Vacation Rentals By Owner In Islamorada, FL

$470.26

Anglers Reef Islamorada home with ocean views, private marina, beach & pool

Islamorada, Florida, United States

Angler's Retreat is a 2 bedroom, 2.5 bathroom single-family home with picturesque ocean views, privacy, and space. The property is in Angler's Reef, a boutique complex of 52 homes donned with quintessential Keys charm. Amenities include lavishly landscaped pathways, a serene, tropical community pool overlooking the Atlantic Ocean (heated in winter), 500 ft of private beach, and a marina with 36 boat slips with a deep water channel out to the Atlantic. Boat slips are available for rent (31' max). The house sleeps up to six comfortably and is appointed with delightful Keys motif, luxury touches, and amenities for the perfect Keys getaway. brbrEnjoy comfort and privacy with two bedrooms located on the 2nd floor, each with its own bathroom and spacious closet. Inside the master bedroom, you'll find a king-sized bed, cable television, dressers, and a private bathroom, including a glass-enclosed stand-up shower with a bench and granite double vanity. The master bedroom also has a walkout, ocean-view balcony with comfortable seating to enjoy the sunrise. The guest bedroom features two queen-sized beds, cable television, and abundant dresser space, and its private bathroom includes a shower with a full bathtub. For your convenience, each upstairs bathroom provides hair dryers and starter toiletries: shampoo, conditioner, bath gel, body lotion, and hand soap. Should you need an extra bed, the downstairs area includes two chairs that pull out to comfortable single sleepers. Additional pillows, bedding, and blankets can be found throughout the home.brbrDownstairs, ocean views off the porch make the perfect setting for morning coffee or 'anytime' cocktails (it is the Keys). The kitchen boasts stainless appliances, a refrigerator with an ice maker, a dishwasher, a stove, and granite counters, and looks into the living room, which includes an oversized couch for movie night on the 75 flat screen and smart TV. Of course, cable, including HBO, WiFi, and telephone, are included. The home is fully stocked with all your needs, so pack light. Items in the home include a coffee maker (Keurig and auto drip), blender, toaster, pots and pans, dishes, utensils, linens, bath towels, beach towels, iron, and even a collection of books and games. The home also has its washer-dryer in the hallway and a gas BBQ grill out back.brbrWe are located in Islamorada, the Sportfishing Capital of the World, just 90 minutes South of Miami. The area is known for its incredible wildlife, artisan shops and restaurants, and extensive waterways for boating, snorkeling, and scuba diving, most notably during the mini-lobster season. Explore by land or sea. You won't be disappointed.brbrWe are one of Islamorada’s limited licensed weekly vacation homes, VR-239.br

2

Bed

2

Bath

6

Sleeps

$1421.76

/ Nightly

Private Vacation Home

Stay at the Pirate House conveniently located on Snake Creek in Venetian Shores

Islamorada, Florida, United States

This unique home is located directly on Snake Creek which is ideal for experiencing the amazing sunsets and convenient for any and all water activities. The property has ample room to dock any size boat in a protected lagoon as well. Easy access to both the Atlantic Ocean and Gulf via Snake Creek make navigation around the area simple and quick.brbrHome features the primary living area which consists of three bedrooms (king size beds) and ample room for an addition bed if needed. brbrThere is also a separate apartment downstairs that sleeps four adults for any party needing additional capacity (for an additional cost).brbrHome comes with all the sheets and towels you'll need for your stay, The kitchen and bathrooms are well stocked. brbrThe downstairs living area has recently been remodeled and makes a great area for outside entertaining and relaxation. In addition to the large pool and hot tub, amenities include a large dining area, pool table, lounging and sitting areas, and two large TV's. Any number of games are provided including a ping pong table as well. Also located in this area is a large capacity ice maker and bin that stores 400 lbs of ice.brbrThe home is located in the highly regarded Venetian Shores community centrally located in the heart of Islamorada (MM 86) and close to many dining and entertainment options. There is a Publix less than two miles to the south as well. Tenants will have access to Founders Park which offers Pickleball and Tennis Courts and a lap pool and beach and other outdoor activities.brbrMinimum of 28-day stays are desirable, but owner will consider shorter stays if necessary.brbrA 40k boat lift is available for an extra fee.

