Vacation Condo Rentals By Owner In Islamorada, FL

Summary:brbrElevated, thoughtfully updated retreat in the heart of Islamorada with rare access to a private boat basin and fishing jetty—perfect for sunset views and relaxing by the water. Set above the trees for a more open, airy feel, yet tucked into a peaceful setting. Enjoy walkable access to restaurants, shops, and breweries, plus fast WiFi and everything needed for a comfortable Keys getaway brbrbrbrThe Space:brbr● 2 bedrooms / 2 bathrooms (620 sq ft)brbr● Primary: King bed + en suite bathroombrbr● Guest room: King bed + separate bathroombrbr● Open living area + small kitchenbrbr● Second-floor setting with a more open, airy feelbrbr● Courtyard-facing (quiet, tucked-away setting)brbr● Shared external laundry room brbrbrbrNote: no closets or dressers—luggage racks and hanging space providedbrbrbrbrThis retreat is part of a unique, private, wooded waterfront property spanning the bay side of the Florida Keys. While the space does not have direct water views, guests have full access to the property, including a boat basin and fishing jetty just a short walk away—perfect for sunsets and relaxing by the water.brbrbrbrGuest Access:brbrGuests have full access to the entire space, as well as the shared property grounds. This includes the boat basin, fishing jetty, and waterfront areas—perfect for relaxing and enjoying sunset views.brbrbrbrThe courtyard and outdoor areas are shared with the downstairs space. A shared laundry area is also available on-site.brbrbrbrParking is available on-site for your convenience. Self check-in is provided via a keypad for a smooth and flexible arrival.brbrbrbrThe Neighborhood:brbrLocated at Mile Marker 82.5 in the heart of Islamorada, this home is in one of the more walkable areas in the Upper Keys. You’re just steps from local shops and a short walk to popular restaurants, bars, and the well-known Islamorada Beer Company.brbrbrbrDespite being close to everything, the property itself is tucked away in a quiet, wooded setting—offering a more relaxed and private feel than most nearby stays.brbrbrbrA detailed guestbook is provided with our favorite recommendations for dining, drinks, and local activities.brbrbrbrGetting Around:brbrWhile this area of Islamorada is more walkable than most in the Keys, we recommend having a vehicle to fully explore nearby attractions, beaches, and surrounding areas.brbrbrbrFor shorter trips, many restaurants, shops, and local spots—including Islamorada Beer Company—are within walking distance. Biking is also a great option, and rentals are available nearby.brbrbrbrOther Things to Note:brbr● Maximum occupancy: 4 guestsbrbr● SHARED courtyard, grill, and laundry with the upstairs unitbrbr● COURTYARD VIEW (no direct ocean view), with full access to the boat basin and fishing jettybrbrbrbrBoat Basin Access (Optional)brbr● Dockage available for ONE vessel up to 24’ MAX (with engine)brbr● Space is shared and not assigned (placement may vary)brbr● Boat ramp available for vessels up to 20’ MAXbrbr● Larger boats cannot be accommodatedbrbr● Marina waiver required prior to arrivalbrbr● Trailer parking available on-sitebrbr● NO JET SKISbrbrbrbrCancellation Policybrbr● 100% refund: 60+ days before check-inbrbr● 50% refund: 30–60 days before check-inbrbr● No refunds within 30 daysbrbrbrbrTravel insurance is strongly recommended.brbrbrbrInteraction with Guests:brbrWe provide self check-in for a smooth and flexible arrival, but we’re always available if you need anything during your stay. We’re local and happy to help with recommendations, questions, or anything that comes up. - Sean

