Vacation Home Rentals By Owner In Islamorada, FL

Welcome to your private oceanfront retreat in Islamorada, Florida Keys. Located in the exclusive gated community of Angler's Reef, this spacious 4-bedroom, 3-bath waterfront vacation home includes a private 31-foot boat slip at no additional cost, stunning Atlantic Ocean views, direct beach access, a resort-style pool, and a newly renovated gourmet kitchen.brbrWhether you're planning a family vacation, fishing trip in the Fishing Capital of the World, boating adventure, or relaxing Florida Keys getaway, this home offers the perfect combination of luxury, comfort, and convenience.brbrWhy Guests Love This Homebrbr✓ Private 31' Boat Slip Included (No Extra Fee)brBring your boat and enjoy easy access to some of the best offshore fishing, reef fishing, backcountry fishing, diving, and snorkeling in the Florida Keys. Your protected private marina slip is just steps from the home, making it easy to head out on the water whenever you choose.brbr✓ Prime Oceanfront LocationbrWake up to breathtaking Atlantic Ocean sunrises and panoramic water views from multiple private balconies and wraparound porches. Enjoy morning coffee overlooking the water or unwind with a sunset cocktail after a day on the boat.brbr✓ Resort AmenitiesbrGuests enjoy access to Angler's Reef's oceanfront swimming pool, sandy beach, marina, and beautifully maintained tropical grounds. Complimentary kayaks and paddleboards are available for exploring the nearby waters and sandbars.brbrThe HomebrDesigned for families and groups, this two-story coastal home comfortably accommodates up to 8 guests.brbrMain LevelbrThe open-concept living area is bright, spacious, and designed to maximize the spectacular ocean views.brbrFeatures include:br• Newly renovated gourmet kitchenbr• Viking stainless steel appliancesbr• Stone countertopsbr• Wine coolerbr• Large pantrybr• Expansive dining areabr• Comfortable waterfront living roombr• Queen bedroombr• Full bathroombr• Washer and dryerbrbrLarge wraparound porches extend the living space outdoors, creating the perfect setting for dining, entertaining, or simply enjoying the ocean breeze.brbrSecond Level: The upper floor includes three additional bedrooms:brbrPrimary Suitebr• King bedbr• Private ensuite bathroom with dual sinksbr• Private covered balconybr• Panoramic Atlantic Ocean viewsbrbrGuest Bedroombr• King bedbr• Balcony accessbr• Ocean viewsbrbrGuest Bedroombr• Queen bedbr• Balcony access in hallwaybrbrA full shared bathroom serves the guest bedrooms.brbrAngler's Reef CommunitybrAngler's Reef is one of Islamorada's most desirable gated waterfront communities, known for its private marina, tropical landscaping, oceanfront pool, and convenient location.brbrNearby activities include:br• World-class sportfishing and charter fishingbr• Offshore and reef fishingbr• Snorkeling and scuba divingbr• Sandbar excursionsbr• Paddleboarding and kayakingbr• Dolphin encountersbr• Waterfront diningbr• Sunset cruisesbr• State parks and nature trailsbrbrYou'll be just minutes from many of Islamorada's most popular restaurants, marinas, breweries, and attractions.brbrIncluded with Your Staybr• Private 31' boat slip (#21)br• Oceanfront community poolbr• Sandy beach accessbr• Kayaks and paddleboardsbr• High-speed Wi-Fibr• Washer and dryerbr• Free parking for 2-3 vehiclesbr• Fully equipped gourmet kitchenbr• Multiple ocean-view balconies and porchesbrbrGuest FavoritesbrEasy dockage for our 31-foot boat.brThe sunrise views from the upper porch were incredible.brPerfect home base for our family fishing vacation.brbrCheck-In: 4:00 PMbrbrBook your Islamorada waterfront vacation today and experience why guests return year after year to enjoy the boating, fishing, and laid-back luxury of the Florida Keys.

