Vacation Rentals By Owner In Islamorada, FL

$317.27

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

$317.27

/ 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

$317.28

/ 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

Bed

Bath

Sleeps

$507

/ Nightly

Private Vacation Home

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

Islamorada, Florida, United States

Hawksbill Cottage - The Hawksbill 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 oceanfront property's amenities: pool, boat basin, tropical sprawling grounds, ping pong table, kayaks, paddle boards, oceanfront shaded tiki area and more. This peaceful garden bungalow is secluded in lush tropical landscaping. It features a king bedroom, bathroom with walk-in shower, kitchen, living room and private patio. The decor and furnishings give it a tranquil feel. The Hawksbill Cottage can be rented separately or in combination with any of the other four homes. There is a cottage above the attached garage, referred to as The Treehouse, that is convenient to rent for family and friends.brVACATION RENTAL LICENSE: 24-0416 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

$295.1

/ Nightly

Apartment

Treehouse Cottage: A cozy 1-bedroom retreat in beautiful Islamorada with kayaks and paddleboards

Islamorada, Florida, United States

Treehouse Cottage - The Treehouse is the upper level of Hawksbill Each cottage has it's own personality and characteristics. All five cottages share the property's amenities: pool, boat basin, tropical sprawling grounds, ping pong table, kayaks, paddle boards, oceanfront shaded tiki area and more. This cozy studio overlooks tropical landscaping and has a very private feel. It features a king-sized bed and kitchenette. The Treehouse Studio can be rented separately or in combination with any of the other four homes.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.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. brVR-253

Bed

Bath

Sleeps

$208.96

/ Nightly

Private Vacation Home

Keys Getaway – 2 Bikes, Heated Pool, Small Beach & Sunset Dock Views

Islamorada, Florida, United States

Escape to Your Florida Keys Getaway – A Slice of Paradise in IslamoradabrWelcome to our beautiful 2-bedroom, 2-bathroom townhome in the heart of the Florida Keys. Whether you're looking for adventure or relaxation, our home offers the perfect balance of both.brbrAmenities & Outdoor FunbrRelax & Unwind – Lounge by the large, heated pool, soak up the sun swimby the dock or take in breathtaking sunsets from the fishing pier/dock.brbrExplore with Ease – Enjoy our two beach cruiser bikes, Kayak from our beach in our 2 single person kayaks brbrStay Active – Play on the pickleball and tennis courts or head next door to Founders Park, which features baseball and soccer fields, a beach volleyball court, a marina, and an Olympic-sized swimming pool.brbrModern Comforts – Stay connected with free Wi-Fi throughout the home and clubhouse. Smart TV's to enjoy streamingbrbrEntertainment for All – Enjoy streaming your favorite shows on smart TVs in the living room and primary bedroom. Plus, we provide board games for memorable family game nights.brbrPrime Location – Islamorada brOur townhome is nestled in Islamorada, known as the Sport Fishing Capital of the World and home to incredible wildlife. Located in a private, gated community with 24/7 security, you’ll be minutes from world-class fishing, diving, and snorkeling.brbrYour Home Away from HomebrSpacious & Comfortable –brbrUpstairs: Two bedrooms accessed via a spiral staircase. The primary bedroom features a king-size bed and a queen sleeper sofa with a Tempur-Pedic mattress. The guest bedroom has a queen-size bed.brbrDownstairs: Open-concept dining and living area with a new queen-size sleeper sofa (also with a Tempur-Pedic mattress).brbrWork-from-Paradise Setup: The primary bedroom has a dedicated workspace with a monitor, keyboard, and mouse, plus strong, reliable Wi-Fi for remote work.brbrFully Equipped Kitchen & Outdoor Dining – Cook a delicious meal in the fully stocked kitchen or fire up the BBQ grill on the back patio. Enjoy your meal at the outdoor dining table with an umbrella, perfect for morning coffee or sunset cocktails.brbrAll the Essentials Provided –brbrLinens, towels, and beach towelsbrbrHairdryers and complimentary starter toiletries (shampoo, conditioner, bath gel, lotion, and hand soap)brbrIn-unit washer & dryer for added conveniencebrbrExtra Perks & Nearby ShoppingbrPublix & Winn Dixie supermarkets are just 4 miles awaybrbrWest Marine & Bass Pro Shops for all your outdoor needsbrbrQuaint local shops and waterfront restaurants to explorebrbrImportant NotesbrDock Use: Our fishing dock is not available for guest boat docking, but it’s a fantastic place to watch for manatees and swap fish tales with fellow guests.brbrAccessibility Notice: Please note that this unit is not disability-friendly. It features a spiral staircase leading to the bedrooms, which may not be suitable for guests with mobility challenges. If you have any concerns about accessibility, please feel free to reach out before booking.brbr brCome experience the best of the Florida Keys—whether it’s adventure-filled days or tranquil nights, this is your perfect getaway.brbrBook your stay today and start making unforgettable memories.

