Vacation Rentals By Owner In Islamorada, FL

Discover tranquility at our Venetian Shores Escape, Islamorada. Nestled in a serene neighborhood, this property boasts a sunlit pool oasis, cozy living spaces, and is perfectly suited for families seeking peace. Immerse in nature's beauty, with easy access to local attractions and ocean adventures. Enjoy the comfort of a fully equipped home where every detail is curated for your relaxation. Here, peaceful moments and family bonding await in a picturesque setting. with showers and hair dryers, guests can relax and unwind in this charming retreat. The living room offers additional space with a cozy sofa bed for extra comfort. Experience the magic of Islamorada at our superb house.

3-bedroom cozy pool home in exclusive Venetian Shores, Islamorada .

Islamorada, Florida, United States

Bed

Bath

6

Sleeps

$576.03

Amenities: Ocean-view balconies, htd pool, game room, level 2 EV chargerbr Gated Peaceful Palms communitybr Water activity-friendly, paddle boards, dock br Located in Islamorada near dining, marinas, and the famous sandbarbr 24/7 guest support team for a seamless staybrbrTHE SPACEbrWelcome to Mirage, a well-appointed vacation rental designed for relaxed stays in the Florida Keys. With multiple levels, private bedroom spaces, and access to shared oceanfront amenities, this home is well suited for families or groups looking for both comfort and convenience.brbrThe main living area is open and easy to navigate, with a natural flow between the kitchen and living space. The kitchen offers seating for five at the counter, while the balcony just off the living room features partial ocean views and a dining table for six, creating a comfortable setting for meals or time outside.brbrThe bedroom layout is thoughtfully arranged across levels. The second-floor bedroom includes a full-size bed with a trundle and is located next to a full bathroom. On the third floor, both the primary suite and an additional guest bedroom feature king-size beds and private ensuite bathrooms, offering added comfort and privacy.brbr⭐ WHAT YOU'LL LOVEbrbr✔ Ocean-view balconies with outdoor seatingbr✔ Primary bedroom features a private balcony br✔ Located in gated Peaceful Palms oceanfront communitybr✔ Access to shared heated pool and dock areabr✔ Paddle boards (2) and beach gear includedbr✔ Kayak/paddleboard launchbr✔ Multiple levels offering privacy for groupsbrbr ️ BEDROOMSbrbrAll bedrooms include premium beds, linens, TVs, and ample storage space.brbrBedroom 1 (Second Floor): Full-size bed with trundle, located next to a full bathroombrbr♛ Primary Bedroom (Third Floor): King-size bed with ensuite bathroom, private balcony accessbrbrBedroom 3 (Third Floor): King-size bed with ensuite bathroombrbr BATHROOMSbrbrBathrooms are stocked with essentials including shampoo, conditioner, body soap, and fresh towels.brbrBathroom 1 (Second Floor): Frameless shower, single vanity, and toiletbrbrBathroom 2 (Primary Ensuite): Double vanity, frameless rain shower, private toilet, and ample counter and storage spacebrbrBathroom 3 (Third Floor Ensuite): Frameless shower, single vanity, and toiletbrbr BONUS SPACEbrbrA first-floor bonus room off the garage provides additional space to gather, featuring an air hockey table, seating area, TV, and a dining table for six. This space offers a casual area for games or downtime separate from the main living area.brbrThe garage includes a level 2 EV charger, paddle boards, beach chairs, and basic workout equipment for guest use.brbr OUTDOOR + WATER ACCESSbrbrMirage is located within the Peaceful Palms oceanfront community, offering access to shared amenities in a private, gated setting.brbrGuests can enjoy the community pool and oceanfront dock area, along with easy access to the water for paddling or boating.brbrCOMMON AREASbrbrHeated pool + lounge chairsbrRestroomsbrOceanfront boat dockbrbr⚠️ IMPORTANT THINGS TO NOTEbrbrBoat Dockage Information: brbr-Complimentary boat dockage (subject to availability) -Dockage is limited, we recommend reserving dockage upon booking. The dock is not in a protected marina and subject to weather conditions.br-We can accommodate boats up to 24'. Contact us to confirm if the dock can accommodate your boat.br-No trailer storage on-sitebr-No boat ramp on-sitebrbr NEIGHBORHOOD OVERVIEWbrbrLocated in Islamorada, Mirage places you in a central location for boating, fishing, and exploring the Florida Keys. Peaceful Palms is a small, gated community with a quiet atmosphere, while still being close to restaurants, marinas, and local attractions.brbrCOMMUNITY GUIDELINESbrbrPeaceful Palms is a private, gated residential community. To ensure a great experience for all guests and neighbors, parties and events are not permitted, quiet hours are enforced, and parking is limited to designated spaces. Additional community guidelines will be shared prior to arrival.brbr POINTS OF INTEREST (distance measured in driving time, non-rush hour)brbr-Publix ( 6 min) br-Islamorada Sandbar (by boat/paddle): One of the most popular gathering spots in the Keysbr-The Square Grouper (10 min): Waterfront dining with local flavorbr-Morada Bay (10 min): Beach café, sunset views, and eventsbr-Robbie's Marina (12 min): Feed the tarpon, book charters, and explorebr-Founders Park (8 min): Beach access, pool, and recreational areasbrbrHOUSE RULESbrCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrbr*All guests must sign our rental agreement as mandated by Florida Law.brbr- Minimum rental age is 25. A valid photo ID must be provided to the company no less than 72 hours before arrival.br- An accurate guest count must be provided.br- NO PETS allowed.br- No parties or events. Unauthorized guests on property will result in fees and/or immediate eviction.br- Quiet hours are from 10:00 PM to 8:00 AM.br- No smoking or vaping. If evidence is discovered of either smoking or vaping, the guest will be subject to a fine of up to $1,000brbrStarter SuppliesbrWe provide trash bags, paper towels, toilet paper, detergent, and bathroom amenities to accommodate this home's maximum occupancy for the first three days of your stay.brbrSame-Day BookingsbrSame-day bookings require company approval. Guests must provide information about their group and purpose of stay. If approved, a government-issued ID is required for verification. Your phone number must match the phone number registered on your account, or your reservation cannot be honored.brSame-day reservations will not be accepted after 2:00 PM. All same-day bookings require a minimum of 3 hours before check-in, and check-in may be extended later than 4:00 PM.brbrRelease of Liability for Recreational EquipmentbrGuests agree to use paddle boards at their own risk. The property management and owners are not liable for any injuries, damages, or losses related to their use. By using these items, guests release the property management and owners from all claims and liabilities.brbrMID-STAY CLEANING REQUIREMENT:br- For all extended stays of 30 nights or longer, a mandatory mid-stay cleaning is required every 30 days.br- If your reservation is 60 days, two mid-stay cleanings will be required, and so on.br- This helps keep the home maintained during longer stays and ensures everything stays in great condition.br- Mid-Stay Cleaning Fee: $285 to be paid by guests.br- We'll reach out after booking to schedule the mid-stay cleaning(s) and send the payment link.