Oceanfront 4BR Retreat w/ Private 31' Boat Slip, Pool & Beach, gourmet kitchen

Islamorada, Florida, United States

Bed

Bath

Sleeps

$695.54

This Beautifully renovated Compound / Property Comes With A recently completed and Magnificent Landscape Oasis , That Begins With the Coral Stones And Fire Bowl Entrance To A Large Golf Putting Green For Everyone In The Family To Enjoy ⛳️, Plenty Of Shaded Areas With Palm Trees a Coral stone Fire Pit and Hammock area With Comfortable Sittings that’s just perfect For Family Gatherings and fishing stories , (including the one that got away) and/or just total relaxation . and Much More . Truly The Perfect Vacation Home For Any Size Family. .Has 3 distinct Sleeping Quarters ,one in the Upper Floor Home ( This Spacious And Accommodating 2nd Floor Suite have its Own Entrance ,King Size Bed , Small Fridge/ Microwave Oven , Nespreso Coffee Maker , Sitting Vanity With Mirror , A 65 In TV And A Large Confortable Scenic And Relaxing Wrap - Around Balcony ). On Ground Floor and With Access from the Swimming Pool Area ,you’ll find Entrance to an Area With Two Beautiful Bedrooms With Queen Size Beds and One Full Bathroom all Attached to The Main house Also On Ground Floor That Have 3 Bedrooms, one of them a Master Bedroom With double Glass Doors , 65 inch TV and direct access and views to Swimming Pool And Harbor. Additionally, Two Full Bathrooms Large Kitchen and Living room with Wall/entertainment unit and a 65 in TV . .Sleep 10-12 Comfortably. Compound located in a Magnificent and rare Canal End With An Extended Waterfront View. Easy Access To Best Hidden Beach In Islamorada With Otherwise no Access to Public except by Boat, It’s Only 3-4 min by Power Boat vs 15 Min Of A Breathtaking Scenery Kayaking ( kayaks provided with the property ) Along The Coast. Enjoying Nature At It’s Best ,Watch The Abundance Of Pelicans, Playing And Passing Dolphins And Gentle Manatees On Your Way. Only 5 Min By Boat To Atlantic Ocean And 15 Min To The World Famous Alligator Reef For Some Of The Best Snorkeling The Florida Keys Have To Offer, There’s Also Anne’s Beach Only 1/4 miles Walking Distance .Enjoy The Newly Build Lagoon Shape Swimming Pool And Tiki Hut For A Refreshing Cocktail Or BBQ . Don’t Feel Like Cooking No Problem , Local Restaurant With Great Food Just short Walking Distance. Yes This Wonderful Property Has It All For A Memorable And Relaxing Vacation. 135 feet of Dockage Good For Multiple Boats .1hour 25 min from Miami Airport, 1hour 25 min from key west. ( New Updated Pictures To Follow Soon ).

Waterfront beautifully renovated 6 Bedrooms 4 Bath , Gated Private Home

Islamorada, Florida, United States

Bed

Bath

12

Sleeps

$521.27

Beautiful coastal boho-style home located in the highly sought-after Venetian Shores neighborhood of Islamorada. This spacious waterfront property offers plenty of dockage and quick access to both the Atlantic Ocean and Florida Bay via Snake Creek, making it a great choice for guests bringing a boat. The dock is equipped with shore power, water, and a fish cleaning station, making it easy to rinse down the boat and prep your catch after a day on the water. Islamarina is conveniently located right at the entrance of the neighborhood, where you can grab fuel, bait, and other essentials before heading out.brbrThe home features a flexible layout with two bedrooms and one bathroom downstairs along with a convenient kitchenette, while the upstairs offers two bedrooms and two bathrooms with the main living space and kitchen.brbrJust off the upstairs living room, you'll find a cute porch with a swing, the perfect spot to relax with your morning coffee or unwind in the evening while enjoying the island breeze.brbrDownstairs, the outdoor space is designed for relaxing after a day on the water, featuring sun loungers, a fire pit, and an in-ground spa, creating your own private Keys-style retreat.brbrWith its relaxed coastal boho style, excellent boating access, and inviting outdoor spaces, this Venetian Shores home is the perfect place to experience the laid-back Islamorada lifestyle.brIf booking more than a year in advance current prices may not reflect the annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Spacious 4-bedroom canal home in Islamorada, perfect for families or groups.

