Vacation Rentals By Owner In Islamorada, FL

Watch the sunrise from your private balconies in both bedrooms overlooking the Atlantic ocean, and walk across the street to amazing sunsets on the Gulf of Mexico in Founder's Park or Marker 88 Restaurant. brbrEnjoy the fully renovated condo with wood floors, marble in both bathrooms, granite countertops, a 55 TV in the living room, high-speed WiFi, and reclaimed wood bar. The kitchen has all the equipment and utensils you need to make a great meal, and a community BBQ is located just below the unit by the water. Clean up is easy with a in-unit dishwasher, washer and dryer.brbrWe are located an hour south of Miami and you will be less than two hours north of Key West - a perfect day trip. Islamorada is the fishing capital of the world, with charter captains available to take you on the water on your whim.brbrThe property has a small exercise room (run or walk on the treadmill while looking at the ocean waves!), a lovely heated pool with lots of loungers and rockers, a beautiful dock and a community BBQ to grill your catch on.brbrWe have a small, friendly, community of 80 units, and are looking forward to hosting great people. Please reach out today so we can discuss your Keys dreams.

Condo

Oceanfront condo in Islamorada, amazing sunrise views, renovated in 2019!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$613.54

Beautiful Port Antigua waterfront home with a 60 foot concrete dock on a wide, clear-water canal. Access to Port Antigua homeowners' boat ramp and private white sandy beach on the Florida Bay. Meticulously maintained residence with third floor suite, with two walk-in closets, spacious spa-style bathroom featuring double sinks, and large balcony with water views. Office/loft space with trundle bed to accommodate 2 extra guests. Main level offers two bedrooms, one bath, custom kitchen, and dining and living room with vaulted Cypress plank ceilings. Substantial waterside screened patio that wraps around the entire 2nd floor. Additional rooms on ground floor which includes 2 bedrooms and one full bath. Featuring a brand new in-ground spa-style saltwater pool with putting green on the side. Also features metal roof, small barbeque and covered patio. A lovely home dubbed 'Banana Republic'.

Gorgeous Keys Vacation Home in Prestigious Neighborhood of Port Antigua

Islamorada, Florida, United States

Bed

Bath

Sleeps

$666.78

Welcome to Peaceful Palms, a 3-bedroom, 3-bathroom townhome that's all about easy, laid-back island living. Tucked away in Islamorada, this spot has everything you need for the perfect getaway—boho coastal vibes, plenty of space to relax, and access to a gorgeous community pool.brbrInside, you'll find bright, open spaces with natural textures and beachy tones that feel like a breath of fresh air. Each bedroom is its own little retreat, and with three bathrooms, no one's waiting in line after a day out in the sun.brbrSpeaking of the sun, the community pool is just steps away, ready for lazy afternoons with a good book or a quick dip to cool off. And when you're ready to explore, you're in the heart of Islamorada—close to amazing restaurants, fun waterfront spots, and some of the best fishing in the world.brbrWhether it's sipping your morning coffee on the balcony or catching the sunset after a full day of adventures, Peaceful Palms is where the best kind of memories are made. Come see for yourself—you won't want to leave!brbrPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Enjoy a serene stay at Peaceful Palms 3 in Islamorada with ocean views.

Islamorada, Florida, United States

3

Bed

3

Bath

6

Sleeps

$229.5

This brilliant house in Islamorada is a wonderful choice for guests seeking a cozy retreat. With 2 bedrooms, 2 bathrooms, pool, and essential amenities like WiFi and AC, this home offers everything you need for a comfortable stay. Whether you're relaxing in the living room or enjoying the outdoor space, you'll feel right at home here. You're sure to make fantastic memories with a stay at our place.

