Vacation Home Rentals By Owner In Islamorada, FL

Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. brbrThis unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club house, fitness center, tennis courts, gas barbeque grills, tennis equipment, beach chairs and coolers.brbrThis spectacular condo offers two master bedrooms with private full bathrooms, additional half bath and full size washer and dryer. Additionally, each bedroom and the living room has flat screen televisions with cable tv. A dvd player is included in the living room. There is free wifi and telephone included for your use. The kitchen has stainless steel appliances, granite countertops and everything you need to prepare and serve a gourmet meal. brbrThe large balcony overlooking the water offers plenty of seating. Enjoy a meal or coffee while you take in the expansive views or enjoy the sunrise. Additionally, you will have a direct view of your boat parked in a private boat slip just steps away. brbrLocated at mile marker 75, this boater’s paradise is just minutes from fishing in the gulf or ocean, diving or snorkeling beautiful reefs, jet skiing, parasailing, kiteboarding or kayaking. brbrCall us to book your vacation of a lifetime.br

Condo

Islamorada Luxury Waterfront Condo with Boat Slip

Islamorada, Florida, United States

Bed

Bath

Sleeps

$537.14

Short Descriptionbrbr Community amenities: heated pool, boat dock, BBQbr Walk to shops, grocery store, parks, restaurantsbr ️ All bedrooms feature ensuite bathroom br 24/7 Guest supportbrbrBayberry Key (Villa #9) is part of Little Basin Villas upscale community of nine luxury vacation villas, located in the heart of the Art District of Islamorada. This is the only Villa that offers an unobstructed water view from the private outdoor terrace and balcony! Boasting a bayside boat dock and private community pool, our villa offers the perfect blend of relaxation and adventure. Enjoy breathtaking sunsets, waterfront views and island décor & foliage. It uniquely offers three bedrooms complete with their own ensuite bathroom, plus a half bath. It is completely furnished and stocked with the essentials needed for an amazing and comfortable vacation. You also have access to our concierge, Guest Experience Team to assist in making the most of your stay.brbr The Spacebrbr ️ Living Room: Open-concept living area that features ample seating w/ sectional sofas, modern beach decor. brbr ️ Kitchen: Sleek peninsula with six stools, top-of-the-line appliances, and a modern white design. Perfect for relaxing and culinary adventures alike.brbr♛ Primary Suite 1 provides a generously sized retreat - with calm accents, king size bed, premium bedding, and a luxe primary ensuite bathroom. An oversized shower and sink offer the comforts of home.brbr ️ Bedrooms feature the following amenities:brbr✔ Premium beds, pillows, linensbr✔ Smart TVsbr✔ Ample closet spacesbrbrBedroom 2: King sized bedbrBedroom 3: Queen sized bedbrbr All full ensuite Bathrooms are generously stocked with:brbr✔ Shampoo & conditionerbr✔ Body soapbr✔ Fluffy towelsbr✔ Toilet tissue brbrPrimary Bathroom 1: Single vanity sink, shower and toiletbrBathroom 2: Single vanity sink, shower and toiletbrBathroom 3: Single vanity sink, shower/tub combo and toiletbrHalf-bathroom: Standing sink, mirror, toiletbrbrOutdoor Paradise brbrEnjoy your coffee or tea on your private outdoor terrace. Top-tier amenities include a bayside boat dock, private community swimming pool, and walking proximity to the best and most popular restaurants, shops, and many other incredible wildlife and fishing attractions. The pool area has lounge furniture, bathrooms, & is heated for year-round swimming. Watch our beautiful sunsets as you sit under the large tiki hut. brbrCommon AreasbrbrPool + lounge chairs brRestroomsbrTiki area + picnic tables + BBQbrBoat dock brbrBoat Dockage Information: *Dockage is not included with rental reservationbrbr-Dockage is limited and based on availability. *We recommend reserving dockage upon booking.brbr-Boat dockage will cost $6 per foot, per day between December 13 - August 9th and $4 per foot, per day between August 10 - December 12. brbr-Floating dock can accommodate 2 boats, for a combined length of 46 feet.brbr-The concrete dock can accommodate 2 boats, for a combined length of 52 feet.brbr- Guest(s) are required to complete a boat dockage agreement form (BDA), to reserve boat dockage.brbr- There is no trailer storage or boat ramp available at Little Basin Villas. Our recommendations for both will be sent along with our boat dockage agreement form.brbrNeighborhood Overviewbrbr*Mile Marker 81.8 on the bayside.brbrBeing located in the heart of Islamorada makes our property accessible to walk to over 10 restaurants, paddle board and kayak the islands, snorkel the reefs and experience the ultimate Keys Life Vacation. There are great bike, running & walking paths in Islamorada….fun for the entire family! brBicycles, paddle boards, & kayaks can be delivered directly to your villa for use during your stay. Islamorada is a serene paradise in the Florida Keys that embodies the essence of island living. With easy access to world-class fishing, diving, and watersports, Islamorada is the ideal destination to experience the natural beauty and laid-back lifestyle of the Keys.brbr Points of Interest: (Distance measured in driving time, non-rush hour) brbr-Islamorada Library Beach Park (1 min walk): Water access on a mangrove channel with amazing play equipment, shaded tables & BBQ facilities. Please note this is temporarily closed for remodel and is expected to open in June 2024.br- Morada Way Arts & Cultural District (3 min): Stroll through art galleries, boutique shops, and enjoy local cuisine at the weekly art walk eventbr- Theater of the Sea (5 min): Enjoy interactive marine shows and swim with dolphins in this unique marine park.br- Robbie's Marina (8 min): Feed the tarpon, dine at waterfront restaurants, and shop for souvenirs at this bustling marina.br- History of Diving Museum (5 min): Explore the fascinating history of scuba diving through exhibits and artifacts.br- Anne's Beach (11 min): Relax on the sandy shores or take a leisurely swim in the calm waters of this picturesque beach.brbrHouse RulesbrbrCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrbr**All guests must sign our rental agreement as mandated by Florida Law.**brbrbr-The minimum rental age is 25. A picture ID must be provided to the company no less than 72 hours (about 3 days) before arrival.br-An accurate guest count must be provided.br-No smoking or vaping. If evidence is discovered of either smoking or vaping, the guest will be subject to a fine of up to $1,000br-No parties or events. If unauthorized persons are discovered on the premises, guests will be subject to additional fees and/or immediate eviction.br-Quiet time is from 10pm - 8ambrbrStarter Supplies:brWe provide trash bags, paper towels, toilet paper, detergent, and bathroom amenities to accommodate this home's maximum occupancy for the first week of your stay. br brSame-Day Bookings: brSame-day bookings require approval from the company. We will ask you to provide information on your group and the purpose of your stay. If your stay is approved, we require a government-issued ID for identity verification. Your phone number must match the phone number on your account, or we will not be able to honor your reservation. Same-day reservations will not be accepted after 2:00pm. All same-day reservations require at least 3 hours before check-in. We may have to extend check-in time to later than 4:00pm.br brPet Policy:brPets are not allowed. brbrMid-Stay Cleaning Requirement:brFor all extended stays of 30 nights or longer, a mandatory mid-stay cleaning is required every 30 days.brIf your reservation is 60 days, two mid-stay cleanings will be required, and so on.brThis helps keep the home maintained during longer stays and ensures everything stays in great condition.brMid-Stay Cleaning Fee: $275brWe'll reach out after booking to schedule the mid-stay cleaning(s) and send the payment link.

