Home Vacation Rentals By Owner In Islamorada, FL

Showing 480 Of 715 Vacation Rentals
Slider Thumb
Exceptional(9)

$387.74

/ Nightly
Private Vacation Home

Incredible Bayside Home in the Florida Keys!

Islamorada, Florida, United States

**To our guests** Nautilus Getaway has always been proud to utilize a contact-less check in process. We use CDC recommended standards for disinfecting in our all our cleaning protocols.brbrAs soon as you walk into this home you will feel like you just walked into a comfortable, cozy home. With its cool laid-back style and subtle sophistication this house doesn't disappoint. The home is newly painted and new gravel. Also the backyard has been updated with new artificial turf, which allows for more entertaining space or sun bathing. The house is situated on a canal and features 3 bedrooms and 2 bathrooms, family room, kitchen, dining area, outside deck off the 2nd floor. Our home is situated 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. The home is a 3/3, and can comfortably sleep six, with three bedrooms and 2 bathrooms upstairs and 1 full-bath downstairs. The Master has a queen bed, and a private bath. The second and third bedroom have queen beds, and a separate bath that is shared. If more room is needed, or for families with older children or adult that cant climb stairs, the lower level is an open floor plan where you can find two sets of bunk beds and sofa sleeper and I full bathroom. Also, you can find on the lower level a laundry room and television to connect any of your favorite game consoles (not provided). A full-size refrigerator for water/soft drinks/beer/bait is located on the first level for easy access to the pool deck. On the pool deck you will find an outdoor barbecue area and gorgeous Tiki Hut with a large pool to soak your worries away. Also, a large 65 foot of dock with Electric & Water; and a fish cleaning station This home provides a private homeowners beach with Tiki Huts, chairs and BBQ Grills. This home is close to the best restaurants, and sightseeing that can be offered in the Florida Keys. brbrPeaceful, quiet and relaxing! Just what is needed to take your mind off of business and a great place to spend the winter months in turquoise, warm waters. Fish, read a book, swim, head to Key West, shop, eat, drink, enjoy the Florida Keys. brbrCome stay in this incredible home and create your own memories!brbr*This is a non-smoking unit. Sorry, no pets. No large groups or individuals under the age of 25.brbr***Service Pets Allowed***brbr****Please feel free to reach out for more information****
Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(90)

$465.11

/ Nightly
Private Vacation Home

CHARMING WATERFRONT OCEANSIDE CANAL HOME-LARGE PROTECTED DOCKAGE-WiFi-SMART TVs.

Islamorada, Florida, United States

WATER FRONT CANAL HOME 3 BEDROOM/ 3 BATH HOME. brBRING YOUR BOAT, LOTS OF PROTECTED DOCKAGE. FULLY UPDATED HOME. HIGH SPEED WiFi and ALL SMART TVs. Coconut trees provide the shade to enjoy the calm breeze as you sit in one of our comfortable adirondack chairs and enjoy the tranquility.brUpdated Wi-Fi with new easy to connect AT&T modem. brDOCK RIGHT AT THE HOUSE! FISHING FUN RIGHT OFF DOCK!brGUEST BATHROOMS RENOVATED AND UPDATED! NICE PROTECTED DOCKAGE.brLOTS TO SEE AND DO CLOSE BY! MANY RESTAURANTS CLOSE BY!brWE MAKE COMMUNICATION EASY AND ALWAYS PROMPTLY RESPOND TO OUR GUESTS.brCLEANLINESS IS MORE IMPORTANT THAN EVER!brHOME IS CLEAN AND FRESH! INTERIOR RECENTLY PAINTED! brBRING YOUR OWN BOAT OR RENT ONE LOCALLY.brbrWEEKLY STAYS ARE WELCOME. LICENSE #VR-113. brbrCharming cozy private waterfront house on Atlantic side canal. brGreat protected dockage and room for your trailer. Newly paved, private road.brbrNew kitchen with all wood cabinets, granite counter tops and stainless appliances. The kitchen is fully equiped with all the essentials.brbrThree bedrooms and three bathrooms. Downstairs bedroom has full bathroom with shower and is separate from upstairs and opens to carport. Home is perfect for four adult plus two kids.brbrWe have lots of great dockage for your boat. The large dock/seawall area extends 90 feet and includes a nice cut-in slip. The dock includes electric, water. There is also a cleaning station on the dock. Also there is plenty of room for trailers on the side of the home. It's all about the boating. brbrThere are several local boat ramp options close by. brbrKeep in mind that trip insurance is available and is recommended.brThere are many options including through VRBO or other mainstream recognizable third party providers.brBe sure to understand the coverage, benefits and limitation of any policy you purchase.brbrbrINSPECTED, PERMITTED & LICENSED BY THE VILLIAGE OF ISLAMORADA # VR-113.brbrKeywords: License #VR-113, Islamorada Florida, Lower Matecumbe, Dockage, Waterfront, WiFi, Internet, clean, Tropical, Home, waterfront, deep dockage, bungalow, shopping, dinning, beach, kayak, scuba, snorkeling, lobsterbrfishing, dock, boat, ocean, bay, Keys, key, Islamorada, Upper Keys, Lower Matecumbe, kitchen, open, clean, bright, comfortable, private, protected, deep water, boating, swimming,! Amazing
Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(15)

$588.94

/ Nightly
Cottage

Experience paradise at Green Cottage, a charming 2-bedroom oceanfront retreat in Islamorada!