Charming 2-bedroom house in welcoming Islamorada with WiFi, AC

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1473.75

Islamorada Rental License: VR - 065 *** SATURDAY TO SATURDAY RENTALS ONLY!brbrIf your preferred dates are not available, check our other home, The Last Resort Too - VRBO #4357870, MM 77, or contact us with an inquiry here, SPECIFYING The Last Resort ToobrbrCHECK OUT A FEW WORDS FROM THE OWNERS BELOW THE INITIAL INFORMATION...brbr4 bed/5 bath beachfront on over 1 acre with a private beach, heated pool & dockbrSeparate upstairs Den area sleeps up to 6 kids.brbr* 7 Day minimum rental - Saturday to Saturday *brSORRY, NO WEDDINGS OR LARGE EVENTS ALLOWED br Max 8 adults + 4 childrenbrYou must be 25 years+ to rent this home and must be staying for the duration of the rental.brbrOur house is one of the most highly sought-after vacation homes in Islamorada that regularly books years in advance. The Last Resort is a firm favorite of multi-generational families and friends looking to create memorable moments that last a lifetime in a lush, private, and tropical setting.brbrAs owners, we have spent 24+ years providing the best possible Keys experience for guests. Michele handles the day-to-day operations of the property and ensures guests have everything they need for a stress-free vacation. We believe that guests should not have to worry about 'extra or hidden' charges, so our rates INCLUDE many of the things other vacation rentals charge for, such as pool heat, BBQ gas, kayaks, and baby equipment. Though the property is self-catering, we supply many household items so you don't have to worry about purchasing them, such as laundry detergent, dishwasher detergent, garbage bags, kitchen paper, cleaning fluids, etc.brbrWe also don't charge a security deposit or pet fee. We operate on an honor & integrity system, giving our guests an authentic Keys experience that keeps them returning year after year as repeat guests.brbrFrom years of international travel with our kids, one of my pet peeves was the amount of equipment that I had to pack just to go on vacation. Another was arriving at houses that were sparsely stocked or having to rent additional equipment. Greg and I made the commitment to provide as many supplies and equipment for our guests, from all kitchen equipment to baby equipment, from hairdryers & straighteners to lifejackets and water shoes, all to alleviate the need for guests to stuff their suitcases and truly make it a 'pack your shorts, flip-flops & toothbrush' kind of house.brbrThe Last Resort is truly in a beautiful setting, and we look forward to the opportunity to host you, your family, and your friends someday.brbrMichele & Gregbrbr.... AND NOW THE HOUSE...brbrBuilt in 1922, this historic Conch Style oceanfront executive retreat boasts overwhelming views of the Atlantic, large open verandas, 165 feet of private sandy beach, a 15 x 30 seaside heated swimming pool, 37 ft. concrete protected dockage on the canal adjacent to the house, and a gated entrance. Quiet seclusion awaits you at this unique destination.brbrThis 4-bedroom, 5-bath home with 4,000 square feet of living area is situated on over an acre in a private, tropical setting. Located in an upscale neighborhood in famed Islamorada, this fine home offers you the ability to relax, entertain, and enjoy the many recreational activities found only in the Florida Keys! br brRecognized by international publications as a preferred location for resort and swimwear photo sessions, the interior is casually furnished, tropically decorated, and offers every imaginable convenience.brbr* Ralph Laurenbr* Victoria's Secretbr* Abercrombie & Fitchbr* Michael Korsbrbr* Opening shot Bloodlinesbr* Promo shot HGTV Dream Homebrbr* Variety of European magazinesbrbrYou'll find an abundance of great island shops, full-service marinas, and popular local restaurants nearby! br brIdeal home for extended families, as most of the living space is on the ground level. Also, wide-covered front and back porches are ideal for outdoor entertaining/relaxing. The rear veranda overlooks breathtaking ocean views, palm trees, and a private sand beach. The front veranda overlooks a beautiful, tropical landscaped yard. Our home also has a rooftop deck overlooking the palm-lined sand beach and brilliant shades of the tropical ocean.brbrAmenities: Two-story home with front and back covered porches, a 15x30 heated in-ground pool, a 165-wide private sand beach, and beautiful landscaping. House includes phone, high-speed wireless Internet/DSL line, dual-zone central air conditioning, ceiling fans in all rooms, 3 cable/smart TVs (both Masters & Living room)(2 smart TVs in the kids' Den, DVD player, and Bluetooth speakerbrbrFull kitchen includes a microwave, dishwasher, refrigerator, beverage fridge, coffee maker & Keurig 2.0, toaster, cooking utensils, and linens provided. 2 washers, 2 dryers, and 2nd fridge in the Laundry room. Jacuzzi tub in the downstairs Master bath.brbr brGas grill (BBQ). Pets are allowed with advanced permission. 37-foot concrete private dockage with mains water and direct ocean access is available on our canal lot adjacent to the oceanfront home, with plenty of room for a boat trailer.brbrThere is one exterior camera on the front porch pointing towards the driveway. and a 2nd camera on the exterior of the laundry room door. There are no other cameras anywhere on or on the property.brbrFeel free to send us an inquiry for any further information before making a booking decision. We are always happy to help.brbrMichele