Villa

Bayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$492.13

Short Descriptionbrbr Community amenities: heated pool, boat dock, BBQbr Walk to shops, grocery store, parks, restaurantsbr ️ All bedrooms feature ensuite bathroom br 24/7 Guest supportbrbrIsla Mirabelle (Villa #7) is part of Little Basin Villas upscale community of nine luxury vacation villas, located in the heart of the Art District of Islamorada. Boasting a bayside boat dock and private community pool, our villa offers the perfect blend of relaxation and adventure. Enjoy breathtaking sunsets, waterfront views and island décor & foliage. It uniquely offers three bedrooms complete with their own ensuite bathroom, plus a half bath. It is fully furnished, and offers a private deck, and a top balcony. This home is fully stocked with everything you need, and a full time Guest Experience Team to assist in making the most of your stay.brbr The Spacebrbr ️ Living Room: Open-concept living area that features ample seating w/ sectional sofas, modern beach decor. brbr ️ Kitchen: Sleek peninsula with six stools, top-of-the-line appliances, and a modern white design. Perfect for relaxing and culinary adventures alike.brbr♛ Primary Suite 1 provides a generously sized retreat - with calm accents, king size bed, premium bedding, and a luxe primary en suite bathroom. An oversized shower and sink offer the comforts of home.brbr ️ Bedrooms feature the following amenities:brbr✔ Premium beds, pillows, linensbr✔ Smart TVsbr✔ Ample closet spacesbrbrBedroom 2: King sized bedbrBedroom 3: Queen sized bedbrbr All full ensuite Bathrooms are generously stocked with:brbr✔ Shampoo & conditionerbr✔ Body soapbr✔ Fluffy towelsbr✔ Toilet tissue brbrPrimary Bathroom 1: Single vanity sink, shower and toiletbrBathroom 2: Single vanity sink, shower and toiletbrBathroom 3: Single vanity sink, shower/tub combo and toiletbrHalf-bathroom: Single sink and toiletbrbrOutdoor Paradise brbrEnjoy your coffee or tea on your private outdoor terrace. Top-tier amenities include a bayside boat dock, private community swimming pool, and walking proximity to the best and most popular restaurants, shops, and many other incredible wildlife and fishing attractions. The pool area has lounge furniture, bathrooms, & is heated for year-round swimming. Watch our beautiful sunsets as you sit under the large tiki hut. brbrCommon AreasbrbrPool + lounge chairs brRestroomsbrTiki area + picnic tables + BBQbrBoat dock brbrBoat Dockage Information: *Dockage is not included with rental reservationbrbr-Dockage is limited and based on availability. *We recommend reserving dockage upon booking.brbr-Boat dockage will cost $6 per foot, per day between December 13 - August 9th and $4 per foot, per day between August 10 - December 12. brbr-Floating dock can accommodate 2 boats, for a combined length of 46 feet.brbr-The concrete dock can accommodate 2 boats, for a combined length of 52 feet.brbr- Guest(s) are required to complete a boat dockage agreement form (BDA), to reserve boat dockage.brbr- There is no trailer storage or boat ramp available at Little Basin Villas. Our recommendations for both will be sent along with our boat dockage agreement form.brbrNeighborhood Overviewbrbr*Mile Marker 81.8 on the bayside.brbrBeing located in the heart of Islamorada makes our property accessible to walk to over 10 restaurants, paddle board and kayak the islands, snorkel the reefs and experience the ultimate Keys Life Vacation. There are great bike, running & walking paths in Islamorada….fun for the entire family! brBicycles, paddle boards, & kayaks can be delivered directly to your villa for use during your stay. Islamorada is a serene paradise in the Florida Keys that embodies the essence of island living. With easy access to world-class fishing, diving, and watersports, Islamorada is the ideal destination to experience the natural beauty and laid-back lifestyle of the Keys.brbr Points of Interest: (Distance measured in driving time, non-rush hour) brbr-Islamorada Library Beach Park (1 min walk): Water access on a mangrove channel with amazing play equipment, shaded tables & BBQ facilities. Please note this is temporarily closed for remodel and is expected to open in June 2024.br- Morada Way Arts & Cultural District (3 min): Stroll through art galleries, boutique shops, and enjoy local cuisine at the weekly art walk eventbr- Theater of the Sea (5 min): Enjoy interactive marine shows and swim with dolphins in this unique marine park.br- Robbie's Marina (8 min): Feed the tarpon, dine at waterfront restaurants, and shop for souvenirs at this bustling marina.br- History of Diving Museum (5 min): Explore the fascinating history of scuba diving through exhibits and artifacts.br- Anne's Beach (11 min): Relax on the sandy shores or take a leisurely swim in the calm waters of this picturesque beach.brbrHouse RulesbrbrCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrbr**All guests must sign our rental agreement as mandated by Florida Law.**br-The minimum rental age is 25. A picture ID must be provided to the company no less than 72 hours (about 3 days) before arrival.br-An accurate guest count must be provided.br-No smoking or vaping. If evidence is discovered of either smoking or vaping, the guest will be subject to a fine of up to $1,000br-No parties or events. If unauthorized persons are discovered on the premises, guests will be subject to additional fees and/or immediate eviction.br-Quiet time is from 10pm - 8ambrbrStarter Supplies:brWe provide trash bags, paper towels, toilet paper, detergent, and bathroom amenities to accommodate this home's maximum occupancy for the first week of your stay. br brSame-Day Bookings: brSame-day bookings require approval from the company. We will ask you to provide information on your group and the purpose of your stay. If your stay is approved, we require a government-issued ID for identity verification. Your phone number must match the phone number on your account, or we will not be able to honor your reservation. Same-day reservations will not be accepted after 2:00pm. All same-day reservations require at least 3 hours before check-in. We may have to extend check-in time to later than 4:00pm.br brPet Policy:brPets are not allowed. brbrMid-Stay Cleaning Requirement:brFor all extended stays of 30 nights or longer, a mandatory mid-stay cleaning is required every 30 days.brIf your reservation is 60 days, two mid-stay cleanings will be required, and so on.brThis helps keep the home maintained during longer stays and ensures everything stays in great condition.brMid-Stay Cleaning Fee: $275brWe'll reach out after booking to schedule the mid-stay cleaning(s) and send the payment link.