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Bath

Sleeps

$191.95

/ Nightly

Private Vacation Home

Beautiful water front home, private dock in Islamorada, World Fishing Capital

Islamorada, Florida, United States

This two-story house is located on an ocean access canal that is literally minutes from the Atlantic Ocean. Guest can dock their boat (max. length of 32') in the backyard and be on the Ocean in just a few minutes. The front of the house faces the Atlantic Ocean with views of the ocean. The home is updated and has an open layout with volume ceilings. The master bedroom has a queen size bed with attached master bathroom. The second bedroom has bunk beds with a trundle, which sleeps 5 people. The great room has a love seat, and a sleeper sofa, which sleeps 2 adults. Guests can enjoy views of the ocean from the balcony. There is covered parking for 2 cars.

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Bath

Sleeps

$2706.47

/ Nightly

Private Vacation Home

Ocean Villa | BeachFront Paradise by Glam Homes

Islamorada, Florida, United States

Summary:brbrThis is a truly unique and spectacular Villa thanks to its breathtaking view of the sea and its warm sandy beach.brbrbrbrOn the stunning beach you will find paddle boards and kayaks (both for rent) and comfortable sun loungers while you sunbathe and enjoy the dreamy sunsets.brbrbrbrGet ready for a private saltwater pool with lush tropical landscaping plus a cozy cabana with a dining table, a cinema (projector) and a lovely fire pit!brbrbrbrThe interior has 4 bedrooms, 4 bathrooms and much more!brbrbrbrLicense # 24-4115brbrbrbrThe Space:brbrBEDROOMSbrbrbrbr1. Master Bedroom with a KING SIZE BED with excellent quality linens. A balcony with an amazing view of the beach and access to a full private bathroom with a hot tub.brbr2. Bedroom with a QUEEN SIZE BED and access to a full private bathroom.brbr3. Bedroom with THREE QUEEN SIZE BEDS and access to a full private bathroom.brbr4. Bedroom with TWO FULL SIZE BEDS and access to a full private bathroom.brbrbrbr*Two extra air mattresses.brbrbrbrAll the bathrooms are stocked with the toiletries our guests will need; towels are also included.brbrbrbrPerfect for large groups.brbrbrbrThe Villa has a cherry hardwood flooring throughout, Also, a fully equipped kitchen with granite/stainless appliances and a gas stove.brbrbrbrTHE VILLA HAS AN OUTDOOR CAMERA TO CONTROL WHO GOES IN AND OUT, ALWAYS LOOKING FOR OUR GUEST SAFETY.brbrbrbr-kayaks and paddle boards are available for rent only we don’t provide them, we have a partnership with a Keys rental for this!brbrbrbrOther Things to Note:brbr- This property is pet friendly.brbr$300 per petbrbr-brbr- If you want the pool to be heated, request it 48 hours prior arrival.brbrbrbr- BUGS & CRITTERS: Please note we routinely spray the property for bugs and insects, however if you do come across any little critters please keep in mind that Florida is a sub-tropical climate. To help prevent this, keep the doors closed.brbrbrbr-Propane tanks for the fire pit and grill will need to be replaced by guests at the moment they use it, if guests found it empty we will refund the refill of the tank, but guests need to take care of propane.brbrbrbr-Unfortunately we are experiencing a strange amount of seaweed at the shore by this time of the year, this is affecting all florida area!