Next available - August 2026 - Oceanfront - Heated Pool - Dock

Islamorada, Florida, United States

Bed

Bath

Sleeps

$295.85

Each furnished room offers premium bedding and free Wi-Fi. Our pet-friendly private beach resort features a boat ramp and paid parking, heated pool with ocean views, terrace lawn games, daily continental breakfast, complimentary self-parking, bike rentals, kayaks, paddleboards, and outdoor BBQ facilities.brbrThis listing is for a room within a hotel.brbr✦ Your room is 380 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.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✦ Outdoor pool is available.brAdditional features:br • Heated poolbrbr✦ Free parking lot.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $29.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 dogs max w/ no breed restrictions. Tax inclusivebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Access To Private Boat Ramp will incur additional charge/nightbrbr✦ Front desk: 8 AM to 9 PM

Apartment

Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed

Islamorada, Florida, United States

Bed

Bath

Sleeps

$273.42

Take a break and experience the laid-back lifestyle in the beautiful Islamorada!brbrThis listing is for a room within a hotel.brbr✦ Your room is 904 sq. ft, equipped with complimentary toiletries, TV.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 18 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✦ Pool is available.brbr✦ Free parking lot – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). per pet, per night. Up to 2 dogs, max 50lbsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ A mandatory resort fee applies per unit, per night, plus applicable taxes.

Hotel

Just What You Were Looking For! Free Breakfast, Onsite Pool, Free Parking

Islamorada, Florida, United States

Bed

Bath

Sleeps

$273.42

Take a break and experience the laid-back lifestyle in the beautiful Islamorada!brbrThis listing is for a room within a hotel.brbr✦ Your room is 904 sq. ft, equipped with complimentary toiletries, TV.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 18 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✦ Pool is available.brbr✦ Free parking lot – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). per pet, per night. Up to 2 dogs, max 50lbsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ A mandatory resort fee applies per unit, per night, plus applicable taxes.

Hotel

Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast

Islamorada, Florida, United States

Bed

Bath

Sleeps

$273.42

Take a break and experience the laid-back lifestyle in the beautiful Islamorada!brbrThis listing is for a room within a hotel.brbr✦ Your room is 904 sq. ft, equipped with complimentary toiletries, TV.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 18 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✦ Pool is available.brbr✦ Free parking lot – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). per pet, per night. Up to 2 dogs, max 50lbsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ A mandatory resort fee applies per unit, per night, plus applicable taxes.

Hotel

Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed

Islamorada, Florida, United States

Bed

Bath

Sleeps

$295.85

Each furnished room offers premium bedding and free Wi-Fi. Our pet-friendly private beach resort features a boat ramp and paid parking, heated pool with ocean views, terrace lawn games, daily continental breakfast, complimentary self-parking, bike rentals, kayaks, paddleboards, and outdoor BBQ facilities.brbrThis listing is for a room within a hotel.brbr✦ Your room is 380 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.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✦ Outdoor pool is available.brAdditional features:br • Heated poolbrbr✦ Free parking lot.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $29.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 dogs max w/ no breed restrictions. Tax inclusivebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Access To Private Boat Ramp will incur additional charge/nightbrbr✦ Front desk: 8 AM to 9 PM

Apartment

Just What You Were Looking For! Free Breakfast, Onsite Pool, Free Parking

Islamorada, Florida, United States

Bed

Bath

4

Sleeps

$295.85

Each furnished room offers premium bedding and free Wi-Fi. Our pet-friendly private beach resort features a boat ramp and paid parking, heated pool with ocean views, terrace lawn games, daily continental breakfast, complimentary self-parking, bike rentals, kayaks, paddleboards, and outdoor BBQ facilities.brbrThis listing is for a room within a hotel.brbr✦ Your room is 380 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.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✦ Outdoor pool is available.brAdditional features:br • Heated poolbrbr✦ Free parking lot.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $29.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 dogs max w/ no breed restrictions. Tax inclusivebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Access To Private Boat Ramp will incur additional charge/nightbrbr✦ Front desk: 8 AM to 9 PM

