Vacation Home Rentals By Owner In Islamorada, FL

Bayfront beautiful double townhouse with stunning bay views. Watch the sunsets from your balcony or from the beach right outside. This one a kind unit offers 4 bedrooms, 3 bathrooms and over 2800 square feet of living and entertaining space. Located inside of Executive Bay Club. Amenities include a sandy beach, large swimming pool, clubhouse, tennis/basketball/ pickleball courts, gated entrance with 24 hour security and much more! Located right next door to the Florida Key's largest and nicest park, Founder's Park. Also within Founder’s Park is the Yacht Harbor and Marina.

Islamorada Bayfront Townhouse in Executive Bay Club

Islamorada, Florida, United States

Bed

Bath

Sleeps

$389.0

Futura Townhome #708 - Enjoy the spectacular view of the Florida Bay from either one of two balconies in this 2-story townhome, located off the master bedroom or the living room. Amenities include Wi-Fi, flat panel TVs in the living room and master bedroom, phone (for local calls), a gas grill, and a charcoal grill. brThere are tons of things to keep you and your family busy without having to leave the Futura Condo complex. There are tennis courts and a swimming pool located on the property. Make yourself at home in our home away from home. Boat dockage available please inquire within. The Futura Yacht Club HOA charges- onsite-$150 per trailer and $50 per boat fee. These fees will not show up on your rental agreement, as the fees are collected upon check in at Futura Yacht Club. brNo smoking and no pets allowed. brVACATION RENTAL LICENSE: 24-0312 Per Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.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.

Futura Townhome 708: Stylish 2BR condo in Islamorada with pool access.

Islamorada, Florida, United States

Bed

Bath

4

Sleeps

$682.76

Discover the beauty of Islamorada from this 4-bedroom house. Inside, guests find a wonderful mix of sleeping options, including a king bed, queen bed, twin bed, and a futon. The three bathrooms offer excellent features like a jetted bathtub and a separate shower, perfect for relaxing after a day of adventure. With air conditioning and heating, the house stays comfortable year-round. Whether you’re cooking up a meal or unwinding in the cozy living space, this amazing home provides a great base for your getaway. You're sure to make fantastic memories with a stay at our place.

Beautiful house in pleasant Islamorada

Islamorada, Florida, United States

4

Bed

Bath

7

Sleeps

$1303.98

Welcome to Islamorada Palm Cove, a private four-bedroom retreat tucked inside a gated enclave in the heart of Islamorada, the Sport Fishing Capital of the World. Set along a protected lagoon with direct access to both Florida Bay and the Atlantic Ocean, this exceptional home offers private boat dockage and a ramp, making it ideal for anglers, divers and boaters alike. Spend your days on the water and your evenings unwinding in the heated and chilled pool, surrounded by lush tropical calm. Inside, the home features impeccable finishes, thoughtful design, and modern-day comforts throughout. The main living areas are bright and inviting, perfect for gathering after a day of adventure. Two of the four bedrooms are privately located downstairs and accessed separately from the main living space, offering added privacy for guests, extended family, or couples traveling together. Though peaceful and secluded, Islamorada Palm Cove is just minutes from downtown, where you’ll find renowned restaurants, local shops, and island culture. World-class sport fishing, fly-fishing, diving, snorkeling, and boating are right at your doorstep, with the coral reef and historic Alligator Lighthouse just offshore. Perfectly positioned for exploring the Keys, the home is approximately 1.5 hours from Miami and 2 hours from Key West, offering easy access while still feeling worlds away.brWhether you’re here for adventure or pure relaxation, Islamorada Palm Cove delivers the best of the Florida Keys—privacy, water access, luxury, and tranquility—all in one unforgettable setting.brThis home is managed by Florida Keys Signature Stays. Note that a 3% non-refundable convenience fee will be applied to all reservations paid by credit card, while check and eCheck payments are exempt from this fee.

