Vacation Home Rentals By Owner In Islamorada, FL

Showing 260 Of 365 Vacation Rentals

$591.78

ISLAMORADA BEACH HOUSE

Islamorada, Florida, United States

Luxury Waterfront Home in Exclusive Port Antigua – Islamorada, FLbrbrEscape to this stunning 4,200 sq. ft. waterfront retreat in the coveted Port Antigua neighborhood of Islamorada, Florida. With breathtaking sunrises from two expansive terraces, this 5-bedroom, 4-bathroom home comfortably accommodates up to 10 guests—perfect for families or groups seeking a serene getaway.brbrFeatures and Amenities:br • Spacious 5 bedrooms and 4 bathrooms, ideal for up to 10 guests.br • Two large terraces offering stunning ocean views.br • Access to a private community boat ramp for easy exploration of the Florida Keys.br • Prime location near top attractions, shops, and restaurants.brbrNearby Attractions:br • 5 minutes to Robbie’s of Islamoradabr • 10 minutes to Bass Pro Shops – World Wide Sportsmanbr • 10 minutes to Publix Super Marketbr • 15 minutes to Theatre of the Seabr • 30 minutes to the famous Seven Mile Bridgebr • 30 minutes to MillionAir Private AirportbrbrEnjoy luxury living in Islamorada with all the comforts of home.brbrContactbrCall 786-227-3354 to schedule a showing or book your stay today!

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Exceptional(84)

$548.84

/ Nightly

Private Vacation Home

Luxury, Elegant, Water Front Home, Heated Pool, Plantation Key, Islamorada

Islamorada, Florida, United States

VILLAGE. RENTAL LICENSE # VR-007brPlease always send email request with dates desired , as sometimes the dates on the calendar are not right.brbrFrom Dec 16 to April 16 are high season weeks/months.brFrom April 17 to Dec 15 are low season weeks/months.br brHouse has access to all water recreational activities , close to open water and yet secluded enough to feel you are all alone in Paradise , you can have your boat dockside gas and full service. brMarinas less than 10 minutes away by water, brbrThe Florida Keys can be considered the American Caribbean and features all the same amenities as other island destinations such as world class sport fishing, scuba diving and snorkeling, boating, sailing, kayaking and eco-tours. Each of our island destinations has some special features. We invite you to visit each area individually and discover our tropical paradise in the Florida Keys.brbrKey Largo offers some of the finest diving and snorkeling in the Florida Keys. One of the main attractions in Key Largo is the John Pennekamp State Park. There are many dive companies that run guided trips to the park and to area sunken wrecks just off Key Largo.brbrIslamorada is the next island destination just south of Key Largo. Islamorada is known for its world class sportfishing. Each season welcomes new fishing tournaments and angling opportunities. Bone fishing is especially popular with large bonefish up into the 10lb. Range. Offshore sport fishing can be equally exciting during the winter months for sailfish just off the reefs of Islamorada.brFounders Park just 10 minutes south of the property with beaches , boat rental , kayak rentals , Olympic size pool , basketball court, tennis court , skating , dock-age , refueling facilities , bar and restaurants .brbrThe Department’s function is to enhance the quality of life for residents by providing safe and attractive parks, recreation areas and activities. There are six Village parks and recreation properties: Founders Park, Library Park Beach, Anne’s Beach, Plantation Tropical Preserve, Green Turtle Hammock Nature Preserve, Plantation Hammocks Preserve, and Southwind's Park. The 45 acre Islamorada Founders Park is the center of the Village’s park system, offering sports programs, recreational Founders Park Pacific Lighthouse Programs and facilities, sports coaching and training and facilities for aquatics, golf, soccer, baseball, tennis, volleyball, swimming, and basketball. The department also provides children’s recreational camps and supervises, organizes, and supports large charitable public special events such as: Friends of the Pool Aquatic Ball, Bougainvillea Ball, July 4th Celebration & Fireworks, Florida Keys Youth and Masters Swim Meets, Special Olympics Swim Meet, Islamorada Chamber of Commerce Holiday Festival and Island Fest, Upper Keys Rotary Nautical Flea Market, University of Miami Sports Hall of Fame & Habitat for Humanity Fishing Tournament, Bay Jam and several Islamorada Community Entertainment amphitheater events, as well as a wide range of numerous smaller special events.brbrGolf at Hawk Keys resort. Various shopping areas and super markets and 5 screen movie theater very close by ,many more activities, to make your vacation one that will never be forgotten. brbrHouse has up to date emergency lighting plus hard wire fire and smoke alarm system all up to code.brbrNew inside pictures posted .brIn addition to the Heated Pool , the inside of the house was totally redone , from new appliances including dishwasher , new flat screen TV's in each of the bedrooms and Living room , custom made Kitchen cabinets , new floors throughout , new bathroom vanities and all new paint inside , new lights, new bunk beds , twins over full with trundles , new mattress in each bed.brbrKeywords: Luxury , Elegant , Newly installed Heated Pool , Waterfront Home ,Plantation Key ,Islamorada Village, Fla Keys. Village Rental License VR-007 .