Villa

Isla Mirabelle: Boutique Resort, FREE Boat Dockage Sep-Oct Only!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$191.23

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 301 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 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

Swim with Dolphins in the Florida Keys! FREE Breakfast & Parking, Marina, Pool!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$216.03

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 290 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 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

Discover Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Parking, Breakfast

Islamorada, Florida, United States

Bed

Bath

Sleeps

$191.23

Private beach resort on breathtaking Islamorada in affluent Florida Keys area.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 301 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 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

Snorkeling & Kayaking Beach Resort! Seaside Villa w/Patio! Marina, Pool, Parking

Islamorada, Florida, United States

Bed

Bath

Sleeps

$404.42

brThis incredible property in Islamorada is the ultimate getaway, offering a spacious and flexible layout with 9 beds—perfect for family reunions, large groups, or anyone seeking a luxurious Florida Keys escape. With 2,000 sq ft of living space under air, plus an additional secured lot for RVs, jet skis, boats, and recreational vehicles, this home is tailored to outdoor enthusiasts and boaters alike.brbrA true boater’s paradise, the property boasts 100' of dockage, a private boat slip, and convenient free on-site boat trailer parking on the adjacent lot. The approximately 5 ft deep canal is perfect for maneuvering a 46.6 ft Bertram, with plenty of room to comfortably turn around, and the open Atlantic Ocean is just 1/8 mile away for easy access to world-class fishing and watersports.brbrInside, the home features a fully stocked kitchen with an additional refrigerator in the laundry room next to the washer and dryer. A bait freezer is also conveniently located on the side patio adjacent to the dock. The flexible sleeping arrangements allow for single beds to be converted to Continental Kings, ensuring comfort for all guests. This Smart Technology home offers multiple areas for socializing, recreation, and relaxation, including three separate patio spaces equipped with shade sails and Edison lights, perfect for enjoying the warm Florida evenings.brbrWhether you’re here for adventure or relaxation, this one-of-a-kind property is designed to offer the best of both worlds, making it the perfect place for an unforgettable stay in the Florida Keys.

Boater's Paradise

Islamorada, Florida, United States

4

Bed

Bath

9

Sleeps

$523.63

This charming 3 bedroom ground-level home is located in the private gated community of Bay Hammock on Upper Matecumbe in Islamorada. Enjoy a heated pool, a comfortable island setting, and the relaxed lifestyle the Florida Keys are known for.brbrBoaters welcome — inquire within about bringing your boat! The community boat basin offers a boat slip available for use, making it easy to get out on the water and enjoy some of the best fishing and boating the Keys have to offer. Perfect for a laid-back getaway in a quiet, private neighborhood.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.