Villa

Mirage | Islamorada Oceanfront Community, 3BR, Near Sandbar, Pool

Islamorada, Florida, United States

Bed

Bath

Sleeps

$697.1

Sunrise Haven is professionally cleaned including all linens and towels. The owners or property manager do not do the cleaning and laundry. brbrIslamorada, Florida, is known as the Sports Fishing Capital of the Florida Keys. The Maison resort property in Islamorada is half way between Key West and mainland Florida. Sunrise Haven, our Atlantic Ocean beach front condo is located near the heart of Islamorada at Mile Marker 80.6 on the quiet, less traveled, Old Federal Highway, not on the busy US-1 Overseas Highway. Walk to great restaurants, the arts district and marinas in Islamorada. The Maison resort property includes 21 condos, in 4 buildings in a U shape around a very large, 86' x 25', resort style pool and hot tub. Enjoy 350 feet of white sand beach. We provide 2 double kayaks, 2 stand-up paddle boards and a kayak cart to aid rolling the kayaks and SUPS to the beach for our guests private usage. The Overseas Highway, US-1, follows Henry Flagler’s famous railroad to Key West that was destroyed in the deadly Labor Day hurricane of 1935. Miami International Airport is an 85 minute drive. Fort Lauderdale International Airport is a 2 hour drive. From Sunrise Haven a visit to Key West is an easy 80 mile, 90 minute drive. “Downtown Islamorada” is home to a number of great restaurants for casual outside, waterside dining or more upscale seafood, chop or steak dinners. You can walk to the Midway Cafe for an outdoor or indoor breakfast or lunch and the opposite way on the Old Hwy to the famous Green Turtle Inn and Restaurant for all three meals. Fishing charters and scuba diving are close by.brbrWhether you are coming to the Keys for a relaxing, restful break from cold weather to lounge around the pool or on the beach, to catch lobster and stone crabs, to go snorkeling or scuba diving, to spend your time fishing the back country for snook, redfish, bonefish and tarpon or to go off shore fishing for dolphin, wahoo, snapper and grouper, Sunrise Haven in Islamorada can be your comfortable home away from home. The panoramic sunrises and moonrises are beautiful from our condo's main balconies, the beach or the pool area. You can also enjoy sunset from our guest bedroom balcony. Our condo is a legal, yearly safety and fire inspected, private rental in Islamorada. Our Islamorada vacation rental license number is 25-0267.br brThe Maison resort property is an exclusive, private gated resort condominium complex located on the Atlantic Ocean side of Upper Matecumbe Key in Islamorada. It has one of the few sand beaches in the Florida Keys. There is no overnight boat dockage or trailer storage available onsite. There is a 155 foot Day Dock from the middle of the beach into the Atlantic available for daytime dockage. Safe Harbor Anglers House Marina, 305-664-5247, at 80500 Overseas Hwy has a nice launching ramp and may be able to store your boat overnight and your trailer. Safe Harbor Islamorada Marina, 305-664-8884, at 80462 Overseas Hwy may also have overnight boat storage and trailer storage. They may be able to bring your boat to the Maison day dock or golf cart you over to the marina. The common areas of the Maison complex have undergone significant recent renovations that includes an 86 foot by 25 foot resort style pool. The 24/7 hot tub looks out over the Atlantic. The beach area has a gas fire pit, lounges, umbrellas, Adirondack chairs and hammocks. The pool area includes updated lounges, tables and umbrellas. There is a beachside Summer Kitchen with a Chickee covered eating area and two 30 inch gas BBQs. You can relax in a hammock, a lounge or at an umbrella shaded table and read a book on the beachside terrace. Snorkel or swim from the beach or the ladder on the day dock platform, fish from the day dock or have fun with our 2 kayaks and 2 stand-up-paddle boards for your private use. Only our condo supplies Stand-Up-Paddle Boards for our guest's usage. We also have some fishing equipment in the parking area storage closet for use on the day dock. Since the equipment is used by guests we cannot guarantee how good the equipment has been maintained. Please try to keep saltwater out of the tackle box. If you buy hooks, sinkers, etc. feel free to leave the excess in the tackle box. Please rinse all equipment including the fishing poles and reels with fresh water after fishing.brbrOur 