Apartment

Elevated Retreat | Sunset Access + Boat Basin

Islamorada, Florida, United States

Bed

Bath

Sleeps

$515.1

Village of Islamorada license #24-0370br138 Anglers Way and boat slip #1 for 26' max boat length for this slip (extra fee)brCall me for more information 305-240-0592br2 large bedrooms amd 2.5 bathrooms. largest floorplan of two bedroom in Anglers.br Community kayaks and paddleboards are avail to use (just have to sign a waiver)brThis large Oceanfront Villa has 2 bedrooms (one with king bed and the other with One QUEEN SIZE BED and twin bunk beds) and 2 full bathrooms located on the 2nd floor, both with private balcony's. Down stairs there is a half bath, a full kitchen with stainless steel appliances, granite counters, living/dining room, wood floors, cable TV, Wi-Fi and 2 open porches with seating.This oceanfront resort is a boutique complex of 52 homes inspired by Key West architecture that was built in 2007. Gate community, located off the Old Hwy at MM 86 in Islamorada. Amenities include a community pool overlooking the Atlantic Ocean and 500ft of private beach. The home’s boat slip is available for rent with a deep channel out to the Atlantic. Be at Alligator Light house or the Famous Islamorada (Holiday Isle) sandbar in minutes. Launch your kayak or paddle board from the private beachbrbrKayaks are now available to all homes (provided by the community) on a first come, first serve basis. A waiver needs to be signed (attached to welcome email) in order to be able to use them.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. Trailers fitting under the carport are able to be stored there. Otherwise, we can recommend local storage lots you can contact.brbrCome on down and put your toes in the sand. It's always better in the Florida Keys.Angler’s Reef is the perfect place for all fishing and diving enthusiasts. Islamorada is known as “The Sport fishing Capital of the World”. Water activities abound including: diving, snorkeling, Para sailing, kiteboarding, paddle boarding, kayaking, and more. You may even spot manatees at the Dock. Fine dining and unique shops are within walking distance: Island Grill (Famous for their tuna nachos) serving breakfast, lunch and dinner oceanfront with live music. For late night entertainment, walk on over to Hog Heaven for a fun night of dancing. Also, within in walking distance is Theatre of the Sea, where you can watch a live dolphin show or even swim with the dolphins!brbrBring your boat (up to 26') max. If you have a larger boat, I will need to put it in another slip and there is an additional fee.

Islamorada-Anglers Reef-LARGE/updated/Views DOCKAGE AVAILABLE

Islamorada, Florida, United States

Bed

Bath

Sleeps

$401.36

Summary:brbrUnique, thoughtfully updated retreat in the heart of Islamorada with rare access to a private boat basin and fishing jetty—perfect for sunset views and relaxing by the water. Walk to top restaurants, breweries, and shops, then return to a peaceful, tucked-away setting. This first-floor unit offers easy access, fast WiFi, and everything you need for a comfortable Keys getaway! brbrbrbrThe Space:brbr● 2 bedrooms / 2 bathrooms (620 sq ft)brbr● Primary: Queen bed + en suite bathroombrbr● Guest room: King bed + separate bathroombrbr● Open living area + small kitchenbrbr● Courtyard-facing (quiet, tucked-away setting)brbrbrbrNote: no closets or dressers—luggage racks and hanging space providedbrbrbrbrThis unit is part of a unique, private, wooded waterfront property spanning the bay side of the Florida Keys. While the unit does not have direct water views, guests have full access to the property, including a boat basin and fishing jetty just a short walk away—perfect for sunsets and relaxing by the water.brbrbrbrGuest Access:brbrGuests have full access to the entire unit, as well as the shared property grounds. This includes the boat basin, fishing jetty, and waterfront areas—perfect for relaxing and enjoying sunset views.brbrbrbrThe courtyard and outdoor areas are shared with the upstairs unit. A shared laundry area is also available on-site.brbrbrbrParking is available on-site for your convenience. Self check-in is provided via a keypad for a smooth, flexible arrival.brbrbrbrThe Neighborhood:brbrLocated at Mile Marker 82.5 in the heart of Islamorada, this retreat is in one of the most walkable areas in the Upper Keys. You’re just steps from local shops and a short walk to popular restaurants, bars, and the well-known Islamorada Beer Company.brbrbrbrDespite being close to everything, the property itself is tucked away in a quiet, wooded setting—offering a more relaxed and private feel than most nearby stays.brbrbrbrA detailed guestbook is provided with our favorite recommendations for dining, drinks, and local activities.brbrbrbrGetting Around:brbrWhile this area of Islamorada is more walkable than most in the Keys, we recommend having a vehicle to fully explore nearby attractions, beaches, and surrounding areas.brbrbrbrFor shorter trips, many restaurants, shops, and local spots—including Islamorada Beer Company—are within walking distance. Biking is also a great option, and rentals are available nearby.brbrbrbrOther Things to Note:brbr● Maximum occupancy: 4 guestsbrbr● SHARED courtyard, grill, and laundry with the upstairs unitbrbr● COURTYARD VIEW (no direct ocean view), with full access to the boat basin and fishing jettybrbrbrbrBoat Basin Access (Optional)brbr● Dockage available for ONE vessel up to 24’ MAX (with engine)brbr● Space is shared and not assigned (placement may vary)brbr● Boat ramp available for vessels up to 20’ MAXbrbr● Larger boats cannot be accommodatedbrbr● Marina waiver required prior to arrivalbrbr● Trailer parking available on-sitebrbr● NO JET SKISbrbrbrbrCancellation Policybrbr● 100% refund: 60+ days before check-inbrbr● 50% refund: 30–60 days before check-inbrbr● No refunds within 30 daysbrbrbrbrTravel insurance is strongly recommended.brbrbrbrInteraction with Guests:brbrWe provide self check-in for a smooth and flexible arrival, but we’re always available if you need anything during your stay. We’re local and happy to help with recommendations, questions, or anything that comes up - Sean