Apartment

Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast

Islamorada, Florida, United States

Bed

Bath

Sleeps

$449.71

Welcome to Villa #110, your perfect getaway! Nestled in the heart of Islamorada, this spacious 2-bedroom villa - one of the largest 2 BR units in the community - offers the ideal blend of comfort and tranquility for your tropical escape. Recently taken under new ownership, the villa is undergoing thoughtful updates to enhance your stay while preserving its laid-back island charm. brbrThis magnificent free standing home is located in Islamorada at Mile Marker 85 in the exclusive gated community of Anglers Reef, a quiet oceanfront community in the Florida Keys. Anglers Reef is a boutique complex of 52 homes inspired by Native Conch & British West Indies architecture. Quaint streets & walking paths wind through this village-styled retreat. Amenities include a resort-like community pool overlooking the Atlantic Ocean, private marina (boat slip can be requested at additional charge) and 500 ft of private beach. Community owned kayaks and paddleboards are available for all guests to use.brbrThis home away from home will meet all of your needs! The villa offers 2 large Master bedrooms located on the 2nd floor. The first bedroom has a king size bed with a private balcony and the second oversized bedroom has two queen size beds with twin size pull-out trundle. Each bedroom has a private en suite bathroom. Plenty of room and privacy to unwind, and the perfect set up for those traveling with children. A rear deck with dining table, new Weber barbeque grill and lavish landscaping allow for restful downtime. Home decor includes stainless appliances, dishwasher, granite counters, hardwood floors, 3 flat screen TVs with premium cable and Wi-Fi. Rental includes all kitchen needs, dishes, glasses, pot/pans, etc. as well as linens / towels / beach towels to set you up for the perfect vacation getaway! Two bicycles are included in the rental. A dedicated driveway with carport accommodates two vehicles.brbrIslamorada is universally known as the “Fishing Capital of the World” and provides amazing fishing opportunities - gulf, backcountry or ocean. Or fish off one of the picturesque Florida Keys bridges! Fishing guides, charters and boat rentals are easily accessible. Fishing is also permitted off our private dock.brbrFor the landlubbers, Anglers Reef offers many opportunities to relax. Enjoy our outdoor deck spaces with a book or cocktail. Swim and sunbathe at our large community pool (heated in winter and cooled in summer!). Or stroll through the community or relax on the private beaches. Something for all!brbrWithin walking distance are Hog Heaven, Smugglers Grill, the Island Grill, Three Rivers Resort Tiki Bar and Starbucks (one of three between Miami and Key West!). There are countless amazing dining opportunities in the Islamorada area.brbrFor recreation, you can swim with dolphins at Theater of the Seas 1/2 mile south or visit Founders Park one mile to the North to swim in the Olympic size swimming pool, use the diving boards, play tennis/pickleball or enjoy their shallow sandy beach. Charter boat tours readily available to visit the Sandbar, tour the area, scuba or snorkel. A short 30-minute drive to the John Pennekamp Coral Reef State Park in Key Largo for amazing snorkeling or to visit the famous Christ of the Deep Statute. The opportunities are endless!brbrPreferred check-in/check-out days are Saturday. Message us if you wish to check in/out on a different day. Our calendar is updated in real time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrNOTE THAT THERE IS CURRENTLY A VRBO GLITCH WITH SOME OF OUR CHECK IN SATURDAY DATES (6/27, 7/4, 7/18, 12/5, 12/12, 12/19/26 AND 1/9, 1/16, 3/20, 3/27/27). WE ARE WORKING WITH VRBO TO CORRECT THIS TECHNICAL ISSUE. IF YOU ARE LOOKING TO CHECK IN ON ANY OF THESE SATURDAYS, PLEASE MESSAGE US. SORRY FOR THE INCONVENIENCE! brbrTIP: Look for discounts on Retail Me Not and Rakuten for your VRBO booking :) brbrWe look forward to welcoming you to our home away from home in the Florida Keys!