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$424.72

/ Nightly

Private Vacation Home

Stunning 3-bedroom home in Islamorada with private heated pool and ocean views.

Islamorada, Florida, United States

Indulge in a retreat to paradise at this exquisite 3-bedroom, 3-bathroom oceanfront home on the captivating shores of Islamorada! This haven not only presents breathtaking ocean views but also features a private pool and a delightful tiki hut, providing an ideal blend of relaxation and outdoor enjoyment. Whether it's sipping morning coffee on the balcony or enjoying sunset cocktails beneath the tiki hut, this house caters to every preference.brbrThe living space sets the tone with a laid-back atmosphere, embodying the essence of island living. Expansive windows frame sweeping ocean panoramas, establishing a tranquil backdrop for your escape. The open-concept design seamlessly links the living and dining areas, creating a cozy space to unwind after a day of sun-soaked adventures.brbrAccommodating up to six guests, the three bedrooms and bathrooms ensure a comfortable stay. Whether you're a family seeking an adventure-packed vacation or a group of friends desiring a laid-back getaway, this oceanfront retreat guarantees a restful night's sleep for all.brbrStep into your private outdoor oasis, where a glistening pool beckons. Take a refreshing dip or soak up the Florida sun on the poolside deck. Adjacent to the pool, the charming tiki hut offers a shaded retreat perfect for enjoying a refreshing drink or simply soaking in the stunning ocean views.brbrBeyond your secluded haven, Islamorada invites water enthusiasts and nature lovers to a myriad of activities. From fishing charters to exploring nearby reefs, the opportunities abound for creating enduring memories in the heart of the Florida Keys.brbrDon't miss the chance to embrace the ultimate oceanfront getaway. Secure your reservation now and submerge yourself in the laid-back allure of Islamorada's coastal paradise!brbrDon't miss the chance to embrace the ultimate oceanfront getaway. Secure your reservation now and submerge yourself in the laid-back allure of Islamorada's coastal paradise!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.

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Bath

Sleeps

Exceptional(10)

$438.29

/ Nightly

Private Vacation Home

By The Sea ~ Islamorada Home with Ocean Views!

Islamorada, Florida, United States

Summary:brCanal front 2/2 with ocean views and relaxing breezes!brbrThe Space:brThis canal front two bedroom two bathroom home offers a large open living area with kitchen and dining rooms opening to a large screened patio with ocean breezes - just a couple of homes away from the open ocean with unobstructed ocean views.brbrbrAs you walk up the exterior steps you enter the main floor patio which is screened in and overlooks the Atlantic ocean. The main living area features a full kitchen, dining area, living space with a pull out couch and television. The main floor also has the guest bedroom with two twin beds. As you go up the spiral staircase you will enter the master suite which has direct ocean views, king size bed, and ensuite bathroom. You also have your own private balcony. The views will leave you awestruck!brbrbrThis home has covered parking for two vehicles and exposed parking for up to two more. The dock has space for up to a 25' boat directly behind the home and a community boat ramp at the end of the street. Washer and dryer are located in their own room outside of the master bedroom on the patio. There is also an observation deck on the roof of the home! brbrbrLower matecumbe is known as one of the fishing capitals of the united states and this home is right in the middle of it. Easy access to both the ocean and bay gives you the most versatile options when it comes to fishing spots. You also have charters available just up the road which will take you to some of the most prime fishing the Florida Keys has to offer! brbrbrThank you for viewing our property and we look forward to hosting your trip!brbrbr brbrbrThis home is managed by The Florida Keys Rental Store. For recommendations or things to do while in the keys, we have all the information you could need. Over 20 years in the business, we know what it takes to make your trip the best one yet!