Islamorada, Florida, United States

Bed

Bath

10

Sleeps

$741.59

Located in Islamorada's premier neighborhood of Venetian Shores, this stunning 4-bedroom, 4-bath waterfront home offers the perfect balance of comfort and coastal style. Inside, you'll find an open-concept layout with a modern kitchen, spacious island, and high-end appliances—ideal for entertaining or family gatherings. The living area opens to beautiful water views, creating a bright and inviting space to relax after a day on the water.brbrThe lower level offers additional flexible living space, including a bonus room that leads directly to the pool deck. There is also an additional room that can easily function as a home office or extra sleeping space, complete with a sofa bed and its own bathroom—perfect for guests or convenient access from the pool area. A laundry room is also located on the lower level for added functionality.brbrOutside, enjoy a heated pool, outdoor kitchen, two outdoor TVs, dining area, and outdoor shower, all surrounded by lush tropical landscaping. For boaters, the property features concrete dockage on a deep-water canal with quick access to both the Atlantic Ocean and Florida Bay through Snake Creek.brbrThis home offers the ultimate Keys lifestyle with modern coastal design, exceptional outdoor living, and unbeatable access to Islamorada's world-class fishing, dining, and local attractions.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.

Luxurious 4BR retreat at 115 Vilabella Drive, Islamorada, with a private pool.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1470.34

Apartment

Ocean View Two Duplex Penthouses / Retreat amenities: tennis court, heated Pool | Vista Key

Islamorada, Florida, United States

Bed

Bath

24

Sleeps

$440.48

Nestled in Islamorada Sport Fishing Capital this fabulous house offers a tranquil retreat for guests seeking comfort and relaxation. With dock for your boat and three bedrooms featuring a king, queen, and twin bed as well as a double sofa bed in the living room there’s plenty of space for everyone. Two bathrooms include both a shower and a bathtub, perfect for unwinding after a day of adventure. Guests enjoy a cool, refreshing atmosphere thanks to air conditioning and heating throughout the home. Whether you’re gathering in the spacious living area or resting in the peaceful bedrooms, this awesome house provides a welcoming escape. Fall in love with Islamorada and enjoy the magic it has to offer.

Marlin Beach 3-bedroom house in Islamorada with private beach, hot tub and dock

Islamorada, Florida, United States

Bed

Bath

Sleeps

$673.46

Located on a cul-de-sac in the charming city of Islamorada, this beautifully- appointed five-bedroom, four and a half-bath home serves as an excellent setting for your tropical getaway. Ideally located in Islamorada on Lower Matecumbe Key, you will have convenient access to breathtaking views, casual and fine dining restaurants, shopping, water sport rentals, and just a short drive to the Bud N’ Mary Marina where you can charter a boat and head out for a deep sea adventure! Port Antigua community offers wide canals, boat ramp, and infamous bay front white sandy beach with tiki huts and picnic tables. These are private amenities and are only accessible by Port Antigua homeowners and guests. brbrAs you enter through the front door you are welcomed into the grand foyer that leads directly out to the pool and dock. Up the staircase you will find an open concept area complete with a spacious kitchen and a designated living room that includes comfortable lounge seating, perfect for a relaxing evening at home! The sliding glass doors off the living room open to reveal a balcony with picturesque views. Imagine sipping your morning coffee or afternoon cocktail while enjoying fresh sea air and an island breeze.brbrThoughtfully designed with you in mind, the intimate dining area sits adjacent to the kitchen with enough seating for six. The roomy kitchen grants space for any budding chef and comes fully-equipped with all the essentials to prepare gourmet, island- inspired meals at home! The large refrigerator, ample countertops and cabinet space ensures sufficient storage for all your necessities. Island-style furnishings and tropical decor sprinkled throughout the home elicit the peaceful vibes of Keys lifestyle.brbrWith five plentiful bedrooms to choose from, everyone in your group will enjoy some privacy in their pleasant accommodations. Each bedroom features comfortable bedding, TV’s with steaming service capabilities, ceiling fans and natural light. You will love waking up to the gentle Keys breeze and soft sunshine! The master suite offers a king size bed, private covered balcony, ensuite bathroom and an oversized closet. The main guest bedroom has a queen bed with an ensuite bathroom. While a second guest bedroom has a queen bed and convenient access to the hall bathroom. The third guest bedroom is located just up the stairs adjacent to the family room. And finally, the pool cabana that can also be utilized as a fifth bedroom as it features a sleeper sofa and full bathroom.brbrThe third floor offers a vast entertainment room, perfect for watching movies with an expansive U-shaped sofa, a bar area complete with mini fridge and cabinets full of games to play. Be sure to go out on the open lanai for peek-a-boo views of the Atlantic.brbrOutside you’ll find an impressive outdoor kitchen and eating area with ample space to entertain. Take a dip in the refreshing swimming pool or soak up some vitamin D in the comfy loungers. The 220 foot concrete dock features a gazebo, a fish cleaning station and two boat lifts. Enjoy your days resting by the water or take advantage of having canal access. This home is sure to check all the boxes for a relaxing and enjoyable vacation.brbrAdditional amenities include a washer and dryer, internet and parking. Learn more by calling us at (305) 664-0077!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.