3 bedroom, 3 full bath multilevel condo is located on the upper two levels of the three story building #3 for added privacy. It has two sunrise ocean/beach/pool facing balconies and another sunset balcony off of the upper floor guest bedroom. Only 2 condos have west facing balconies. All three bedrooms have room darkening window treatments. The upper level contains the master bedroom/bath, the first guest bedroom/bath, and full laundry room. The master bedroom has a wet bar/mini-kitchen with refrigerator, coffee maker, electric tea kettle, walk-in closet, hotel style safe, sunrise, ocean facing balcony and a huge master bathroom with a large jetted tub, separate shower area and double vanities. The upper level guest bedroom has two double beds, a small exterior deck with nice views of sunset and accesses the second full bathroom. The lower level has the open dining area, kitchen and great room with a wet bar, wine cooler and a wall mounted HDTV with DVR, DVD and stereo system. The northeast wall of the great room is two sets of sliding glass doors that open onto the balcony with a relaxing seating area for 6 adults and a glass top table with 6 chairs for outdoor dining. The lower level second guest bedroom has a queen bed with access to the third full bathroom. The kitchen has granite counter tops, tile back splashes, quality appliances, wine cooler and an eat-in/bar area with stools. The kitchen is stocked with all necessary small appliances, cookware, serving pieces, cutlery, etc. All bedrooms have HDTVs, cable boxes and room darkening window treatments. You can nap at any hour of the day.brbrSunrise Haven has the X-1 Comcast Cable system with voice remote activation and XFI residential Internet access. You do not need to know the channel number, you just speak into the remote ESPN or ABC or NBC or a movie name and the cable box will respond to the HD channel.brbrMost of our high season rentals are Saturday to Saturday but the weekly rental can be any 7 consecutive days depending upon the season. Sunrise Haven can accommodate 6 adults & NO children or 4 adults & 2 children or 2 adults & 4 children. We cannot accommodate more than 6 adults which includes teenagers.brbrNeed baby gear during your stay We have some baby gear that is available to our guests. brThis includes a full sized crib, high chair, and a couple of pack-n-plays. We do not have enough to supply both of our vacation rental properties in Islamorada, so check with us first We have set up an account with BabyQuip to help our guests with obtaining baby stuff to make their vacation easier and safer.brbrRent cribs, car seats, strollers, toys and more from BabyQuip! As seen on Shark Tank, BabyQuip offers clean, sanitized, and safe baby gear in Islamorada. Visit Sunrise Haven’s unique link https://www.babyquip.com/a/wst21v to make a reservation.brbrIt is likely the only disappointment you will experience at Sunrise Haven is having to depart at the end of your vacation stay. Many of our guests return yearly, some for a month or more, but most for a week. You can join our group of loyal guests.brbrIf you are looking for a weekly Islamorada vacation rental property that can accept boats overnight, please look at Sunset Reef, our bay side 4 bd, 4 1/2 ba private estate at MM 76, www.vrbo.com/809744 or www.HomeAway.com/809744. We also have a Park City/Deer Valley, Utah 4 bd, 4 1/2 ba vacation rental home, www.vrbo.com/206330 or www.HomeAway.com/206330.

Condo

Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock

Islamorada, Florida, United States

Bed

Bath

Sleeps

$151.49

Drive down south to enjoy the tranquil and beautiful Florida Keys. Enjoy a cozy and spacious townhome in the heart of Islamorada. Located within a gated community with 24 hr. security. Includes fully equipped kitchen w/ granite countertops, microwave and s/s appliances; With washer & dryer, plasma TV, electric outdoor grill, cable, and phone. Sleeps up to 8 - oversized master bedroom w/ one king bed, TV, walk-in closet and loft access with 2 twin beds. Second bedroom includes 2 double beds & balcony. Two pack-n-plays, baby tub, and portable high chair available. Outdoor sitting area/patio and private beach,pool, 2 tennis courts, clubhouse, playground, and bbq grill within community grounds. Enjoy FL Keys sunsets as you fish from pier or sip on your favorite cocktail. Boat ramp and marina available next door at Founder's park or nearby marinas for your convenience.