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$487.32

/ Nightly

Private Vacation Home

Waterfront / Ocean Access Canal / Kamp Key / Homes

Islamorada, Florida, United States

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Exceptional(6)

$650.15

/ Nightly

Private Vacation Home

Island pool home awaits in Islamorada's Port Antigua

Islamorada, Florida, United States

Your island pool home awaits in Islamorada's Port Antigua! 3,500 square foot, 4 bedroom, 3 bathroom, high ceilings, tile & hardwood floors, state of the art kitchen w/ concrete counters & top of the line stainless appliances. Open, spacious and perfect for entertaining is how this home was designed. Walk out the great room french doors into an intimate pool setting with custom chickee & lounge area decorated with a vibe of Gilligan's Island meets The Ritz Carlton. Out back is 65ft of yacht dockage w/ shore power & water for water toys. Rare 2 car garage with golf cart, fishing rods, ping pong table/ game room, and bicycles provided. Private beach 1 minute by golf cart & ramp for owners in this golf cart approved community on Lower Matecumbe in Islamorada, the Village of Islands.

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Exceptional(26)

$504.64

/ Nightly

Private Vacation Home

Bayview Villa- Pet-Friendly Waterfront Paradise. A fisherman's dream!

Islamorada, Florida, United States

We have recently completed an inside and outside renovation. The Bayview Villa is a private, secluded villa facing Florida Bay and in view of the fabulous Everglades and gorgeous sunsets. Quick access to offshore fishing. Located in a lush tropical hammock in a quiet, one acre residential area (rare). The villa is approx. 30 feet from the water. The property contains a wading beach and a free marina with night lights, power and water. An enclosed patio offers private outdoor grill and dining.brbrThe villa itself comes with a fully-equipped new stainless kitchen, full size LG washer and dryer, linens, two queen and one king beds, Cable TV, and a dining room. French doors in the dining area face the bay, spacious 700 square foot patio,and marina giving the feeling of the outdoors being in. Beautiful glass block showers with pebble floors are in both baths. brbrIslamorada proudly calls itself the 'Fishing Capital of the World' but there is so much more to do

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Exceptional(3)

$207.85

/ Nightly

Private Vacation Home

Radiant waterfront retreat with remarkable views, patio, tennis court, & grill

Islamorada, Florida, United States

Step into your own slice of paradise at this sunlit, open-concept home overlooking the turquoise waters of the Florida Keys. With enchanting views from nearly every room, Tollgate Tides is the perfect retreat for a surf trip with friends, a romantic couples' getaway, or a family vacation by the shore.brbr⭐ Location Highlightsbr • Robbie's of Islamorada (10 miles): Feed the famous tarpon, book a fishing charter, or browse local artisan shops.br • Long Key State Park (10 miles): A must for kayaking, snorkeling, and beach picnics.br • Windley Key Fossil Reef Geological State Park: Walk through ancient coral trails and enjoy prime birding.br • Local seafood dining: Savor the catch of the day at waterfront restaurants or take a sunset cruise for unforgettable views.brbr Why You'll Love Itbr • Outdoor living: Spacious waterfront patio for grilling your fresh catch, alfresco dining, or simply soaking in the coastal breeze.br • Gourmet kitchen: Fully equipped with stainless steel appliances, a wine fridge, and bar/island seating perfect for gathering.br • Relaxation: End your day with a soak in the jetted tub or stream your favorite movies with HBO and Netflix.br • Activities for all: Sneak in a tennis match on the shared courts, explore nearby state parks, or enjoy family time with games in the living area.br • Everyday comforts: Private washer/dryer, central AC, and wide-clearance access for ease of mobility.brbr Amenities at a Glancebr • High-speed internet + streaming (HBO & Netflix)br • Oceanfront views from balcony, deck & patiobr • Shared tennis courtsbr • Jetted tub for ultimate relaxationbr • Fully equipped kitchen with wine fridgebr • Private washer/dryer & central ACbr • Snowbird-friendly for extended staysbrbr✨ Tollgate Tides blends comfort and adventure in one perfect waterfront escape. Whether you're here for fishing, snorkeling, sunset cruises, or simply soaking up the tropical vibe, you'll find everything you need to make unforgettable Florida Keys memories.brbrThings to KnowbrCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrAll guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AMbrNo smoking is permitted anywhere on the premises.