Islamorada, Florida, United States

Green Cottage - The Green 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 peaceful cottage is nestled in lush landscaping and offers pool and ocean views from the open living and dining room. The 2/1 layout includes a master bedroom furnished with a queen bed and a guest room with bunk beds in a full/twin configuration. The Green Cottage can be rented separately or in combination with any of the four other homes.brVACATION RENTAL LICENSE: 24-0385brIf 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.
Bed 2

Bed

Bath 1

Bath

Sleep 5

Sleeps

Slider Thumb
Exceptional(5)

$1012.82

/ Nightly
Private Vacation Home

Alligator Reef - Conch Home: Stunning 3BR retreat in Islamorada with open water views.

Islamorada, Florida, United States

Welcome to Alligator Reef, a gated oceanfront property offering two homes that can be rented individually or together—perfect for families or groups traveling to the Keys.brThe Conch Home is a spacious 3 bedroom, 2 bathroom home featuring its own private fenced heated and chilled pool, outdoor kitchen and bar area, ping pong table, and plenty of space for relaxing and entertaining. Conch also includes bicycles for guests to explore the surrounding area.brLocated just in front of the Conch Home is the Lobster House, a comfortable 2 bedroom, 2 bathroom home that provides additional space for larger groups or extended family.brBoth homes share the beautiful oceanfront grounds which include a sandy lounging area, fire pit, observation dock, kayaks, and paddleboards—perfect for enjoying the water and soaking up the laid-back Keys lifestyle.brWhether you're looking for a private family getaway or a larger group retreat, you can book the Conch House on its own or reserve both homes together for the full Alligator Reef experience.brFamily fun for everyone, all set right on the ocean in the heart of the Florida Keys. brVACATION RENTAL LICENSE: 24-0389 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.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. 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.
Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(47)

$562.17

/ Nightly
Private Vacation Home

Keys Paradise with Private Beach and Pool

Islamorada, Florida, United States

NOTE:br--PLEASE SEND AN INQUIRY TO BE SURE YOUR DATES ARE AVAILABLE. br--DOCKAGE AVAILABLE AT FOUNDERS PARK MARINA RIGHT NEXT DOOR FOR A FEE. NO DOCKAGE AND NO TRAILERS ALLOWED ON PROPERTY. (Condo rules, not ours!!)brbrLuxury resort amenities with all the comforts of home! brGorgeous, spacious condo with modern updates just steps from the crystalline waters of the Florida Bay. Updated kitchen appliances, granite counter tops and fully equipped with all the extras you might imagine make the kitchen a gourmet cook's delight. Breakfast bar and large wooden table accommodate up to 10 comfortably in the adjoined dining area. The open floor plan makes it a great space to sit with your family and friends while others are preparing food in the kitchen in one of three couches and three comfy chairs. You'll find one full bath downstairs and another upstairs, both completely remodeled this year with tile and luxury finish.brbrEnjoy sitting under the stars or making your favorite barbecue foods on the private outdoor patio equipped with large gas grill, surrounded by greenery and shaded by palms. Just off the patio, but hidden by the greenery is one of the complex's two tennis courts. And only a few steps away is the pool and club house where you can swim in the large, heated pool or just relax in the shade in one of the many lounge chairs. brbrThe enormous master bedroom hosts a dreamy king bed with orthopedic mattress and memory foam top and is decorated with classy Keys style, and a Queen bed up in the loft space, as well as plenty of room for a queen air mattress down below if you need it. brThe second bedroom has a Queen beds, and two twin (bunk) beds. Wooden ceilings with inset lights are a highlight of the high-end updates made in the recent remodel. There's plenty of space for everyone to relax and enjoy the escape to paradise.brbrMarvel at the most spectacular sunsets on the planet from our private beach, just a minute walk from the front door. Jump from the wooden dock to swim in the clear blue water, or just enjoy watching the variety of colorful reef fish, rays, nurse sharks, and even frequent visits from manatees! Fishing is great right off the dock, too.brbrYou won't ever have to go far to enjoy the best that Islamorada has to offer. Walk easily to nearby Founders Park, where you will find a large sandy beach with beach volleyball, a play ground, an olympic sized pool, a walking/ running path, an outdoor gym, soccer and baseball fields, and a marina. Various restaurants are within a mile of the property and the heart of downtown Islamorada is 4 miles to the south. brbrOther amenities include parking for up to 2 vehicles, high speed WIFI, smart TV, and a large washer and dryer onsite so you can pack light.brbrNote: The bed configuration is different than the photos but the same beds are all there, as follows: Large bedroom with King bed and a Queen bed up in the loft. Space for queen air mattress if needed. Second bedroom has a queen and two twin bunks.
Bed 2

