Vacation Home Rentals By Owner In Islamorada, FL

Angler's Reef is located at MM85 in Islamorada, the heart of the Florida Keys. Our gated community is made up of 52 luxury waterfront villas accompanied by a boat basin with 36 slips, and a pool among the many amenities.brbrEnjoy the expansive views and ocean breezes from the wrap around balconies on the first and second story. Fully remodeled chef's kitchen with top of the line appliances, quartzite counters, eat at bar, large pantry and extra beverage/bar fridge. Kitchen is fully stocked with cookware, dishes and appliances. Gas grill outside. Starter toilet paper and paper towels, basic cleaning items, drip and Keurig coffee makers, and basic spices in kitchen are included.brbrOne bedroom downstairs with queen bed and ensuite bath. Upstairs bedroom #1 has a queen bed. Upstairs bedroom #2 has 2 full beds. Hall bath and washer/dryer upstairs. Primary bedroom upstairs has king bed, private bath and amazing wrap around porch. Linens, bath towels and beach towels are all provided and replaced often.brbrBoat slip fits boat up to 31ft and is included with your rental. The community also provides kayaks for your enjoyment (first come/first served). No trailer parking onsite.brbrSmart TV to log in to your favorite streaming services, wifi, board games, some childrens' toys provided. Highchair and pack n' play for our littlest guests. brbrPictures and description are representative of accommodations provided but are subject to change. brbrNo pets allowed! Service animals will be accommodated but prior notice and HOA approval is needed. Please contact owner PRIOR to arrival for accommodation. brbrLicense #VR-226

Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.

Islamorada, Florida, United States

4

Bed

3

Bath

8

Sleeps

$237.86

Discover your ideal getaway at this charming seascape in Islamorada! This lovely 3-bedroom, 3-bathroom townhome, complete with an additional loft, accommodates up to 10 guests. With ample amenities to keep you busy such as pickleball, tennis, pool, and beach you’ll be ready to spend your days soaking up the sun and salty air at this bay-side retreat.brbrAs you enter, you'll find a contemporary kitchen outfitted with stainless steel appliances and a coffee bar. The open layout seamlessly connects the kitchen, dining area, and living space, making it great for gatherings. The main floor also features a laundry area, a full bath, and a back patio equipped with a grill. Venture upstairs to discover a master suite with a king-size bed and en-suite bathroom. There are two more guest bedroom, one with a queen bed, and another with a full size bunk and twin size bunk— both sharing a full bath. Additionally, this floor offers a loft with two twin beds, accessible via a ladder. brbrExecutive Bay Club is conveniently located next to Founder's Park, which features an Olympic-sized swimming pool, a children's splash pad, a beach, picnic areas, playgrounds, fitness and walking trails, a basketball court, soccer fields, baseball diamonds, pickleball courts, and a golf driving cage. If you require docking facilities, Plantation Yacht Harbor Marina boasts secure marina access with 80 boat slips available for daily, weekly, monthly, or annual rental. Amenities at the marina include electric, water, sewage pump-out, and fuel sales, along with a boat ramp and dedicated trailer parking. You'll also be just a short distance from some of the best dining and attractions in the Keys, including Marker 88, MEAT Eatery and Taproom, and Rain Barrel Village.brbrAt Executive Bay Club, the activities are endless. The pool and clubhouse were fully remodeled in summer 2025, offering fresh, modern accommodations for guests to enjoy. Spend the day lounging at the private beach, cool off in the sparkling pool, play a round of tennis, or take a sunset stroll to the end of the dock. brbrHave any questions Feel free to ask away! Coastal Vacation Rentals of the Florida Keys is located in the heart of Islamorada and has a full office staff to ensure you have the best vacation possible.brbrReservation Deposit & Cancellations: A reservation deposit equal to one-half (50%) of the total reservation amount is due at the time of booking. TENANT shall be entitled to a refund of the one-half (50%) reservation deposit, less any non-refundable fees, if the reservation is cancelled at least 60 days prior to the occupancy date. The remaining balance, including any required security deposit, is due no later than 60 days prior to the occupancy date. If the cancellation occurs within 60 days of the occupancy date, the full reservation amount shall be non-refundable. If the booking is made less than 60 days prior to the occupancy date, the full reservation amount shall be due at the time of booking, and TENANT shall not be entitled to a refund of any amounts paid in the event of cancellation. As an exception to the foregoing, TENANT shall be entitled to a refund of all amounts paid if COASTAL re-rents the property for the same amount and for the full rental period. If the property is re-rented for fewer days or at a lower rate, COASTAL may deduct from the refund the difference between the total amount due under TENANT’s original reservation (including all taxes and fees) and the amount received from the subsequent rental. brbrInstant quote prices and calendar availability are subject to change without notice and are not guaranteed. Please contact Coastal Vacation Rentals of the Florida Keys to speak to one of our associates to confirm pricing and availability.