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$353.01

/ Nightly

Private Vacation Home

NEW! Waterfront, 3 Bedroom, 3 Bath. Keys Living, Peaceful Retreat

Islamorada, Florida, United States

This home is the definition of 'Keys' living. Situated on an oversized lot this 3 bedroom, 3 bath home offers 68 feet of dockage including a 10,000 lb. boat lift, a spacious wraparound porch overlooking the canal, outdoor entertainment area including a large tiki hut with TV. The main living area offers 2 bedrooms, 2 bathrooms, a well-maintained kitchen, and an open concept living area perfect for entertaining. With vaulted ceilings, multiple sliding glass doors, and expansive gable windows, this home feels light, bright, and airy. As a bonus, the downstairs offers a private studio apartment with a bathroom and private entry. Placed in one of the most desirable boating locations, you are minutes away from some of the best fishing spots in the world. brEnjoying the natural beauty of the florida keys. Watch the sunrise from Anne's beach, enjoy an abundance of wildlife right in the canal with visiting manatees, parrotfish and pelicans. 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. Located in one of Lower Matecumbe's favorite neighborhoods, Tollgate Shores is only minutes away from downtown Islamorada, Founders Park and Marathon. brbrAnne's Beach - ‪6 min walk‬brRobbie’s of Islamorada - ‪6 min drive‬brFiesta Key - ‪7 min drive‬brBud n' Mary's Dive Center - ‪10 min drive‬

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Exceptional(1)

$540.79

/ Nightly

Private Vacation Home

Spacious 4BR canal home in Islamorada with private heated pool and beach access.

Islamorada, Florida, United States

Welcome to your Islamorada escape in the highly sought-after Port Antigua community. This canal-front pool home is set up perfectly for families and groups who want space, dockage, and that true Keys outdoor lifestyle.brbrUpstairs features 2 bedrooms and 2 bathrooms with a comfortable, open living space designed for relaxing after a day on the water.brbrDownstairs offers a separate 2 bedroom, 1 bath suite with a kitchenette — ideal for extended family, friends, or multi-generation stays while still giving everyone their own space.brbrStep outside and you'll find what makes this home special:br• Heated pool for year-round enjoymentbr• Outdoor kitchen perfect for grilling the day's catchbr• 65 feet of dockagebr• Quick boating access to the Ocean or Baybr• Access to the private Port Antigua homeowners beachbrbrBring your boat, enjoy the sunsets, and settle into the laid-back Keys lifestyle. This is the kind of home guests come back to year after year.brIf booking more than a year in advance current prices may not reflect annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brbrPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

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Exceptional(3)

$307.57

/ Nightly

Private Vacation Home

Relax in this 3-bedroom canal home with stunning views in Islamorada!

Islamorada, Florida, United States

141 Ocean Lane - The Beach Fixes Everything. That's the sign that greets visitors as they enter the living room of this newest Freewheeler Vacations home. But while the beach certainly is nice, an awesome vista doesn't hurt either. Located on a narrow residential peninsula in Lower Matecumbe Key, the two-bedroom, two-bathroom house offers a 270-degree view of the Atlantic. Check out that view as you lounge in the living area, take an afternoon snack in the kitchen or when you rise from bed in either the master bedroom or the upstairs guestroom. Better yet, you can enjoy the surroundings while you grill out on the screened porch that wraps around nearly the entire home. brThe main upstairs living space contains a master king bedroom with attached bath and a queen guestroom. The tiled kitchen and living room offer ample cooking space, another flat screen TV and two-sided views of the sea. For an added bonus this home comes with kayaks and bikes for your everyday adventure!! brThere's plenty of outdoor action beyond the porch as well. Lounge on the outdoor dock (30') and tie off your boat for almost instant access to Islamorada's famed oceanside fishing grounds. When your day on the water is done, prep your catch at the home's private fish cleaning station. brbrNear the house is the small Anne's Beach. There are nature trails, boardwalks to small lunch and BBQ areas, private sandy areas hidden in the mangroves and parking. The home is also near Robbie's Marina (where they feed the Tarpon), Bud n' Mary's Marina and Caloosa Cove Marina. You won't have a problem finding a marina for boat rentals or a fishing guide (Deep Sea or Backcountry). You are only minutes away from Downtown Islamorada where Worldwide Sportsman and the Islamorada Fish Company are located yet you are in a quiet area of town.brbrYou will be able to truly enjoy your vacation! This is a great house that our tenants seem to love and will want to return to year after year! Located at Mile Marker 76, this home is available for monthly rentals. brbrIf booking more than a year in advance current prices may not reflect the annual cost of living increase. Many 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.