Apartment

Sunset Access + Boat Basin | Walkable Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$723.07

Islamorada Vacation Rental LICENSE #: 26-1243brbrSpacious five bedroom home on huge canal. Tons of dockage, bait freezer, and fish cleaning station!! SUPER PRIVATE!!! brbrAmazing waterfront restaurants close by!!! Boat rental and paddle board/kayak company that will deliver boat to dock for your stay. brbrDream home in they keys is a 4000 square foot home on water with heated/chilled Pool. Located in an exclusive area of all waterfront homes. This immaculate two-story home offers a luxurious and very private setting. It has 5 large bedrooms and three baths. Equipped with four king beds, one queen bed, one queen sofa sleeper, a futon and four singles. All top quality mattresses. All down beddering and sheets 800 or higher. Both the down stairs and up stairs have tv and dvd. Three of the bedrooms have TV's. The kitchen is extremely spacious and well-equipped. brThe screened verandah overlooks the pool and water area filled with blooming tropical landscaping. The veranda has two seating areas and a large teak table that can extend to 10 feet and seat 12 comfortably. Just a sliding glass door from the kitchen. Windows and sliding glass doors make up most of the house providing the feeling of living at one with the tropics. brbrThe outdoor entertainment area is complete with heated pool, barbecue grill and 100 foot of dock space on deep natural, crystal clear canal which is right at channel two.brBeautiful Tiki Hut to enjoy our wonderful weather.brbrMy cancellation policy is I ask for a booking deposit (VRBO takes THEIR fee) at this time, I then as for the balance 60 days prior to your stay. As long as I can rebook your dates I refund 100%. VRBO also refunds their service fee when I refund 100%. VRBO does not give me this option on their site. I send you a contract when you book, detailing this. brKeywords: House

Waterfront Oasis 2Mins2BeachTons dockage VERY Private Immediate ocean/bay access

Islamorada, Florida, United States

5

Bed

Bath

12

Sleeps

$793.13

Located in the sweet spot of the Florida Keys - Islamorada. Custom built and designed by an Award winning architect in 2019. Wonderful floor to ceiling glass captures amazing ocean views. Warm reclaimed teak flooring. Fabulous ocean front views, 4 outdoor ocean view patios plus 1 small outdoor Master bath deck. Chef appointed kitchen with Wolf stove and Subzero fridge. Wolf wine cooler and warming oven. Ocean front Master bedroom has its own private balcony and bathroom suite. Guest bedroom has ocean front views and private bath. Other guest bedroom has queen bed and private bath. brbrVanishing edge pool on all sides and spa. Pool & spa heat, bubble jets and lights are controlled from your iPhone. 50 foot of beachfront property, great for paddle boarding, kayaking, kiteboarding and snorkeling. Bicycles and paddle boards included. Great loft space with lots of natural light from clerestory glass. 3,050 ft.² of livable space on three levels.brbrIncluded is a 23 foot Contender boat docked next door at our resort property for guest use. Boating experience is required.brbr

Ocean Front Contemporary Beach House, Islamorada.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$719.96

Welcome to 104 Leoni Drive, a stunning new home in the highly sought-after Venetian Shores neighborhood of Islamorada. This 4-bedroom retreat has it all—a private pool, deepwater dockage, and a prime waterfront location with easy access to both the Ocean and Florida Bay.brbrStep inside, and you'll immediately feel at home. The open-concept living area is bright, airy, and beautifully designed, with high-end finishes and plenty of natural light. The gourmet kitchen has everything you need to whip up meals after a day on the water, and the spacious living room is perfect for unwinding in the evenings.brbrEach bedroom is thoughtfully designed for comfort, with plush bedding and stylish touches. The primary suite is a true retreat, featuring a private balcony with incredible waterfront views—the perfect spot for your morning coffee or an evening cocktail.brbrOutside, the pool invites you to soak up the Florida sun, while the private dock makes it easy to head out for a day of boating, fishing, or just relaxing by the water. With deepwater access via Snake Creek, you'll be on the ocean or bay in no time.brbrLocated in one of the best neighborhoods in Islamorada, you're just minutes from great restaurants, shopping, and all the fun the Keys have to offer. Whether you're here for adventure or just to kick back and relax, this home is the perfect place to do it all.brbrBook your stay today and experience the best of waterfront living in the Florida Keys! 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.

Luxury Waterfront Escape- Brand New Home In Venetian Shores

Islamorada, Florida, United States

Bed

Bath

8

Sleeps

$337.5

Discover the beauty of Islamorada from this charming 1-bedroom hotel. The cozy room features 2 full beds, perfect for a relaxing stay. With amenities like heating and AC, guests can unwind after a day of exploring. The bathroom includes a shower and a hair dryer for added convenience. Our place is equipped for both long or short stays to make your holiday one to remember.

