach Road

Key Largo, Florida, United States

Experience Key Largo’s charm in our Partial Waterfront Room in the Hammock Wing, featuring two queen beds, a mini-fridge, daily housekeeping, and all essentials for comfort. After paddle-boarding, snorkeling, or savoring bayside views, unwind in this cozy retreat where adventure and relaxation meet at your doorstep.brbrThis listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 1050 sq. ft, equipped with complimentary toiletries, high definition 32-inch TV, available with Premium cable.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Outdoor shared pool available all year, opened from 8:00AM to 9:00PM.brbr✦ Paid parking lot – 1 space(s), available for $23 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $200 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $49.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. Pets allowed for $75 per night up to 100lbsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The current early departure fee is one night charge, subject to change.brbr✦ Bag handling/porterage available for a fee per room, roundtrip.brbr✦ Other available parking options for a fee: Valet, Oversize Vehicles/Boat Trailers & Day Parking/Event Parking
Bed 2

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Bath 2

Bath

Sleep 8

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$1814.56

/ Nightly
Hotel

3 Coconut Wing Waterfront Room with Two Queens

Key Largo, Florida, United States

Ideal for families or friends, our Waterfront Room in the Coconut Wing features two queen beds and all the essentials for comfort. Step outside to the bay for paddleboarding, fishing, or simply soaking in the scenery. With daily housekeeping and amenities like a mini-fridge, this room is your gateway to an unforgettable Key Largo escape.brbrThis listing is for 3 separate rooms within a hotel. The price shown in the listing covers all 3 rooms.brbr✦ Each room is 1200 sq. ft, equipped with complimentary toiletries, high definition 32-inch TV, available with Premium cable.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Outdoor shared pool available all year, opened from 8:00AM to 9:00PM.brbr✦ Paid parking lot – 1 space(s), available for $23 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $300 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $49.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. Pets allowed for $75 per night up to 100lbsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The current early departure fee is one night charge, subject to change.brbr✦ Bag handling/porterage available for a fee per room, roundtrip.brbr✦ Other available parking options for a fee: Valet, Oversize Vehicles/Boat Trailers & Day Parking/Event Parking
Bed 3

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Bath 3

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Sleep 12

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$345.75

/ Nightly
Condo

Key Largo hidden gem!! Rare Moon Bay condo with 2.5 baths!!

Key Largo, Florida, United States

Moon Bay is the secret gem of the Keys! It's never crowded, maintained beautifully, and offers breathtaking views with the best sunsets in the world! Relax in the heated pool or lay out on the beach. We love to walk out to the end of the boat docks, sit under the tiki hut, and watch the marine life, or fish for snapper. Boat rentals are available nearby, and if you're a boater you'll be in heaven navigating the waters around the keys! You'll be a stone's throw away from John Pennekamp Coral Reef State Park, which offers beaches, snorkeling, fishing excursions and more! Roughly five miles offshore is the world famous Christ of the Abyss, which is a statue of Christ under the crystal clear water about 15 feet down inside a coral reef! Travel further down highway 1 and experience the other Keys attractions, with unlimited dining choices. The Lazy Lobster and Snooks are highly recommended! We recommend you take a day to travel down to Key West. It's about a 2.5 hour drive from the condo, but SO worth it! Just the drive there is unexplainable, with blue ocean on either side of you for the majority of it. There are plenty of places to see and stop on the way, from awesome shopping to wildlife parks, a turtle hospital, the list is endless. Once you arrive in Key West be sure and take a walk down famous Duval Street.brWhen you experience vacationing in the Keys, you'll want to come back. Our condo is remodeled and furnished to high standards, with tile and stone floors and showers, granite countertops, kitchen aid appliances, power blinds, high speed Wi-Fi, and full-size washer and dryer. With each bedroom having its own full bathroom, making getting ready alot easier for families. Our condo is only 1 of 3 with 2 full bathrooms plus a half bath!! My personal cell phone number is listed in the unit to contact me for any reason. We appreciate you renting from us, and we're confident that you'll be able to give us a positive review, and hopefully return!brWhen booking, please keep in mind that the bunk beds will accomodate kids or very small adults. The max recommended weight is 150lbs. Thank you SO MUCH!!!!
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Bath 2

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Sleep 6

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Exceptional(10)