Bed

Bath

Sleeps

$442.63

/ Nightly

Private Vacation Home

Bayside Retreat: Enjoy stunning open water views in this 3-bedroom home in Islamorada.

Islamorada, Florida, United States

Bayside Retreat - Completely renovated bayfront duplex home. This bayfront home consists of three bedrooms and three baths in Lower Matecumbe. With charming island decor and the open concept living room, kitchen and dining area, the home is light and airy. The screened balcony directly off the kitchen enables you to enjoy outdoor dining with beautiful bay views. The master en-suite with a king bed and bay views, and the guest room with two twin beds are located on the main level. The loft queen en-suite on the second level with sliding doors leading out to an open balcony offers open Gulf views to the west and ocean views on the east. This home offers both ocean views and bay views from the kitchen and living room. Dockage for smaller boats and skiffs up to 24' with easy bay access and ocean access through Channel 5 Bridge. Enjoy paddle boarding and kayaking right from the bayfront beach area. There are 2 paddle boards for your enjoyment at the property. Enjoy the refreshing bayside pool.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.

3

Bed

3

Bath

6

Sleeps

$272.14

/ Nightly

Private Vacation Home

Lovely 2-bedroom house in ocean front resort.

Islamorada, Florida, United States

This Islamorada house boasts 2 inviting bedrooms with 1 full bed and 1 king bed. The serene atmosphere and lovely decor make it a phenomenal retreat for guests. With amenities like a washing machine, hair dryer, WiFi, and AC, you'll feel right at home. The 2 bathrooms offer additional comforts like a bidet. Plus, there's an extra living space with a sofa bed for added convenience. It's easy to see why you'll be able to unwind at our place. While your experience will be private, you will have full access to all of the Sun Outdoors' resort amenities and activities. Including, 2 heated pool, clubhouse, game lawn, billiards, and much more! A social calendar for all guests is always available for those that wish to be more social!brA min of 28 nights is required for these homes.