Executive Bay Club R8 ~ 3 Bed / 3 Bath + Loft Townhouse on Plantation Key

Islamorada, Florida, United States

Bed

Bath

Sleeps

$202.84

This is a quaint, ocean side condo with full amenities and easy access for fishing, diving, snorkeling and much more.The apartment sleeps 2-4. It has a king bed in the bedroom, a pull out sofa bed in the living room, a fully equipped kitchen, a garage with additional fridge/freezer. Boat/trailer storage in boat yard included on availability and easy ramp access. Fish cleaning table and BBQ grill also on property.brbrThere is an ocean of things to do for everyone. Shopping, Keys themed restaurants both inexpensive and high-end all over the islands. There is swimming, tennis, pickle ball, snorkeling, diving, bird watching, historical interest, botanical, culture, kayaking, wildlife and pondering life. The property is a nature lovers dream with an occasional manatee in the canal, iguanas that sun themselves on the dock, pelicans, egrets and osprey that fly in for a hello there.brbrWe can accommodate a registered 25 ft boat, dockage is included in the rental on availability. There is a heated pool, tennis court, shuffle board and more.brbrThe area is world renowned for bonefish, permit, tarpon fishing and offshore fishing for dolphin, tuna, wahoo, swordfish, sailfish, etc. etc. etc. This can be your own personal paradise.

Condo

Ocean Side Condo In Paradise Mm 76.5-Islamorada, Fl (28 day minimum required)

Islamorada, Florida, United States

Bed

Bath

Sleeps

$479.26

**Please contact owner directly via email if dates do not appear on calendar** There is also an in-laws quarter 1/1 available. Inquire withinbrbrEnjoy the Florida Keys from our beautiful spacious 3 bedroom 2 bath home in the fishing capital of the world, Islamorada Florida. **FAST WIFI** Our home features a large master bedroom with a private master bathroom, king size bed, TV and desk for those that need to work and play. There are two other bedrooms. Both have TV's, one has King size bed, the other a Twin over Full Bunk Bed with an additional Twin Trundle underneath. In addition there is a Sleeper Sofa in the living room. Our home also features an over-sized balcony on the 2nd floor with a dining table, BBQ, and ample seating. Downstairs there is a covered patio area where you can play Foosball or enjoy a cocktail under our mango tree. The downstairs patio area also features a sitting area, BBQ, and dining table. The home is very spacious with a fully updated kitchen that is attached to a large living room. If cooking is your thing we have everything that you need to make a delicious home cooked meal. There are also many local restaurants that you can visit or order take out. One of our favorite spots is the Islamorada Fish Company where you can shop, watch the sunset, have a cocktail or sit under the tiki hut and have delicious meal. Our family enjoys many afternoons fishing, and exploring the Florida bay and Atlantic ocean. There are many local places to visit and interact with nature. If you are looking for comfort you have found your home away from home. Our balcony is one of our favorite spots in our home it over looks the canal where you can enjoy your morning coffee, have lunch, take a nap or watch the manatees as they often like to visit. Our home also features a large dock which easily accommodates your boat, or jet skis. We are on a deep water canal with easy access to the bay or ocean within minutes. We have a fish cleaning station as well as an ice machine and a bait freezer. There is a convenient private ramp where you can launch your water toys. One of our favorite community features is our PRIVATE beach which you can access via car, bike, walking or boat. The beach is only accessible to residents of our community. Catch an early sunrise or sit and watch as the sun sets over the bay, it is truly inspirational and breathtaking. After watching the sunset come back home and enjoy a quiet evening playing board games, reading a book or simply catching the breeze. Our home is very kid friendly, (we have 5 kids) so the home is fully equipped with board games, Foosball table, books, mini basketball hoop, dart game and an X BOX 360 with family ,sports and dancing games! If fishing is your thing this is the home for you, if relaxing is your thing this is the home for you, if you have children young or teenagers this is the home for you. Our family has enjoyed many great times and we have made many wonderful memories here! We look forward to you and your loved ones enjoying our little piece of paradise!