Islamorada Palm Cove | Private Waterfront Escape

Islamorada, Florida, United States

Bed

Bath

Sleeps

$585.0

Discover Your Slice of Islamorada Paradise!brbrContact Us Directly for AvailabilitybrbrWelcome to our newly remodeled, canal-front haven in Islamorada, the Fishing Capital of the World. Ideal for families or friends, this 3-bedroom, 2-bath retreat offers all the luxuries and amenities you need for an unforgettable stay in the Florida Keys.brbrHome Highlights:brbr*Spacious Master Suite: King bed, private bathroom, Smart TV, and balcony for quiet morning moments.brbr*Comfortable Guest Rooms: One with a king bed and Smart TV; the other with a Twin-over-Full bunk plus a Twin trundle and Smart TV, great for groups.brbr*Extra Sleeping Space: Sleeper sofa in the family room for added flexibility.brbr*Custom Closets in each room with ample storage space.brRelax & Entertain Outdoors:brbr*60-Foot Private Dock: Perfect for boating and easy access to open waters.brbr*Private Pool & Pergola: Enjoy poolside lounging or gather under the pergola equipped with a grill, dining table, fire pit, and 60-inch Smart TV—ideal for outdoor movie nights or catching the big game.brbr*Large Upstairs Balcony: Cozy seating to savor morning coffee or evening cocktails.brbrTop-Notch Amenities:brbr*High-speed internet & Smart UHD TVs in every bedroom (Netflix, Hulu, Prime Video, and more)brbr*Large-capacity washer & dryerbrbr*Fully-equipped kitchen: Keurig, toaster oven, rice cooker, cookware, and tablewarebrbr*Essentials: Laundry detergent, dish soap, hand sanitizer, and disinfectant spraybrbr*Commercial ice maker for keeping drinks chilledbrbr*Outdoor propane grill for al fresco diningbrbrExtra Fun for Guests:brbr*2 Paddleboards for exploring the canal and nearby watersbr*2 Adult Cruiser Bikes for scenic rides around the neighborhoodbrbrOur beautiful Islamorada home is fully updated, thoughtfully equipped, and ready to make your stay in the Keys relaxing, fun, and memorable. We look forward to sharing our little piece of paradise with you!brbrbrbrbrbrbr

Luxury Islamorada Oasis: Pool, Dock, Fire Pit, King Beds & Canal Views

Islamorada, Florida, United States

Bed

Bath

Sleeps

$250.76

Your cozy getaway awaits in Islamorada at this superb house. With 2 bedrooms including 1 king, 1 queen, and 2 twin beds you and your family will find comfort and relaxation in this serene retreat. Enjoy the convenience of amenities like kayaks and private beach access. A storage area downstairs with a bait/fish freezer plus a refrigerator. Store your fishing & diving equipment too. Our place is equipped for long stays, large boats and pets are welcomed!

Captains Quarters is a charming canal front Keys house in delightful Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$445.17

VRL# 26-0132 We are one of Islamorada’s limited number of licensed weekly vacation homes.brbrThis magnificent home with direct amazing ocean views is located in Islamorada at Mile Marker 85 in the gated community of Anglers Reef.brbrA relaxing retreat, with amenities that include lavishly landscaped pathways, a serene tropical community pool overlooking the Atlantic Ocean (heated in winter and chilled in Sumer), private beach, private marina with 36 boat slips. brbr*****PREMIUM BOAT SLIP AND TRAILER STORAGE ARE INCLUDED WITH WEEKLY RENTAL OF OUR UNIT********brbrBoat size can not exceed 31” max- with a deep water Chanel out to the Atlantic.brbrThis island style keys getaway home sleeps up to six comfortably.brEnjoy comfort and privacy with two bedroom en-suites located on second floor.brInside the Master bedroom , you’ll find a king -sized bed, tasteful linens, cable ,television ,dressers, spacious closet, private bath with double vanity.brThe master bedroom also has a walkout, ocean-view balcony with gorgeous post-card views.brThe guest bedroom comfortably features 2 queen-sized beds, cable television,dressers, private bathroom includes shower with full bathtub.brbrFor your convenience, each upstairs bathroom includes hair dryers,brComplimentary starter spa toiletries:shampoo,conditioner,bath gel,body lotion, and hand soap.brWasher/dryer in addition to all linens, towels, and beach towels provided as well.brShould you need an extra bed, the downstairs area includes a queen-sized sleeper sofa with additional linens ,pillows, and blankets.brbrDownstairs, stunning ocean views off the porch make the perfect setting for morning cup of coffee or eve cocktails.brKitchen boast stainless steel appliances,granite counter tops-well equipped with Keurig coffee maker, blender,toaster,dinnerware,flatware,barware,cooking utensils, pots and pans.brDining room seating for 6, powder room, comfortable sofas maximize pool and ocean side views.brFlat screen TV’s, complimentary Wi-Fi/internet, and rich wood flooring throughout home ,coastal decor with a boutique style feel.brbrWeber BBQ grill, with full gas tank, 2 designated parking stalls, with single covered car port.brA seaside retreat offering relaxation at its finest.brPerfect for families or couples seeking to make the best of their Florida Keys vacation.brAnglers Reef offers a nearby Publix, convenience stores,restaurants,diving, fishing,snorkeling,kayaking,parasailing, kite-surfing, and so much more!

Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch

Islamorada, Florida, United States

Bed

Bath

Sleeps

$419.94

Relax in this beautiful and comfortably updated bayside home in Port Antigua. Port Antigua is the Lower Keys best kept secret. A mile-long private beach shared only with Port Antigua residents. It's crystal clear waters, Tiki huts, picnic tables, and BBQ will provide all the relaxation you need. Relax in this designer waterfront cul de sac home with 4 bedrooms, 3.5 bathrooms, and 95' of dockage. The home is fully equipped with everything you need from fast WIFI, linens, towels, cooking, large capacity washer/dryer, BBQ, ice chest, etc. Take pleasure in all the amenities this home has to offer with breathtaking sunset views, this home is one you must enjoy for your families vacation. Copy and Paste video on YouTube: https://www.youtube.com/watch v=-HVPkMfAJpgbr

Breezy Beach Waterfront home in Port Antigua

Islamorada, Florida, United States

Bed

Bath

Sleeps

$411.36

Relax, Recharge & Explore – Detached Islamorada Cottage w/ Pool, Paddleboards & Fire Pit ☀️brWelcome to your own private cottage in paradise — perfectly located in Islamorada, just a mile from the legendary Robbie’s Marina, where feeding massive tarpon, grabbing a drink at the Hungry Tarpon, or hopping on a snorkeling charter is all part of a normal day.brThis detached 2-bedroom, 1-bathroom cottage is ideal for couples, friends, solo adventurers, or small families looking for a laid-back, comfortable, and affordable Keys escape. It’s part of a quiet, boutique property with just 7 cottages total, so you get the space and peace of a private place with shared perks like a stunning pool just steps away.brbr Two bedrooms, both with queen beds and clean, simple decorbrbr A full kitchen stocked with essentials – fridge, oven, microwave, pots/pans, utensils, coffee maker, and morebrbr Comfortable living area to relax after a day on the waterbrbr Fast, reliable WiFi – whether you’re working remotely or uploading your snorkeling videosbrbr Air conditioning throughout the spacebrbr Fresh linens, bath towels, and starter toiletries provided. br Outdoor Living – Florida Keys Stylebr You’ll have your own:br✔️ Fire pit – light it up for s’mores, a nightcap, or just to unwind under the starsbr✔️ Grill – perfect for cooking up the day’s catch or some island-style BBQbr✔️ Outdoor seating surrounded by tropical greenerybrThis is your spot to sip your morning coffee or enjoy a cocktail after a day of exploring.br ‍♂️ Resort-Style Pool (Without the Crowds)brThe pool area is a gem – beautifully maintained and shared with only 6 other cottages, so it’s never crowded. Plenty of space to lounge, float, soak up the sun, or take a dip before heading out to dinner.br Free Paddleboards IncludedbrWant to explore the crystal-clear waters the Keys are famous for We include paddleboards FREE for guest use! You can easily launch from a nearby ramp and head out to discover mangroves, spot wildlife, or just glide across the turquoise sea. No rentals, no hassle – just grab and go.br Location, Location, LocationbrYou’re right in the heart of Islamorada, known as the Sportfishing Capital of the World, but there's so much more here than just fishing.br✔️ Robbie’s Marina – just 1 mile away! Feed the tarpon, rent a boat, book a jet ski, or shop the quirky local marketbr✔️ Anne’s Beach – a beautiful, family-friendly stretch of sandy coastline just a 5-minute drivebr✔️ The Art District – home to local galleries, artisan shops, cafes, and laid-back island vibesbr✔️ Close to amazing restaurants and tiki bars – fresh seafood, sunset views, tropical cocktailsbr✔️ Easy access to snorkeling, diving, kayaking, and boat toursbrWhether you’re here to explore or just kick back with a drink in your hand, you’re in the perfect spot.br☀️ What Guests Love About the Cottage:br It’s private, peaceful, and relaxedbrbr The pool is beautiful and never crowdedbrbr You can paddleboard without having to rent anythingbrbr The outdoor firepit and grill make it feel like your own little backyard in paradisebrbr The location makes it easy to get anywhere on the island – beaches, marinas, restaurants, all nearbybrbr Other Things to Note:br Parking is included and right outside your doorbrbr Pool towels are providedbrbr No smoking inside the cottagebrbr We’re happy to give local recommendations – we live here and love it!