Charming and Cozy Townhouse in the Fl Keys with Pool and Beach Access

Islamorada, Florida, United States

Bed

Bath

Sleeps

$797.27

Enjoy a peaceful stay at this 3-bedroom house in Islamorada. The bedrooms feature a queen bed, bunk bed, and king bed, ensuring a comfortable night's sleep for all guests. With amenities like a hair dryer, heating, AC, and iron, you'll have everything you need for a relaxing getaway. The 2 bathrooms offer a shower and jetted bathtub for ultimate relaxation. Experience the magic of Islamorada at our welcoming house. This home has over 75 foot dock. State of the art fish station. Come and relax with the whole family in luxury. Paddle board straight from the home while others stay in the pool or go fishing. The most peaceful backyard I have stayed in. This home is beautiful in and out and it's in the heart of Islamorada. Only minutes away from all the restaurants and stores.

Luxury vacation home. This is Paradise. Perfect for all family occasions.

Islamorada, Florida, United States

Bed

Bath

10

Sleeps

$1421.76

This unique home is located directly on Snake Creek which is ideal for experiencing the amazing sunsets and convenient for any and all water activities. The property has ample room to dock any size boat in a protected lagoon as well. Easy access to both the Atlantic Ocean and Gulf via Snake Creek make navigation around the area simple and quick.brbrHome features the primary living area which consists of three bedrooms (king size beds) and ample room for an addition bed if needed. brbrThere is also a separate apartment downstairs that sleeps four adults for any party needing additional capacity (for an additional cost).brbrHome comes with all the sheets and towels you'll need for your stay, The kitchen and bathrooms are well stocked. brbrThe downstairs living area has recently been remodeled and makes a great area for outside entertaining and relaxation. In addition to the large pool and hot tub, amenities include a large dining area, pool table, lounging and sitting areas, and two large TV's. Any number of games are provided including a ping pong table as well. Also located in this area is a large capacity ice maker and bin that stores 400 lbs of ice.brbrThe home is located in the highly regarded Venetian Shores community centrally located in the heart of Islamorada (MM 86) and close to many dining and entertainment options. There is a Publix less than two miles to the south as well. Tenants will have access to Founders Park which offers Pickleball and Tennis Courts and a lap pool and beach and other outdoor activities.brbrMinimum of 28-day stays are desirable, but owner will consider shorter stays if necessary.brbrA 40k boat lift is available for an extra fee.

Stay at the Pirate House conveniently located on Snake Creek in Venetian Shores

Islamorada, Florida, United States

Bed

Bath

8

Sleeps

$1289.23

Welcome to Flamingo Bay, where luxury, space, and jaw-dropping beauty come together on the sparkling open waters of Florida Bay in Islamorada. This massive private estate is a true showstopper, with three separate buildings designed for comfort, fun, and unforgettable memories. The main home features four spacious bedrooms, two full kitchens, an elevator, and a bright Florida sunroom that opens out to the pool. A separate two-bedroom, two-bath guest house with its own kitchenette offers the perfect retreat for friends or family, while the game house brings the entertainment with a pool table, dart board, TV, and bar area. Step outside and you'll find paradise—your own private pool and hot tub, kayaks and paddleboards for exploring the bay, and a tiki hut at the end of the dock that feels like it was made for watching the most spectacular sunsets you've ever seen. Whether your days are spent fishing, boating, snorkeling, or simply soaking in the Keys sunshine, Flamingo Bay is more than a place to stay—it's an experience you'll never forget.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.

Flamingo Bay: Stunning 6BR home with breathtaking open water views in Islamorada.

Islamorada, Florida, United States

6

Bed

8

Bath

12

Sleeps

$1233.0

Welcome to 116 Gulfside Drive — a breathtaking waterfront retreat in one of Islamorada's most desirable neighborhoods. From the moment you walk through the door, panoramic bay views draw you in, flooding the home with natural light and capturing the beauty of the Florida Keys.brbrThe main level offers bright, open living spaces designed for both style and comfort, along with three beautifully appointed bedrooms. Downstairs, a private apartment-style fourth bedroom with its own entrance is perfect for guests, in-laws, or anyone wanting extra privacy.brbrStep outside and discover where this home truly shines. Lush tropical landscaping frames a sparkling pool and spa, creating your own resort-like oasis. Multiple outdoor seating areas make it easy to relax, entertain, and savor the unforgettable sunsets over the bay.brbrFor boaters, this property is pure paradise—tie up at your own floating dock or keep your vessel in a private slip at the Venetian Shores Marina, offering quick, bridge-free access to both the ocean and Florida Bay via Snake Creek.brbrPerfectly situated on a peaceful street yet just minutes from world-class fishing, dining, and shopping, this home delivers the very best of Islamorada living. Whether you're setting out on the water, enjoying a cocktail at sunset, or simply unwinding in paradise, 116 Gulfside Drive offers a Keys experience you'll never forget.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.