Bed

Bath

Sleeps

$1409.53

/ Nightly

Private Vacation Home

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

Islamorada, Florida, United States

The Sapodilla House - The Sapodilla House is one of Islamorada's gems. This tropical, sprawling estate has every amenity and then some. Enjoy island living at its finest from the moment you drive through the private gates.brThe spacious main house is beautifully furnished and equipped with everything you will need. Cook island inspired meals in the high-end kitchen and choose to dine in the formal dining area, breakfast nook with garden views or outside under the tiki hut. The main house features three king ensuites, and a kids' room with full-size bunk beds and your own personal mini arcade. Enjoy the company of family and friends in one of the conversation areas or over a game of pool. The detached pool house includes an additional king bedroom and bathroom. brStep outdoors and the lush, tropical landscaping will have you feeling like you're at your own private resort. Outdoor entertainment areas include an expansive outdoor kitchen (including a bonus grilling area with charcoal and smoker grills), crystal-clear swimming pool and spa, a rooftop sundeck and a fully equipped dock. Dockage with water, shore power and a fish cleaning station right at your reach. Paddle boards and kayaks available for your use. 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.

5

Bed

5

Bath

10

Sleeps

$1289.23

/ Nightly

Private Vacation Home

Flamingo Bay: Stunning 6BR home with breathtaking open water views in Islamorada.

Islamorada, Florida, United States

Welcome to Flamingo Bay, where luxury, space, and jaw-dropping beauty come together on the sparkling open waters of Florida Bay in Islamorada. This massive private estate is a true showstopper, with three separate buildings designed for comfort, fun, and unforgettable memories. The main home features four spacious bedrooms, two full kitchens, an elevator, and a bright Florida sunroom that opens out to the pool. A separate two-bedroom, two-bath guest house with its own kitchenette offers the perfect retreat for friends or family, while the game house brings the entertainment with a pool table, dart board, TV, and bar area. Step outside and you'll find paradise—your own private pool and hot tub, kayaks and paddleboards for exploring the bay, and a tiki hut at the end of the dock that feels like it was made for watching the most spectacular sunsets you've ever seen. Whether your days are spent fishing, boating, snorkeling, or simply soaking in the Keys sunshine, Flamingo Bay is more than a place to stay—it's an experience you'll never forget.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.

6

Bed

8

Bath

12

Sleeps

$1268.66

/ Nightly

Private Vacation Home

Bellavista: Luxurious 4-bedroom home with stunning open water views in Islamorada.

Islamorada, Florida, United States

Welcome to 116 Gulfside Drive — a breathtaking waterfront retreat in one of Islamorada's most desirable neighborhoods. From the moment you walk through the door, panoramic bay views draw you in, flooding the home with natural light and capturing the beauty of the Florida Keys.brbrThe main level offers bright, open living spaces designed for both style and comfort, along with three beautifully appointed bedrooms. Downstairs, a private apartment-style fourth bedroom with its own entrance is perfect for guests, in-laws, or anyone wanting extra privacy.brbrStep outside and discover where this home truly shines. Lush tropical landscaping frames a sparkling pool and spa, creating your own resort-like oasis. Multiple outdoor seating areas make it easy to relax, entertain, and savor the unforgettable sunsets over the bay.brbrFor boaters, this property is pure paradise—tie up at your own floating dock or keep your vessel in a private slip at the Venetian Shores Marina, offering quick, bridge-free access to both the ocean and Florida Bay via Snake Creek.brbrPerfectly situated on a peaceful street yet just minutes from world-class fishing, dining, and shopping, this home delivers the very best of Islamorada living. Whether you're setting out on the water, enjoying a cocktail at sunset, or simply unwinding in paradise, 116 Gulfside Drive offers a Keys experience you'll never forget.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.

4

Bed

3

Bath

8

Sleeps

$294.71

/ Nightly

Apartment

Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking

Islamorada, Florida, United States

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 330 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

1

Bed

1

Bath

2

Sleeps

$294.71

/ Nightly

Apartment

Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast

Islamorada, Florida, United States

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 330 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

1

Bed

1

Bath

2

Sleeps

$294.71

/ Nightly

Apartment

Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast

Islamorada, Florida, United States

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 330 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

1

Bed

1

Bath

2

Sleeps

$636.38

/ Nightly

Condo

Bay Harbour A-101 in Islamorada: Stunning 3BR condo with waterfront views.