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Exceptional(11)

$232.76

/ Nightly

Private Vacation Home

Islamorada Paradise! Luxury Townhouse! Sleeps 4-6 Boat Slip And Pool

Islamorada, Florida, United States

This Modern Upscale duplex Home Has All The Amenities For A Wonderful And Special Vacation. King Size Master Bedroom And Queen Size Second Bedroom,sofa Bed In Living Room,extra folding bed, 4 Balconies, Gas BBQ, Satellite TV and WiFi. Carport For Two Cars. Pool, Tiki Hut. End Unit Provides Extra Sunlight And More Privacy. Boat slip .Boat rental available Washer Dryer in unit. Storage shed.Bike path at our door.Security front gate

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Exceptional(7)

$253.13

/ Nightly

Private Vacation Home

Beautiful 2/2 Islamorada Home Directly on Florida Bay (28 Day Minimum Rental)

Islamorada, Florida, United States

Our home is in Islamorada, in the middle Florida Keys. To be more specific, we are on Lower Matecumbe Key, which is the southernmost island in Islamorada, at exactly Mile Marker 74, on the bayside. Our home is a 2/2, and can comfortably sleep four, with two bedrooms upstairs. The Master has a queen bed, and a private bath. The second bedroom has twin beds, and a separate bath. If more room is needed, or for families with young kids or teenagers, it's possible for at least two to camp out on comfortable air mattresses upstairs in the family room. Downstairs there is a laundry room/workshop, and a more rustic game room/bar with a refrigerator for water/soft drinks/beer/bait.

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$333.63

/ Nightly

Private Vacation Home

Waterfront Escape Featuring Private Pool, Hot Tub & 50 ft. Boat Dock

Islamorada, Florida, United States

Your Waterfront Escape in the Heart of Islamorada Awaits!brbrWelcome to your dream getaway in the Florida Keys—where turquoise waters, tropical breezes, and that unmistakable “island time” feeling set the tone for an unforgettable stay. Nestled right on the water in beautiful Islamorada, this spacious 3-bedroom home offers the perfect blend of relaxation, adventure, and true Keys lifestyle.brbrStep outside to your private waterfront deck, thoughtfully furnished for lounging, sipping morning coffee, & beginning the day with one of Islamorada's famous sunrises. Gather for meals in the outdoor dining area, where warm breezes and water views create the perfect backdrop for unforgettable moments.brbrEnjoy exclusive key-card entry to Port Antigua's resident access beach and 50 foot boat ramp, giving you the true Florida Keys experience. Spend your days lounging on the sugar-soft sandbar, relaxing under tiki huts, grilling at the charcoal BBQ stations, or enjoying a picnic at the waterfront tables. When you get home, cool off in the sparkling private pool, unwind in the hot tub after a day of exploring the islands, or challenge your crew to a friendly match at the ping-pong table. Whether you're soaking up the sun or slowing down under the stars, this home is built for relaxation.brbrIslamorada—known as the “Sport Fishing Capital of the World”—offers endless opportunities to enjoy the ocean. Spend your days snorkeling vibrant reefs, chartering a fishing boat, kayaking through mangroves, or simply embracing the laid-back island lifestyle that makes the Keys so special. Delicious seafood restaurants, waterfront bars, boutiques, and local attractions are just minutes away.brbrWith three comfortable bedrooms and an inviting open layout, there's plenty of space for families or groups to unwind. Large windows highlight the water views, while coastal-inspired décor brings the beauty of the Keys indoors.brbrWhether you're here for adventure, relaxation, or a little of both, this Islamorada retreat gives you the best of waterfront living in one of the most iconic destinations in the Florida Keys. Your island escape starts here!