Spacious Home in Islamorada with boat dock, private beach, & Fast

Islamorada, Florida, United States

Bed

Bath

Sleeps

$573.55

Come Play! Your 70-foot private dock provides instant access to fun – whether boating, fishing, swimming or relaxing under the shady, palm-roof “Chickee.” Enjoy your privacy with independent upstairs/downstairs units - friends, family, or guests will appreciate the extra bed, bath, living room and refrigerator downstairs.brThe Dock: 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 foot 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. br*****Love Fishing ***** Enjoy casting right from the dock for yellow tail, red snapper or grouper. Cast-offshore for sport fishing in the Gulf Stream. The world famous “hump,” an underwater mountain just 11 miles from the dock, has made Islamorada fishing world famous; catch marlin, sailfish, black-fin tuna, mahi-mahi, wahoo and many more ocean treasures.brbrOr just as easily, go backcountry fishing in Florida Bay and catch speckled trout or tarpon. A fish cleaning station at the end of the dock lets you clean your catch whenever your reeling arm is rested and ready.brbr*****Love Swimming, Snorkeling or Diving ***** Enjoy endless swimming right from the dock where the water is clean and refreshing, and the beverages are never far away. Living reefs and sunken wrecks are easily enjoyed by everyone, just three miles from the dock in 3-15 ft of water. Enjoy colorful tropical fish, coral rock formations and sea fans. Certified divers will enjoy the drop-off just five miles out, where the 20-30 foot reefs transition to 60+ feet, and sea life changes. And the world famous Islamorada Sandbar is just a 10 minute boat ride away for the daily water social.br brThe House: We only rent the house to one party at a time – so the upstairs and downstairs units are yours! Upstairs has Two Bedrooms, with a king size bed in the Master, a queen in the other guest suite, and a queen size sofabed in the living room There is one Bathroom upstairs and one downstairs. Downstairs has one Bedroom with a king size bed and a queen size sofa bed. Enjoy the convenience of a first floor bathroom, and refrigerator, sink and Microwave – perfect for those lazy outside days!brbrEnsure everyone's comfort with separate air conditioning systems for the upstairs and downstairs. You’ll find all of the conveniences you expect – comfortable accommodations, fresh linens, plenty of kitchen utensils, laundry machines, and a gas barbeque grill.brbrYou will also find some unique conveniences, like plenty of room to park your boat trailer, extra dock capacity next door, an open lot next door for unobstructed breezes, a shaded palm-roof “chickee”, and private fish cleaning station. There are hanging chairs and a plush hammock for enjoying the outdoor experience... In all, there is room to stretch out and relax without being crowded by others.brbrFounders Park is 3000 feet from the house: an easy walk or drive, where you can enter free with your rental contract and enjoy the beach, walking paths, and family playgrounds. They provide small-fee access to swimming in the Olympic size pool - complete with diving boards, lap-lanes, and a separate splashpad 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 week.brbrCome and stay. Upstairs or down– this is a great place to play.brbrKeywords: Waterfront Home

Boat, Fish, Swim from Your Own 70' Dock!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$247.5

Are you ready for modern day pirate life Wonder how the locals live Well then we can show you ! Redneck paradise, Primitive stay experience 4:20 & pet friendly. “ glamping on water”. Private cabin on our boat hosted directed & maintained by us onboard during your stay. fishing from anchorage, snorkeling, lobstering & swimming, cook & catch meals, nightly dinner, morning coffee & pastries included. A true local experience! Includes parking & shuttle to & from boat. Additional amenities available for additional fee such as reef trips , dingy rental, kayaking. Deck swabbing at no additional charge!

House Boat

“ The Ultimate redneck” boat experience

Islamorada, Florida, United States

1

Bed

Sleeps

Exceptional(46)

$426.53

The ocean is your front yard at this modern, luxurious townhome hidden away in a small, private seaside community. Enjoy the pool, the beach, the dock and the peacocks! Walk to restaurants or cook at home on your private grill. We are work-from-vacation-home friendly with desk, chair, high speed wifi. Amazing fishing, boating, sightseeing, relaxing and dining experiences are all around you here, come visit and invent your perfect vacation!brbrWelcome to your oceanfront townhome on Millionaire's Row in Islamorada, the Sport Fishing Capital of the World! Take in the sweeping ocean views on every level from the living room, the master bedroom, the screened porches and the rooftop deck. Enjoy the front yard sunrise in the morning and moonrise at night. Amazing bayside sunsets await you on the rooftop deck.brbrYour newly remodeled modern kitchen is equipped with every convenience including stainless appliances, a washer and a dryer, restaurant quality cookware and cutlery (yes, sharp knives and cutting boards!), full place settings for 8 and a large family table. Small appliances include a drip coffee maker, Keurig coffee maker, 4-slice toaster, blender, mixer, slow-cookers. Downstairs you'll find a private 3-burner gas grill with extra propane.brbrNeed to work on your vacation Pop up your desk and pull up your swivel chair anywhere you like, connect to the 100Mbps wifi and enjoy the ocean view.brbrYou'll find big-screen flat panel TVs in the living room and the bedrooms, each equipped with a Roku. Watch cable channels, hundreds of on-demand movies and shows, stream Netflix, Disney, Apple+, etc. A wall-mounted iPad in the kitchen handles TV and streaming duties as well as weather/wind/tide forecasts, recipes, news, sports.brbrThere are hundreds of dining experiences to choose from within minutes of your location, from outdoor picnic tables to ocean- or bay-front verandas to indoor dining and everything in between. Brunch, food trucks, seafood, Italian, pizza, sushi, diner counter seating, white-linen fine dining... Islamorada has it all.brbrYou'll have a guest pass for Founders Park, just a mile south of your townhome bayside. Enjoy the sandy beach, swim or snorkel with colorful fish, visit the olympic pool and the splash park. You'll also have access to the pickle ball and tennis courts, the running trails, the ball fields, batting and golf cages, and the hammock hiking trails.