Key Lime Cottage in Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$681.7

We are proud to announce- Castaway Island has been named for KW people’s choice awards as a FINALIST for Best Vacation Rental in the Florida Keys. . Being named top three of over 6,000 vacation rentals is the honor of a lifetime. Experience the ultimate tropical getaway in our enchanting bungalow, boasting 82 consecutive 10/10 guest reviews! Our hosts' lifetime in hospitality shines through in the meticulous restoration and thoughtful amenities, ensuring an unparalleled vacation experience. Discover your home away from home, where every detail is designed to exceed your expectations.

TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP

Islamorada, Florida, United States

Bed

Bath

Sleeps

$757.77

Front-Row Ocean Views – A Location That Cannot Be ReplicatedbrbrWelcome to Paradise Palms—the crown jewel of the exclusive Peaceful Palms gated community. Perfectly positioned just steps from the water, this newly built three-story home offers sweeping panoramic views and a rare third-floor oceanfront balcony.brbrWake up to sweeping views of the Islamorada Sandbar and Alligator Reef Lighthouse, nature unfolds right outside your door.brbrEvery sunrise and sunset becomes part of your stay.brbrDesigned for Comfort, Style & Connectionbr• 2 Expansive Oceanfront Balconies – Coffee at sunrise, cocktails at sunsetbr• True Oceanview Kitchen – Rare full ocean-view layout, fully stocked with premium appliancesbr• Oceanfront Living Room – 77” 4K OLED TV, designer furnishings, seamless indoor-outdoor feelbr• Curated Interiors – Clean, coastal luxury with thoughtful, high-end finishes throughoutbr• Pet-Free, Pristine Environment – Guarantees the highest standards of cleanlinessbrbr3 Bedrooms | Sleeps Comfortably with Space to Spread Outbr• Primary Oceanfront Suite (3rd Floor) – Tempur-Pedic King, private balcony, workspace, spa-style ensuite with rain showerbr• Second Oceanview Suite (3rd Floor) – Tempur-Pedic King, twin pull-out sofa, spa-style ensuite with ocean viewsbr• Bunk Room (Main Floor) – Full-over-full Tempur-Pedic bunks + trundle—perfect for kids or additional guestsbrbrThe Ultimate Bonus: Entertainment Retreat – A fully air-conditioned lower-level space designed for endless fun:br• 86” 4K Smart TVbr• Gaming systembr• Full-size ping pong tablebr• Lounge area + bonus fridgebr• Board games, books, puzzlesbr• Plus outdoor fun: cornhole + spikeballbrbrDock + Water Access (A Guest Favorite)br• Boat slip for vessels up to 24 ft (18” max draft at low tide, reservation required)br• Water + electricity at dockbr• Complimentary paddleboards + kayakbr• Oceanfront community pool with loungers, umbrellas & restroombrbrWhile onsite trailer parking is not provided, we will be delighted to share nearby accommodations for your convenience.brbrWhy Guests Choose Paradise Palmsbrbr“The location was the best one on the property. You see the ocean from every balcony and window.”br“The location was perfect, close proximity to fantastic restaurants and plenty of things