Bellavista: Luxurious 4-bedroom home with stunning open water views in Islamorada.

Islamorada, Florida, United States

4

Bed

Bath

8

Sleeps

$306.95

Your home away from home in Islamorada with 3 bedrooms plus a loft. This cool townhome features a king bed, queen bed, 2 twin beds, and full bed (Loft) to accommodate all guests. Enjoy the convenience of a washing machine, hair dryer, iron, heating, AC, and WiFi during your stay. Located in the best building of EBC, within seconds from the pool and the bayside beach area! We have a marina where you can watch the boats come in and/or the beautiful sunsets. Community has a heated pool, pickle ball courts, and next door there is FOUNDERS PARK that has many amenities and activities for all!brMake your holiday one for the books with a stay at our place.

Charming 3-bedroom townhome in fabulous Islamorada seconds from the bay!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$269.39

Welcome to Paradise Cottage!!brbrThis downstairs portion of a dual family dwelling is fully renovated a 1/1 cottage with breathtaking oceanfront views. brSleeps four comfortably. brPrivate bedroom with queen bed. brLiving room has two full size futons.brNew kitchen with all stainless steel appliances. brVery cozy and great views to enjoy in your dream vacation. brAmenities provided are kayaks, bicycles, grills, boat ramp and boat dockage for your use with no extra fees. brbrPrivate boat dock and convenient boat ramp. Amenities for your boat includes water and electricity(only 110volts) by the dock, brush and soap, extra fenders, and a small freezer for bait and ice. Trailer parking is available on our acre and a quarter property. The ramp and dock use are part of the rental amenities!brbrRelax and enjoy ocean views and gorgeous sunsets from the comfort of our multiple loungers. brbrPlenty of parking for all of your toys in my acre and a quarter property(boat, trailer, car, etc). brbrBBQ areas with plenty of seating and a separate picnic table perfect for lunch and snack time. brbrBath towelsbrBed linensbrHair dryerbrWifibrCable brTV in living room and bedroom. brWasher and dryerbrAll appliances in kitchenbrCoffee maker (K-cup and drip )brToasterbrBlenderbrPots and pansbrbrClose to all attractions and best restaurants. brbrThose who want to charter a fishing captain upon request please contact Captain Avila or other captains from Whahoo Marina.

Cottage

Oceanfront Private Cottage!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$681.49

⭐️5 bedroom 4 bathrooms (One bathroom by pool)br⭐️Canal home in Venetian Shores with access to bay and oceanbr⭐️100 foot of dockage on 100 foot wide deep canal. Ask about bringing your own boatbr⭐️Location of canal is off Snake Creek near MM86br⭐️ Beautiful large pool with hot tub in tropical settingbr⭐️ Tiki bar and lounge areas x 2 for you lounging pleasurebr⭐️We have all the comforts of home in a beautiful tropical setting br⭐️Please message us to discuss your needs for your stay! We love hearing from what brings you to the Keys and how we can help!brWelcome to Golden Resort of Islamorada in the beautiful Florida Keys. Our large 3600 square foot home is a 5 bedroom 4 bath canal home located in Venetian Shores with 100 feet of dockage and easy access to the bay and the ocean via Snake Creek. Our home is perfect for your extended stay in Islamorada. Upstairs we have 3 bedrooms. Master king bedroom has it's own private bathroom, another king bedroom that shares the hall bathroom with another bedroom that has 2 queen beds. There is a beautiful kitchen with oven, microwave, stove, refrigerator and dishwasher as well as a small breakfast area for dining and large pantry. Another dining room is off the living room. There is a full washer and dryer as well. Lastly there is a screened in porch with outdoor dining available as well as a sitting area for enjoying the sunsets! Our living room has a large 75 inch smart TV is available for your viewing please. Internet is At&t Fiber for fast streaming capabilities. Our downstairs has another full equipped kitchen with oven, microwave, dishwasher, stove and refrigerator. Also in the kitchen is another washer and dryer set. Downstairs dining area is available both inside and outside. There is a king room and a queen room with bunk beds and a hall bathroom for these 2 bedrooms to share. Outside we have a resort style pool that can be heated in the winter for an extra charge. Next to the pool are 2 tiki areas with bar and couches for lounging. We also have a sun deck for enjoying the warm Islamorada sun. We are located near MM 86 in Islamorada. If you would like to bring your boat please message us.