2

Bed

2

Bath

6

Sleeps

$545.63

/ Nightly

Condo

Bay Harbour 209C ~ Chic 3 Bed / 2.5 Bath Condo with Ocean Views in Islamorada

Islamorada, Florida, United States

Welcome to Pressure Drop! brbrThis beautiful ocean-view condo features three bedrooms and two full bathrooms, making it an ideal choice for families or groups of friends. Modern amenities and coastal decor throughout create a cozy, welcoming environment for your stay. The spacious living room showcases stunning ocean views and opens to a large screened-in balcony, perfect for enjoying sunrises or feeling the salty breeze. The fully equipped kitchen includes additional features like an office nook and bar seating. The master bedroom offers a king-sized bed and a private bathroom complete with a walk-in shower, jetted tub, double vanity sinks, and a water closet. The second and third bedrooms are furnished with queen beds, sharing a full bathroom. Additional conveniences include a washer and dryer, central air conditioning, streaming TV’s, and high-speed internet throughout the condo.br brSituated in the desirable Bay Harbour community on Lower Matecumbe Key, this resort-style community offers amenities such as a pool, jacuzzi, fitness center, and tennis and pickleball courts. Anglers will appreciate boat slips that can be reserved for an additional fee (must be reserved in advance). With direct access to Florida Bay, you can easily venture out to Everglades National Park to fish for snook, redfish, bonefish, and permit, or take a short trip to the ocean for sailfish, mahi-mahi, snapper, wahoo, and more! The famous Islamorada sandbar is nearby, offering crystal-clear waters and a laid-back atmosphere. During spring and summer, try your luck at Channel 2 or Channel 5 bridge for the renowned “Silver Kings” (tarpon) for an exhilarating catch. While there is no trailer parking on-site, Seabird Marina offers options for trailer parking.br brAt the top of the neighborhood, you'll find a local seafood market with fresh lobster, fish, shrimp, and more. Just 1.5 miles south is Anne’s Beach, a hidden gem featuring a winding boardwalk through mangroves and sheltered picnic areas where you can enjoy lunch while taking in the ocean views. Anne’s Beach is also popular with windsurfers, and on breezy days, it’s entertaining to watch them glide across the water. The expansive shallow areas make wading and enjoying the warm, turquoise waters a delightful year-round activity.br brIslamorada, located in the heart of the Florida Keys, offers a prime vacation destination. Whether you enjoy deep-sea fishing, exploring backcountry shallows, diving or snorkeling vibrant reefs, sailing, kayaking, parasailing, or windsurfing, there’s something for everyone. Just five minutes north is the famous Robbies, where you can find fishing and snorkeling charters, a restaurant and bar, shops, and rentals for parasailing, kayaks, and paddleboards. You can even hand-feed the massive tarpon! Habanos is another local favorite, offering oceanfront dining and classic Cuban cuisine. Downtown Islamorada is only ten minutes north, featuring a variety of restaurants, breweries, shops, activities, and grocery stores. Key West is a scenic 1.5-hour drive to the south.brbrTake advantage of a local’s secret and park your vehicle and utilize the Islamorada Freebee; Our local rideshare service offering door-to-door transportation service to and from your favorite Islamorada destinations with environmentally friendly electric vehicles. It’s not only a fun alternative transportation option – it reduces traffic congestion, addresses drinking and driving, and reduces the Village’s carbon footprint. Two Tesla Model X vehicles can accommodate up to seven passengers and one larger vehicle that can accommodate a wheelchair and up to nine passengers. brbrHave any questions Feel free to ask away! Coastal Vacation Rentals of the Florida Keys is located in the heart of Islamorada and has a full office staff to ensure you have the best vacation possible.brbrReservation Deposit & Cancellations: A reservation deposit equal to one-half (50%) of the total reservation amount is due at the time of booking. TENANT shall be entitled to a refund of the one-half (50%) reservation deposit, less any non-refundable fees, if the reservation is cancelled at least 60 days prior to the occupancy date. The remaining balance, including any required security deposit, is due no later than 60 days prior to the occupancy date. If the cancellation occurs within 60 days of the occupancy date, the full reservation amount shall be non-refundable. If the booking is made less than 60 days prior to the occupancy date, the full reservation amount shall be due at the time of booking, and TENANT shall not be entitled to a refund of any amounts paid in the event of cancellation. As an exception to the foregoing, TENANT shall be entitled to a refund of all amounts paid if COASTAL re-rents the property for the same amount and for the full rental period. If the property is re-rented for fewer days or at a lower rate, COASTAL may deduct from the refund the difference between the total amount due under TENANT’s original reservation (including all taxes and fees) and the amount received from the subsequent rental. brbrInstant quote prices and calendar availability are subject to change without notice and are not guaranteed. Please contact Coastal Vacation Rentals of the Florida Keys to speak to one of our associates to confirm pricing and availability.brbrIslamorada Vacation Rental License: 26-5029