Islamorada, Florida, United States

Bay Harbour A-101 - Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 people. Master bedroom has a king bed with direct access to the waterfront balcony. Second bedroom has a queen bed and the third has two twin beds. Brand new flat screen HD TVs in living room, master and queen guest! Gourmet kitchen has granite countertops, stainless steel appliances and a great selection of cookware and utensils. Open floor plan with wet bar and formal dining room. Enjoy your morning coffee or afternoon cocktail with the gentle ocean breeze on the wonderful screened in waterfront balcony. This unit is the model for all of Bay Harbour and is professionally decorated and furnished. brThe condo includes all linens and is equipped with a full washer and dryer. Also included is the use of a 50-foot boat slip in a protected harbor with four-foot control depth. The large screened in balcony looks directly at your boat slip. There is immediate bay access and quick ocean access via Channel Two and Channel Five bridges. Fish cleaning stations, shore power and water are also on the slips. A marina is located across the harbor with gas, diesel and bait. brPrivate gated community with a large, heated pool, jetted spa, two lighted tennis courts, pickleball court, clubhouse with fitness center. New stainless gas grills are conveniently located at the clubhouse for grilling your catch! brIslamorada is conveniently located 90 minutes from Miami and Key West. During your visit you can feed the tarpon at Robbie's, enjoy a spectacular sunset at the Lorelei or swim with the dolphins at Theater of the Sea. brIslamorada is the “Sport Fishing Capital of the World”. Tarpon, bonefish, permit, mahi mahi, sailfish and sword fish abound in the tropical waters surrounding Islamorada. Flats fishing or blue water offshore fishing options are at your fingertips with Islamorada having the biggest fishing fleet in all of the Keys! At Bud n Mary's you will find a great selection of deep-sea charters. Or if you prefer the backcountry, visit Worldwide Sportsman for a variety of different guides. brSo, whether you want to fish, snorkel, dive or just sit by the pool and relax, this condo has something for you. brPlease note: Bay Harbour does not allow parking on site for boat trailers. brVACATION RENTAL LICENSE: 24-0324 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.

Bed

Bath

Sleeps

$503.34

/ Nightly

Private Vacation Home

Pool Home in Venetian Shores

Islamorada, Florida, United States

Spacious, open layout designed for ultimate comfort and convenience. The fully equipped kitchen flows seamlessly into the cozy living and dining areas, all boasting breathtaking canal views. Enjoy your morning coffee on the terrace as you watch the sunrise over the pool and waterway—this is truly island living at its best.brbrThe home offers three bedrooms upstairs, including a spacious primary suite with a bath and a luxurious closet. The two guest bedrooms share a full bath with dual vanities. Downstairs, the additional family room and fourth bedroom offer even more space to spread out. A wet bar off the pool area makes entertaining a breeze, and the private, fenced backyard provides a true tropical escape with lush turf, a Tiki hut, and a stunning pool area.brbrThis property is ideally located for boating enthusiasts, with a boat ramp at the local Founder’s Park. Direct access to Snake Creek, the Bay, and the Ocean makes this the perfect base for water lovers.brbrConveniently located near shopping, dining, schools, art galleries, and local breweries, this home offers the ultimate combination of tranquility and proximity to all the best of Islamorada. brbrBedroom 1 - King BedbrBedroom 2 - Queen BedbrBedroom 3 - Queen BedbrBedroom 4 - Bunk Bed - 2 Queen Mattresses