to do.”br“The kids LOVED the bonus space downstairs to play ping pong and hang out.”br“I want to live in this home forever! THE VIEWS… WOW!”br“Unrivaled oceanfront positioning—you can’t get closer to the water than this!”br“All I can say is WOW! We travel a lot, have stayed in dozens of vacation rentals all over the country as well as internationally. And this is the best place we’ve ever stayed in by far!”br“You can tell so much care went into every detail, and everything felt spotless and welcoming from the moment we walked in.”br“The views from every window were incredible. Everything about this home was comfortable and top-notch.”br“My boys especially loved playing ping-pong in the game room and fishing off the dock in front of the house. They caught fish every day!”br“AMAZING! 6 adults stayed at Paradise Palms for a week and we were not ready to return home! The space is dreamy with stunning views!”br“Gorgeous decor, comfortable, and so spacious! 3 floors of fabulousness! From ping pong battles, corn hole domination, lazing by the poolside, hanging inside and watching football or walking to Starbucks and the marina…… this place did not disappoint!”br“We have stayed in many rentals all over the country and this home is one of the best we've ever stayed in.”brbrGet a true glimpse of living at Paradise Palms from the words of a guest, “Paradise Perfection: I have stayed in vacation rentals for decades... and this topped them all. We had an absolute blast and never wanted to leave. The panoramic ocean views were spectacular! The owners have furnished this place with incredible generosity and luxury, both style and comfort. We had 6 guests and plenty of room for everyone - especially loved the extra entertainment room. From the yummy linens, luxurious towels and spotless amenities; every detail was perfection. A private five-star resort experience all to ourselves. The location couldn't be better; a perfect balance of tranquility and convenience. We slept like babies as the location is QUIET and the beds were TEMPUR-PEDIC BLISS! As foodies, we loved being within walking distance of amazing restaurants and activities. We booked again and have referred our friends - this is a rare gem as it is oceanside, spacious, and brand new!”brbrWalkable Location + Local Favoritesbr• Walk to dining, marina, and activitiesbr• 5-minute walk to Starbucksbr• 1 mile to Publixbr• Complimentary Freebee Tesla rides throughout IslamoradabrbrNearby must-do’s:br• Robbie’s Marina (feed the tarpon)br• Theater of the Sea (walkable!)br• Alligator Reef snorkeling & divingbr• Morada Way Arts Districtbr• Founders Park (beach, pool, playgrounds)brbrA Stay That Feels Different – From the unmatched proximity to the water to the thoughtful details throughout the home, Paradise Palms offers a level of experience that goes beyond a typical vacation rental.brbrWe would be honored to host you. Your comfort and satisfaction are our top priorities. Let us help you turn your vacation dreams into reality.brbrVacation Rental License: 26-5235 | DBPR: DWE505412