Impressive Resort Like 5 Bedroom / 4.5 Baths with Pool & Dockage in Islamorada!

Islamorada, Florida, United States

5

Bed

Bath

10

Sleeps

$624.0

Hidden gem in Venetian Shores with incredible bay views and stunning sunsets. This spacious and private property sits on a large fenced-in lot and offers the perfect setting for a relaxing Islamorada getaway.brbrThe outdoor space is truly special, featuring a heated pool, plenty of lounge seating, and beautiful open views of Florida Bay. Upstairs, the covered porch with a dining table overlooks the water, making it the perfect spot for morning coffee, outdoor meals, or watching the sunset over the bay.brbrThe main home upstairs offers 3 bedrooms and 2.5 bathrooms, along with bright living spaces that take full advantage of the beautiful water views. Downstairs there is a separate 1-bedroom, 1-bath apartment with a kitchenette, ideal for guests who want extra space or privacy. The downstairs apartment can be added to the rental for an additional $2,500.brbrThe property also features a rare walk-in sandy beach area along the bay, along with an observation dock perfect for sitting by the water, launching a kayak, or simply enjoying the peaceful surroundings.brbrWith its private setting, expansive outdoor space, heated pool, and incredible bay views, this Venetian Shores home is a truly special place to experience the Florida Keys.br1 small Pet will be considered at this home. (Please inquire.)brAlso note, this beautiful home is available for monthly rentals only.brIf booking more than a year in advance current prices may not reflect the annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Luxurious 4BR home with open water views in Islamorada, perfect for families.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$493.29

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 8 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 is a bunk room as it has four queen size bunk beds! Sleeps 8 people! 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. 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.brbrFounders Park is 3000 feet from the house: an easy walk or drive, or use one of the three beach cruisers we provide. 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 stay.brbrNon-shedding dogs (2 max) allowed with prior approval and $300 non-refundable fee. br28 day minimum - contact owner for more info and rates for long-term stays.br

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

Islamorada, Florida, United States

Bed

Bath

Sleeps

$167.56

Take it easy at this unique and tranquil getaway. Enjoy this well equipped 2 bedroom, 2 bath home. Enjoy beautiful sunsets . Fish, swim or snorkel while enjoying the bay view. close to some of the best restaurants and attractions in Islamorada. Walk to Founders Park to enjoy a beautiful beach, walking trails, picnic areas and playgrounds. Located in a private gated community with 24 hour security. No pets allowed. I am happy to offer early check in and late check out (if available/usually available) please ask if you need this accommodation. Available for a 28 day stay or more.

Pool, Beach and Tennis Court! Fishing, swimming and relaxation!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$423.99