Villa

NewListing Canal Home Snake Creek with Bay&Ocean Access Tiki&Pool 100ft Dockage

Islamorada, Florida, United States

5

Bed

4

Bath

14

Sleeps

$309.38

1940s Old Keys Fishing Cottage with dockage available. Large Waterfront property and walking distance to world famous Lorelei Cabana Bar & Restaurant as well as local breweries too ! This 1940s original Keys Fishing Cottage is not fancy, as the ad's photos show, but in great location and has everything you need for a great Islamorada getaway. We can arrange custom days of stay if you are booking a sunset/sandbar/fishing charter with our family. Enjoy the peace and privacy of the large, natural waters edge property with the convenience of being minutes away from some of the best dining and outdoor activities in the Florida Keys. Dockage is available on site for additional charge with free trailer storage. Relax in our 1940's Old Florida Keys style cottage which is updated while still maintaining its original look and feel ~ Original open beam ceilings and hard wood floors. Wi-Fi . Central air. King size bed in bedroom. There is one bath with original 1940s tile on walls, laundry area with full size washer and dryer. There is a second room that offers a desk for remote work and sitting area as well. We want you to enjoy your experience in the beautiful Florida Keys !! We are lifetime residents and our children born and raised here as well. This property is located conveniently within walking distance or at most ,less than half a mile to most Islamorada restaurants and local breweries. Kayak rentals and paddleboard rental is available for delivery to property. Great area for kayaking and paddle boarding. Launch right from water's edge of property. Please contact me prior to booking with any questions as I always want to make sure that the cottage is a good fit for prospective renters. Dockage is available at property for up to 35' boat for a fee of $50 per day with free trailer parking on premise payable upon arrival. No children please as the property is not fenced along the extensive water frontage and is not suitable. Thanks for checking out our listing :) If you book you will have a great time! *** Dockage Fee of $50 per day payable upon arrival and is NOT included in VRBO reservation fees and can be discounted dependent on length of your stay. You will have a fun time!! One Pet under 20 lbs welcome.. PLEASE ADD TO YOUR RESERVATION WHEN BOOKING. Thanks so much for liking our place ! :)

Cottage

WATERFRONT FISHING COTTAGE/ DOCKAGE + Walking distance to world famous Lorelei

Islamorada, Florida, United States

Bed

Bath

Sleeps

$955.58

Summary:brStunning ocean views from all living levels & a waterfront pool!brbrThe Space:brWelcome to the captivating Marlin House, an extraordinary 4-bedroom, 4-bath retreat nestled in the scenic paradise of Islamorada. Prepare to be enthralled by its exquisite design, unparalleled amenities, and sweeping ocean vistas that grace every level of this remarkable abode. Your journey begins as you pass through the gates of Tarpon Point, an exclusive enclave comprised of just twelve oceanfront residences. Within this private sanctuary lies Marlin House, waiting to envelop you in a world of sheer luxury.brbrAs you step foot inside Marlin House and ascend to the main living level, a symphony of awe-inspiring ocean views unfolds before your eyes. The sheer beauty of the surrounding turquoise waters will leave you breathless. Adjacent to the living area, an elegant dining room and a chef's kitchen beckon, promising unforgettable culinary experiences and convivial gatherings. This level also houses the first of three splendid guest bedrooms, each adorned with expansive closets to ensure ample storage space. In addition, every bedroom and the living room boast internet-enabled smart televisions, offering seamless access to your preferred streaming services.brbrVenture up to the third living level, where two more resplendent guest bedrooms await, each boasting its own ensuite bath. As you stroll down the hall from the guest bedrooms, prepare to be captivated by the main bedroom, a sanctuary that epitomizes refined coastal living. With its breathtaking ocean panoramas, a sprawling private balcony, a cozy reading nook, and a generously sized closet, this tranquil haven invites you to unwind in blissful serenity. The ensuite bathroom is an oasis of indulgence, featuring a sumptuous soaking tub and lavish Toto fixtures, ensuring a pampering experience beyond compare.brbrBeyond the confines of Marlin House, the gated property offers a wealth of amenities designed to enhance your stay. Immerse yourself in the refreshing embrace of the community waterfront pool, bask in the sun-drenched beach area, or cast a line from the fishing pier, all while enveloped in the meticulously landscaped grounds that surround this coastal retreat.brbrMarlin House beckons, promising an escape to a world where luxury meets coastal splendor. Experience the epitome of refined living, where every detail has been carefully curated to exceed your expectations. Unleash your senses to the breathtaking ocean views, savor the state-of-the-art amenities, and allow yourself to be swept away by the sheer beauty that awaits within these hallowed walls. Your perfect getaway starts here, at Marlin House, where memories are made and dreams come true.brbrThis home is managed by The Florida Keys Rental Store. For recommendations or things to do while in the keys, we have all the information you could need. Over 20 years in the business, we know what it takes to make your trip the best one yet!brbrNotice to Guests:brTarpon Point is not a rental community or resort. The homes are private homes and are the private property of the owners, some of whom live there full time. You need to be aware that you are sharing common areas with owners of the Tarpon Point Community. As a guest, it is imperative you ensure all of your party are respectful of both the private property in and around each home and respectful in your use of the common areas

