Vacation Rentals By Owner In Islamorada, FL

$927.0

Island Oasis Stay | 1 King Bed | Near Islamorada Beaches

Islamorada, Florida, United States

Set along the scenic Overseas Highway in Islamorada, this oceanside resort offers easy access to Florida Keys attractions like local beaches and marine parks. Guests can enjoy waterfront views and a tranquil setting ideal for exploring the natural beauty of the area.brbrThis listing is for a room within a hotel.brbr✦ Your room is 370 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 shared pool available all year, opened from 10:00AM to 10:00PM.brbr✦ 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 $150 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). Max 2 pets/room; pet form due at check-inbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

1

Bed

1

Bath

4

Sleeps

$587.23

/ Nightly

Hotel

Oceanfront Islamorada Stay | 3 mi to Keys Brewing | Brewery Tour Nearby

Islamorada, Florida, United States

Located on the scenic Overseas Highway in Islamorada, this oceanside resort offers direct access to the Florida Keys' stunning beaches and waters. Enjoy proximity to local dining and water-based activities, making it an ideal choice for exploring the area's natural beauty and marine attractions.brbrThis listing is for a room within a hotel.brbr✦ Your room is 370 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 shared pool available all year, opened from 10:00AM to 10:00PM.brbr✦ 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 $150 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). Max 2 pets/room; pet form due at check-inbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

1

Bed

1

Bath

4

Sleeps

$1905.76

/ Nightly

Hotel

Islander Resort Oceanside | 4 Units | 5 mi to Windley Reef

Islamorada, Florida, United States

Located on the scenic Overseas Highway in Islamorada, this resort offers direct ocean access and close proximity to popular spots like the Florida Keys National Marine Sanctuary. Guests can enjoy on-site dining and water activities, making it an ideal destination for those seeking a vibrant coastal experience.brbrThis listing is for 4 separate rooms within a hotel. The price shown in the listing covers all 4 rooms.brbr✦ Each room is 370 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.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 shared pool available all year, opened from 10:00AM to 10:00PM.brbr✦ 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 $600 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). Max 2 pets/room; pet form due at check-inbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

4

Bed

4

Bath

16

Sleeps

$1219.55

/ Nightly

Hotel

Coastalstay w/ Gym Onsite | 5 mi to Annes Beach | Sunset Swimming

Islamorada, Florida, United States

Located on Overseas Highway in Islamorada, this oceanside resort offers easy access to Florida Keys attractions and water activities. Guests can enjoy serene ocean views and a convenient location near local dining and entertainment options.brbrThis listing is for a room within a hotel.brbr✦ Your room is 370 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 shared pool available all year, opened from 10:00AM to 10:00PM.brbr✦ 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 $150 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). Max 2 pets/room; pet form due at check-inbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

1

Bed

1

Bath

2

Sleeps

$1654.91

/ Nightly

Hotel

Islandstay Kitchen Pool Gym | 5 mi to Windley Reef | Hiking & Kayak Fun

Islamorada, Florida, United States

Set along the scenic Overseas Highway in Islamorada, this oceanside resort offers direct access to beautiful beaches and water activities. Enjoy proximity to local dining and attractions in the Florida Keys, making it an ideal spot for a memorable coastal getaway.brbrThis listing is for a room within a hotel.brbr✦ Your room is 760 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 shared pool available all year, opened from 10:00AM to 10:00PM.brbr✦ 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 $150 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). Max 2 pets/room; pet form due at check-inbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

1

Bed

1

Bath

2

Sleeps

$1429.88

/ Nightly

Hotel

Seaview Kitchen Pool Gym | 4 mi to Theater Sea | Swim with Dolphins

Islamorada, Florida, United States

Situated on the scenic Overseas Highway in Islamorada, this resort offers direct access to beautiful ocean views and water activities. Guests can enjoy a range of on-site amenities while being close to popular Florida Keys attractions like the Theater of the Sea and local dining spots.brbrThis listing is for a room within a hotel.brbr✦ Your room is 760 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 shared pool available all year, opened from 10:00AM to 10:00PM.brbr✦ 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 $150 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). Max 2 pets/room; pet form due at check-inbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