Bed

Bath 2

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(12)

$490.17

/ Nightly
Private Vacation Home

Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip

Islamorada, Florida, United States

Boat slip #13 is included in this rental.brOcean view property in the Village of Islamorada located in the Florida Keys at Mile Marker 85. The property is in a gated community filled with quaint streets and walking paths throughout the perfectly manicured grounds. A heated/cooled pool cascading over a 52' beach front property overlooking the Atlantic Ocean. Enjoy the convenience of having your private dock for a 31' boat with electricity and water included. Boat slip #13 is just steps away from a refreshing dip in the pool.brbrThis home features high ceilings both upstairs and down and an open floor plan on the first floor. The kitchen is well-equipped with granite counters, stainless steel appliances and adjoins a comfortable dining area and living room. The dining area includes bar seating for two and a dining table for four and the living room is equipped with a sectional sofa with a pull-out-bed, an accent chair, coffee table and a flat screen. Hardwood floors throughout. brbrThe master suite upstairs features a king size bed, flat screen tv and a private bathroom with a walk-in shower. Additionally, the master suite has a private balcony. The guest suite features one queen bed, a pull-out sofa, closet, private bathroom with walk-in-shower and a private balcony. A stacked washer and dryer are located on the second floor for the guest's convenience.brbrbrNote: I also have a 4-bedroom rental home with a boat dock included on the front row just across from the pool with a full view of the ocean. VRBO Listing 359378
Bed 2

Bed

Bath 3

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(2)

$444.52

/ Nightly
Private Vacation Home

2BR/2.5BA Angler's Reef Conch Villa 103 With Private Beach and Pool Access

Islamorada, Florida, United States

In the heart of the Florida Keys - Islamorada - an ancient reef awaits your arrival, where its waters brim with earth's most abundant marine life and it is nobly touted as "The Sport Fishing Capital of the World." Greeting you along its shore, native palms wave in a Caribbean breeze, framing dramatic ocean views where a spectacular pool meets the Atlantic. Preserved in the barefoot beauty of another time, Angler's Reef brings together quaint streets and walking paths to unite a community of homes crafted in the style of Native Conch and the British West Indies; Here private, deep water docks channel boats to the Mecca of fishing - famed Alligator Reef - just three miles to the south.brbrLocated in the center of the sport fishing and boating universe, Angler's Reef offers all the amenities of a classic-sport fishing resort, including:brbrGated entry for privacy and securitybr36 privately owned protected deep water docksbr500 feet of private beachfrontbrCrafted in the style of Key West Conch and the British West Indies: metal roof, spacious porch and classic gingerbread trimbrTile floors & morebrHeated Oceanfront pool with Mens & Womens BathhousebrClose proximity to several state and national parksbrNearby seafood restaurants serving the freshest catch of the daybrNearby Snake Creek Marina for water sports, fishing and boating servicesbrBoat trailer parking available along the Old Highway median outside the property gatebrAdditional auto parking available along the Old Highway median outside the property gate
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb

$797.63

/ Nightly
Hotel

Breathtaking Bayfront Villa w/ Private Patio & Living Area, Perfect For Couple

Islamorada, Florida, United States

This listing is for a room within a hotel.brbr✦ Your room is 1042 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.brbr✦ Cleaning services availability and frequency vary by staybrbrThere 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✦ Fitness center is available.brbr✦ Outdoor shared pool is available, opened from 8:00AM to 10:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $60.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $100.00 (per night). $100 per night. Up to two pets/roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.
Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps

Slider Thumb

$726.75

/ Nightly
Hotel

Stunning Bay View Villa in Florida Keys | Beach Getaway w/ Scenic Outdoor Pool

Islamorada, Florida, United States

This listing is for a room within a hotel.brbr✦ Your room is 1042 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.brbr✦ Cleaning services availability and frequency vary by staybrbrThere 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✦ Fitness center is available.brbr✦ Outdoor shared pool is available, opened from 8:00AM to 10:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $60.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $100.00 (per night). $100 per night. Up to two pets/roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.
Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(6)

$553.46

/ Nightly
Hotel

Picture-Perfect Villas Offering Pool Relaxation & Ocean Adventures Nearby

Islamorada, Florida, United States

This listing is for a room within a hotel.brbr✦ Your room is 1042 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.brbr✦ Cleaning services availability and frequency vary by staybrbrThere 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✦ Fitness center is available.brbr✦ Outdoor shared pool is available, opened from 8:00AM to 10:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $60.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $100.00 (per night). $100 per night. Up to two pets/roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.
Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps

Home Most popular vacation rentals in Islamorada