Marlin House @ Tarpon Point

Islamorada, Florida, United States

Bed

Bath

Sleeps

$403.39

brPrivate, secluded villa faces Florida Bay in view of the fabulous Everglades. Located in a lush tropical hammock in a quiet residential area (rare), the villa is approx. 50 feet from the water. The property contains a wading beach and a free marina with night lights, power and water.brbrFree onsite boat ramp, marina, and trailer parking.brbrThe villa itself comes with a fully-equipped kitchen, washer and dryer, linens, queen and king beds, Cable TV, VCR, and a Florida room for dining. Windows in the living room and bedroom cover two thirds of the wall giving the feeling of the outdoors being in during the day and easy open/close window coverings provide privacy at night. This is a small house, near the water, no high-rise, no canal, and no density of people problem. This is a laid-back atmosphere for those who desire it.brbrLocated on Upper Matecumbe Key, the downtown area of Islamorada, the property is quiet and hidden. Boats up to 25' are secure in our protected marina. Most trailers are able to launch from the property but a few extra-wide may have to use nearby launching places. There is trailer parking on the property as well as two parking places per unit. There are seven units on the property.brbrbrFree use of the village park(tennis, pickle ball, beach, pool, and dog park) is provided to guests. There are three state parks in the Islamorada area and the owner will provide passes. You are within walking distance to the best restaurants, shopping, and attractions. Free electric taxis are able to take you anywhere in town. Grocery, fishing and boating supplies are conveniently close.br brIslamorada proudly calls itself the 'Fishing Capital of the World' and fishermen love us!brLocated close to the best backcountry fishing on the edge of the Everglades, we are also able to easily access reef and blue water fishing. Our immediate bay provides fun catching tarpon and easy fishing on our seawall at night is a guest favorite. Owner has names of boat rental places and guides for all types of fishing and snorkeling. Next door to us is Back Country Cowboy. They rent kayaks, canoes, paddle boards, as well as bicycles. our bay is the perfect, protected area for all water activities. Oceanside, we have some of the best snorkeling and scuba areas in the Keys!brbrThere's never a dull moment at our marina. We have an Osprey nest nearby. If you clean fish, you'll have lots of bird friends. Other visitors are manatees, octopi, and nurse sharks.brThis property is treasured by guests and owners alike. The privacy is wonderful, the property peaceful, and the villas kept clean and updated. Most of our guests come year after year. Some have met friends one year and make the same dates together the next year. The size of the property is perfect- not too big, just right.brbrThree or four years ago, Fox News had a US Best Sunsets contest. Someone submitted one of our guest's pictures and we recognized it! Our sunset won over thousands submitted. Come and enjoy the best The Keys has to offer. Best location, best property, best fishing, and the best sunsets.

Villa located on the water Free marina, and trailer parking.

Islamorada, Florida, United States

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Bath

Sleeps

$447.59

This Keys Home is Located in Beautiful Port Antigua. 4 Br/ 3 Ba Sleeps 8 Comfortably. All Rooms Have Queen Sized Beds. Large Kitchen and Dining Room. Large Gathering Areas Throughout the House. There is Also a Barbecue and Gas Stove Downstairs. Features 60' Dock for Your Boat With Deep Water Access to the Florida Gulf and Atlantic Ocean in Minutes. Enjoy Fishing in the fishing Capital of the World. Private Beach Access With Tiki Huts and Barbecues for Your Use. Golf Cart and Multiple Bicycles Available.

Port Antigua Waterfront Home With Private Beach Access

Islamorada, Florida, United States

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Bath

Sleeps

$305.31

This spacious two bedroom, two bath condominium overlooking the ocean is located on a quiet 12 acre private gated community. Includes a 30 foot boat slip in a protected marina with direct access to the ocean. Eat in kitchen with breakfast bar open to living area that looks out over the water. Expansive patio for open air dining or lounging. Main bedroom has an ocean view, opens to screened patio, a king sized bed, private bath with soaking tub and walk in shower. The split floor plan design provides a private additional bedroom with a spacious bathroom. Ideal for remote workers, retirees wishing to spend winter in a warm, sunny locale or families looking for an adventurous escape. Large heated community pool and hot tub. Lighted tennis courts. Onsite boat ramp. Club house features a large community room and full gym. Outdoor covered dining area with picnic tables, a gas grill, and ice machine.

Condo

Ocean Harbour Condominium is an Oceanfront Fisherman's Paradise in Islamorada

Islamorada, Florida, United States

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Bath

Sleeps

$1595.07

Little Bay Compound - Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units, accommodating a total of 18 people. brbrThe Upper & Lower Duplex are each 1,500 sq ft units, each with two bedrooms, two full baths, full modern kitchen, laundry, family room, and 10' x 40' porch overlooking the bay. Each unit accommodates 6 people (upper master bedroom: king and twin murphy, Guest bedroom: two twins, sofa sleeper) (lower master bedroom: queen and twin murphy, guest bedroom: two twins, sofa sleeper)brbrThe Cottage is a bright and airy 1,250 sq ft unit with a huge master bedroom (king & sofa bed), 2nd sunroom with sofa bed and twin murphy bed, two full baths, laundry room, and combined family room, kitchen, & great room. The Cottage accommodates 6 people. brAll units come equipped with central a/c and ceiling fans, loads of outdoor furniture and BBQs for each unit, large private boat basin with 12' X 25' Chickee hut and 12' X 25' Pergola, bait prep station, freshwater shower and power on the dock. The spacious front yard is enhanced by Tropical Landscaping and offers a large circular driveway with plenty of parking for cars and trailers. Located in the heart of Islamorada within walking distance to water & land activities, restaurants, shops, and more! brIf booking more than a year in advance current prices may not reflect 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. 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.brVR#- 24-0336, 24-0334, 24-0335 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.