Peacock Shores Islamorada - Vacation On The Beach!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$403.45

Sea Glass Cottage 2b 2b canal front home.brbrBring your boat or two, and enjoy your vacation or holiday relaxing and playing in the world famous Florida Keys. The Sea Glass cottage, is a beautiful canal front, keys style home on a over sized corner lot with ample parking for guests. The cottage provides our guests with direct bay or ocean access in minutes via Tavernier Creek. brbrIt is centrally located and close to Tavernier Creek Marina, a 10-acre facility that provides boat access to a full service marina. In addition, you can grab some delicious Cuban cuisine at Habanos On The Creek, fuel up or service your boat at the marina, or grab your bait supplies at Chris's Bait and Tackle for a fantastic day of fishing, diving or just enjoying the turquoise waters of the beautiful Florida Keys. brbrThe Sea Glass Cottage boasts 2 bedrooms and 2 baths. Completely remodeled with all upgraded finishes throughout. Features include beautiful cottage style wood like flooring throughout, new cottage style kitchen with built in dining, stocked coffee bar and adjacent seating to relax in the morning or evening, beautifully decorated living room with fireplace with access to patio, master bedroom located directly off front patio providing beautiful morning sunrise views. Master features a king size bed, walk in closet and completely remodeled and upgraded private bath with shower. Guest bedroom provides cottage style furnishings with comfortable queen size bed and full size sleeper sofa with view to the canal. Guest bath also completely remodeled with new cottage style decor and bathtub. brbrThe house has two separate docks that have been completely replaced and rebuilt with top of the line decking, that will accommodate up to a 60ft boat and the other up to 20ft. Never run out of space for your toys. Fish cleaning station and covered outdoor seating area to relax. Downstairs storage room provides ample space to store fishing gear, bikes, etc. brbr4 adult size brand new Panama Jack beach cruisers are available for use during your stay along with 2 adult size kayaks and 2 children's kayaks.brbrOutdoor showerbrbrNeighborhood park with kayak launching rampsbrbrMonthly and seasonal rentals welcome. brbrLocated in a well established, quiet family neighborhood. Please respect our neighbors. Guest are asked to refrain from loud parties, no destructive behavior or drugs!!! If police are called to residence during your stay, you will be ask to leave and forfeit remaining rent. Renters are responsible for cleanliness of home during your rental stay. brbrArea is perfect for walking, jogging, biking and kayaking. There is a small neighborhood grocery store with a great selection of meats and wines, BB&T bank, restaurant/bar, gas station and marina within walking distance from the residence. Additionally, there are several restaurants, dress and gift shops, dive center, paddle board and kayak rentals, dive and fish charters, seafood store, church, and a once a week farmers market.brbrThere is also a shopping center which includes Winn-Dixie, restaurants, bar, post office, movie theater, CVS, McDonald's, Dunkin Doughnuts, AT&T and Mariners Baptist Hospital. 3 miles from the house is Founders Community park with beach, playground, soccer field, outdoor gym, tennis courts, boat ramp and swimming pool.brbrCome and enjoy the wonders of the Florida keys. 28 Day minimum rentalbrbrThe Sea Glass Cottage boasts 2 bedrooms and 2 baths. Completely remodeled with all upgraded finishes throughout. Features include beautiful cottage style wood like flooring throughout, new cottage style kitchen with built in dining for 8, coffee bar and adjacent seating to relax in the morning or evening, beautifully decorated living room with fireplace with access to patio, master bedroom located directly off front patio providing beautiful morning sunrise views. Master features a king size bed, walk in closet and completely remodeled and upgraded private bath with shower. Guest bedroom provides cottage style furnishings with comfortable queen size bed and sleeper sofa with view to the canal. Guest bath also completely remodeled with new cottage style decor and bathtub.brbrKahiki Harbour is a well established, quiet family neighborhood. Please respect our neighbors. Guest are asked to refrain from loud parties, no destructive behavior or drugs!!! If police are called to residence during your stay, you will be ask to leave and forfeit remaining rent. Renters are responsible for cleanliness of home during your rental stay. Owner will be responsible for yard maintenance.brbrArea is perfect for walking, jogging and biking. (bikes provided) There is a small neighborhood grocery store with a great selection of meats and wines, BB&T bank, restaurant/bar, gas station and marina within walking distance from the residence. Additionally across from Kahiki Harbour {rt 1} there are several restaurants, dress and gift shops, dive center, paddle board and kayak rentals, dive and fish charters, seafood store, church, and a once a week produce and market.brbrWith-in one mile from neighborhood there is also a shopping center which includes Winn-Dixie, restaurants, bar, post office, movie theater, CVS, McDonald's, Dunkin Doughnuts, AT&T and Mariners Baptist Hospital. 2 miles from the house is Founders Community park with beach, boat ramp and swimming pool.brbrCome and enjoy the wonders of the Florida keys.