Bed

Bath

Sleeps

$920.41

/ Nightly

Private Vacation Home

The Beach House-Luxury Oceanfront Home, Outstanding Views, Pool & Beach

Islamorada, Florida, United States

Welcome to ‘The Beach House’ at Tarpon Point in Islamorada – This luxurious oceanfront home is in a private gated enclave of 12 houses. This home sits directly on ‘The Beach’. Being the end home, it is nestled next to lush mangroves and the ocean offering a lot more privacy. It is also the largest model with an additional Family Room and more square footage overall - giving everyone plenty of room to mingle or just chill. brbrThere are beautiful ocean views including of Indian Key Historic State Park and the Alligator Lighthouse. An ocean access channel runs just out front and you can watch the dolphins, manatees or spinner sharks swim by. Enjoy your morning coffee and a phenomenal sunrise from one of the multiple oceanfront decks. Afternoons, lounge around the heated & chilled oceanfront pool taking in the panoramic views or launch your kayak from the private beach area and paddle over to Indian Key. For those who like to fish, the observation pier offers a place to catch your next dinner.brbrAlthough no permanent dockage is provided, world renown Robbie’s is just across the street and does offer transient dockage as well as watersports rentals, fishing & snorkeling charters and a restaurant. Within a few miles are other options for your boat and dining as well. Your fishing guide is welcomed to dock at the pier to pick you up & drop you off.brbrOn the main level of The Beach House is the Great Room which offers amazing ocean views with plenty of room for everyone to gather. This room opens to a covered deck to take in the vista and ocean breezes. On cooler nights (yes, even in The Keys) enjoy the fireplace in the Living Room. The Osprey Nest in your front yard is active during the winter months and it is mesmerizing to watch Mom, Dad and babies interact. brbrThe Gourmet Kitchen offers a Wolf 6 burner gas stove/electric oven; microwave draw and warming oven. Bosch Silence dishwasher and Sub-Zero Refrigerator. A Butler’s Pantry is off the kitchen with full size washer/dryer and plenty of storage for all your provisions. There is an extra microwave, coffee makers and ice maker as well. The kitchen is very well equipped whether whipping up a gourmet fish dinner with your latest ‘catch’ or whipping up a batch of margaritas.brbrTucked between the kitchen and rear Bedroom Suite is a large Family Room with a bar offering a wine cooler and undercounter refrigerator draws. The perfect place to make your evening cocktails, hold game night or watch your favorite sports games on the large screen TV. Plenty of puzzles, games and books are on hand for all ages. This is the only rental home in Tarpon Point to offer this additional living space.brbrAfter a long day of play, take a luxurious spa shower or enjoy some quiet time on your personal deck/balcony. There are four ensuite bedrooms (3 with private decks/balconies), all with spa showers. There is an additional ½ bath on main living floor. brbrThe large Primary Suite situated on the oceanfront on the top floor has panoramic ocean views with a private terrace. For quiet time, the sitting nook, gives you a bird’s eye view of The Osprey Family or a place to finish your favorite beach read. There is also a second fireplace. Refresh in the spa shower or relax in the whirlpool tub. This is the life!brbrA three-stop elevator starts at the ground level with a large covered brick patio where the entire family can prepare and enjoy al fresco dining with the cooler ocean breezes. Gas BBQ, dining table for 8 and a sectional sofa round out the ground level. Lounge in the sun, play corn hole or bocci. Kayaks and fishing rods are also available.brbrThe ‘Beach House’ offers the highest level of amenities, furnishings and is designed to make your vacation a truly relaxing and memorable one. This is an owner direct rental and therefore there are no additional fees. You will have direct contact with us at all times to handle any issues or questions. We are proud of our testimonials that this home and our responsiveness have been above and beyond our guest’s expectations. We invite you to share our love of our home by ‘The Beach’.brbrOther amenities: Full house generator, California closets, Wi-Fi, Plenty of Parking, lush landscaping. 3382 square feet of interior living spacebrbrWe invite you to share our love of this home by the beach.brbr~*~*~*~Saturday Changeover~*~*~*~brbrSorry, no animals per HOA rulesbrbrWe invite you to share our love of this home by the beach.brbrBe sure to search The Beach House At Tarpon Point to learn more!brbrVR 26-0041

4

Bed

4

Bath

8

Sleeps

$315.0

/ Nightly

Private Vacation Home

FULLY RENOVATED piece of paradise. 2 bdrs, 2 king beds, 1 Queen bed 2 full baths

Islamorada, Florida, United States

FULLY RENOVATED piece of paradise. 2 bdrs, 2 king beds, 1 Queen bed 2 full bathrooms and a loft for gaming etc. freshly painted all new furniture & fixtures, all new. Inside you have washer/dryer stainless steel appliances fully equipped kitchen. Dishwasher, microwave everything for your comfort. The premises is a gated community with private beach, boat ramps, Olympic pool clubhouse, Nearby shopping, restaurants, Gas etc.