Welcome to REELaxation! Everything you need for your Islamorada vacation is here. Picture this, gazing at the Atlantic Ocean from the heated resort style pool, watching the sunrise from one of the 2 private beaches, kayaking or paddle boarding to the famous Islamorada sandbar, catching dinner off the dock, soaking it all in on the porch seating with ocean views, reading a book on one of the 2 balconies and then having dinner nearby with some of the most amazing sunset views you will find. Imagine bringing all that to life in your own memory filled Islamorada vacation.brbrIn the middle row of Angler’s Reef, this 2-bedroom home accommodates up to 6 with the sleeper sofa. REELaxation offers kitchen supplies, Weber 3-burner gas grill, AC, heating, WiFi, and a washing machine/dryer for your convenience and 2 parking spaces with covered carport. Boat slips can be reserved for additional fee, if available. brbrREELaxation is within walking distance to several waterfront restaurants, Theatre of the Sea is around the corner, Robbie's is just up the road to hand feed the tarpon and Key West is within driving distance of a day trip. Located at mile marker 85, on the ocean side, you have so many options that are very easily accessible. Islamorada is a fisherman's dream with the back country water and the gulf stream each just a short boat ride away. Catch pelagic species like a tuna, sailfish, marlin, mahi or wahoo in the morning and close the day out in the back country with a tarpon, bonefish, trout, redfish, snook or snapper.brbrREELaxation is our only vacation rental and with an extensive background in customer service, extraordinary guest service and helping to make lifetime memories are our goal. We look forward to assisting in any way we can and making your next Keys vacation an unforgettable one! brbrBook now and enjoy everything this fabulous house has to offer. Do not hesitate to reach out to us with any questions that you may have.

PRIME LOCATION Islamorada Anglers Reef Oceanview Private Beaches, Pool & Marina

Islamorada, Florida, United States

Bed

Bath

Sleeps

$432.17

Village of Islamorada license #24-0369br131 Anglers Way, Islamorada, FLbrThis Villa has 2 bedrooms (one with king bed and the other with One QUEEN SIZE BED and pull out couch) and 2 full bathrooms located on the 2nd floor, both with private balcony's. Down stairs there is a half bath, a full kitchen with stainless steel appliances, granite counters, living/dining room, New tile floors, cable TV, Wi-Fi and open porch with seating.br2 bikes included in rate. Community kayaks and paddleboards are avail to use (just have to sign a waiver).brCall me for more information 305-240-0592.brbrThis oceanfront resort is a boutique complex of 52 homes inspired by Key West architecture that was built in 2007. Gated community, located off the Old Hwy at MM 86 in Islamorada. Amenities include a community pool overlooking the Atlantic Ocean and 500ft of private beach. brBoat slips are available for rent (for additional fee)for up to 31' boat with a deep channel out to the Atlantic. Trailer storage is no longer available outside gate please ask for storage recommendations. Be at Alligator Light house or the Famous Islamorada (Holiday Isle) sandbar in minutes. Launch your kayak or paddle board from the private beachbrbrCome on down and put your toes in the sand. It's always better in the Florida Keys.Angler’s Reef is the perfect place for all fishing and diving enthusiasts. Islamorada is known as “The Sport fishing Capital of the World”. Water activities abound including: diving, snorkeling, Para sailing, kiteboarding, paddle boarding, kayaking, and more. You may even spot manatees at the marina. Fine dining and unique shops are within walking distance: Island Grill (Famous for their tuna nachos) serving breakfast, lunch and dinner oceanfront with live music. For late night entertainment, walk on over to Hog Heaven for a fun night of dancing. Also, within in walking distance is Theatre of the Sea, where you can watch a live dolphin show or even swim with the dolphins!

Anglers Reef Islamorada Vacation Rental 2/2.5 updated 131 Anglers Way

Islamorada, Florida, United States

Bed

Bath

Sleeps

$867.44

This listing is for a room within a hotel.brbr✦ Your room is 888 sq. ft, equipped with complimentary toiletries, standard quality 37-inch TV, available with Standard cable, and Premium cable.brbr✦ Cleaning services included in the nightly price.brbrThere 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✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Outdoor shared pool available all year, opened from 8:00AM to 5:30PM.brAdditional features:br • Heated poolbrbr✦ Free parking lot – 1 space(s).brbr✦ Shuttle service is available upon reservation between 7:00AM and 11:00AM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $50 nonrefundable fee per pet per day/ max 2 petsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Refundable security deposit charged nightly. brbr✦ Complimentary shuttle within 4 miles. brbr✦ Early check-in & late check-out subject to availability for a fee.br br✦ Smoking prohibited indoors; designated smoking areas provided.