Closest Oceanfront Home - 3 Stories, Views & Dock - Paradise Palms

Islamorada, Florida, United States

Bed

Bath

8

Sleeps

$458.87

The Salty B is located in the popular neighborhood of Venetian Shores! Canal front home on Snake Creek gives you fast access to both Ocean & Bay, fuel, bait, and provisions.brbrKey Features of Salty B:brbr- The House: Upstairs has Two Bedrooms, with a king-size bed in the Master, and a Full/Twin Bunks (2) in the other guest suite, There is one Bathroom upstairs and one downstairs. Downstairs has a queen-sized Murphy bed Enjoy the convenience of a first-floor bathroom, and refrigerator, sink, and Microwave – perfect for those lazy outside days!brbr- The Dock: Have your boats or yacht waiting just outside your door. Large, deep-draft sailboats or yachts are easily accommodated with a waterway 20 feet deep and 100 feet wide. Even tall vessels travel quickly between the Ocean and Florida Bay using the drawbridge just 1000 yards from the dock. With gas, bait, and tackle shops located before the bridge, your convenience is assured. Your 35-foot private dock provides instant access to fun – whether boating, fishing, swimming, or relaxingbrbrFounders Park is 3000 feet from the house. An easy walk or drive, where you can enter for free with your rental contract and enjoy the beach, walking paths, and family playgrounds. They provide small-fee access to swimming in the Olympic-sized pool, complete with diving boards, lap lanes, and a separate splash pad for kids. Founders Park is convenient for launching/loading boats at the boat ramp for nominal fees ($3/person pool, $20/ launch or loading boats). Larger boats are recommended to put in at the Harry Harris boat Ramp at mile marker 92.5 - just 6.5 miles from your rental & dock for the stay.brbr- Pet Friendlybrbr- Minimum 28-day rental

Pet Friendly 2 Bedroom in Venetian Shores Sleeps 10

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1015.14

Welcome to HeartofMorada!brbrStep into a private world in Islamorada's most coveted location. Heart of Morada sits in Coral Cove — a gated community of just 8 homes — giving you a private heated saltwater pool with waterfall, your own boat dock with electric and water hookups, and near-exclusive use of a second community pool and fire pit with sweeping sunset views.brbrGuests regularly paddleboard with manatees right off the dock each morning, and fall asleep to the sound of live music drifting over from Lorelei next door. This is the Florida Keys experience that gets people talking.brbrThe Homebrbr3 bedrooms, all king beds (2 Tempurpedic adjustable), 3 full ensuite baths + half bathbrbrSleeps up to 6 guestsbrbrTwo-story open-concept design with Bosch appliances, wine refrigerator, and kitchen island seating for 6brbr75 HDTV, premium sound system, high-speed 500 Mbps Wi-FibrWhat's IncludedbrbrPrivate heated saltwater pool with waterfall — open 24 hoursbrbrDedicated boat dock with electric + water (slip your own boat or rent)brbrCommunity pool + fire pit lounge — nearly always private to youbrbr4 bikes, 3 kayaks, 1 paddleboard, life vests for 6brbrBait freezer for fishingbrbrTesla and NEMA 50-14 EV chargerbrbrDog-friendly — bowls providedbrbrThe LocationbrWalk 2 minutes to Lorelei for waterfront sunset cocktails and live music. Bike to Florida Keys Brewing Co, History of Diving Museum, and Islamorada's best restaurants. World-class fishing charters, snorkeling, and sandbar trips depart from nearby marinas.brThe heart of Islamorada — right outside your door.brbr★ DOG-FRIENDLY HOME ★brBring your furry friends along for an exciting vacation. They'll enjoy and run around the patio outdoors while you relax in the pool. A $350 dog fee applies.brbr★ NO SMOKING ★brPlease refrain from smoking inside the home or community! Any smoking evidence will result in odor removal and furniture cleaning fees.brbr★ BOOKING ★brA signed rental agreement and a security deposit are required for booking, and follow Airbnb and VRBO policies.brbr★ OUTDOOR CAMERAS ★br3 cameras outside the property protect the driveway/rear gate where amenities are provided, the top floor out to the street, and the front door. The footage is only reviewed if there is any issue reported.