Bed

Bath

Sleeps

$1148.36

/ Nightly

Private Vacation Home

Book Now! Discounted Pricing Last Minute Availability

Islamorada, Florida, United States

Remarkable home nestled in the heart of Islamorada where you will find large outdoor spaces with outdoor dining and private lounge areas with private salt water pool and outdoor kitchen. Spacious interior with large open kitchen including convection oven, wine fridge and large island with seating area, living room with comfortable large sofa, smart TV and separate dining. Occupies 8. One Spacious bedroom with on suite and large shower downstairs and three upstairs. Master Bedroom upstairs boasts a large master bath spectacularly designed with large wet bath featuring a shower and floating bathtub for soaking in a spa like setting. Sleep in luxury with comfy linens and blackout curtains in all bedrooms all with smart TV’s, king size beds on 3 of them and 1 with 2 full size beds. Extensive upstairs terrace with access from the master bedroom and guest bedroom includes a sitting area to take in the wonderful night breezes and extraordinary sunset views. Quiet street and private beach next to the luxurious Cheeca Lodge. Walk to many restaurants and shops, close to water activities, marinas, Founders park, and wonderful cafes and shops. Supermarket nearby, golf cart rentals, bike rentals and kayaks. Show your reservation for free entry to Founders Park offering pickle ball, beach, kids playground and lots more. brbrOCEANSIDE IS A NEW DEVELOPED COMMUNITY AND THERE IS SOME TEMPORARY CONSTRUCTION ONGOING ON THE LAST TWO HOMES CLOSEST TO BEACH CONFINED TO SPECIFIC AREAS BUT THERE IS NO ACCESS TO BEACH/PIER CURRENTLY. DURING THIS TIME WE ARE OFFERING GUESTS PASSES TO THE ISLANDER RESORT STEPS FROM OUR PROPERTY. PLEASE INQUIRE WITH HOST. APOLOGIZE FOR THIS TEMPORARY INCONVENIENCE AND REST ASSURED IT WILL NOT AFFECT YOUR VACATION EXPERIENCE. brbrVisit Islamorada Chamber of Commerce website for calendar and list of local events.brhttps://islamoradachamber.com/brbrNotable residents of Islamorada:brInclude Miguel Cabrera, Gene Hackman, Jimmy Johnson, and Ted Williams. If you think the area looks familiar, you may recognize it from the Netflix TV Series BLOODLINE which was filmed in Islamorada.brbrIslamorada is known as the Sport-Fishing Capital of the World. And recently the island was named one of the 17 most romantic destinations in the U.S.brbrIf you are interested in golf carts this is their site islamoradaluxurycarts.com 305-394-5350 for rentals, let them know we sent you. There is also a Freebee transportation .You can download it in the App Store to get you around for free. brbrThere are also bike and kayak rentals nearby as well as fishing charters, boat tours, tiki tours, water sports, etc. All info is in the welcome binder in the house.

4

Bed

4

Bath

8

Sleeps

$340.88

/ Nightly

Apartment

Premium Units w/ Ocean Views & Balcony! Marina, 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 398 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Outdoor pool is available.brAdditional features:br • Heated poolbrbr✦ Free parking lot.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $29.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 dogs max w/ no breed restrictions. Tax inclusivebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Access To Private Boat Ramp will incur additional charge/nightbrbr✦ Front desk: 8 AM to 9 PM

1

Bed

1

Bath

4

Sleeps

$396.04

/ Nightly

Apartment

Spacious Villa! Private Beach Access, 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 355 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

4

Sleeps

$396.04

/ Nightly

Apartment

Sportfishing in Florida Keys! Large Unit w/ Private Beach Access! 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 355 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

4

Sleeps

$340.88

/ Nightly

Apartment

Spacious Unit w/ Kitchenette & Balcony! Marina, 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 398 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Outdoor pool is available.brAdditional features:br • Heated poolbrbr✦ Free parking lot.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $29.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 dogs max w/ no breed restrictions. Tax inclusivebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Access To Private Boat Ramp will incur additional charge/nightbrbr✦ Front desk: 8 AM to 9 PM