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Exceptional(11)

$469.51

/ Nightly

Private Vacation Home

Beautiful Harbor Front Oceanside Home on the Atlantic Ocean

Islamorada, Florida, United States

Oceanside 3/3 located in a beautiful naturally protected harbor on the Atlantic Ocean. See manatee, tarpon and many beautiful species of bird and fish in this amazing natural preserve, Enjoy a scenic sunset over the harbor or ocean views while relaxing in the 2nd floor living room. Enjoy new furnishings, bedding, electronics, appliances & more. Soak and relax in a new heated swimming pool with an 8 person hot tub. A true gem of the Florida Keys with resort style amenities and privacy of private island. This home is kept fresh and meticulously maintained. Monthly or 28 day minimum calendar bookings only. Outdoor ring cameras in front and back of property for safety and security purposes only.

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Sleeps

Exceptional(1)

$609.83

/ Nightly

Private Vacation Home

Venetian Shores Pool Home

Islamorada, Florida, United States

Desirable Venetian Shores neighborhood. Newly renovated home with open concept kitchen, dining and living room. Convenient access either bay or ocean with protected dockage. This canal front home has 2 king en-suites upstairs and a relaxing screen porch off of the living room. There is a downstairs apartment with 2 bedrooms and 1 bathroom and small kitchen area. The pool is situated canal side and perfect after a long day of boating. Enjoy grilling your catch in your outdoor canal side kitchen. There is a 28 day minimum requirement on this home…please do not request or ask for altered time as it will not be accepted.

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$515.95

/ Nightly

Private Vacation Home

Feel the breeze of the keys

Islamorada, Florida, United States

**HOUSE HAS BEEN RENOVATED AND PICTURES TO COME**brPerfect Vacation Home in Islamorada, the center of the Keys Island. The house is ideal for a large family get away, or a small intimate escape. It is perfectly situated between canals providing guests with an unforgettable keys breeze. You are conveniently located near supermarkets, restaurants, and fun activities, like Theatre of the Sea. Take a walk to the community private beach which is only accessible through key access. The house is equipped with 75 total dock space with approximately 35 feet of that dock space to accommodate your boat. It has been updated with a new pool and resort style yard for your enjoyment. Beautiful open views and quick access to ocean. The house is located in one of the most well known fishing areas, Islamorada, renowned for the best fishing areas.brbr

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Exceptional(59)

$2119.45

/ Nightly

Private Vacation Home

Next available August 15th, 2026 - Stunning Oceanfront Estate - Private Pool

Islamorada, Florida, United States

License # 204.brbr| ** 3 payment schedule available** | No Pet Charges | No security deposit |brSATURDAY TO SATURDAY ONLY BOOKINGSbrbrEscape to this welcoming house in picturesque Islamorada. This fantastic property boasts 6 bedrooms, including 5 king beds, 4 custom bunks, 2 cribs, a toddler bed, and more. With 6.5 bathrooms offering amenities like a jetted bathtub, this place is perfect for large groups or families. The Master bedroom offers two additional twin beds on the sun porch and a nursery nook with a crib and toddler bed, making a wonderful family suite. brbrThe Last Resort Too is our sister home to the original Last Resort, offering the ability to cater to larger families and groups. Set on over two acres of prime oceanfront land, complete with a heated swimming pool, 200 ft of beach, and a walking/fishing dock. Nestled behind privacy gates, you will feel right at home in this exclusive enclave of Islamorada. *Please note: V-boats do not have clearance for this dock, flat bottom, and pontoons only. * Please check with us for V-Boat accommodations.brbrThis house can book up to two years in advance and is already taking bookings for 2027.brbr** The owner, who has been part of VRBO since 2004, will be managing the home directly from 2026. As an already established listing on VRBO, reviews do not transfer to this new 2026 listing.

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Exceptional(4)

$548.6

/ Nightly

Private Vacation Home

Charming 2-bedroom open water view home in Islamorada, perfect for 6 guests.