Hotel

Room #3 in Charming hotel with AC in sunny Islamorada

Islamorada, Florida, United States

1

Bed

1

Bath

Sleeps

$1237.52

This listing is for 3 separate rooms within a hotel. The price shown in the listing covers all 3 rooms.brbr✦ Each room is 950 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services availability and frequency vary by staybrbrThere 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 is available, opened from 8:00AM to 10:00PM.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 $60.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $100.00 (per night). $100 per night. Up to two pets/roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Hotel

Three Villa w/ Living Area & Private Patio | Close to Theater of the Sea

Islamorada, Florida, United States

Bed

Bath

18

Sleeps

$140.63

Unwind in Islamorada at this brilliant apartment. With two cozy bedrooms featuring queen beds, guests enjoy plenty of space to relax. The two bathrooms include refreshing showers and handy hair dryers for added comfort. Stay comfortable year-round with heating and air conditioning throughout the apartment. Whether you’re winding down after a day of adventure or starting fresh in the morning, this amazing spot offers a perfect home base. We’ll be available to answer any questions while you stay at our place.

Apartment

Charming 2-bedroom apartment with AC in beautiful Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1588.39

The recently renovated Oceanside Cottage is located directly on the ocean with amazing morning sunrises over the ocean. The full moon rise over the water in front of the house is breathtaking! brbr2 Bedroom - 2 bath Modern Cottage: brThe cottage has a beautiful cook's kitchen equipped with brand new appliances. Each bathroom is entirely new with modern fixtures including glass showers. There are 2 bedrooms, each with a private full bathroom. The brand new king sized mattress sets are known as the famous Westin Heavenly. Each bedroom has a beautiful view of the water through a private sliding glass door that leads to a oceanfront deck. The pool sits squarely in front of the cottage and has a stunning white marble pool ledge patio overlooking the ocean.brbrA constant onshore breeze drifts through the house with pure, invigorating ocean scents. The house sits across from the Alligator Lighthouse, an amazing snorkeling spot, and snorkeling at Cheeca Rocks is just a few moments anyway by boat. The dock easily accommodates one bay style boat with immediate access to deep water. brIslamorada has fantastic restaurants, cafés, bakeries, marinas, charters, and needless to say it is the fishing capital of the world. There is so much to enjoy!brbr2 Paddle boards and 2 kayaks are included with rental as the waters off the house are perfect for exploring by kayak. There is a teak cabana for rest and relaxation by the pool. brbrThe house is a 100% non-smoking property.brbrAbout the owner: Islamorada is absolute paradise - we love the island and happy to share the vacation house with guests looking to escape to a patch of paradise in the Keys. The is property is exclusively offered as a vacation rental so it is similar to staying at a hotel and is exceptionally clean and easy to enjoy.brbrWe privately own a total of 5 boutique vacation rentals in Islamorada:brVRBO listing #1576833 (5 bedroom)brVRBO listing #1054019 (5 bedroom)brVRBO listing #1977457 (7 bedroom)brVRBO listing #3363008 (6 bedroom)brVRBO listing #689629 (5 bedroom)brbrLICENSE #: 26-0147 - Islamorada

Cottage

Oceanfront Cottage With Stunning Pool & Dockage in Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1534.63

