Vacation Rentals By Owner In Islamorada, FL

Our house is located in Islamorada, FL, the fishing capital of the world. Our single-family, Key-style home is located in an exclusive gated community of 50 island homes called Angler's Reef. The community includes a beautiful oceanfront pool, a private marina, and two stunning man-made beaches, a rarity in the Florida Keys. A famous sandbar amid turquoise waters is located right in front of the community and can be reached by kayak or boat.brbrOur island home is cleaned professionally and we maintain a non-smoking pet-free environment. The house sleeps four and has a Master bedroom with an en-suite Master bathroom and a large private balcony. The large second bedroom is also a master suite featuring an en-suite bathroom with a tub and a small private balcony. The living area includes a formal dining room and living room, as well as a modern open kitchen. A large sofa can accommodate one or two children if more sleeping space is needed. A large private porch amid lush tropical gardens with BBQ and white wood rocking chairs. The house is tastefully decorated and equipped for all your needs to enjoy a perfect vacation.brbrOur village offers restaurants for all tastes and prices as well as fun adventures for singles, couples and families. We have numerous unique boutiques and shops, where you can also find rare items. But most important is that you will have the time of your life in our beautiful place in Angler's Reef!brbrNote: Children welcome, non smoking only, pets not allowed, wheelchair inaccesible

GREAT Christmas week 12/20-27 DISCOUNTED SPECIAL RATE- 2 bedroom beautiful house

Islamorada, Florida, United States

Bed

Bath

Sleeps

$630

Contact owner for rates and availability (305-431-2006).brRelax in Islamorada, Florida Keys... 'Sport Fishing Capital of the World.' Enjoy deep blue water or back country fishing. Dive, snorkel, and swim on a clear, white, sandy beach (rare in the Keys!). Walk/jog among beautiful waterfront homes. Sip wine while gazing at glorious sunsets while surrounded by coconut palms.brbrManatees, tarpon, mangrove snappers, and other native fish species swim the waters off our dock. Beautiful tropical vegetation, shore birds, and other marine life are all around you. You will cherish the memories of your stay in this 'Island Paradise.' Islamorada is known as 'The Purple Isle' and is located in the heart of the Florida Keys - midway between bustling Miami and laid-back Key West.brbrThis charming island home on a deep-water canal features high-beamed ceilings and a 'loft.' The walk-around deck, open floor plan, and kitchen designed for entertaining make this home an excellent choice for a carefree vacation. The home is newly furnished and redecorated and has two spacious bedrooms each with a private bath. The home is equipped with High Speed Wireless Internet Access.brbrThe home's 70-foot boat dock gives easy bay and ocean access and the private beach is a few steps away with your own private access.brbrKeywords: Beach House

GREAT LOCATION !!! White Marlin Beach House, Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$710

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 (May 2021) 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. Master bedroom 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. The community also provides kayaks for your enjoyment (first come/first served).brbrCable, wifi, board games, some childrens' toys provided. Highchair, booster seat, pack n' play and infant tub for our littlest guests. brbrPictures and description are representative of accommodations provided but are subject to change. brbrLicense #VR-226

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

Islamorada, Florida, United States

4

Bed

3

Bath

8

Sleeps

$421

Fully renovated 5-bedroom 3-bathroom vacation style home for rent in Islamorada on a canal. It is located near the white Marlin Beach. Comes completely furnished with a beautiful coastal design that will make you feel on vacation 24/7. 2 bedrooms are on the first floor with a bathroom and their own living room. It has an outside staircase access to the second floor where there is an open concept spacious kitchen and the other three bedrooms. This property also has a crystal-clear pool and a dock to park your boat. Property is being offered at $12,000 a month. 28 Night Minimum