1

Bed

1

Bath

2

Sleeps

$914.58

/ Nightly

Hotel

Bayview Pool Gym | 6 mi to Robbies | Fish Feeding & Boating

Islamorada, Florida, United States

Set along the scenic Overseas Highway in Islamorada, this oceanside resort offers easy access to beautiful beaches and local attractions like the Theater of the Sea. Enjoy a tranquil stay with stunning ocean views, perfect for exploring the Florida Keys.brbrThis listing is for a room within a hotel.brbr✦ Your room is 760 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 shared pool available all year, opened from 10:00AM to 10:00PM.brbr✦ 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 $150 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). Max 2 pets/room; pet form due at check-inbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

1

Bed

1

Bath

2

Sleeps

$2752.85

/ Nightly

Hotel

Tropic Kitchen Pool Gym | 3 mi to Keys Brewing | Brewery Tour Nearby

Islamorada, Florida, United States

Experience oceanfront tranquility at this resort located on Overseas Highway in Islamorada. Enjoy easy access to nearby beaches and local dining, making it an ideal base for exploring the Florida Keys.brbrThis listing is for a room within a hotel.brbr✦ Your room is 1070 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 shared pool available all year, opened from 10:00AM to 10:00PM.brbr✦ 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 $150 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). Max 2 pets/room; pet form due at check-inbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

2

Bed

2

Bath

6

Sleeps

$1051.9

/ Nightly

Hotel

Oceanstay w/ Pool Access | 2 mi to Founders Pk | Bike & Picnic Outdoors

Islamorada, Florida, United States

Situated along the scenic Overseas Highway in Islamorada, this resort offers easy access to local beaches and marine attractions. Enjoy the tranquil ocean views and proximity to popular fishing spots, making it ideal for a seaside escape.brbrThis listing is for a room within a hotel.brbr✦ Your room is 400 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 shared pool available all year, opened from 10:00AM to 10:00PM.brbr✦ 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 $150 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). Max 2 pets/room; pet form due at check-inbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

1

Bed

1

Bath

4

Sleeps

$958.54

/ Nightly

Hotel

Reefview w/ Onsite Gym | 7 mi to San Pedro Pk | Dive & Explore Waters

Islamorada, Florida, United States

Set along the scenic Overseas Highway in Islamorada, this oceanside resort offers easy access to local beaches and water activities. Guests can enjoy spacious accommodations and a tranquil environment perfect for exploring the Florida Keys.brbrThis listing is for a room within a hotel.brbr✦ Your room is 400 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 shared pool available all year, opened from 10:00AM to 10:00PM.brbr✦ 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 $150 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). Max 2 pets/room; pet form due at check-inbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

1

Bed

1

Bath

4

Sleeps

$1056.32

/ Nightly

Hotel

Sunrise Stay | 6 mi to Hurricane Mon | Scenic Walks & Tours

Islamorada, Florida, United States

Set along the stunning Overseas Highway in Islamorada, this oceanside resort offers easy access to local beaches and marine activities. Enjoy waterfront views and a prime location perfect for exploring the Florida Keys’ natural beauty and vibrant fishing spots.brbrThis listing is for a room within a hotel.brbr✦ Your room is 760 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 shared pool available all year, opened from 10:00AM to 10:00PM.brbr✦ 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 $150 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). Max 2 pets/room; pet form due at check-inbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

1

Bed

1

Bath

2

Sleeps

$1191.33

/ Nightly

Hotel

Coastal Kitchen Pool Gym | 5 mi to Annes Beach | Swim & Relax on Shore

Islamorada, Florida, United States

Experience beachfront tranquility at this oceanside resort in Islamorada, offering easy access to local dining and watersports. Steps from the Atlantic Ocean, it’s an ideal base for exploring the Florida Keys’ vibrant marine life and scenic attractions.brbrThis listing is for a room within a hotel.brbr✦ Your room is 1070 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 shared pool available all year, opened from 10:00AM to 10:00PM.brbr✦ 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 $150 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). Max 2 pets/room; pet form due at check-inbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

1

Bed

1

Bath

4

Sleeps

$277.18

/ Nightly

Private Vacation Home

Relax in this oceanside, pet-friendly 2BR home! Min 28-Day Reservation Required

Islamorada, Florida, United States

This home has amazing views of the Atlantic and has two bedrooms and two baths. The vibe is tasteful and relaxing - just bring your suitcase. brbrWhile here, you will have full access to all of the Sun Outdoors Islamorada resort amenities and activities. Including a heated, waterfront, resort-style pool, clubhouse, outdoor game lawn, billiards, and oceanfront tanning chairs and boardwalk. A social calendar for all guests is always available for those who wish to be more social, while fine dining is only a minute's drive in Islamorada.brbrMinimum stay: 28 nights. Boat slips may be booked for an additional fee. Disclaimer: Photos represent the general style and quality of our homes. Each unit is individually owned and decorated, so furnishings and décor may vary slightly. All meet resort standards for comfort and cleanliness.