TED’S PLACEbrbrLicense # VR052 - Minimum Stay 1 Week, Saturday thru Saturday – Unbeatable Location - 1.5 acres – Bayfront – Gated & Secluded – Walking Distance to Lorelei and other great spots - 5/4 Home with Heated Infinity Pool and Hot Tub – Protected Dockage for Boats up to 30’ – Easy safe and secure parking for your boat trailer - Stunning Views – Great Amenities inc. Paddleboards, Kayaks, Gym, Outdoor Grill Station & Bar, Sunset Cabana, Smart TV’s, Indoor & Outdoor Sonos Sound System, Pool Table, Ping Pong, Shuffleboard, Cornhole, Firepit.brbrDesigned to be the ultimate vacation home for couples, families with teenage children or groups of fishing friends. brbrPlease note that Ted's Place has multiple deep water features within close proximity of the house. brbrbrTHE LOCATIONbrbrTed’s Place – the spectacular former estate of Ted Williams is superbly situated at Mile Marker 82 in the heart of fabulous Islamorada – the Village of Islands, the Sportfishing Capital of the World and recently described by the Miami Herald as ‘the Cool Key’.brbrIts central location on Upper Matecumbe Key means easy access to the best that Islamorada has to offer. A short stroll to the end of the street takes you to the Islamorada Fishing Club or the Lorelei Restaurant and Cabana Bar – popular hangouts for locals and visitors alike. Explore further afield and you will find many of the area’s top-rated marina’s, restaurants, craft breweries, tiki bars, art galleries and boutiques.brbrSet well away from the busy Overseas Highway, this gated estate fronts directly on to glorious Florida Bay for breathtaking sunsets and panoramic views of shimmering, teal waters, mangrove islands and the turquoise horizon.brbrIslamorada is uniquely positioned at the confluence of the Atlantic, the Gulf of Mexico and the Everglades National Park. For fishing friends and families this is a seriously fishy venue. The world record producing bonefish flats of Shell Key are seconds away from the dock, a few minutes further takes one to the tarpon hotspots of Florida Bay or the Oceanside flats. The fertile fishing grounds of the Gulfstream are easily accessed via nearby Whale Harbor Channel. Opportunities for lobstering, snorkeling, kayaking, paddle boarding and nature watching abound right outside your door. brbrWhen Baseball legend Ted Williams moved to the Keys in the fifties, he had the pick of the best waterfront locations to call home. He chose here. After spending a week treading in his footsteps, you will understand why. brbrTHE ESTATEbrbrSpanning 1.5 acres and accessed via an electric gate on quiet Madeira Road, Ted’s Place is truly a tropical paradise. A long, winding driveway leads you through expansive, mature gardens populated with hundreds of native trees, shrubs and flowering plants, all designed to attract an abundance of butterflies and birdlife. Towering, swaying palms surround the main home, rambling Bourgainvillea provide vibrant splashes of color and comical curly-tailed lizards stand sentry on the stone garden walls.brbrAccessing the bayside of the estate you are immediately struck by the infinity-edged swimming pool and spa and an assortment of patio’s, decks, outdoor dining areas and a bar area - all laid out to maximize the spectacular open water views.brbrA small mangrove island protects the sea wall and dockage creating a shallow lagoon that shields boats from excessive wind and waves. It’s also an ideal place to kayak and paddle board on windy days. Most days an Osprey perches on the largest palm, surveying the lagoon for its preferred prey of Mullet. Schools of large Snapper and Parrotfish hang out in the shade of the floating dock and families of Manatee’s visit on a frequent basis. If you are lucky you may witness dolphins playing beyond the island in the deeper waters of the Bay.brbrIf you are not transfixed by the natural beauty of it all, there are many further outdoor features to occupy your time – a small gym located in the garden room, a pool table, darts board and ring toss in the bar area, shuffleboard on the porch, ping pong in the entryway, corn hole in the yard and a fire pit for toasting marshmallows on cooler winter evenings.brbrIf you are tired of the Ted’s Place you are tired of life. Kick back, relax and enjoy this serene oasis.brbrTHE HISTORIC HOMEbrbrTed Williams was the quintessential all-American hero. His achievements as a baseball hitter for the Boston Red Sox remain unsurpassed to this day. In between setting all time batting records he served his country with distinction as a fearless fighter pilot during World War II. Upon his retirement from baseball he headed south to Islamorada where he quickly distinguished himself as one of the best fisherman the Keys had ever seen. The media attention Williams brought with him truly put Islamorada on the map as one of the leading sportfishing destinations in the world.brbrTed Williams evidently loved the Keys and its people. The fact that he lived in this house for forty years makes Ted’s Place one of the most historically significant homes in the Upper Keys.brbrToday, the original concrete shell of Williams house still forms the superstructure. But beyond that, subsequent owners have upgraded the interior and exterior to create 5,400 sq/ft of living space (3,600 sq/ft interior and 1800 sq/ft of porches, balconies and terraces) laid out and equipped for contemporary lifestyles, but careful to preserve the Old Florida charm. The ground floor of the home offers an open plan living design and features a well equipped kitchen by the modern masters, Bulthaup and a dining area furnished in the minimalist mid-century modern style with superb views towards the water. Large sliding glass doors bring the outdoors in to the living areas and provide plenty of natural light. One en-suite bedroom makes up the ground floor.brbrUpstairs, there are a further four bedrooms and three bathrooms. The master suite is as large as some condominiums in the Keys and opens on to a large balcony overlooking Florida Bay. All bathrooms are equipped with the best power showers and porcelain from Hans Grohe and Duravit. Large Smart TV’s are situated in the living room and master bedroom and Wi-fi is available throughout the home. Please note the 5th bedroom has two twin beds - the other 4 bedrooms have King beds..brbrThe owner of this home is an avid saltwater fly fisherman and this is reflected in the fine artwork by notable marine artists such as Al Barnes, Tim Borski, Jorge Martinez and Roge Fowler that adorns many wall spaces.brbrTo stay at Ted’s Place is to immerse oneself in the natural beauty of the Florida Keys whilst still enjoying the creature comforts one would expect from modern living. You may find you never want or need to leave the Estate except perhaps by boat – any of the many great fishing guides in the area will be happy to pick you up by skiff or bay boat right at the dock.