Beautiful Islamorada Waterfront Homen

Islamorada, Florida, United States

Bed

Bath

Sleeps

$666

Welcome Back!! I temporarily took the property off the market during COVID and for renovations. I am looking forward to having my returning guest come back and visit.brPlease look at the (video icon) in the picture to view the video of the homes location. A tropical boater's and angler's paradise, this Key West styled luxury villa in Islamorada boasts the best fishing in South Florida. With tangerine sunsets glistening across the calm ocean waters, an afternoon boat ride is as easy as walking out your back door. Dolphin and turtles are common. Deep water access, boat dock, nearby marina with fuel, bait and tackle shop, nearby waterfront restaurants and short boat ride (seen from the balcony) to the famous sand bar located behind Holiday Isle weekend hot spot.brbrThis is the developer unit with the largest fully equipped kitchen in the development. Large living room with a beautiful view of the ocean, 3 BR's, den, 2 1/2 luxury baths, sleeps 10 comfortably. Wood floors, glass designer tile throughout, california closets, covered parking with an additional parking spot. Upper and lower decks overlook ocean view. Flat screen TV's, cable, internet service. (Kitchen utensils, dishes and linens are plentiful). Security gate for privacy and peace of mindbrbrCommunity pool and dock space with electric and water hook-up.brbrNote: I also have a 2-bedroom rental home in Anglers Reef neighborhood with a boat dock included. VRBO Listing 3578196brbrKeywords: Breath taking views. Sunrise in the morning on the back balcony. Deep water access to a private dock. View of the Pool. Very relaxing.

Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip

Islamorada, Florida, United States

Bed

Bath

Sleeps

$635

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

4

Bed

Bath

6

Sleeps

$564

***June 2022 - Installed a new AC with Germicidal UV light air purifier, which improves air quality by sterilizing mold, bacteria, allergens and viruses: and of course, our housekeeping staff complies with the latest cleaning and disinfecting CDC guidelines. *** brbrANGLERS REEF is a quiet oceanfront community of Key West inspired homes, streets, and walking paths, that wind through a quaint village-style retreat. Located at Mile Marker 85 by Theater of the Sea, Windley Key Geographical Site, Snake Creek Marina & some of the best bars and restaurants in Islamorada. brbrGREAT LOCATION brThe house is in a quiet section of the community, away from the highway and just 2 homes from the ocean. Our porches are shaded and face a tree-lined yard with a view of the ocean.brbrOCEANFRONT RESORT-STYLE SWIMMING POOLbrThe pool is both heated & chilled so that it is always a perfect 87 degrees.brbrTWO PRIVATE SANDY BEACHESbrThe South Beach has a shoreline & ocean access. A tandem kayak sits on the beach for your use, (additional kayak, paddleboards, jet ski & boat rentals are available close by and available for drop-off to your beach or dock).br brThe North Beach, a white sandy beach, is located just steps from the house. brbrDEEP WATER MARINAbrOur boat slip, with direct ocean access, is available for rent and is also just steps away from the house. But whether or not you use our slip, the marina is part of the community and enjoyed by all guests.brbrOUR HOUSEbrBuilt in 2007, this home, is bright and cheery with tile floors, high ceilings, and many large windows. It is newly decorated for the Keys and surrounded by lush tropical landscaping.brThe main floor has an open plan with, tile floors, granite counters, stainless appliances, flat screen TV w/DVD players, cable with ALL PREMIUM CHANNELS, A DVR, Fast WiFi & a SONOS wireless speaker system.brbrThere are 2 bedroom suites with flat screen TV’s and private baths located on the 2nd floor. Both baths have frameless glass showers and granite vanities. Rear bedroom has an ocean view and a private porch.brbrISLAMORADAbrParks in Islamorada, Village of Islands: Just 2 miles north is Islamorada Founders Park at MM 87 Bayside, which offers activity or relaxation for the whole family. An Olympic-sized pool with diving area, a shallow water beach, water sports rentals, ball fields, fishing jetty, bocce, tennis and basketball courts, vita course with 18 exercise stations, multi-purpose path, skate park and dog park all are within the 40-acre park. Fees may apply. Village municipal parks also include the Islamorada Library Beach and Anne’s Beach. There is the Windley Key State Geological Site, a state park, at the site of a former coral rock quarry. In addition to shady walks through unique foliage, fossils of sea creatures can be seen throughout the park. A free guidebook is available at the visitors center for use during your stay in the park. Islamorada also offers an 18-mile bicycle path that extends the length of the Village.brbrScuba/Snorkel!: Islamorada, long recognized as the 'Sport Fishing Capital of the World,' is now an icon among sport divers for a similar reason: a massive population of tropical marine life. High-profile coral heads and broad ledges shelter huge congregates of French grunt and goat fish, while regal queen angelfish casually graze amid the reef recesses. Friendly green moray eels swim freely along the spur-and-groove channels, and reclusive nurse sharks lurk beneath the overhangs. Islamorada offers a wide variety of shallow coral reefs, mini walls, shipwrecks, and even an underwater habitat for scientific research, the Aquarius. To learn more about Islamorada or any other manner of local lore, stop by the Chamber of Commerce at MM 82.5.br

OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

Islamorada, Florida, United States

Bed

Bath

Sleeps

$659

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

$388

**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

$203

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

$353

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

$478

Windley Cottage is a private home in the small gated community of Angler's Reef in Islamorada. This welcoming, tastefully-decorated home is located at mile marker 85, 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. Whether you’re looking for a couples’ retreat or an exciting Keys experience with the family, this home is the answer! Its central location is perfect for exploring all of the Florida Keys!brbrWe have amenities for all ages! Enjoy a swim in our temperature-controlled pool. Paddle out to the sandbar on our 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. Fish or 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! Play pickle ball, tennis, swing, or swim at nearby Founders' Park. 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, 3paddle ball courts, bocce, tennis, and basketball courts, an exercise course with 18 stations, and a multi-purpose path within the 40-acre park. Bring your rental agreement for free entry to the park. Other 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 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. When you find the perfect dates for your stay, simply click on Book Now. brbrSTR#-24-0163brFL DBPR #DWE5403337brbrNOTE: We also own a vacation rental property on Cape Cod, MA. Visit Vrbo listing 3757615 for photos and more information. br

OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1,049

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

$1,447

OSPREY BAY VILLA! Wonderful Bay front Home in the heart of Islamorada in the fabulous Florida Keys for rent by the week, or month; offering Incredible Panoramic Bay and Sunset Views. Heated pool & hot tub, sunning decks galore. Deep water dock & boat basin. Elegant, yet casual, spacious living room with coral rock fireplace, wet bar, open dining room, atrium garden,& gourmet kitchen. Sleeps 10-12 people comfortably. Private south wing offers 3 bedrooms; 1 with1 king bed, 1 with 1 queen bed, another 1 with 2 queen beds, and 1 full bathroom with bathtub & separate shower, double vanity sinks etc. Separate bedroom with two twin beds, tv, a/c, etc. adjacent to kitchen. Spacious second level master bedroom suite with king bed & it's own master bath & vanity room, fireplace & bay side veranda. Third full bathroom with vanity and shower downstairs has an entrance from the wet bar/living room area & also exits to and from the heated pool. Lush tropical landscape & expansive waterfront lawn & dock area with its own small beach for wading into bay, for snorkeling or for an easy launch for kayaks and paddleboards. This vacation home is secluded, yet situated in a perfect location for walking to classic restaurants & local shops. brCome, Relax & Enjoy!brbrKeywords: House

Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$190

Come and experience the beauty and tranquility of the Florida Keys at Executive Bay Club! Enjoy gorgeous views from this private, gated community, located in the renowned Sport Fishing Capital of the World, Islamorada at Mile Marker 87. Spend your days swimming and snorkeling in crystal-clear waters filled with abundant marine life, lounging on the beach, perfecting your serve on the two tennis/pickleball courts, or fishing from the dock! Plus, with your rental agreement, take advantage of free access to Founder's Park next door, which offers a beach with ideal snorkeling conditions, trails for running, walking, and biking, and the chance to take in free concerts and other events. You won’t want to miss out on this amazing opportunity to enjoy the Florida Keys, book your stay at EBC today!brbrThis is townhouse M3 and it accommodates 8 guests comfortably. Upstairs there are two bedrooms, one has a king bed and the other has 3 sets of bunk beds (great for kids).brbrThere is also a loft bedroom with 2 twin beds that can be pushed together to form a king bed. This is a perfect sleeping spot for kids and young adults alike. brbrThere is a full bathroom is upstairs and a full bathroom is downstairs to refresh after a day of exploring. brbrGather in the living room on the sofa to watch a movie together on the flat-screen TV or enjoy a meal in the dining area that seats 6 plus 2 people on the kitchen counter. brbrThe kitchen comes fully equipped with all the necessary items to prepare and serve your meals. Outside, there is a BBQ and outdoor seating.brbrAmenities at the EBC include a communal heated pool, clubhouse, communal charcoal BBQ grills, picnic tables, beach, etc. Fishing allowed from the dock, but you may need a fishing license. brbrBONUS with your rental agreement you have free access to Founder's Park next door where you can enjoy the beach and snorkeling, etc. They often have free concerts and other free events too. The park has trails for running, walking and biking and more!brbrIf you would like to bring your boat your can dock it at Founders Park for a reasonable fee, which is right next door to the Executive Bay Club. NO docking allowed at the EBC marina. brbr**NO SMOKING ALLOWED IN THE UNIT**brToiletries are not included.brYou must be 25 years old or older to book this property. NO work crews allowed. Family rentals only.