Hotel

Come Create Memories w/ 1BR Fun Adventures at this Paradise! Outdoor Pool!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$258.94

Located in Islamorada, mile marker 87 right in the middle of beautiful Florida Key's. This Executive Bay Club Condo provides full 3 bed 2 bath accommodations with community amenities that include an outdoor swimming pool, free private parking, multiple tennis and pickleball courts. Huge Dock to see most amazing sunsets as well as go fishing along with beach access is available (No Boats Allowed with Rental).

Apartment

Islamorada Escape - Executive Bay w/Pool, Fishing Dock, Beach, Tennis/Pickleball

Islamorada, Florida, United States

Bed

Bath

Sleeps

$353.15

Welcome to island time at beautiful Anglers Reef, the perfect way to experience and relax in the Florida Keys. Our home, the Drop Off, is our little bit of island paradise. Anglers Reef is a village of 52 single-family homes in an exclusive gated community located at MM 85. Whether you are looking for a couples retreat or a family excursion, Anglers Reef provides the experience you are looking for. brbrACTIVITIES:brYou can take in the beauty of the island while walking or biking the quaint neighborhood streets and along the marina boardwalk. Return from your bike ride to take a refreshing dip in our temperature controlled pool with beautiful views of the Atlantic Ocean. At one of the two beaches, enjoy complimentary paddle boards and kayaks, which you can use to venture to the nearby sandbar or to fish or investigate the mangrove lined shoreline. Plus, there are many shops and premier restaurants with in walking distance.br brBOATING AND FISHING: brIslamorada is appropriately referred to as The Sport Fishing Capital of the World as world class fishing opportunities surround the area. You can dock your boat in one of the private slips at the marina or charter a fishing excursion nearby for ultimate fishing opportunities. However, fishing is only one of the many water activities you can enjoy from Anglers Reef. There is world class site seeing, snorkeling, diving, and boating opportunities everywhere. Plus, you may even run into one of the local Manatees that frequent the marina. Please contact property owner for boat slip rental information and rates. brbrHOUSE:brOur beautiful home has 2 Bedrooms, 2.5 Bathrooms, A/C, Granite work tops, modern stainless steel appliances, including gas BBQ. Open porches and balconies, rich hard wood floors, open plan dining area with ample seating, tasteful décor and fully furnished rooms. A truly unique place to stay in the keys, with an island paradise feel.

Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip.

Islamorada, Florida, United States

Bed

1

Bath

Sleeps

$2472.56

Welcome to Caribee Beach House!brbrDiscover the enchanting charm of Caribee Beach House, where the timeless allure of old-school Islamorada beautifully melds with stylish comforts. Tucked away in the heart of downtown Islamorada, this hidden gem offers an extraordinary retreat with 200 feet of private water frontage, a spacious 100-foot dock, and stunning views of Alligator Lighthouse.brbrBring your entire crew to this sprawling estate that boasts six bedrooms and five bathrooms, comfortably accommodating up to 14 guests. The fully equipped kitchen awaits your culinary inspiration, whether you're whipping up family favorites or cooking your fresh catch of the day!brbrStep outside to be mesmerized by sweeping ocean vistas that promise to take your breath away. The expansive yard, adorned with lush greenery and twinkling bistro lights, creates a magical ambiance perfect for unforgettable evenings. Jump into the stunning heated and chilled pool, complete with a baja shelf with loungers and umbrellas. brbrFor those looking to stay active, challenge your guests to a friendly match on your very own pickleball court that also doubles as a basketball court, or enjoy a round of mini putt on the custom putting green, adding a playful touch to your vacation! After the games, unwind around the fire pit on your private sandy beach for cozy bonfire memories. Your very own 100-foot dock is ideal for docking your boat, heading out for an early morning fishing trip, or taking a serene sunset cruise. Should you be craving adventure, kayaks, paddle boards, and bikes are available for rent, delivered directly to the property for your convenience.brbrbrIf you choose to explore beyond the beautiful grounds, you’ll find Lazy Days Restaurant within walking distance, offering exquisite seafood and breathtaking oceanfront dining. Also nearby is Bud N’ Mary’s Fishing Marina, home to the oldest and largest fishing fleet in the Florida Keys. Here, you can book off-shore and in-shore fishing charters or embark on eco-tours and diving adventures.brbrTake advantage of a local’s secret and park your vehicle and utilize the Islamorada Freebee; Our local rideshare service offering door-to-door transportation service to and from your favorite Islamorada destinations with environmentally friendly electric vehicles. It’s not only a fun alternative transportation option – it reduces traffic congestion, addresses drinking and driving, and reduces the Village’s carbon footprint. Two Tesla Model X vehicles can accommodate up to seven passengers and one larger vehicle that can accommodate a wheelchair and up to nine passengers. brbrWe also offer daily housekeeping, pre arrival grocery shopping, and golf cart rentals to make your stay as easy and enjoyable as possible.brbrThis property has a rich history, established in the 1950s, and has been lovingly revitalized to preserve its eclectic charm while enhancing its captivating grandeur. Your unforgettable escape awaits at Caribee Beach House! brbrAs part of nature’s vibrant tapestry, Sargassum seaweed may occasionally collect along the shores of the Florida Keys, including Islamorada. This natural phenomenon supports a thriving marine ecosystem, serving as a nursery for sea life and enriching the local environment.brbrCheck-in must be on a weekday. Weekend arrivals (Saturday or Sunday) start at $18,000/week plus taxes and fees. Prices and availability are subject to change without notice. Contact Coastal Vacation Rentals of the Florida Keys to confirm pricing and availability. Holiday weeks may incur peak pricing without notice.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.brbrVacation Rental License: 26-0205