Iconic Ted Williams Estate. Bayfront, Heated Infinity Pool & Hot Tub, Dockage.

Islamorada, Florida, United States

5

Bed

Bath

10

Sleeps

$155.05

PROPERTY NAME: The Palms #417br79901 Overseas Highway, Islamorada, FLbrbrLOCATION: Oceanside Condominium brbrMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedbrbrMILE MARKER: 79.9brbrDETAILS: The Palms of Islamorada is a condo complex consisting of 84 units and is located directly on the Atlantic Ocean. The complex features separate his and hers mini-gyms, heated pool, hot tub, tiki for gatherings and lots of lounge chairs so soaking up the wonderful sunshine. This one bedroom unit has partial views of the ocean and a good view of the Florida Bay. It is perfectly proportioned - large living area and large bedroom and dressing area with separate linen closet and walk-in closet. The kitchen and baths have been updated. You'll be glad you chose this unit for your holiday in the Keys. Bedding is king. This property is professionally managed by Keys Holiday Rentals.brbrSleeping Arrangements: Sleeps 2-3 comfortablybrPrimary Bedroom: King, Ensuite Shower/ Tub CombobrBathroom 2: ShowerbrbrAmenities Include: Community pool and hot tub, Indoor community area/kitchen, gym, Outdoor lounge chairs.brbrActivities: Beach, Swimming, Boating, Offshore Fishing, On Shore Fishing, Paddle Boarding, Museums, Wildlife Reserves, Art, Shopping, Historic Tours and Culinary Adventures.brbrENHANCED CLEANING, DISINFECTION AND SANITIZATION: Our number one priority is the wellbeing and safety of our guests. We have contactless check-ins and check-outs. Our properties are cleaned and sanitized by professionally trained and equipped housekeepers who provide quality service, security and personal accountability. We use CDC housekeeping protocols, approved disinfectants and personal protection equipment. Our properties are private, well maintained, hygienic and sanitized. A whole safe and private space just for you and your family. brbrRESERVATIONS ARE NOT CONFIRMED UNTIL THE REQUIRED CONDOMINIUM ASSOCIATION APPLICATION IS APPROVED.

Condo

Updated Unit with Beautiful Florida Bay Sunsets

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1102.08

Heart of Morada - This unique townhome is located bay front at Mile Marker 81.5 on U.S. Highway 1 in the heart of downtown Islamorada. Just beyond the discreet gates, an easy walk or bike ride away, is all that this Florida Keys village has to offer boutiques, galleries, dining, spa relaxation, beaches and the ultimate saltwater fishing experiences. Kayak, paddleboard or boat for a day of flats fishing right from your backyard. Or simply enjoy home in lush tropical surroundings at your private pool. 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. brVR-24-2069 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.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.

Experience luxury at Heart of Morada, a 3-bedroom condo in beautiful Islamorada.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$980.78

SANCTUARY FOUND… At the intersection of two very wide sparkling canals sits this lovely, four bedroom, two and a half bathroom Spanish, Modern home in desirable Port Antigua. brbrThis owner operated property is always clean, comfortable and relaxing.brbrEndless water views delight in every direction – incredible sunsets from the master suite and from the screened-in porch just off the living room. Nice open floor plan, newly tiled floors throughout. Professional tropical landscaping graces this 8000 square foot, parcel. After a long day of fishing, diving or shopping you can relax in the heated swimming pool. A second refrigerator and restaurant style icemaker on the ground level are available for your use. They are located in a very large lockable storage area that can also be used to store your fishing equipment, dive gear, bicycles or any other items you may bring for your vacation. Beach chairs and beach towels are provided for you to enjoy Port Antigua's private beach and sandbar. A screened porch with dual ceiling fans provides the perfect location to relax and watch the sunset over the Florida Bay.brbrThis Non-Smoking home is located on a lovely, quiet cul-de-sac with community beach. The location offers easy boat access to the Florida Bay and the Atlantic Ocean through Channel 5 or Indian Key. Boats may be docked at no charge on the 144ft. seawall on the property. The dock is equipped with water and electric. Canal depth is five plus feet.brbrThe house has gone through some major renovations over the past few years. New central A/C and Heat, all new windows and doors, new railing and fenced yard area, new tile inside and out, new grilling deck just off of the screen porch. The kitchen is fully equipped with just about everything you will need cook your catch.brbrDue to HOA regulations, all rentals are for a minimum of 28 days and must start on the 1st, 2nd or 3rd of the month. Sublets of the rental are prohibited.brbrThe pet fee is non-refundable. The cleaning fee includes a mid-stay cleaning.