Bed

Bath

Sleeps

$476.54

/ Nightly

Condo

3 Bedroom Islamorada Condo w/ 30' Boat Slip & Ocean Views!

Islamorada, Florida, United States

Welcome to Mother Ocean! brbrThis stunning ocean view condo boasts three bedrooms and two full bathrooms, making it perfect for a family or group of friends. It features modern amenities and coastal decor throughout, providing a comfortable and inviting atmosphere for your stay. The spacious living room offers captivating views of the ocean, and opens up to a large screened-in balcony where you can enjoy watching the morning sunrise or spot manatees in the afternoon. The fully equipped kitchen comes with a few extra features such as a coffee bar, air fryer oven and bar seating. The master bedroom has a king-sized bed and its own private bathroom that boasts a walk-in shower, jetted tub, double vanity sinks and a water closet. The second and third bedrooms offer queen and full-sized beds and share a full bathroom. Other amenities include a washer and dryer, central air conditioning, cable TV, and high-speed internet throughout. brbrThe condo is located in the sought after Bay Harbour community on Lower Matecumbe Key. This resort style community offers a pool, hot tub, fitness center and tennis and pickleball courts. If you're an angler, you'll appreciate the 30’ deep water dock with water, electricity, fish cleaning stations, and a locked storage closet for your gear. You can rent a boat, kayaks, or paddleboards, and they can be delivered directly to your own dock. With direct access to the Florida Bay, you can head straight out to the Everglades National Park and fish the flats for snook, redfish, bonefish and permit. Or, take a quick ride to the oceanside for sailfish, mahi-mahi, snapper, wahoo and more! With close proximity to the famous Islamorada sandbar, you can experience the unforgettable crystal clear waters and relaxed atmosphere. During spring and summer, fish Channel 2 or Channel 5 bridge for the world famous “Silver Kings” (tarpon) for a fierce fight. Dockage must be reserved prior to arrival and is included in the rate. There is no trailer parking on-site, but you can try Seabird Marina for trailer parking options.brbrAt the top of the neighborhood is a local seafood market with fresh local lobster, fish, shrimp and more. 1.5 miles south you will find Anne’s Beach; A hidden gem featuring a winding boardwalk that meanders through the mangroves and sheltered picnic areas where you can have lunch while watching the ocean! Anne’s Beach is also a popular place with windsurfers, and if it’s a breezy day, it’s fun to watch them swoop and soar. Because of the expansive area of shallows in the area, the best activity is to wade and enjoy the year round warm turquoise waters.brbrIslamorada is located in the heart of the Florida Keys, offering a prime location for your vacation. Whether you prefer deep-sea fishing, exploring the backcountry shallows, diving or snorkeling the vibrant reefs, sailing, kayaking, parasailing, or windsurfing, there's something for everyone to enjoy. Just 5 minutes north is the world famous Robbies, which offers fishing and snorkel charters, a restaurant and bar, shops, parasailing, kayaks and paddle board rentals. You can even hand feed the enormous tarpon! Habanos is another local favorite, where you can experience oceanfront dining and classic Cuban cuisine. Downtown Islamorada is only 10 minutes north and offers endless restaurants, breweries, shopping, activities and grocery stores. Key West is a beautiful 1.5 hour drive 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. brbrThis could be just the getaway you need, for more information contact us at (305) 664-0077.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 #: 26-0098

Bed

Bath

Sleeps

$372.19

/ Nightly

Private Vacation Home

Discover comfort at 139 Venetian Way, a spacious 4BR getaway in Islamorada.

Islamorada, Florida, United States

Enjoy this quiet, peaceful retreat in the desirable Venetian Shores neighborhood of Islamorada. Located on a quiet plugged canal, this spacious home offers a relaxing setting perfect for unwinding and enjoying the Florida Keys lifestyle.brbrThe home features 4 bedrooms and 3 bathrooms, providing plenty of space for families or groups to spread out comfortably. Outside, you'll find a heated pool and generous outdoor space ideal for relaxing in the sun, dining outside, or enjoying the warm island breeze.brbrWith its peaceful location and roomy layout, this Venetian Shores home is the perfect place to relax and enjoy your time in the Keys.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.