Sea Glass Cottage Beautiful Canal Front Home

Islamorada, Florida, United States

Bed

Bath

6

Sleeps

$913.87

Village of Islamorada - Vacation Rental License No. 24-0248brbrThis home is remodeled every year in some way or form...We try to make it interesting and fun particularly for our repeat customers. Our objective is to provide the most rewarding and awesome experience possible. From the most comfortable beds you can find, to the various cooking options and outdoor eating choices. You can pretty much live outside with all the amenities for outdoor living provided at this vacation rental. brbrThis property is NOT AVAILABLE for any special events including WEDDINGSbrbr

Private Beachfront Paradise

Islamorada, Florida, United States

Bed

Bath

Sleeps

$223.34

It's not every day that you come across a rental like this. This delightful and fun 2 bedroom, 1.5 located in Lower Matecumbe offers a private beach, dockage, and enough charm as you can squeeze in. brbrThe main living space, located on the second floor, has a great open layout making it the perfect space to both entertain and unwind after a long day on the water. With wall-to-wall windows, peekaboo bay views, lively and fun décor, charming wood accents this condo is the perfect home away from home. The third floor offers a guest bedroom with two twin beds, bathroom, and master bedroom with a cozy reading nook and windows with the perfect bay view. The laid-back yet eclectic vibe of this home is gratifying to all and must be experienced.brbrEnjoy your own little slice of paradise from the beach. One of the very few beaches in the Florida Keys, Sandy Pointe offers soft sand, crystal clear waters, and the best sunsets on the island. Feeling more adventurous Hop on your boat and go fishing or take a boat ride to lunch. Placed in one of the most desirable boating locations, you are minutes away from some of the best fishing spots in the world. Enjoy backcountry fishing right in your backyard or hop over to the oceanside via Channel 5 Bridge. brbrLocated in one of Lower Matecumbe's favorite neighborhoods, Sandy Pointe is only minutes away from downtown Islamorada and Marathon. brbr28 day minimum, please inquire for rates and availability. brbrDockage is available on a first come first serve basis. 30' max length. brbrSandy Pointe 108 ~ MM74 Bayside

Zesty Lower Matecumbe Condo with Private Beach & Dockage

Islamorada, Florida, United States

Bed

Bath

Sleeps

$675.0

This beautiful, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a beautiful upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of home. It is extra clean and modernly furnished.brbrUpstairs there are three bedrooms and two baths. Downstairs there is a totally independent, one-bedroom, one-bath apartment. The house is PERFECT for those traveling with different age groups, in-laws, teenagers, or two families. The house is fully equipped with everything you will need to make your vacation a 'PERFECT' one.brbrSpend your days soaking up the sun and your evenings relaxing in the jacuzzi or in our HEATED swimming pool. THIS IS PARADISE! Being just one-and-one-half hour from Miami and one-and-one-half hour from Key West, you can easily spend a full day in either of the two, and be back on time to watch the beautiful sunset.brbrWe are just one mile from world-famous Holiday Isles, TIKI BAR. There you can sit out by the beach, or take a dip in the pool. Their live entertainment and contests give your vacation the full island effect. As if diving, snorkeling, sunning, boating, and swimming all day were not enough, do not forget to spend an afternoon swimming with the dolphins or the stingrays. Also, just one minute from the house.brbrCome and spend you PERFECT vacation at THE PERFECT GETAWAY!!!brbrPOOL HEATING WEEKLY CHARGE OF $300 AVAILABLE UPON REQUEST. RENTER MUST NOTIFY OWNER AND PAY FOR HEATING CHARGE IN ADVANCE TO ASSURE THAT POOL IS HEATED IN ADVANCE. AFTER CHECK IN, POOL HEATING CHARGE IS $400, AS POOL COMPANY HAS TO RETURN TO LOCATION TO TURN ON THE HEATER.brbrBOAT AVAILABLE FOR RENT. ARRANGEMENTS MUST BE MADE IN ADVANCE.