Gated Keys Home | Dock, Heated Pool & 2 Pools | Pet-OK

Islamorada, Florida, United States

Bed

Bath

Sleeps

$193.46

Enjoy breathtaking sunset from your own private beach.brCottage nautical townhouse with your outside terrace. brBest restaurants in the keys are in Islamorada. Directly next door to Founders Park walking distance. Club house, pool, marina totally renovated

Keys Cozy Townhouse

Islamorada, Florida, United States

Bed

Bath

Sleeps

$515.75

Beautiful designer-appointed oceanside canal home located at Mile Marker 76.5 on Lower Matecumbe Key in Islamorada. Situated as the second home from the point, the property enjoys beautiful ocean views and a peaceful setting while still being close to everything Islamorada has to offer.brbrThe home features a bright, open layout with modern décor and water views from nearly every window. The fully equipped kitchen includes a dishwasher, microwave, coffeemaker, toaster, and blender—everything you need to prepare meals after a day on the water. The home also offers Wi-Fi and two flat-screen TVs for your comfort.brbrBoaters will appreciate the protected dockage for up to two boats, including 30 feet of dockage and a fish cleaning station, making it easy to enjoy Islamorada's world-class fishing.brbrThe location is ideal for exploring the area. Anne's Beach is just nearby, offering nature trails, boardwalks, picnic and BBQ areas, and sandy spots tucked into the mangroves. You're also just minutes from Robbie's Marina, Bud N' Mary's, and Caloosa Cove Marina, making it easy to book a fishing charter, rent a boat, or enjoy local dining.brbrDespite being close to everything, the home sits in a quiet part of town while still only minutes from “Downtown Islamorada,” including Worldwide Sportsman and the Islamorada Fish Company.brbrThis property has become a favorite for many guests, with visitors returning year after year to enjoy this special spot in the Keys.brbrPlease note: if booking more than one year in advance, pricing may be subject to annual cost-of-living adjustments. Reservations are confirmed after speaking directly with our team.brVACATION RENTAL LICENSE: 24-0300 Per Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.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.

Enjoy a serene stay at 137 LeSerra Lane, a 3-bedroom canal retreat in Islamorada.

Islamorada, Florida, United States

Bed

Bath

6

Sleeps

$1175.49

Behold this exquisite oceanfront pool residence, which has been flawlessly renovated. Nestled in a remarkable location with direct access to a sandy beach and a private dock, this noteworthy home boasts two bedrooms and two baths on the upper level, while the lower level comprises a spacious entertainment area alongside a bedroom and a bath. Embracing an expansive half-acre lot with 100' ocean frontage, the property showcases breathtaking vistas across the majestic Atlantic Ocean. Prepare to be captivated--this residence cannot be missed!

Oceanfront 3 bedroom with dock

Islamorada, Florida, United States

Bed

Bath

Sleeps

$675.0

Oceanfront Paradise in Anglers Reef, Islamorada – Florida Keys Vacation RentalbrbrExperience the ultimate Florida Keys vacation in this stunning 3-bedroom oceanfront rental in Anglers Reef, Islamorada, featuring brand new furniture throughout and a master bedroom with direct ocean and pool views. Enjoy a resort-style pool, private beach, and boat dock, making it the perfect getaway for families, friends, or boating enthusiasts. The home's boat slip is available for rent with a deep channel out to the Atlantic ($500 per week. Let owner know after booking to add dock).brbrThe Home – Luxury & Comfort by the SeabrbrSleeps up to 8 guests comfortablybrbrMaster bedroom: private porch with direct ocean and pool viewsbrbrSecond bedroom upstairs: queen bed + full/full bunkbrbrThird bedroom downstairs: queen bedbrbrModern coastal interior with:brbrBrand new furniture throughoutbrbrFully equipped kitchen with stainless steel appliances & granite countertopsbrbrBamboo and tile flooringbrbrHigh-speed WiFi and streaming TVsbrbrFull washer and dryerbrbrExclusive Community & AmenitiesbrbrLocated in the gated Anglers Reef community, a boutique oceanfront complex of 52 homesbrbrBeautiful Native Conch and British West Indies architecturebrbrCommunity pool with panoramic Atlantic Ocean viewsbrbr500 feet of private beach for sunbathing and swimmingbrbrKayak launch from the beach & private boat dock for deep-water Florida Keys fishing and boatingbrbrFishing, Water Sports & Outdoor FunbrbrWorld-class fishing and boating adventures just steps awaybrbrFish species include snapper, tarpon, mahi, tuna, and morebrbrKayak and paddleboard rentals available in the communitybrbrPerfect for snorkeling, scuba diving, or simply relaxing by the poolbrbrNearby Attractions – Explore IslamoradabrbrIslamorada, the Sport Fishing Capital of the WorldbrbrWalk to local favorites: Hog Heaven, Smugglers Grill, Island GrillbrbrShort drive to:brbrTheater of the Sea (swim with dolphins)brbrFounders Park (Olympic pool & recreation)brbrNearby reefs for snorkeling and scuba divingbrbrWhy You’ll Love This Florida Keys Vacation RentalbrWhether you’re seeking adventure, relaxation, or quality family time, this Islamorada oceanfront home offers the ultimate Florida Keys getaway. Enjoy direct ocean and pool views from the master bedroom, brand new furniture throughout, private beach access, and resort-style amenities, creating the perfect vacation retreat.brbrWe would love to share our home with people who love the water as much as we do, and we are here to make your vacation amazing. Book now for your next Florida Keys vacation—your oceanfront paradise awaits!