Discover One Too Mini, a cozy 3-bedroom getaway in Islamorada, perfect for 8!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$409.56

Futura Townhome #731 - Enjoy the spectacular view of the Florida Bay from this beautiful townhome. This townhome is a two bedroom two and a half bath unit. There are tons of things to keep you and your family busy without having to leave the Futura Condo complex. There are tennis courts and a swimming pool located on the property. Make yourself at home in our home away from home. Boat dockage available please inquire within. The Futura Yacht Club HOA charges- onsite-$150 per trailer and $50 per boat fee. These fees will not show up on your rental agreement, as the fees are collected upon check in at Futura Yacht Club. brVACATION RENTAL LICENSE: VR 24-0413 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.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 Futura Townhome 731 in Islamorada, with heated pool and modern amenities.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$257.63

August to November, take $500 off regular price! World Famous Beacon Reef Condo (a gated community) Oceanfront Islamorada, Florida (Max 4 Persons /monthly rentals only!!) Come and enjoy our 2nd home in Paradise! FREE BOAT DOCKAGE (with proof of insurance) In the fishing capital of the world, Islamorada. Conveniently located, walk to local restaurants. Come into our beautifully furnished 2 BR 2 BA Condo on the second floor.(First is parking only) Convenient Staircase from back porch directly down to grounds. Only units on this floor have the convenience of using private stairs to grounds others have to use the lobby and elevator. The master bedroom and outside patio gives a beautiful view of the OCEAN. Wake up to the sunrise. Inside find a fully equipped kitchen with extras as is ou 2nd home, An inside washer/dryer. Games, books, comfortable furniture, and smart TVs throughout. Tile floors for easy care. Go out into the mild weather & wander among our beautiful tropical gardens, bring your drink down to the waters edge or curl up with a good book. Sandy BEACH boasts lounge chairs under Tiki huts and wonderful chaise lounges and tables around the pool. Fish or swim from the beautiful newly rebuilt T-dock with electric and water at each slip and ice machines on the dock. A big cleaning station for your fresh catch. Most restaurants will cook it for you. Or just hang out and watch the fishermen come in. Don’t forget to Bring your boat or rent one at the numerous places nearby, FREE DOCKAGE! Water and electric included at each slip.brbrDon't miss the state of the art work out room equipped with an inferred SAUNA, so after a vigorous workout or a day on the water, relax and get rejuvenated in the therapeutic SAUNA and relieve any aches in the hot tub.brbrSwim in our heated fresh water pool with zero entry or lounge in our huge therapeutic Jacuzzi. Have a party under the thatched Tiki roofed 'room', can be open air, or clear plastic curtains roll down to keep the wind and weather out. It is fully equipped with ice machine, fridge, sink, grills, a smoker, tables, chairs and benches and a serving bar with a sink, ice machine and refrigerator.! A paradise you will want to come back to again and again. Play cards or eat with friends. Spontaneous parties have been known to erupt as one of the many grills lights up!brbrKeywords: Beacon Reef, Condo, Islamorada, fishing, oceanfront, sandy beach, boating, swimming, pool, beach front, ocean front

Condo

BOOK YOUR DREAM VACATION at BEACON REEF - SPECIAL SUMMER DEAL

Islamorada, Florida, United States

Bed

Bath

Sleeps

$366.01

A perfect Keys home located in the heart of Islamorada in the sought-after Port Antigua community with access to the homeowner's private beach. This updated home is spacious with 2 bedrooms and 2 bathrooms. There is a huge balcony with a sitting area, dining table, and BBQ where you can enjoy your morning coffee or after-dinner drink with a view of the canal. Port Antigua is a quiet and friendly neighborhood that will ensure your peaceful stay. Fish off the dock, bask in the sun, and enjoy the private pool or bring your small boat (no lift). There is a community ramp where you can launch your boat and enjoy the incredible water of the Florida Keys. Bike riding is also available along the Port Antigua streets. Enjoy the beautiful sunsets on the beach while you sip your favorite drink, or walk along the sandy beach as you enjoy the tranquil moments at the Florida Keys. You can also enjoy excellent restaurants minutes away or visit Dolphin Research Center or Island Dolphin Care to experience the beauty of dolphins. In addition, Key West is only a short drive where you can spend a day exploring. Whether you choose to relax or adventure, our home will be a perfect fit.brbr*Long term rental welcomed br*No pets allowedbr*Non smoking homebr