The Perfect Getaway with Swimming Pool, Jacuzzi and Boatslip

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1510.57

OSPREY BAY VILLA – Your private bayfront escape in the heart of Islamorada, Florida Keys! brbrRelax and enjoy incredible panoramic bay and sunset views from this elegant yet casual Old Keys Charm home, designed for the perfect family or group getaway. With a heated pool, hot tub, and deep-water dock, you’ll experience the best of island living—whether you’re soaking up the sun, exploring by boat, or strolling to local restaurants and shops.brbrKEY FEATURES:brbr*5 bedrooms, sleeps 10–12 guestsbr - 2 king bedrooms (including master suite)br - 1 queen bedroombr - 2 bedrooms with 2 queen bedsbr* 3 full bathroomsbr - Master bath with separate vanity roombr - Full bath with bathtub + separate shower, double sinksbr - Pool-level bath with shower + direct outdoor accessbr* Fully equipped gourmet kitchen with open dining room and atrium gardenbr* Spacious living room with coral rock fireplace + wet barbr* Second-level master suite with private bayfront veranda + fireplacebr* Multiple sunning decks, heated pool, and hot tubbr* Deep-water dock + boat basin (perfect for boating, snorkeling, kayaking & paddleboarding)br* Lush tropical landscaping + private sandy beach area for wadingbr* Incredible sunset views from expansive waterfront lawn and outdoor spacesbr* Secluded yet walkable to iconic Islamorada restaurants and local shopsbrbrCome, Relax & Enjoy!brYour perfect Florida Keys vacation awaits.

Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$694.42

Experience waterfront FL Keys living at its finest at The Seascape, a modern, newly constructed retreat nestled directly on the ocean where every morning begins in color, and every evening ends in calm. Here, the ocean isn’t just a view. It’s a presence. Come make memories at Islamorada's iconic tiki bar sandbar, legendary fishery, or gather on sunlit shores to relax and revel in life’s simplest joys with stunning views, direct water access, and a stylish escape from the everyday.brbrLocated in a secure, gated enclave, The Seascape provides one of the closest waterfront experiences available in the Florida Keys, complete with private dockage and sweeping ocean views. Spanning over 2,000 square feet, this spacious three-bedroom residence boasts two expansive oceanview balconies, a private exclusive entertainment lounge, and interiors curated for both relaxation and refined living. Whether you’re planning a family vacation or a retreat with friends, The Seascape is your launch point for making lifelong memories. Keep your eyes open for dolphins, manatees, and pelicans, or gaze across the water toward the iconic Alligator Reef Lighthouse and Islamorada Sandbar.brbrStylish Interiors with the Comforts of Home in MindbrThe Seascape was designed for both relaxation and entertainment, featuring:br✔ Two large balconies overlooking the ocean—perfect for outdoor dining, a morning coffee or an evening glass of winebr✔ A fully stocked designer kitchen with stainless steel KitchenAid appliancesbr✔ A bright living area with oversized sectional seating and a 65 OLED 4K TVbr✔ Thoughtful details and elegant decor throughout every roombrbrThree Private Tranquil Bedrooms with Room for Everyonebr✔ Primary Suite – King bed, private patio that extends the bedroom to the ocean front with comfortable egg chairs, and ensuite bath with a walk-in rainfall shower br✔ Second Bedroom – King bed with ensuite bath with a walk-in rainfall shower br✔ Third Bedroom – Ideal for kids or additional guests, featuring a full-size bunk bed with a pull-out trundle and ensuite bath with a walk-in rainfall showerbrbrBonus Entertainment Space – Exclusive to This HomebrUnwind in your private lower-level entertainment retreat, complete with:br✔ 55 4K Smart TV with gaming systembr✔ Ping pong table, pop a shot, mini-putt matt, board games, books, and morebr✔ Lounge area with sectional seating and bean bagsbr✔ Outdoor games like cornhole for fun in the sunbrbrPool, Private Dockage & Water Gear Includedbr✔ Dock space for boats up to 26 ft (advance reservation required)br✔ Kayaks and paddleboards available for guest usebr✔ Enjoy the community’s heated oceanfront pool with lounge chairs and a sun shelfbr*Options for nearby trailer storage will be provided since we cannot accommodate trailers onsite.brbrNearby Attractions Include:br✔ Feed the tarpon at Robbie’s Marinabr✔ Visit dolphins and sea lions at the walkable Theater of the Seabr✔ Snorkel vibrant coral reefs and local shipwrecksbr✔ Offshore fishing charters at nearby Bud n Mary's and whale Harbor marina to best enjoy the sportfishing capital of the worldbr✔ Relax at Islamorada Library Beach or Founders Park (free guest access!)br✔ Explore the charming shops and galleries of Morada WaybrbrThis awesome home comes with AC, a washing machine, WiFi, heating, and even a fitness room. With 3 bathrooms and a hair dryer, guests will have everything they need for a comfortable stay. Our place is equipped for both long or short stays to make your holiday one to remember.

NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony

Islamorada, Florida, United States

Bed

Bath

Sleeps

$412.72

Windley Cottage is a welcoming, tastefully-decorated home located at mile marker 85. It's away from the highway, and just steps from the pool and docks. The “Bahamian conch style home provides irresistible charm and comfort tucked in among lush landscaping. Angler's Reef is centrally located, perfect for exploring all of the Florida Keys!brWhether you’re looking for a couples’ retreat or an exciting Keys experience with the family, this home is the answer! Flexible bed arrangements. Call 239-250-4135 for more information. IbrWe have amenities for all ages! Enjoy a swim in our temperature-controlled pool. Paddle out to the sandbar on our complimentary paddle boards or kayaks. Cycle to the many gift shops and restaurants. Scuba or snorkel the nearby coral reefs and shipwrecks, rich with underwater wonders. Dive near the popular Alligator Reef Lighthouse, which is visible and easily accessible from Angler's Reef. For a fee, dock your boat in our protected lagoon with direct, deep-channel access on the Atlantic. Nearby marinas offer boat/jet ski rentals, fishing/scuba/snorkeling charters, and party boats for fun on the water. Whether you fish from shore or our docks, flats-fish in the back bays, or deep-water fish for big game, Islamorada has it all! Swim with the dolphins and learn about the local marine life at Theater of the Sea (1/2 mile from our home). Dine at one of the fabulous nearby restaurants, many offering nightly entertainment.brbrJust 2 miles north is Islamorada Founders Park at MM 87 Bayside. The park offers a shallow water beach, ball fields, playground, fishing jetty, driving cage, 3 paddle ball courts, bocce, tennis, a large playground, basketball courts, an exercise course with 18 stations, and a multi-purpose path within the 40-acre park. brbrOther municipal parks include the Islamorada Library Beach and Anne’s Beach. The Windley Key State Geological Site, a state park, is a former coral rock quarry, where fossils of sea creatures can be seen throughout the park.brbrAfter a busy day, enjoy a glass of wine on one of our two private beaches. Play a board game on the back porch. Dim the pendant lights in the great room and turn on the fireplace as you cuddle up to watch your favorite movie after a busy day. brbr Just pack a few clothes and your toothbrush and head down to the Florida Keys for the vacation of a lifetime in the comfort and luxury of Windley Cottage! See why people from all over the world get sand in their toes and return here again and again!brbr Contactless check-in and check-out is on Saturdays. Please contact us if you want a different day. Our calendar is updated in real-time and posted rates are accurate. brbrSTR#-24-0163brFL DBPR #DWE5403337brbrNOTE: We also own a vacation rental property on Cape Cod, MA. Visit Vrbo listing 3757615 for photos and further information of this property.