Port Antigua South Islamorada Canal Front Home with Pool Dock & Private Beach

ISLAMORADA, Florida, United States

Bed

Bath

Sleeps

$1606.37

Welcome to Oasis4rent!brbrEscape to 2.75 acres of private oceanfront paradise in the heart of Islamorada. Two beautifully appointed homes sit directly on the Atlantic with 200 feet of sandy beachfront, a heated saltwater infinity pool, and views of Alligator Reef Light on the horizon.brbrThe PropertybrbrMain House: 1 king bedroom (Tempurpedic adjustable), 1.5 baths, full kitchen, wrap-around porchbrbrGuest House: 2 bedrooms (queen + queen/full), 1 bath, full kitchen, ocean-view living roombrbrSleeps up to 8 guests across 3 bedrooms and 4 bedsbrbrWhat Makes This SpecialbrbrPrivate sandy beach — swim, kayak, or paddleboard from your backyardbrbrHeated saltwater infinity pool with unobstructed Atlantic viewsbrbr100+ palm trees, 60+ lit at night — the Keys' most stunning evening ambiancebrbr6 high-end bikes for exploring Upper Matecumbebrbr4 kayaks, 2 paddleboards, bocce ball, and cornholebrbrTesla and NEMA 14-50 EV chargerbrbrEnterprise-grade Wi-Fi covering the entire estatebrbrGated entrance for complete privacybrbrThe LocationbrWalk or bike to Italian Food Company, Bayside Gourmet, local breweries, and art galleries. Less than a mile from Publix. World-class fishing, snorkeling, and diving charters depart from nearby marinas.brPet-Friendly — Dogs welcome ($350 fee). They will love the fenced, grassy yard.brCoffee on the porch at sunrise. Dolphins passing just offshore. Margaritas by the pool at sunset. This is why it is called The Oasis.

Oceanfront Keys Escape | Private Beach & Pool | 3 Acres

Islamorada, Florida, United States

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Bath

Sleeps

$517.5

Located in Islamorada, this peaceful 2-bedroom house. Ocean front -Private beach is a welcoming retreat for guests. this fantastic property offers an outdoor kitchen and living area for a relaxing stay. Enjoy amenities like The 2 bathrooms feature a bathtub and a jetted bathtub facing the ocean for ultimate relaxation. Pet friendy . Top of the line furnishings and linens . brSeven eight six 457-1795

Villa

Beautiful ocean front private beach 2-bedroom house gorgeous views Isla morada

Islamorada, Florida, United States

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Bath

Sleeps

$770.63

ONE-OF-A-KIND VACATION HOME. Elegant living at its finest. You will never want to visit any other place. Large open space throughout the entire house. Beautiful dining area, open kitchen and spacious living room. Private pool. Porch with water view. Complimentary private beach for White Marlin Beach residents and guests.