2

Bed

2

Bath

6

Sleeps

$1364.2

/ Nightly

Private Vacation Home

Oceanfront Keys Escape | Private Beach & Pool | 3 Acres

Islamorada, Florida, United States

Welcome to Oasis4rent!brbrEscape to 2.75 acres of private oceanfront paradise in the heart of Islamorada. Two beautifully appointed homes sit directly on the Atlantic with 200 feet of sandy beachfront, a heated saltwater infinity pool, and views of Alligator Reef Light on the horizon.brbrThe PropertybrbrMain House: 1 king bedroom (Tempurpedic adjustable), 1.5 baths, full kitchen, wrap-around porchbrbrGuest House: 2 bedrooms (queen + queen/full), 1 bath, full kitchen, ocean-view living roombrbrSleeps up to 8 guests across 3 bedrooms and 4 bedsbrbrWhat Makes This SpecialbrbrPrivate sandy beach — swim, kayak, or paddleboard from your backyardbrbrHeated saltwater infinity pool with unobstructed Atlantic viewsbrbr100+ palm trees, 60+ lit at night — the Keys' most stunning evening ambiancebrbr6 high-end bikes for exploring Upper Matecumbebrbr4 kayaks, 2 paddleboards, bocce ball, and cornholebrbrTesla and NEMA 14-50 EV chargerbrbrEnterprise-grade Wi-Fi covering the entire estatebrbrGated entrance for complete privacybrbrThe LocationbrWalk or bike to Italian Food Company, Bayside Gourmet, local breweries, and art galleries. Less than a mile from Publix. World-class fishing, snorkeling, and diving charters depart from nearby marinas.brPet-Friendly — Dogs welcome ($350 fee). They will love the fenced, grassy yard.brCoffee on the porch at sunrise. Dolphins passing just offshore. Margaritas by the pool at sunset. This is why it is called The Oasis.

3

Bed

1

Bath

8

Sleeps

$495.02

/ Nightly

Private Vacation Home

Best location in downtown Islamorada. 2 Houses with Beach access!

Islamorada, Florida, United States

Unbelievable location in Islamorada Florida Keys! You have beach access and boat trailer parking. This listing is for 2 houses - 1 property. The 2 homes are right next to each other offering plenty of space for your group getaway. Walk to the beach and walk or bike to great restaurants, marinas and shopping. The beach is a 2 minute walk down the street as well as the famous Islamorada Brewing Co! The home comfortably sleeps 10 people. We are a local family who is happy to help with your Island Getaway!

6

Bed

5

Bath

18

Sleeps

$1777.44

/ Nightly

Hotel

Your Idyllic Getaway Awaits! Breathtaking Beachfront, Outdoor Pool | 3 Units

Islamorada, Florida, United States

This listing is for 3 separate rooms within a hotel. The price shown in the listing covers all 3 rooms.brbr✦ Each room is 950 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.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 $300 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.

6

Bed

6

Bath

18

Sleeps

$388.9

/ Nightly

Private Vacation Home

3-bedroom, 3-bath Canal front home with private pool in Islamorada, Florida Keys

Islamorada, Florida, United States

Nestled at the quiet west end of Islamorada, minutes from the Channel 2 and Channel 5 bridges famed for Tarpon fishing, this delightful recently updated canal-front house with a heated/chilled private pool offers a tranquil escape for guests. There's plenty of space for everyone to unwind in the hammock, hang by the pool, fish on the dock, or take the kayaks out for a morning catch or afternoon sunset. With a downstairs apartment, second living room, and kitchen, this home is perfect for a multi-generational family or two families traveling together. Imagine waking up to the serene surroundings and enjoying a cup of coffee on the screened-in porch. Don't forget to enjoy the afternoon sunset from the front deck. The home is a short walk to Anne's Beach, Caloosa Cove Marina, and two restaurants. Come rent our place for at least 28 days per city ordinance and enjoy all the wonders Islamorada offers. You don't have to actually stay 28 days; our rates are less than most 2-week rentals.

3

Bed

3

Bath

10

Sleeps

$306.44

/ Nightly

Private Vacation Home

Charming 3-bedroom townhome in fabulous Islamorada seconds from the bay!

Islamorada, Florida, United States

Your home away from home in Islamorada with 3 bedrooms plus a loft. This cool townhome features a king bed, queen bed, 2 twin beds, and full bed (Loft) to accommodate all guests. Enjoy the convenience of a washing machine, hair dryer, iron, heating, AC, and WiFi during your stay. Located in the best building of EBC, within seconds from the pool and the bayside beach area! We have a marina where you can watch the boats come in and/or the beautiful sunsets. Community has a heated pool, pickle ball courts, and next door there is FOUNDERS PARK that has many amenities and activities for all!brMake your holiday one for the books with a stay at our place.

Bed

Bath

Sleeps

$392.95

/ Nightly

Villa

Serenity by the Sea!! Anglers Reef with Boat Slip Available!!

