Islamorada, FL Short term rentals

1222 available short term rental offers

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Islamorada, FL short term rentals
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Best Short term and Weekly rentals in Islamorada, FL

Discover Short-Term Rentals by the Sea in Islamorada, FL

Plan a relaxing maritime getaway at coastal short-term rentals in Islamorada, FL, situated short distances from local shoreside communities.

Florida Keys Tour! Private Beach Access W/ Marina! Pets Allowed, Free Breakfast - Islamorada, FL
No reviews

Florida Keys Tour! Private Beach Access W/ Marina! Pets Allowed, Free Breakfast

apartment, Islamorada, Village of Islands
This one-bedroom, one-bathroom apartment in Islamorada's downtown district offers direct ocean access and is located a 3-minute walk to Windley Key Fossil Reef Geological State Park and a 9-minute walk to Hog Heaven.
This pet-friendly condo accommodates up to two guests and features air conditioning, Wi-Fi, a swimming pool, and on-site parking for your convenience.

Check Out 5-Star Lodgings in Islamorada, FL

Experience the height of comfort in Islamorada, FL with high-end properties designed to be memorable.

Oceanfront King Suite Beach Walkout Room - Islamorada, FL
8.9 95 reviews

Oceanfront King Suite Beach Walkout Room

B&B, Islamorada, Village of Islands
The Drop Anchor Resort & Marina is located in Islamorada, Florida, directly on the oceanfront with beach walkout access, making it a perfect choice for travelers looking to experience the beauty of the Florida Keys. The resort has received high ratings for its location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay.
The King Suite at The Drop Anchor Resort & Marina comfortably accommodates up to four guests, making it ideal for families or groups of friends. The suite features a king-size bed, a sofa bed, a kitchen with a fridge and microwave, air conditioning, a swimming pool, parking, and internet access, offering everything needed for a relaxing and enjoyable vacation.

Frequently Asked Questions about short term rentals in Islamorada, FL

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Search Family Short-Term Rentals in Islamorada, FL

Family beach days in Islamorada, FL are easier when your rental offers enough square footage for everyone to relax.

Florida Keys Condo With Pool, Beach Access, Marina, Pickleball & More - Islamorada, FL
9.6 21 reviews

Florida Keys Condo With Pool, Beach Access, Marina, Pickleball & More

apartment, Tavernier
This Tavernier condo, situated between Islamorada and Key Largo, offers a 5-minute walk to the beach, nearby kayak/paddleboard rentals, and proximity to John Pennekamp Coral Reef State Park and the History of Diving Museum.
The two-bedroom, two-bathroom unit sleeps six, features two balconies with ocean views, a full kitchen, a swimming pool, jacuzzi, and includes access to tennis and pickleball courts, a playground, and grills.
Bayview Isle Place - Islamorada, FL
10 1 review

Bayview Isle Place

apartment, Islamorada, Village of Islands
This Islamorada vacation rental is located near Snake Creek, about one mile north of Founders Park, offering easy access to its beach, pool, marina, and picnic areas.
The 4-bedroom, 3-bathroom home features a refreshing pool, wrap-around porch, and endless Snake Creek views, comfortably accommodating up to six guests and providing proximity to Islamorada's dining and attractions like the Theater of the Sea and the Diving Museum.
500 Burton Drive Tavernier, Key Largo - Islamorada, FL
9.9 225 reviews

500 Burton Drive Tavernier, Key Largo

apartment, Tavernier
This Tavernier apartment is located on the Atlantic Ocean, between Key Largo and Islamorada, offering a peaceful setting surrounded by protected mangroves. The rental has consistently received excellent ratings for location, cleanliness, and overall user experience.
The 850 square foot suite has two bedrooms, two bathrooms, and can comfortably sleep six guests. The property offers a range of amenities including a pool, beach access, a bar, a sauna, and a full kitchen, providing everything you need for a relaxing and enjoyable stay.
Paradise Found! - Islamorada, FL
9.2 5 reviews

Paradise Found!

apartment, Islamorada, Village of Islands
This family-friendly villa in Islamorada, Village of Islands, is conveniently located less than two hours from Fort Lauderdale and Miami, offering easy access to dining, groceries, and local attractions.
This 4-bedroom, 3-bathroom villa accommodates up to 8 guests and features a private pool, backyard tiki bar, fire pit, game room with a pool table, and a brand new dock with a boat lift and fish cleaning station, ideal for anglers.