Caribee Beach House ~ Private Islamorada Beach Estate W/ Heated Pool & Dockage

Islamorada, Florida, United States

Bed

Bath

Sleeps

$691.09

Beautiful 4-bedroom, 3.5 bath home in Angler's Reef. Located at MM85, this tastefully decorated, open floor plan features a newly renovated gourmet kitchen including all of the amenities you’ll need for a perfect stay – updated appliances, quartz countertops and breakfast bar. Enjoy viewing some of the local artwork as you stroll throughout the home. We pride our home for hosting large groups and the newly added large sectional pulls out as additional sleeping space. A queen bedroom with en-suite bathroom is conveniently located on the first floor. There is also a stylish powder bathroom on the first floor off the kitchen and living area. The 8-person dining table is a perfect space to play cards and enjoy meals with your friends and family, while the kitchen island seats 5 people. A console table off the kitchen offers all the essential openers, koozies, martini shaker and plenty of games for a fun vacation! brbrThe porch off the family room offers ocean views, 2 comfortable chairs w/side table, an outdoor dining table seating 4-people and a grill. brbrThe second floor includes 3 bedrooms. Upstairs, the master bedroom features a four-poster king bed, en-suite bathroom with double sinks and an updated shower with bench. The master bedroom opens up to its own private covered porch with spectacular views of the ocean, 2 sofa lounge and 3 club chairs. The two upstairs bedrooms offer queen beds with a partial ocean view. There’s a full bathroom located between these two rooms. You’ll conveniently find a laundry closet with washer and dryer in the upstairs hallway that also offers a steamer and iron. All bedrooms include TV’s and wireless internet service provided. brbrThis rental includes boat slip #14, which can accommodate boats up to 31 feet in length. Angler’s Reef is a wonderfully maintained and gated community in Islamorada, the fishing capital of the world. In Islamorada you can swim with dolphins, go dive the reefs, sport fish or just simply enjoy the salt-water life and great restaurants.

4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL

Islamorada, Florida, United States

Bed

Bath

Sleeps

$210.49

Your chance to experience one of Islamorada's most sought-after communities has arrived! Brand new to the rental pool, this beautifully renovated townhome in Executive Bay Club (Unit C3) is the perfect escape for the winter season.brThe Owners have recently purchased and are in the process of refurnishing with all-new coastal-chic décor — photos coming soon! You'll love the modern updates, bright open spaces, and resort-style amenities.brEBC has it all: a newly refreshed pool and lounge area (looking AMAZING!), tennis and pickleball courts, and a stunning clubhouse overlooking the bay.brNow booking for the winter season — come enjoy the relaxed, island lifestyle at Executive Bay Club, where every day feels like vacation.brIf booking more than a year in advance current prices may not reflect the annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Charming 2 bedroom townhome at Executive Bay Club!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$574.56