Beautiful vacation home in the heart of Islamorada , Florida Keys

Islamorada, Florida, United States

Bed

Bath

Sleeps

$199

Vacation like a local! This charming 2 bedroom, 2 bath home is located in one of Islamorada’s quaintest and quietest neighborhoods of just 40 residences.brbrThis home is bright and tropically decorated. The master suite features a private bath with shower. The second bedroom shares the hall bath with the main living area. brbrThe backyard has a large Tiki Hut to sit and enjoy the beautiful weather and an outdoor fenced in shower to rinse off after a day on the water or a bike ride. brbrThere is a large closed in air-conditioned porch right off the kitchen where you can enjoy your morning coffee as you start your day or sit and unwind at the end of each day. From the porch, you can see the private park exclusively for the neighborhood.brbrClose to restaurants, charter boats and outdoor activities. brbrThis home is the perfect spot for a Florida Keys retreat.

Off the beaten path in one of Islamorada’s hidden gem of a community!.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$762.55

Leatherback Cottage - The Leatherback Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all with their own personality and characteristics. All five cottages share the property's amenities: pool, boat basin, tropical sprawling grounds, ping pong table, kayaks, paddle boards and more. The main living area is located on the upper level of this oceanfront cottage and has open ocean views throughout. The open concept kitchen, living and dining room are great for entertaining. The main level has two bedrooms and two baths. The lower level is a separate living area with 2 sets of bunk beds, a living room, kitchenette and bathroom. It can be added when renting the upstairs for an additional $600 weekly. The Leatherback Cottage can be rented separately or in combination with any of the four other homes.brVACATION RENTAL LICENSE: 24-0386brIf 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. 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.

Leatherback Cottage: Adorable 2-bedroom oceanfront pool home with open water views in Islamorada.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$291.09

Kemp Cottage - The Kemp Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all with their own personality and characteristics. All five cottages share the property's amenities: pool, boat basin, tropical sprawling grounds, ping pong table, kayaks, paddle boards and more. This romantic garden studio cottage is nestled into lush tropical landscaping. It is perfect for a couple's getaway or a writer's retreat. The Kemp Cottage can be rented separately or in combination with any of the four other homes.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. brVR# 24-0134brbrPlease 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.

Cozy 1-bedroom Kemp Cottage in peaceful Islamorada, perfect for a romantic getaway.

Islamorada, Florida, United States

1

Bed

1

Bath

2

Sleeps

$200.46

Come to Paradise and Enjoy it in comfort.! Located on Mile Marker 87 in Islamorada ( Fishing Capital of the World ), part of the Wonderful Florida Keys. Executive Bay Club is a Private Gated Community with 24 Hr Security, Heated Pool and Club House, Tennis Courts, Private Beach, Fishing off your own Dock and incredible sunsets. Our Two Story Unit is beautifully decorated and furnished, Granite Kitchen counter tops, all new stainless steel appliances , complete with everything you need. Large Living Room and Dining Room with large flat panel LCD TV , and Outside Patio with a relaxing atmosphere. Master Bedroom (Queen Size Bed, Full Bathroom & LED TV ), Second Bedroom Has 2 Twin Size Beds, Half Bathroom downstairs. brbrThis unit is in a great location, a short walk to the water, pool, clubhouse, fishing pier and tennis courts. Partial bay view from back patio!brbrbrFounders Park and Marina is right next door, a Few Steps Away which offers an unlimited number of activities: White Sandy Beach and Marina with boat slips and ramp, Olympic Size Pool, Cycling and Walking Trails and much more. brbrCentrally located just minutes away: large grocery stores and shops, Pharmacy, Hospital, Cinemas, Fine Dining and Incredible Eats right on the Water, Dolphin Shows when you visit Theater of the Sea, Incredible State Parks and Reefs, world Famous Tiki Bar !! Miami is 1 hour away and Key West 1 1/2 hours. brbrAll this is available and waiting for you to enjoy and relax !!!