Top Dog-Friendly Lodgings in Islamorada, FL

Traveling with a dog is simpler in these Islamorada, FL rentals, which feature proximity to pet-friendly shores.

Snowbird Deal: Tavernier Canal Home W/ Dock  28+ Day Keys Getaway! - Islamorada, FL
No reviews

Snowbird Deal: Tavernier Canal Home W/ Dock 28+ Day Keys Getaway!

apartment, Islamorada, Village of Islands
This Plantation Key Colony vacation home in Islamorada, Florida Keys, is conveniently located within two miles of the Florida Keys Dive Center, Old Road Gallery, and Mariners Hospital, and six miles from Islamorada County Park and Rain Barrel Village.
This two-bedroom, two-bathroom house sleeps six and offers a fully equipped kitchen, in-house laundry, a Jacuzzi, terrace, and outdoor barbecue grills; nearby attractions include diving, art galleries, and parks.

Best Islamorada, FL lodging with a balcony

Breathtaking Oceanfront Escapeendless Views +Pool - Islamorada, FL
9.8 137 reviews

Breathtaking Oceanfront Escapeendless Views +Pool

apartment, Tavernier
Second Floor Den Suite  Sunny Islamorada Escape, Pool, Beach, Marina, Sleeps 6 - Islamorada, FL
No reviews

Second Floor Den Suite Sunny Islamorada Escape, Pool, Beach, Marina, Sleeps 6

apartment, Islamorada, Village of Islands
93 M² Condo ∙ 2 Bedrooms ∙ 4 Guests - Islamorada, FL
9.0 6 reviews

93 M² Condo ∙ 2 Bedrooms ∙ 4 Guests

apartment, Islamorada, Village of Islands
Nauti Hideaway Ocean Pointe 2314 - Islamorada, FL
10 3 reviews

Nauti Hideaway Ocean Pointe 2314

apartment, Tavernier

Best Islamorada, FL lodging with a kitchen

Aquamarine Oceanview+special Rates+ Dock+pool+gym+spa+1535 Star Reviews!!! - Islamorada, FL
10 159 reviews

Aquamarine Oceanview+special Rates+ Dock+pool+gym+spa+1535 Star Reviews!!!

apartment, Islamorada, Village of Islands
Bright & Sunny Suite W/ Magnificent Ocean Views - Islamorada, FL
9.8 103 reviews

Bright & Sunny Suite W/ Magnificent Ocean Views

apartment, Tavernier
Deluxe Oceanfront 1/1 Sleeps 4. Cafe & Pool Bar. - Islamorada, FL
9.7 131 reviews

Deluxe Oceanfront 1/1 Sleeps 4. Cafe & Pool Bar.

apartment, Tavernier
Drop Anchor Resort & Marina - Islamorada, FL
8.6 1687 reviews

Drop Anchor Resort & Marina

glamping, Islamorada, Village of Islands

Best Islamorada, FL lodging with laundry available

Boho Chic Ocean Pointe 3214 - Islamorada, FL
9.4 7 reviews

Boho Chic Ocean Pointe 3214

apartment, Tavernier
Tropical Getaway W/private Beach 1 Bd Condo - Islamorada, FL
8.0 12 reviews

Tropical Getaway W/private Beach 1 Bd Condo

apartment, Tavernier
Couples' Retreat 1br W/ Ocean View & Balcony - Islamorada, FL
No reviews

Couples' Retreat 1br W/ Ocean View & Balcony

apartment, Tavernier
Castaway Key - Oceanfront Condo With Double Balconies & Marina Access - Islamorada, FL
10 144 reviews

Castaway Key - Oceanfront Condo With Double Balconies & Marina Access

apartment, Tavernier
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