Islamorada, Florida, United States

brThis beautiful villa is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84 and has access to one of the few privately owned boat slips. The homes boat slip is available for rent for an additional $350/week, paid after booking and gives you access to the deep water channel right in front of the community. The marina is capable of accommodating boats up to 31' in total length.brbrAngler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean. The detached villas are set along quaint streets and walking paths, where nothing is more than a few steps from your front door.brbrThe community amenities include a heated pool with outdoor bathrooms. Chaise lounge chairs and tables to sun and relax overlooking the beautiful blue waters of the Atlantic Ocean. There are two private beaches just a few short steps from every home that flank the marina and the privately owned boat slip which is available for rent. One beach has water access to launch a kayak or paddle board, which are provided, and the other beach is nestled among the protected mangroves where you can watch the gorgeous sunrise while sitting in an adirondack chair with your morning coffee. The lush landscape surrounds you with amazing palm trees, beautiful bougainvillea and some of the most colorful and gorgeous tropical foliage that only the Florida Keys can offer. The quiet gated community is ideal for families with kids of all ages as there is no road traffic. brbrBuilt in 2007, this villa is one of the larger exterior units and has 2 bedrooms located on the 2nd floor, both with private bathrooms. The 1st floor offers a wide open layout with a duel peninsula kitchen centered between dining and living rooms with french doors opening to the back patio. The house has many upgrades, such as stainless appliances, granite counters, rich hardwood floors, crown molding, 3 flat screen TVs, cable & WiFi.brThe Islamorada area is world famous for sport fishing and Angler's Reef has deep water boat docks perfectly poised for any aquatic excursion.brbr** Fully licensed by the Village of Islamorada for Vacation Rentals, license # 26-0183. brbrThe surrounding area has some of the best restaurants in the keys. Such as Lazy Days, Ziggie & Mad Dogs and Chef Michaels- just to name a few. The local watersports are endless and include all types of fishing from charters and boat rentals to jet skiing, paddle boarding, kayaking, and kite surfing.

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Bath

Sleeps

$464.63

/ Nightly

Apartment

Breathtaking ocean views for your Paradise vacations

Islamorada, Florida, United States

Due to COVID-19 and the precedented times we are living, our home will provide hand sanitizer and have the whole house sanitized when one guest leaves and another enters. We take pride in having our home immaculate and now we are taking extreme measures to have our guests feel safe during their stay. brbrThis upstairs portion of a dual family fully renovated home with two bedrooms and two baths will comfortably sleep eight to provide you a dream vacation you will never forget!! brFully stocked new kitchen with granite counter tops and a huge island for entertaining and feeding your whole family comfortably. brAll new stainless steel appliances and new plates,cutlery,utensils,and glasses.brLiving room has two queen sleeper sofas and new 60 in smart TV.brIn hallway closet it has new washer and dryer for your conviniance during your stay.brTwo master bedrooms with new queen beds and each has their private baths. Each bedroom has a 42 inch smart TV.brEverywhere your walk in the house you will have a spectacular view of the ocean!!!brThis property also provides you own private dock and ramp for your conviniance with no extra fees. Our shed provides extra fenders to protect boats, brush and soap, electricity and water by dock, and a small freezer for bait and ice. For more outdoor fun you will be able to use the four kayaks and four bicycles provided to explore the ocean and sight see.brbrThose who want to charter a fishing captain upon request please contact Captain Avila 305-495-3322.

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$269.39

/ Nightly

Cottage

Oceanfront Private Cottage!

Islamorada, Florida, United States

Welcome to Paradise Cottage!!brbrThis downstairs portion of a dual family dwelling is fully renovated a 1/1 cottage with breathtaking oceanfront views. brSleeps four comfortably. brPrivate bedroom with queen bed. brLiving room has two full size futons.brNew kitchen with all stainless steel appliances. brVery cozy and great views to enjoy in your dream vacation. brAmenities provided are kayaks, bicycles, grills, boat ramp and boat dockage for your use with no extra fees. brbrPrivate boat dock and convenient boat ramp. Amenities for your boat includes water and electricity(only 110volts) by the dock, brush and soap, extra fenders, and a small freezer for bait and ice. Trailer parking is available on our acre and a quarter property. The ramp and dock use are part of the rental amenities!brbrRelax and enjoy ocean views and gorgeous sunsets from the comfort of our multiple loungers. brbrPlenty of parking for all of your toys in my acre and a quarter property(boat, trailer, car, etc). brbrBBQ areas with plenty of seating and a separate picnic table perfect for lunch and snack time. brbrBath towelsbrBed linensbrHair dryerbrWifibrCable brTV in living room and bedroom. brWasher and dryerbrAll appliances in kitchenbrCoffee maker (K-cup and drip )brToasterbrBlenderbrPots and pansbrbrClose to all attractions and best restaurants. brbrThose who want to charter a fishing captain upon request please contact Captain Avila or other captains from Whahoo Marina.

1

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1

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4

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