Villa

Executive Bay - Next to Beach and Pool!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1600.73

Sea Ranch - Two adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada at mile marker 83. This stunning property is truly a tropical paradise with a private, sandy beach and observing pier. Relax at the beach or cool down in the beachside pool. The front home sits waterfront with two bedrooms and two bathrooms. The cottage sits back on the property with two bedrooms and one bathroom. Entertain in the pool room with pool table, wet bar, poker table and more. brThe ocean front paradise is also a 'Destination/Wedding Location!' $8,000/week & $24,000.00/month. brbrThe viewing dock is just that, it is too shallow for boats, so boats are prohibited. 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.

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

Islamorada, Florida, United States

4

Bed

Bath

12

Sleeps

$459.7

Welcome to Flamingo Cottage! The pretty cottage is located in Islamorada, the heart of the Keys. brA part of the interior of the cottage is in wood that gives you the feeling of being in a boat. It is a lovely and cozy cottage for reading, thinking and contemplating the sea. brThe cottage is part of a very residential and peaceful area with a front view on the sea.brThe tropical garden offers a nice intimacy, it is pleasant to enjoy the pool and the tiki bar area hidden from neighbors.br

Cottage

Cosy Cottage in Islamorada with private garden & pool - 6 pers.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$517.69

Islamorada is considered the fishing capitol of the world!You can do deep sea,offshore game and back country fishing!Its bountiful reefs contain a wide variety of sea life ready to explore on your next scuba or snorkeling adventure. There are numerous diving and fishing charter boats ready to take you to the action!Visit the The Theatre of the Sea MM84.5 for a fun and informative way to learn about our under sea life,they also offer tours that let you swim with dolphins, sea lions and rays!Visit The History of Diving Museum MM83, which tells the international story of mankind’s attempts to explore, understand and venture under the sea.Take a tour on the Historical Lignumvitae Key Botanical State Park MM78.5 accessible by private boat, kayak, canoe or tour boat for a day of nature exploration and visit the Matheson House, built in 1919 to get of glimpse of early key living.Stop by Robbie's or Bud and Mary's marina and feed the giant Tarpons in the wild!You are sure to have a great timebrbrbrTrailer Storage: Trailer storage is available from Bayside Storage 2 minutes away for a small fee, ask manager for details. However you may choose to store your trailer with anyone of your choosing. Trailers may not be parked on house property. The nearest ramp is located at Founders Park about 1 mile away.brbrBeach: The nearest beach is located at Founders Park about 1 mile away. For our boater guests the 'sand bar' is located in front of Holiday Isle ocean side about 8-10 minute boat ride south of the property. MINIMUM 28 DAY STAY

Islamorada's Finest Canal Front 'One Story' Vacation Home WiFi-HDTV-NO STAIRS

ISLAMORADA, Florida, United States

Bed

Bath

Sleeps

$726.22

Oceanview Maison Matecumbe #306 - Maison Matecumbe is an exclusive gated and private boutique townhome complex. This wonderful unit offers an open floor and three inviting bedrooms and three baths. The master en suite has a king bed, second guest room has two full beds, and the lower-level guest room has a queen bed. Newly renovated kitchen opens up to the dining and living room. The patio offers beautiful ocean views. Lounge by the newly renovated tropically landscaped pool, or on a hammock on the white sandy beach overlooking the Atlantic. Outside oceanfront kitchen, tiki hut and hot tub. Centrally located close to great restaurants, marinas, cafes and boutiques. 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. brVACATION RENTAL LICENSE: VR-124 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

Oceanview 3-bedroom condo in Islamorada with ocean views, perfect for 6 guests!

Islamorada, Florida, United States

Bed