Experience luxury at Little Bay Compound in Islamorada with stunning views.

Islamorada, Florida, United States

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Bath

Sleeps

$397.77

- VR#258 - Saturday check-in. 2 bedroom and 2.5 bath at 117 Anglers Way with Boat Slip #36 available.brbrAwesome family get-a-away in beautiful Islamorada. The ocean views from the back decks are amazing. The Oceanfront pool is serene! The gated community is a family-friendly immaculately kept park-like setting. Perfect for evening strolls. Located in walking distance to swim with the dolphins at Theater of the Sea and local restaurants and bars, Anglers Reef is the perfect family get away for boaters, kayaker's, paddlers, foodies, historians, honeymooners, couples, snowbirds or anyone that wants to experience the Florida Keys.brbrThere is no other neighborhood like Anglers Reef in Islamorada. It has beautiful Key West style pastel colored homes inside a resort community, with garden-like flora and fauna, such as bougainvillea, meticulously maintained. There is a fantastic oceanfront swimming pool and boat docks with views over the Atlantic Ocean that will take your breath away! Just minutes from many local shops, bars and restaurants. Access to the ocean does not get any easier than at Anglers Reef. When we first found Anglers Reef on vacation six years ago we were sold and never went anywhere else.brbrThe Lucky Lobster:brbrThere Are 52 Homes at Angler's Reef with 36 Boat Slips. It is a Safe, Gated Community with very little traffic, truly an oasis. brbrYou will know you are someplace special when you see our 2-bedroom, 2.5-bathroom house surrounded by wonderful landscaping- amazing palms, bougainvillea, and some of the most colorful tropical foliage that only the tropical Florida Keys can offer.brbrThe Lucky Lobster’s first floor offers a spacious, wide open layout with a couch with sleeper. Granite counter tops and all updated appliances, this open kitchen is stocked with pots and pans, utensils, plates, a Keurig Coffee Pot & everything you will need to prepare anything you desire. Stay entertained during your downtime by watching your programming of choice on any of the home’s 3 flat screen TVs with cable or surf the web via the complimentary wireless internet access. There are also community kayaks and SUP available for use (please see waiver).brbrChildren of all ages will love the pool and the fact that there is no road traffic. The geckos and fish will keep young kids entertained for hours!brbrThroughout your visit, you and your companions will get to enjoy outstanding recreational facilities at Angler’s Reef. These community amenities include a heated swimming pool with outdoor bathrooms, chaise lounges, chairs/tables overlooking the breathtaking blue waters of the Atlantic Ocean, boat slips available for rent and kayaks/SUP for your use. Look forward to soaking up the sun at either of the 2 private beaches, located just a few short steps away from every home that flank the marina. The world-famous Islamorada “sandbar” and Alligator Reef are just a short boat ride from the marina. You also have free access to Founders Park with your reservation. The park features an Olympic size swimming pool, beach, sand volleyball courts, splash pad play area, tennis courts, playgrounds and an outdoor fitness park/walking trail. Come to Angler’s Reef and experience paradise! brbrRegistration Number: vr#258

Anglers Reef Islamorada - 2:2.5, Boat Slip, Pool & Beach

Islamorada, Florida, United States

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Bath

6

Sleeps

$534.74

This canal front home is located in the prestigious Venetian Shores neighborhood. The perfect location right off of Snake Creek, which gives you fast access to both Ocean & Bay, fuel, bait, and provisions.brbrThis beautiful, updated canal home has two bedrooms, two baths upstairs and a one-bath studio apartment downstairs. It offers various sleeping arrangements. 8 people can be accommodated upstairs and 4 people downstairs.brbrThe House:brUpstairs has Two Bedrooms, a king-size bed in the Master with en-suite bathroom, a twin/full/twin bunk bed in the other guest suite. There is also a nice size guest bathroom upstairs. The couch upstairs has a large pull out couch and there is a day bed in the sunroom area with 2 twin beds.brbrDownstairs has a queen size hide-a-bed, as well as a large pull-out couch. Enjoy the convenience of a first-floor bathroom and a full, updated kitchen. Perfect for entertaining!brbrThe home is fully stocked with all kitchen supplies and upscale appliances (Cuisinart toaster oven/airfryer, convection oven, espresso machine, coffee maker, Ninja blender, all new knives and pots/pans). New washer/dryer in laundry room, games for family fun including: ping-pong table, corn hole set, darts, 3 cruiser bikes, and 2 kayaks). Pool is maintained each week has a cooler and heater and is lit at night. Outdoor table converts to a fire pit. Traeger grill is also provided.brbrThe Dock: Your 35-foot private dock with a boat lift provides instant access to fun – whether boating, fishing, swimming, or relaxing. Boatlift can accommodate up to 14,000 lbs. Have your boats or yacht waiting just outside your door. Large, deep-draft sailboats or yachts are easily accommodated with a waterway 20 ft 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.

Canal front home in Venetian Shores. Perfect for families. A boater's paradise!

Islamorada, Florida, United States

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