Villa

Oversized Islamorada Villa 110 in Gated Anglers Reef: Pool, Kayaks, Bikes, Beach

Islamorada, Florida, United States

Bed

Bath

Sleeps

$899.83

Maison Matecumbe #307 - Maison Matecumbe is an exclusive gated and private boutique complex comprised of 9 units. Centrally located right in the heart of Islamorada within walking and biking distance to many restaurants, cafes, shopping, marinas and Islamorada's Art District. The unit has been totally renovated, brand new kitchen, beautiful bathrooms, decor and bedding. The unit offers an open lower level living room with kitchen and guest bedroom and full bath. Beautiful views of the Atlantic from the screened balcony. The upper level has a king master en suite and third bedroom with two queen beds. Newly renovated swimming pool and hot tub to spend your days lounging along with Maison's beach, outdoor kitchen, tiki hut and spa. brVACATION RENTAL LICENSE: 24-0074brIf booking more than a year in advance current prices may not reflect annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brbrPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Condo

Experience luxury at Maison 307 in Islamorada, 3 bedrooms with resort-style pool.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$414.75

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

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

Islamorada, Florida, United States

3

Bed

Bath

6

Sleeps

$297.8

This brand new home is sitting quietly behind a controlled access gate with a private balcony overlooking the Atlantic Ocean. Full two bedroom, two bath floor plan, has an upscale decor package and is fully furnished - with an optional work-from-vacation home set up in bedroom 2.brWhile your experience will be private, you will have full access to all of the Sun Outdoors Islamorada resort amenities and activities. Including, but not limited to, heated pool, clubhouse, outdoor game lawn, billiards, and ocean front tanning chairs and boardwalk. A social calendar for all guests is always available for those that wish to be more social, while fine dining is only a minutes drive in Islamorada.brIslamorada is the fishing capitol of the world, and you will easily find plenty of nice dining locally. Founders park is directly across the street for those that wish to walk over and have a day at the beach, or just play some pickle ball.brbrCheck out the video of our home below:brhttps://youtu.be/vs-ChBQAxzc

Hotel Resort

Brand New Home, Resort Location, Pet Friendly, Oceanview

Islamorada, Florida, United States

Bed

Bath

Sleeps

$668.72

Welcome to a one-of-a-kind Florida Keys escape! This unique home, originally used as the Islamorada Courthouse, has been thoughtfully transformed into a stunning waterfront getaway while keeping its historic charm. Located in the heart of Islamorada, this property offers access to what the Keys are known for: the best fishing, dining, and great sunsets.brbrFor the comfort and safety of all guests, our accommodation is designed for guests aged 12 years and older. Pets are not permitted.brbrEscape to this bright and welcoming 3-bedroom, 2-bathroom home, perfectly designed for relaxation and connection. Located right on the water, this Keys-style getaway blends indoor comfort with unbeatable outdoor living.brbrHighlights of your stay:br✔ Smoke Free environmentbr✔ Three comfortable bedrooms with cozy beddingbr✔ Two full bathrooms (no ensuite)br✔ A stylish and comfortable living room with ample seating for winding down after a day in the sunbr✔ A full kitchen with all the essentials, plus a dining table for six for shared meals and game nights.br✔ A screened in porch overlooking the water.brbrStep outside to your private waterfront tiki hut, fully outfitted with:br✔ Outdoor TV for game days or movie nightsbr✔ Refrigerator & ice maker for easy refreshmentsbr✔ Dining and lounge areas ideal for morning coffee, sunset dinners, or just soaking up the breeze.brbrOur waterfront property offers private boat dockage for vessels up to 30 feet, so feel free to bring your boat and make the most of your stay! From your own backyard, you can easily cruise through the crystal-clear waters of the Florida Keys, discover hidden sandbars, fish in world-class spots, or enjoy stunning sunsets from the water. Whether you're island-hopping or just exploring the beautiful surrounding areas, your adventure starts right here!brbrThe villa is stocked with all the basics you will need to start enjoying your vacation right away without any worries. The villa also boasts amenities like an iron/iron board, a hairdryer, beach towels, umbrella, and beach chairs. To start your day, there is a Keurig duo coffee maker (K-cup and drip), french press, and a kettle.brbrThe design of the villa consists of two separate units — one on the ground floor (yours) and another on the upper floor. Both units have separate entrances and are not connected in any way. All outdoor amenities are exclusive for you and your guests. brbrBook your stay now and enjoy waterfront living, island breezes, and all the comforts of home—Keys-style!