ISLAMORADA DREAM

Islamorada, Florida, United States

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Bath

8

Sleeps

$460.14

INTERIOR LOT—-NO ROAD NOISE—-BOAT SLIP AVAILABLE———Interior Painted Jan 2024---New Furniture in Family Room---Beautifully Decorated and So Comfortable!brbr*** This is a great house---beautifully furnished/well kept. Oceanview with two porches!***brbr*** NO ROAD NOISE. This house does not back up to the Overseas Hwy and is very quiet and secluded within Anglers Reef! ***brbr*** Please email and I'll answer any questions you have! ***brbr***** PLS BOOK YOUR WEEK(S) EARLY AS MANY WEEKS FILL UP 6-12 MONTHS AHEADbrbrWe are one of Islamorada's limited number of licensed weekly vacation homes, VR #25-0258 (State License #DWE5404378).brbrAngler's Reef is Islamorada's premier resort community located at MM85 (on the Ocean side) in the heart of the Florida Keys. Islamorada is known as the SportFishing Capital of the World. Our boutique gated community is made up of 52 luxury waterfront villas, inspired by Native Conch and British West Indies architecture, accompanied by a boat basin with 36 slips, a large heated pool, two sandy beaches, and quiet palm tree-lined streets. Quick boat ride or short kayak ride over to the world famous Islamorada Sandbar for fun in the sun or the Alligator Reef Lighthouse for snorkeling!brbrIslamorada is known as the Sport Fishing Capital of the World. The Gulfstream flows past the Florida Keys from 10-20 miles offshore and brings seasonal visitors like mahi, tuna, wahoo, dolphin, sailfish and marlin close enough to shore for small-boat fishermen. Tarpon and bonefish are also plentiful in the backcountry. There are plenty of captains that will provide day-trips for you if you are not bringing a boat along on vacation. Also, boat rentals are definitely available, if you'd rather be your own captain for the week (or two). brbrThe home's boat slip (with electric and water) fits a vessel up to 31 ft. (max ht of 9 ft) and is available for an additional cost of $500+/week. Deep channel out to the Atlantic. The neighborhood of Anglers Reef has stand-up-paddle boards and kayaks for use by renters. A Kayak waiver will be required in order to take advantage of these during your stay. brbrWater sports include diving, snorkeling, parasailing, windsurfing, kayaking, paddle boarding and more. Fine dining close by includes Ziggie & Mad Dogs, Chef Michael's, Morada Bay, Cheeca Lodge along with fun spots like Hog Heaven and Robbie's (to feed the tarpon). Bayside Gourmet is just down the road. It is #1 on Trip Advisor and a must-do for a wonderful meal! There is a Publix grocery just 1 mile south of Anglers Reef. brbrTheatre of The Sea (for dolphin and sea lion shows and interactive exhibits) is located nearby. Marathon is just a short ride down the Overseas Highway where you can visit the Dolphin Research Center and The Turtle Hospital for fun activities for adults and kids alike. brbrThree state parks that are worth a visit are close-by as well: brJohn Pennekamp Coral Reef State ParkbrBahia Honda State ParkbrLong Key State ParkbrbrKey West is less than two hours away. Definitely worth the drive!brbrEnjoy the expansive views and ocean breezes from the porches/balconies on the first and second stories. Upgraded Chef's kitchen with top of the line appliances, granite counters, and eat at bar. Kitchen is fully stocked with cookware, dishes and appliances. Weber gas grill outside. brbrOn the second floor, there are two suites which will sleep 6 comfortably. brThe Master Suite has a king bed, private bath and amazing porch with ocean views.brThe Guest Suite has 2 queen beds with private bath.brWasher/Dryer upstairs. brbrLinens, bath towels and beach towels are all provided and replaced often. We have lots of puzzles and games available. brbrBoat Trailer Storage is available close by. Ask owner for details. brbrCable and WIFI included.brbrTwo available covered parking spaces. brbrRentals are Saturday-Saturday. Exceptions please inquire with owner. brbrPictures and description are representative of accommodations provided but are subject to change.brbr***no trailer parking in carports***brbrNO PETS ALLOWED BY COMMUNITY LAWS

Anglers Reef Islamorada Ocean Views DOCK Beach Pool Boat Slip NO ROAD NOISE!

Islamorada, Florida, United States

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Bath

Sleeps

$1182.86

Welcome to Islamorada- the Fishing Capital of the World.brbrOceanfront living doesn't get better than this. In the heart of Islamorada, this vacation home is located on the exclusive Millionaire's Row street. Once you enter into the private oceanfront estate, you have arrived in paradise!brbrThe house has two levels which are accessed via the outside staircase.brbrThe main floor is upstairs where you will find the living room, dining room, kitchen, laundry room and sun room with spectacular ocean views. There is also a reading nook in the sunroom with a small book library. Also upstairs is a master bedroom with a king bed, TV, and en suite bathroom. The second bedroom has two full size beds and a TV. There is a hall bathroom with a bathtub and separate shower. For the coffee lovers, we have provided a coffee bar. You can choose to make your coffee with a standard coffee pot, a Keurig, or a Nespresso machine. Enjoy!brbrThe first floor, patio level, boasts two bedrooms. The first spacious bedroom which is steps away from the pool and has an ocean view, features a king bed, a twin bed, TV, and a small refrigerator. The second bedroom has two full size beds and a TV. Both bedrooms share a large bathroom with a shared closet.brbrOn a hot day in the Florida Keys, it is nice to take a swim in the pool overlooking the Atlantic Ocean. The pool can be heated in the winter months at no additional charge. There are plenty of chaise loungers if you'd prefer to relax and catch some rays.brThe kids will have a great time playing in the sand and building sand castles with the sand toys provided. You can always take up a game of ping pong under the covered patio. brAnd of course, you'll probably want to take a dip in the ocean. The water is shallow so you can walk right in over the seawall and go for a swim. Depending on the tide, there could be some seaweed.brbrNamed for its stunning 350 foot pier, be sure to be on the lookout for the many fish and sea creatures in the ocean as you walk to the end.brbrFor your convenience, we provide:brbrInside the house:br- Ceiling fan in each bedroom, living room, and sun roombr- Smart TVs with 300+ channelsbr- Hair dryer in each bathroombr- High speed Internet with WIFIbr- Each bathroom has a pump bottle of shampoo, conditioner, and body wash.br- Welcome supplies pack of paper towels, toilet paper, small dish soap, and kitchen sponge.brbrOutdoors:br- 2 kayaks with life jacketsbr- Outdoor gas bbq and charcoal bbqbr- Outdoor bait freezerbr- Ping-pong tablebr- Sand toys for the childrenbrbr** Sleeps 10br** 7 Night Minimum / Saturday to Saturday Only**br** Pets permitted with prior approval**

Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

Islamorada, Florida, United States

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