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.

Private 3-bedroom Brand New Apartment In Tavernier, Key Largo - Islamorada, FL
9.8 6 reviews

Private 3-bedroom Brand New Apartment In Tavernier, Key Largo

apartment, Tavernier
This apartment in Tavernier is located a short distance from Hurricane Monument and Indian Key Historic State Park, and close to John Pennekamp Coral Reef State Park.
This 900 sq ft rental offers 3 bedrooms, 2 bathrooms, and accommodates up to 6 guests with a fully equipped kitchen, air conditioning, WiFi, and parking.

Check Out 5-Star Lodgings in Islamorada, FL

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

Book Your Dream Vacation At  Beacon Reef - Special Summer Deal - Islamorada, FL
9.4 9 reviews

Book Your Dream Vacation At Beacon Reef - Special Summer Deal

apartment, Islamorada, Village of Islands
This beachfront condo is located in Matecumbe, just a short distance from the History of Diving Museum, Windley Key Fossil Reef Geological State Park, and Matecumbe United Methodist Church. It boasts excellent user ratings, making it a popular choice for travelers. This two-bedroom, two-bathroom apartment spans 1000 square feet and can comfortably accommodate up to four guests. You'll enjoy access to a range of amenities, including a swimming pool, jacuzzi, fitness center, and a fully equipped kitchen.

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.

Two Panoramic Ocean Views From The Living Room And Master Bedroom In This Condo - Islamorada, FL
9.8 247 reviews

Two Panoramic Ocean Views From The Living Room And Master Bedroom In This Condo

apartment, Tavernier
This Tavernier condo is conveniently located just a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to nearby attractions and a relaxing beachfront setting. It has received excellent user ratings, making it a popular choice for travelers.
This two-bedroom, two-bathroom rental comfortably accommodates up to six guests. It features a fully equipped kitchen, a private balcony, a swimming pool, a jacuzzi, and a tennis court, ensuring a comfortable and enjoyable stay.
Flakey's - Islamorada, FL
9.9 217 reviews

Flakey's

apartment, Islamorada, Village of Islands
This Islamorada rental is located on Morada Way in the Art and Culture district, just a short walk from the World Wide Sportsman Marina and directly across the street from Morada Bay. The accommodation has excellent user, location, and cleanliness ratings.
The two-bedroom, one-bathroom rental can accommodate up to six guests. The rental features a fully equipped kitchen, two balconies, fast WiFi, Xfinity cable, and a backyard garden that hosts live music and art classes.
Light, Bright & Nautical Condo At Ocean Pointe - Islamorada, FL
9.9 178 reviews

Light, Bright & Nautical Condo At Ocean Pointe

apartment, Tavernier
This waterfront condo in Tavernier is located just a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the beautiful Florida Keys. This rental has earned excellent ratings for its cleanliness, location, and overall user experience.
The 950-square-foot apartment comfortably sleeps four guests in its two bedrooms and two bathrooms. Enjoy swimming, relaxing in the Jacuzzi, grilling outdoors, and taking advantage of the tennis court, all while taking in the stunning waterfront views from your private balcony.
Enjoy Happy Tarpon:  Boat Dock - Private Pool - Islamorada Sunsets & Family Fun! - Islamorada, FL
10 64 reviews

Enjoy Happy Tarpon: Boat Dock - Private Pool - Islamorada Sunsets & Family Fun!

apartment, Islamorada, Village of Islands
This Islamorada vacation home is located in Matecumbe, a half-block from the Lorelei Restaurant and Marina, offering easy access to other restaurants and shops.
The 2400-square-foot house features three bedrooms, four bathrooms, a private heated pool, a deep-water boat dock accommodating boats up to 28 feet, and sleeps up to six guests, perfect for families or groups enjoying Islamorada's fishing and watersports.

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.

Anglers Reef Is Oceanfront, Blue Marlin House2/2.5 - Islamorada, FL
9.7 42 reviews

Anglers Reef Is Oceanfront, Blue Marlin House2/2.5

apartment, Islamorada, Village of Islands
The Blue Marlin house, a two-bedroom, two-bathroom vacation rental in Islamorada's exclusive Anglers Reef neighborhood, is located approximately 100 feet from an oceanfront community pool.
This Key West-style home sleeps six, boasts a full kitchen with dishwasher, offers complimentary paddleboards, kayaks, and bicycles, and is near Islamorada's attractions and restaurants.

Best Islamorada, FL lodging with a balcony

Closest Oceanfront Home - 3 Stories, Views & Dock - Paradise Palms - Islamorada, FL
10 13 reviews

Closest Oceanfront Home - 3 Stories, Views & Dock - Paradise Palms

apartment, Islamorada, Village of Islands
Key Largo-islamorada Area-1 Br, 1 Bath -Privately Owned Condo -Fab Reviews! - Islamorada, FL
10 199 reviews

Key Largo-islamorada Area-1 Br, 1 Bath -Privately Owned Condo -Fab Reviews!

apartment, Tavernier
Spacious Unit W/ Kitchenette & Balcony! Marina, Pets Allowed, Free Breakfast - Islamorada, FL
No reviews

Spacious Unit W/ Kitchenette & Balcony! Marina, Pets Allowed, Free Breakfast

apartment, Islamorada, Village of Islands
Vacation At Its Finest! 2 Convenient Units, Free Parking, Breakfast, Onsite Pool - Islamorada, FL
No reviews

Vacation At Its Finest! 2 Convenient Units, Free Parking, Breakfast, Onsite Pool

apartment, Islamorada, Village of Islands

Best Islamorada, FL lodging with a kitchen

Friends' Getaway 2br W/ Ocean View, Pool & Beach - Islamorada, FL
No reviews

Friends' Getaway 2br W/ Ocean View, Pool & Beach

apartment, Tavernier
Tropical Escape | Sea Gulls 407 ~ Weekly Rental - Islamorada, FL
9.6 52 reviews

Tropical Escape | Sea Gulls 407 ~ Weekly Rental

apartment, Islamorada, Village of Islands
Family-friendly Vacay! Spacious Unit, Outdoor Pool, Steps From The Beach! - Islamorada, FL
9.4 3 reviews

Family-friendly Vacay! Spacious Unit, Outdoor Pool, Steps From The Beach!

apartment, Tavernier
Oceanside  Anglers Reef Home- Gated Community- Pool, Dock, Private Beach - Islamorada, FL
10 193 reviews

Oceanside Anglers Reef Home- Gated Community- Pool, Dock, Private Beach

apartment, Islamorada, Village of Islands

Best Islamorada, FL lodging with laundry available

Spectacular 2 Bedroom With A Beautiful Ocean View. - Islamorada, FL
9.8 295 reviews

Spectacular 2 Bedroom With A Beautiful Ocean View.

apartment, Tavernier
1br Condo W/ Pool, Beach, Near Pennekamp Park - Islamorada, FL
8.0 1 review

1br Condo W/ Pool, Beach, Near Pennekamp Park

apartment, Tavernier
Oceanfront Estate - Private Beach, Pool, & Dock - Islamorada, FL
10 4 reviews

Oceanfront Estate - Private Beach, Pool, & Dock

apartment, Islamorada, Village of Islands
Off The Charts-waterfront Tiki Bar & Private Dock - Islamorada, FL
10 14 reviews

Off The Charts-waterfront Tiki Bar & Private Dock

apartment, Islamorada, Village of Islands
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