Off The Charts-Waterfront Tiki Bar & Private Dock

Islamorada, Florida, United States

Bed

Bath

Sleeps

$514.7

br112 Anglers WaybrIslamorada Village vacation rental #24-0371brCall me for more information 305-240-0592. (2 houses side by side available)brThere is no other neighborhood like Anglers Reef in Islamorada. It's beautiful Key West style pastel colored homes inside resort community, with garden like flora and fauna such as bougainvillea meticulously maintained, with a fantastic oceanfront swimming pool and boat docks and views over the Atlantic Ocean that will take your breath away. Just minutes from many local shops, bars and restaurants. Access to the ocean does not get any easier than at Anglers Reef. When we first found Anglers Reef on vacation ten years ago we were sold and never went anywhere else. br The Yellow Tail House:brThere Are 52 Homes at Angler's Reef With Only 36 Boat Slips. Our home has the option for you to bring your own boat and use the dock (additional cost) . It is a Safe, Gated Community with very little traffic, truly an oasis. Enjoy coffee or cocktail on one of four porches, (each bedroom upstairs has its own balcony and bathroom). brYou will tell you are someplace special when you see our 2-bedroom, 2.5-bathroom house, surrounded by wonderful landscaping, amazing palms, bougainvillea, and some of the most colorful tropical foliage that only the tropical Florida Keys can offer. (have 2 houses one next door to this one, so plan your family event and both)brbrYellow Tail's first floor offers a spacious, wide open layout with an over-sized sectional couch. Granite counter tops, all updated appliances, kitchen is stocked with pots and pans, utensils plates, a Keurig Coffee Pot! & everything you will need to prepare anything. Stay entertained during your downtime by watching your programming of choice on any of the home’s 3 flat screen TVs with HULU and a Netflix Subscription, or surf the web via the complimentary wireless internet access. We also offer two bikes and community Paddle Boards and Kayaks that you are available for you to ride. brThe second floor offers a spacious Primary Bedroom with comfortable King size bed and an en-suite bathroom. There is a balcony and a television for you to enjoy. brFull size washer and dryer is in the hallway for your convenience.brThe Guest bedroom has a brand new Queen over King BunkBed with new comfy mattresses (Jan 2024). This room also has an en-suite bathroom with bath tub and a TV and balcony.brbrChildren of all ages will love the pool and the fact that there is no road traffic, and the geckos will keep young kids entertained for hours!brbrThroughout your visit, you and your companions will get to enjoy outstanding recreational facilities at Angler’s Reef. These community amenities include a heated swimming pool with outdoor bathrooms, chaise lounge chairs and tables overlooking the breathtaking blue waters of the Atlantic Ocean, and boat slips available for rent. Look forward to soaking up the sun at either of the 2 private beaches, located just a few short steps away from every home that flank the marina. Also the world famous Islamorada sandbar and Alligator Reef are a short boat ride from the opening of the channel. brNext door is the Blue Marlin House. For large parties or families both can be rented together, their layout is identical and both share high end furnishings.brbr A dock is available also for an additional costbrbrPlease note, as of Aug 1, 2024. you will no longer be able to store a trailer outside the gate on the grass any longer. Trailers fitting under the carport are able to be stored there. Otherwise, we can recommend local storage lots you can contact.br

Anglers Reef Islamorada, Bikes,Kayak,Paddle Boards DOCK available-Pool

Islamorada, Florida, United States

Bed

Bath

Sleeps

$534.38

This amazing house boat in Islamorada is a unique and pleasant retreat for guests. With 2 cozy bedrooms and a comfortable living room with a sofa bed, this floating oasis offers a relaxing stay. Enjoy the convenience of WiFi and AC during your stay. Whether you're looking to unwind on the water or explore the local attractions, this excellent property is the perfect choice for your vacation. We look forward to welcoming you to our place.

House Boat

Charming house boat with 2 bedrooms and WiFi, AC in wonderful Islamorada

Islamorada, Florida, United States

Bed

Bath

4

Sleeps

$161.21

Bayfront Sand Pebbles #304 - A desirable Islamorada condo complex with a total of only 16 units. This two-bedroom two bath unit is tucked away on the bay right in the heart of Islamorada. Beautiful sunsets & water views from your living room, kitchen & master bedroom. Enjoy the spacious lanai and refreshing breezes! Relax at the pool or venture through the mangrove nature walk. Islamorada Marina, Square Grouper and Midway Cafe are all in walking distance. 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.

Condo

Relax in this 2-bedroom bayfront condo in the heart of Islamorada!

Islamorada, Florida, United States

Bed