$497.38

/ Nightly
Apartment

Marina Vista Gem • Modern 2BR/2BA • Steps to Pickleball

Key Largo, Florida, United States

TAKE A VIRTUAL TOUR OF THE ENTIRE UNIT BEFORE BOOKING http:www.youtube.com/@Keylargotravels brbrThis property is managed by KEYLARGOTRAVELS We own several remodeled high-end units in Key Largo. Please check out all of our units. Just enter the property ID on the search bar: 4336501, 1160742, 783868, 1616926 & 4793739.brbrSLEEPING ARRANGEMENTS: 2-En-Suite Bedrooms Primary Bedroom: King bed | Sleeps 2 | Full private bathroom Guest Bedroom: 2 Full Size Beds Full private guest bathroombrbrMARINA INFO: BOAT SLIP AVAILABLE AT ADDITIONAL COST OF $4.25/ft/day ✔TENNIS & PICKLE BALL WITH LIGHTS ✔SALT WATER LAGOON ✔RAMP AVAILABLE AT NO ADDITIONAL COST FREE TRAILER STORAGE YOU MUST SHOW PROOF IF LIABILITY INS PRIOR TO ARRIVING, FIRST COME FIRST SERVE, THE DEVELOPEMENT RESERVES THE RIGHT TO TURN YOU AWAY IF BOAT PARKING IS FULL. ALSO YOU CAN ONLY DROP AND RETURN WITH HIGH TIDE. YOU MUST BE MINDFUL OF THE TIDES.brbrAMENITIES: - 3 Heated Swimming Pools - Saltwater Lagoon - Ideal for kids to swim safely and spot marine life - Includes a floating swim platform - Jetty for fishing and sunset views - Charcoal grill stations throughout the property - Beach area with palm trees and lounge spots - Kids’ playground brbrbrbrCoastal Getaway ✔ONE STORY BRAND NEW SPACIOUS CONDO WITH ELEVATOR ✔ Newly Renovated Condo | Private Beach Access | Marina & Boat Ramp | Tennis and Pickleball ☀️ | Full private bathroom Large one Story open Floor Plan PLEASE READ OUR REVIEWS★★★★★ Please Note: We truly love animals and respect the importance of service animals. However, due to our daughter’s severe, life-threatening (anaphylactic) allergies, we are unable to accommodate any animals on the property — including service animals. This is also a home we personally use frequently, and her safety depends on maintaining an allergen-free environment. We sincerely appreciate your understanding and compassion. This is our summer home that we absolutely love. We raised our daughters in this beautiful development and have nothing but beautiful memories here. We pray you have the same experience and are blessed on your vacation.
Bed 2

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Bath 2

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Sleep 7

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Exceptional(4)

$232.28

/ Nightly
Private Vacation Home

Waterfront Key Largo – Private Dock, Tiki Oasis & Pet Friendly – Sleeps 6

Key Largo, Florida, United States

Welcome to your private Key Largo waterfront retreat—a calm, beautifully appointed haven designed for comfort, privacy, and refined island living. Located on the peaceful Bayside Canal in the Pirates Cove community at MM98, this home offers an elevated blend of boutique style, relaxed coastal charm, and the slow-living rhythm that makes the Upper Florida Keys so special. Perfectly suited for snowbirds seeking a long, sun-filled stay, couples looking for a romantic escape, high-income travelers who appreciate quality, and guests who value outdoor living, boating, and a quiet, scenic environment. Step into a bright, inviting coastal interior with two serene bedrooms, one and a half baths, a king primary suite, a queen guest room for visiting friends or family, and a full sleeper sofa. Large windows bring in natural light and frame tranquil canal views. The kitchen is fully equipped with essentials and a Keurig, and fast Wi-Fi makes it easy to work remotely or settle in for an extended stay. The real heart of the home is the outdoor waterfront oasis—your own private space to relax, dine, and enjoy the best of Keys living. A shaded Tiki Hut sits just steps from the water, perfect for morning coffee, sunset cocktails, or quiet afternoons with a book. The 50-foot private dock offers effortless access for boating, fishing, and wildlife viewing. Guests regularly spot manatees, tarpon, dolphins, and tropical birdlife right from the dock. Kayaks and bikes are provided to explore the canals, mangroves, and surrounding area. A private on-site ramp is ideal for launching small watercraft, while a nearby community ramp supports larger boats. Whether heading to Florida Bay, Blackwater Sound, Buttonwood Bay, or the backcountry flats, this home offers one of the most convenient, scenic boating locations in Key Largo. The fenced yard adds comfort and peace of mind for pets and makes outdoor time even more enjoyable. When you’re ready to explore, you’re just minutes from John Pennekamp Coral Reef State Park, local beaches, sandbars, dolphin encounters, and iconic Keys sunsets at Sunset Cove. Some of the region’s best waterfront dining is close by, including Snook’s Bayside, Lazy Lobster, Bayside Grill, The Big Chill, and The Fish House. Snowbirds and long-stay guests especially appreciate the peaceful neighborhood, reliable Wi-Fi, outdoor workspace options, fully equipped kitchen, proximity to grocery stores and essentials, and the overall ease of living—making this home an ideal choice for multi-week or month-long stays. Whether you’re escaping winter, planning a romantic getaway, inviting friends to join you for a long weekend, or simply looking to unwind in a quiet, scenic setting, this Key Largo waterfront home offers the perfect balance of privacy, comfort, and elevated outdoor living. Homes with private docks, Tiki Huts, wildlife viewing, and calm canal settings book quickly, especially during peak season. Reserve your stay and experience the Key Largo lifestyle at its most relaxing and refined.
Bed 2

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Bath 1

Bath

Sleep 6

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