Imagine: morning coffee on the balcony, ocean breeze in your hair, then a night in your own hidden speakeasy with karaoke and cocktails. Turtle Cove is Islamorada's most unique 3-bed, 3-bath retreat — luxury linens, 3 private ensuite baths, pool, dock, paddleboards, and bikes included. The Keys trip your group will never forget. Check availability now.brbrOnly at Turtle CovebrAmenities no other vacation rental in Islamorada offersbrbr- Private speakeasy lounge hidden on Level 1 — bar tops, mood lighting, and a vibe unlike anything else in the Keysbr- Karaoke stage — yes, a real stage. Belt your heart out after the kids go to bedbr- High-end game room: shuffleboard, air hockey, and corn hole steps from the patiobr- Private BBQ patio with al fresco dining and fire pit — your own outdoor living roombr- EV charging included — one of the only Islamorada rentals with a dedicated chargerbrbrBedrooms — luxury bedding & private ensuite in every roombr3 bedrooms · 3 ensuite baths · sleeps 8 · no shared bathroomsbrbr- Every bedroom has its own private ensuite bathroombr— no sharing, no waiting, no compromise. Each guest has their own space from the moment they arrive.br- Luxury linens on every bed — hotel-quality sheets, plush pillows, and premium duvet sets so you wake up rested and ready for an adventure-filled daybr- Primary king suite (Level 3): king bed dressed in premium linens · private ensuite bath · balcony with partial water views and ocean breezebr- Double-queen bedroom (Level 3): two queen beds with luxury bedding · private ensuite bath — perfect for kids, a second couple, or friends sharing a roombr- Queen bedroom (Level 2): queen bed with premium bedding · private ensuite bathbr- In-unit washer/dryer — pack light, leave fresh, laundry supplies providedbrbrWater, sun & adventurebrEverything included — no rentals, no extra feesbrbr- Partial ocean views from multiple balconies — catch the sunrise with your morning coffeebr- Dock access for boats up to 26 ft (first-come, first-served — ask us to confirm availability)br- Community pool steps from your doorbr- 2 paddleboards included — launch straight from the propertybr- 4 bikes ready to ride — explore the island car-freebr- Private fishing lessons available as a bookable add-onbrbrThe layoutbr3 bedrooms · 3 ensuite baths · sleeps 8brbr- Level 1: Private speakeasy · karaoke stage · games · BBQ patio with outdoor seating · garage gym · paddleboards & bikesbr- Level 2: Full kitchen · family room · balcony with dining · queen bedroom with ensuite bathbr- Level 3: Primary king suite with ensuite · double-queen bedroom with ensuite · luxury bedding throughout · in-unit laundry · balcony with partial water views & ocean breezebrbrWhy Islamorada brStill deciding where in the Keys to stay Here's why this is the sweet spotbrbr- The Sportfishing Capital of the World — world-class fishing, diving, and snorkeling right outside your doorbr- Perfectly positioned between Miami/Fort Lauderdale and Key West — the Upper Keys sweet spotbr- Freebee on-demand rides: Free electric rideshare (Tesla Model X) runs 7am–midnight daily throughout the village — get to dinner, bars, and beaches without moving your car free of charge (tips encouraged)br- Fly in by seaplane: Tropic Ocean Airways announced charter seaplane service from Fort Lauderdale direct to the Florida Keys — skip the traffic and arrive in stylebr- Walk or bike to top restaurants, beach bars, Anne's Beach, and Robbie's Marinabr- Gated Peaceful Palms community — private, secure, and beautifully maintainedbrbrGood to know before you bookbrPolicies, access & licensingbrbr- Smart lock self check-in — your personalized code arrives before arrivalbr- 1 dedicated parking spot directly in front of the unitbr- Dock space available on a first-come, first-served basis for boats 26 ft and under — contact us to confirm availability or get recommendations for nearby dockagebr- A rental agreement is required at booking to confirm terms and conditionsbr- Exterior security camera on property for your peace of mindbr- FL DBPR License: DWE5405520 · Islamorada Village License: 26-5090

Luxury 3/3·Secret Speakeasy·BBQ Patio·Dock·Pool

Islamorada, Florida, United States

Bed

Bath