Exec Bay townhouse w/heated pool, marina, beach

Islamorada, Florida, United States

Bed

Bath

Sleeps

$517

The perfect island get-away in beautiful Islamorada, the Fishing Capital of the World. Desirable Venetian Shores is an exclusive waterfront community you will love to explore by land and by sea. Our home is located on a wide canal with direct views of famous Snake Creek and immediate access to the ocean or bay. Relax in the private pool set in a tropical oasis with exotic palm collection. Enjoy time with family or friends poolside with plenty of space to lounge, read, relax or dine alfresco. Fish off the dock and enjoy the sea life including eels, manatees, tarpon, tropical fish and porpoise. Perfect set up for families or friends with private first floor bedroom and full bath with separate entrance. Everything you need is right at home. Gourmet kitchen with new appliances. Take a long walk around the neighborhood or a paddle board trip down the canal. br Islamorada has First class dining including The Island Grill and their famous Tuna nachos, Mad Dog Ziggies, Green Turtle Inn and Chef Michael’s. Attractions include Theater of the Sea, Diving Museum and beautiful waterfront State and National parks. brbrThe dock for your boat (LIMITED TO 22 ft BOAT) has direct access to the bay or the ocean in 5 minutes.

Prestigious Venetian Shores with private Pool and Snake Creek View

Islamorada, Florida, United States

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$279

Home sits in the Sun Outdoors Islamorada Resort. New 2b/2b home w/ a boat slip within the private marina . Home has a view of the Atlantic Ocean. Home sleeps 6 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 open kitchen living area a private deck with awesome views. A min of 28 nights is required for these units.

Oceanview 2b/2b w/ Boatslip

Islamorada, Florida, United States

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Select Dates for Price

Condo

Luxury One Bedroom Condo #4

Islamorada, Florida, United States

One Bedroom 700 Square Feet Condo brOne Bedroom, One Bathroom Condo, Separate Living Space and Fully Equipped Kitchen. Outdoor Fire pit under palm trees with Adirondack Chairs. Ideal location in Islamorada FL.br(Four units in building- this one is on the top floor to the right of the entrance)brThe complex is located a MM 80 on the ocean side and does not have a swimming pool. Public beach is 7 miles South at Anne's beach and 7 miles North at Founder's Park.

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$544

Welcome to 128 Anglers Way: Morada Daydreaming. Our home away from home in the Angler's Reef exclusive gated community is calling you. This house has 2 bedrooms upstairs, each with it's own full bath and private balcony. Washer and dryer combo is conveniently located upstairs near the bedrooms. The house is family friendly and includes a pack and play.brbrThe main level open floor plan features peek a boo ocean views. It also contains a half bath, a full kitchen with stainless steel appliances (including a double oven), granite countertops, Brazilian cherry hardwood floors, and a living/dining combo. A cozy outdoor seating area and gas grill is provided off the back porch.brbrAngler's Reef is a premier resort style complex at MM 85 with only 52 houses. The neighborhood includes a heated community pool that overlooks the ocean, complimentary kayaks and paddle boards (first come, first served upon signing a waiver), private marina, and a private 500 foot beach. If a boat slip is required, we can assist you in renting one for boats up to 31' in length. The neighborhood is lushly landscaped and our unit comes with two assigned parking spaces. The unit includes two bicycles for use as well. The location is ideal with many wonderful restaurants and attractions nearby - several within walking distance. brbrbrbr

Rare January Special in Islamorada Anglers Reef

Islamorada, Florida, United States