OCEANSIDE ANGLERS REEF HOME- Gated Community with Pool, Dock, Private Beach

Islamorada, Florida, United States

Bed

Bath

Sleeps

$419.4

Be our guest at a one of a kind, 2 years new, boutique style accommodations in one of the most beautiful areas of the Florida Keys. Serenity. Luxury. Privacy. Peaceful. All amenities in this lavish first floor apartment abound, for the discerning couple. Honeymooners, couples celebrating an anniversary or wanting a quiet get-away from the hustle and bustle of city life or snow. Welcome! From luxury (Comphy) sheets found only in the finest hotels and spas, to pool, towels, body wash, shampoo, and conditioner. Just pack your tooth brush and bathing suit, we'll take care of the rest. The outdoor area has an outdoor summer kitchen with bar b q, refrigerator, small freezer, outdoor sink, side burner for concocting your own creations, outdoor dining area or bring your dinner indoors; order in or feast at many fine dining establishments. Feel like a King and Queen in your own cozy, quiet, slice of paradise, hideaway, spa-like retreat. Sleep like a baby with black out blinds in the master bedroom, and living room for the privacy you seek, or let the abundant sun light shine in. 85 big screen tv for cable and streaming. Washer and Dryer inside the apartment, fully stocked with organic earth friendly products. Microwave/Oven, dinnerware, kitchen utensils, cookware, silverware, stemware, and anything you would need to cook meals inside or outside. Minutes from the world's best fishing, restaurants, and water attractions. Just 1.5 hours from Miami International Airport, 45 minutes from Marathon Airport, or 1.5 hours from Key West. Casa Contessa jr, is located inside a private golf cart friendly community with boat ramp, and private beach. Located on a wide canal on the Gulf side, with an easy scenic 2 minute ride to open Gulf and Ocean waters. Minutes away from world famous Alligator Reef light house with glistening clear water for swimming. Private boat dock space in back yard for an up to 26' boat (upon request inquiries welcome for additional charge due to added water consumption and costs). Minutes from major marinas such as Caloosa Cove, Safe Harbour, Whale Harbour and many more to choose from if you prefer dry storing your watercraft and ready for you to just hop on (call marinas ahead of booking to reserve your spot due to availability). Many services are also available upon request with additional pre-contracted special pricing, such as a private in house massage (we know the best masseuse on the island), additional housekeeping, back country and deep sea fishing charters with the best on the island, Two Conch, Bud & Mary's, and many more, private transportation from Miami International Airport available if needed (additional charges apply inquiries welcome). Home has security camera pointing to boat, pool equipment on the side of the house, front door, and has motion detection lighting on perimeter for safety and lighting should you walk around the side of the house. brbrPeaceful Paradise awaits, we are ready to welcome you!brbrThank you for stopping by!brbrJanet and Jose (your friendly hosts)

Apartment

Port Antigua NEW Luxury one bedroom/2 bath apt with pool

Islamorada, Florida, United States

Bed

Bath

Sleeps

$440.42

The Artist's Cottage at Anglers Reef #136 - This beautiful home is located in Angler's Reef, a gated oceanfront community located in Islamorada. The owner has shared his own personal artwork throughout the unit for guests to enjoy. Angler's Reef is known for its beautiful tropical landscaping and colorful houses. It features a heated oceanfront swimming pool and beach. This two bedroom, two-and-a-half-bathroom unit has a very welcoming feel. Enjoy quiet mornings on the porch and days spent at the beach and pool.brVACATION RENTAL LICENSE: 24-0392brIf 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. 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.

Condo

Discover Angler's Reef 136: a stylish 2-bedroom condo in the heart of Islamorada.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$679.26

Sure you can drive another 1.5 hours to reach Marathon but why would you do that when the best restaurants and events are right here in Islamorada. Stay in a beautiful home in one of the best communities in the Florida Keys, Venetian Shores. You can watch from your veranda tarpons jumping, sea turtles, and manatees . Sip a cocktail and watch your favorite tv show in your own private pool, or hammock away your day while reading a good book. Creating delicious meals is easy using the outdoor kitchen and you will never have to go for an ice bag run because you have a big ice maker at your disposal. The best restaurants, dive shops, fishing spots, and entertainment is just minutes away. If you would like to stay for less time, that can be accommodated by charging you a monthly rate. We only rent monthly .

Endless Summer Awaits!

Islamorada, Florida, United States

4

Bed

3

Bath

12

Sleeps

$942.77

This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 1042 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 $200 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.

Villa

Deactivated due to Bad Review and Low Productivity compared to other listings.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$273.06

Home is located in an ocean front resort. This 2 bedroom 2 bath home is pet friendly. Home has amazing views of the Atlantic Ocean. Home sleeps 4 persons and is designed to make its guests feel at home, offering upgraded features as in stainless steel appliances, a farm sink, quartz countertops, and plenty of storage. The floorplan has an open kitchen living floorplan and a private deck with awesome views.brbrMinimum stay: 28 nights. Boat slips may be booked for an additional fee. Disclaimer: Photos represent the general style and quality of our homes. Each unit is individually owned and decorated, so furnishings and décor may vary slightly. All meet resort standards for comfort and cleanliness.

Oceanview 2BR home in a pet-friendly resort! Minimum 28-Day Reservation Required

Islamorada, Florida, United States

Bed