Anglers Reef Islamorada Oceanfront 3BR Pool Front Home Private Beach & Boat Dock

Islamorada, Florida, United States

Bed

Bath

Sleeps

$601.73

Located in the highly desirable Venetian Shores neighborhood, this canal-front home offers quick access to both the Ocean and Florida Bay via Snake Creek — ideal for boating and fishing enthusiasts.brbrUpstairs features a comfortable two-bedroom, one-bath layout with a screened porch just off the living room, perfect for relaxing after a day on the water.brbrDownstairs offers a separate one-bedroom, one-bath apartment complete with its own full kitchen and living area — a great setup for extended family or guests.brbrThe property boasts 70 feet of dockage, providing plenty of room for your boat and easy access to open water.brbrMany of our guests return year after year to enjoy this location and setup.brbrPlease note: Reservations are not confirmed until you have spoken directly with our office.brVR#- 24-0377 Per Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.brbrPlease 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.

Charming 3BR canal home in Islamorada, perfect for your tropical getaway!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$577.65

Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef (Unit # 114) at mile marker 85 in Islamorada of the Florida Keys. Luxurious beach decor, plush furnishings, spacious accommodations that comfortably sleep 6 adults and children of all ages will feel right at home with the many kid friendly features.brOutfitted with his and her beach cruiser bikes, a pair of paddleboard/kayak crossovers, fishing equipment, pool toys, beach toys, snorkeling gear and much more, you'll have the equipment necessary to experience the Florida Keys to the fullest.brAnglers Reef is a tropical paradise, complete with two private beaches, boat dock, pool and walking paths winding through luscious palms. A relaxing getaway on the Atlantic, overlooking a stunning turquoise grass flat that the Keys are world famous for. Just a short walk to several Restaurants and Marinas, this vacation home is situated on Windley Key, which boasts the largest marine wildlife park, Theater of the Sea, where you can pet a dolphin or shake hands with a Sea Lion.brIslamorada is known as, The Sport Fishing Capital of the World, and is also a watersports mecca, with world class coral reefs to snorkel or dive within a mile of shore, a steady wind that is ideal for kite boarding, parasailing and windsurfing, and the boating and paddling opportunities are limitless. A boat slip can be arranged to be rented for an additional fee.brbrPlease note, as of Aug 1, 2024. you will no longer be able to store a trailer outside the gate on the grass any longer. we can recommend local storage lots you can contact.brbrThe abundance of 5 star reviews tell the story of this home. This is an extraordinary vacation rental in a tropical oasis setting of Anglers Reef Islamorada Florida Keys. brMake sure you watch the video below of this property too!brbrIslamorada Village of Islands Vacation Rental License No: VR227brbrPlease note: Boat slip in not included. If you need a slip, please let property manager know so she can work on a rental. Boat max 31' length and 9' height restrictions.

Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool

Islamorada, Florida, United States