1

Bed

1

Bath

4

Sleeps

$2185.14

/ Nightly

Private Vacation Home

Islamorada Retreat / Waterfront, Pool & Boat Dock

Islamorada, Florida, United States

Wander Islamorada Retreat offers an exceptional collection of amenities designed for comfort, entertainment, and relaxation. Outside, guests can enjoy a stunning heated waterfront pool surrounded by a tropical lounge area and a tiki cabana for shaded relaxation. The property features a 35-foot-wide deep-water dock, perfect for accommodating larger boats—an especially valuable feature for Islamorada travelers looking to explore the Keys by water or enjoy world-class fishing and boating. Guests also have access to two paddleboards and two kayaks for on-the-water adventures, as well as ample parking with dedicated boat trailer space. Additional conveniences include laundry facilities, elegant indoor and outdoor dining areas, and thoughtfully designed spaces that blend island charm with elevated comfort.brbrSet in the heart of the Florida Keys, this area offers endless opportunities for relaxation and adventure. Spend your days snorkeling or diving in the crystal-clear waters of the nearby reefs, kayaking through mangrove tunnels, or embarking on a world-class fishing excursion in the sportfishing capital of the world. Explore the local marinas, art galleries, and boutiques that showcase the island’s creative spirit, or enjoy fresh seafood and tropical cocktails at vibrant waterfront restaurants. For a touch of nature, visit the nearby parks and beaches for paddleboarding, sunset walks, and dolphin spotting.brbrHOUSE RULESbrHosting parties and events is prohibited in this home.brbrPET POLICYbrOur pet fee is $350/stay charged at check-out. The fee goes to the cleaner for the extra work required after a pet stays. Pets are strictly prohibited in beds, indoor or outdoor furniture, or spa facilities. Pet owners will be responsible for damage and charged through their payment on file.

7

Bed

5

Bath

15

Sleeps

$1274.87

/ Nightly

Private Vacation Home

Stunning 5-bedroom Ocean's Edge home in Tavernier, perfect for up to 10 guests.

Islamorada, Florida, United States

Experience the ultimate coastal getaway at this spectacular 5 bedroom, 5.5 bathroom oceanfront home, complete with deep water dockage. This stunning retreat offers the perfect blend of elegance and entertainment, making it an ideal destination for families and friends. brbrStep inside to find an open concept living space bathed in natural light. The kitchen is a chef's dream, equipped with top-of-the-line appliances, a large island, and plenty of counter space. The spacious dining area and cozy living room provide the perfect settings for gatherings and relaxation. Relax and watch the ocean's movements from the comfort of your couch, with expansive windows leading to a balcony right off the living room. brbrEach of the five bedrooms is a private sanctuary, offering luxurious bedding, and stunning views. The master suite is a true retreat, with a private balcony, a spa-like bathroom, and a walk-in closet. brbrThe expansive outdoor area is designed for leisure and fun. Lounge by the pool, take a dip in the hot tub, or enjoy a morning cup of coffee while enjoying the sunrise and ocean breeze. The deep water dockage invites you to explore the sea, and the rooftop putting green offers a unique spot for entertainment.brbrThis oceanfront luxury home promises an unforgettable vacation experience, combining top-tier amenities with the natural beauty of the coast. Whether you're seeking adventure or relaxation, this stunning retreat provides everything you need for a perfect getaway. Book now and start creating lasting memories in this idyllic paradise!

Bed

Bath

Sleeps

$266.7

/ Nightly

Private Vacation Home

Best Location in Islamorada!! Beach access - Boat trailer parking!

Islamorada, Florida, United States

Gorgeous and highly appointed luxury Island villa with beach access. You are right in the middle of it all with this perfect location. Walk or bike to some of the best restaurants and shopping Islamorada has to offer.

Bed

Bath

Sleeps

$357.53

/ Nightly

Condo

Ocean & Bay Views. Welcome To Paradise!

Islamorada, Florida, United States

Sleeps 4, 1 Bedroom - King Bed, 2 Full Bathrooms, Queen Sleeper Sofa, 2 TVs, Balcony, fully stocked kitchen, towels & linens provided, coin laundry available, elevators. Newly remodeled unit. Assigned, Covered Parking. Gated Community. Men’s & Women’s Fitness Centers, Club House, Pool & Jacuzzi, Ocean Front, Boat Ramp, Steps in to ocean. Great for Paddleboard & Kayaking. Walking distance to several restaurants. Minutes from several marinas. Best scuba diving & deep sea fishing in Keys!brbrKayak available to our guests. brbrMarina located just next door.

1

Bed

1

Bath

2

Sleeps

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