Islamorada, Florida, United States

Little Bay Lower Level - Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units. The Lower Duplex is a 1,500 sq ft unit with two bedrooms, two full baths, full modern kitchen, laundry, family room, and 10' x 40' porch overlooking the Bay. Master bedroom: queen and twin murphy bed. Guest bedroom: two twins. Living room: sofa sleeper brbrThis unit comes equipped with central a/c and ceiling fans. The Lower Duplex shares with the other two units loads of outdoor furniture and BBQ, large private boat basin with 12' X 25' Chickee hut and 12' X 25' Pergola, bait prep station, freshwater shower and power on the dock. The spacious front yard is enhanced by Tropical Landscaping and offers a large circular driveway with plenty of parking for cars and trailers. brLocated in heart of Islamorada within walking distance to water & land activities, restaurants, shops, and more! The Lower Duplex can be rented individually or in combination with the entire Little Bay Compound. brbrIf booking more than a year in advance current prices may not reflect annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brbrPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.brVR-24-0335 Per Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.

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Exceptional(6)

$456.64

/ Nightly

Private Vacation Home

132 Anglers Reef Islamorada- POOL, DOCK, BIKES INCL

Islamorada, Florida, United States

VR License #24-4011br132 Anglers Way is an Adorable Key West style home in Anglers Reef. Small gated community located at MM 85 in Islamorada. Beautiful oceanfront pool, two beaches and a very convenient marina just stops from your front porch. brCall me for more information 305-240-0592.br Two bedrooms and two and a half baths with all the comforts of home. The master bedroom is a king size bed and the guest bedroom has two twin size beds with twin trundles underneath. brThere is a very nice living room with a sleeper sofa and dining room set up downstairs and all the things you would need to create a gourmet meal in the kitchen.brbrDock included in pricing. 31'max length and 9' bridge height.brbrPlease 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.

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Exceptional(6)

$1588.39

/ Nightly

Cottage

Oceanfront Cottage With Stunning Pool & Dockage in Islamorada

Islamorada, Florida, United States

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Bath

Sleeps

Exceptional(6)

$1719.90

/ Nightly

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Islamorada, Florida, United States

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Exceptional(6)

$1716.73

/ Nightly

Private vacation home

Royal Palm South 3 Bedrooms, 3 Baths, Ocean Front, Marina

Islamorada, Florida, United States

Bed

Bath

Sleeps

Exceptional(6)

$1606.37

/ Nightly

Private vacation home

Oceanfront Keys Escape | Private Beach & Pool | 3 Acres

Islamorada, Florida, United States

Bed

Bath

Sleeps

Exceptional(6)

$1600.73

/ Nightly

Private vacation home

Discover Sea Ranch in Islamorada: spacious 4BR home with private pool and stunning views.

Islamorada, Florida, United States

Bed

Bath

Sleeps

Exceptional(6)

$1595.07

/ Nightly

Private vacation home

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

Islamorada, Florida, United States

Bed

Bath

Sleeps

Exceptional(6)

$1510.57

/ Nightly

Private vacation home

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

Islamorada, Florida, United States

Bed

Bath

Sleeps

Exceptional(6)

$1409.53

/ Nightly

Private vacation home

Experience luxury at The Sapodilla House, a stunning 5-bedroom waterfront retreat in Islamorada.

Islamorada, Florida, United States

Bed

Bath

Sleeps

Exceptional(6)

$1433.51

/ Nightly

Condo

Experience luxury at Coastal Cove Villa, a 4-bedroom retreat in beautiful Islamorada!

Islamorada, Florida, United States

Bed

Bath

Sleeps

Exceptional(6)

$1948.66

/ Nightly

Private vacation home

New - Oceanfront Estate - Private Beach - Heated Pool - Stunning

Islamorada, Florida, United States

Bed

Bath

Sleeps

Vacation Home Rentals By Owner In Islamorada, FL

$591.78

$548.84

$424.72

$438.29

$487.32

$650.15

$504.64

$207.85

$353.01

$540.79

$307.57

$232.76

$253.13

$333.63

$469.51

$609.83

$515.95

$2119.45

$548.6

$456.64

Rent a place that suits your needs

Most popular vacation rentals in Islamorada

$1588.39

$1719.90

$1716.73

$1606.37

$1600.73

$1595.07

$1510.57

$1409.53

$1433.51

$1948.66

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