4

Bed

3

Bath

8

Sleeps

$444.89

/ Nightly

Private Vacation Home

Surf Shack | Islamorada Beach Bungalow

Islamorada, Florida, United States

Welcome to Surf Shack, your laid-back beach bungalow escape in the heart of Islamorada. Tucked along a quiet street in downtown, this cozy retreat blends classic Florida Keys charm with everything you need for an unforgettable stay—just steps from a beautiful white sandy beach reserved exclusively for residents.brInside, Surf Shack offers two comfortable bedrooms and two full baths. The vibe is relaxed and inviting, with coastal touches that make it feel like your own private island hideaway. After a day in the sun, rinse off in the outdoor shower, then unwind with dinner in the outdoor dining area as the warm Keys air settles in.brFor water lovers, this location is hard to beat. Launch your boat right from the neighborhood ramp, with dockage and trailer storage available for your convenience. Spend your days kite surfing just off the beach, experiencing world class offshore fishing and back country fly fishing, wreck diving, snorkeling vibrant reefs, kayaking through mangroves, or heading out to the famous Islamorada sandbar for a day of fun on the water. Eco tours and endless adventures are all within easy reach.brWhen you’re ready to explore on land, you’re within walking distance of some of Islamorada’s best restaurants, local shops, and island hotspots—no long drives required.brTo make your stay even more seamless, concierge services are available to help arrange excursions, dining, charters, and more.brWhether you’re here for adventure, relaxation, or a bit of both, Surf Shack is your perfect home base for experiencing the magic of the Florida Keys.brThis home is managed by Florida Keys Signature Stays. Note that a 3% non-refundable convenience fee will be applied to all reservations paid by credit card, while check and eCheck payments are exempt from this fee.

Bed

Bath

Sleeps

$292.88

/ Nightly

Condo

Eclectic Easeful Stay At The Keys!

Islamorada, Florida, United States

Come and enjoy this spacious, airy, and recently renovated condo at Summer Sea in beautiful Tavernier, Florida. The building boasts amazing amenities like an olympic-sized, heated pool, gym, game room, party room, and a gorgeous bay-front marina. This location is the best the Florida Keys has to offer, such as award winning restaurants and world class fishing. Come and enjoy a true piece of paradise.

3

Bed

1

Bath

6

Sleeps

$1120.48

/ Nightly

Hotel

Sunset Stay | 3 mi to Diving Museum | Explore Marine Life

Islamorada, Florida, United States

Set along the scenic Overseas Highway in Islamorada, this resort offers direct access to beautiful ocean views and water activities. Enjoy a tranquil stay near popular spots like the Theater of the Sea and local dining options, making it ideal for those looking to explore the Florida Keys.brbrThis listing is for a room within a hotel.brbr✦ Your room is 370 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 shared pool available all year, opened from 10:00AM to 10:00PM.brbr✦ 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 $150 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). Max 2 pets/room; pet form due at check-inbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

1

Bed

1

Bath

2

Sleeps

$925.9

/ Nightly

Hotel

Ocean Escape | 2 mi to Founders Pk | Bike Coastal Paths

Islamorada, Florida, United States

Located on the scenic Overseas Highway in Islamorada, this resort offers easy access to the area's beautiful beaches and popular fishing spots. Guests can enjoy a waterfront setting perfect for exploring the Florida Keys' natural attractions and vibrant local culture.brbrThis listing is for a room within a hotel.brbr✦ Your room is 370 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 shared pool available all year, opened from 10:00AM to 10:00PM.brbr✦ 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 $150 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). Max 2 pets/room; pet form due at check-inbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

1

Bed

1

Bath

2

Sleeps

$1086.75

/ Nightly

Hotel

Islander Resort Stay | 7 mi to San Pedro Pk | Dive & Explore Waters

Islamorada, Florida, United States

Set along the scenic Overseas Highway in Islamorada, this resort offers a tranquil oceanfront retreat with direct beach access. Enjoy nearby attractions like the Florida Keys Wild Bird Rehabilitation Center and local dining, making it an ideal spot for nature lovers and those seeking waterfront activities.brbrThis listing is for a room within a hotel.brbr✦ Your room is 370 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 shared pool available all year, opened from 10:00AM to 10:00PM.brbr✦ 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 $150 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). Max 2 pets/room; pet form due at check-inbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

1

Bed

1

Bath

4

Sleeps

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