
Islamorada long stay rentals
Stay a week, a month or longer in a comfortable place all your own
Relax—Vrbo takes the hassle out of booking monthly rentals in Islamorada. The wide selection available and useful search filters make finding your home away from home a breeze. Whether you're looking for fast Wi-Fi for remote working, a fully equipped kitchen for home cooking, or a pool where you can relax with a good book, you're sure to find it on Vrbo. Many long-term rentals in Islamorada are great for kids and welcome four-legged friends, too. What's more, some offer monthly discounts on extended-stay homes and weekly discounts on shorter-term rentals.
Featured long stay living spaces - Islamorada
Showing deals for:Sep 14 - Oct 12
Image gallery for Islamorada Oasis, Luxurious 4 bedroom 3 bath home. Heated pool! Boat Lift option

Islamorada Oasis, Luxurious 4 bedroom 3 bath home. Heated pool! Boat Lift option
Tavernier
Image gallery for Venetian Shores Escape! Heated Pool, 3BR, 70ft Dock, Dog-Friendly!

Venetian Shores Escape! Heated Pool, 3BR, 70ft Dock, Dog-Friendly!
Islamorada
Image gallery for Charming bungalow in Tavernier perfect for a relaxing getaway

Charming bungalow in Tavernier perfect for a relaxing getaway
Tavernier
Image gallery for Beautiful Bayfront Home with Amazing Sunsets

Beautiful Bayfront Home with Amazing Sunsets
Islamorada
Image gallery for ISLAMORADA BEACH HOUSE

ISLAMORADA BEACH HOUSE
Islamorada
Image gallery for 3/3 directly on Ocean.Pickle ball,BBQ,Beach,pools,marina. Choose summer dates.

3/3 directly on Ocean.Pickle ball,BBQ,Beach,pools,marina. Choose summer dates.
Key Largo
Image gallery for Island pool home awaits in Islamorada's Port Antigua

Island pool home awaits in Islamorada's Port Antigua
Islamorada
Image gallery for Amazing Sandy Beach Sunsets + New Pool + Best Location w/ Park - Bikes & Kayaks

Amazing Sandy Beach Sunsets + New Pool + Best Location w/ Park - Bikes & Kayaks
Islamorada
Image gallery for Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views
Islamorada
Image gallery for Breathtaking Ocean views! Owners who care. “Sangria Sunrise”! 10% off charters!

Breathtaking Ocean views! Owners who care. “Sangria Sunrise”! 10% off charters!
Tavernier
Image gallery for Key Largo, Kawama Yacht Club Newly Renovated

Key Largo, Kawama Yacht Club Newly Renovated
Key Largo
Image gallery for Charming and Cozy Townhouse in the Fl Keys with Pool and Beach Access

Charming and Cozy Townhouse in the Fl Keys with Pool and Beach Access
Islamorada
Image gallery for Islamorada Bay Harbour 2/2.5 Condo Free DOCK included MONTHLY DISCOUNTS!

Islamorada Bay Harbour 2/2.5 Condo Free DOCK included MONTHLY DISCOUNTS!
Islamorada
Image gallery for Sublime Oceanfront Condo at Ocean Pointe

Sublime Oceanfront Condo at Ocean Pointe
Tavernier
Image gallery for Sunsets on the bay at Villa Mia

Sunsets on the bay at Villa Mia
Tavernier
Image gallery for OCEANVIEW / OCEANFRONT APARTMENT WITH RESORT AMENITIES, KEY LARGO, TAVERNIER

OCEANVIEW / OCEANFRONT APARTMENT WITH RESORT AMENITIES, KEY LARGO, TAVERNIER
Tavernier
Image gallery for 🌴 Casa 157 @ White Marlin Beach

🌴 Casa 157 @ White Marlin Beach
Islamorada
Image gallery for Stay where you play, On the water w/Boat dock & Trailer parking. Pet friendly!

Stay where you play, On the water w/Boat dock & Trailer parking. Pet friendly!
Long Key
Image gallery for Luxury home, Heated pool, Hot tub, Chefs kitchen, Sundeck, 100 ft of dockage.

Luxury home, Heated pool, Hot tub, Chefs kitchen, Sundeck, 100 ft of dockage.
Tavernier
Image gallery for Anglers Reef Islamorada 2/2.5 DOCK AVAILABLE Bikes, Kayak available, Pool

Anglers Reef Islamorada 2/2.5 DOCK AVAILABLE Bikes, Kayak available, Pool
Islamorada
Image gallery for Ocean view!

Ocean view!
Key Largo
Image gallery for Bay Harbour Islamorada Oceanfront Views 3/2.5 UPDATED condo DOCK

Bay Harbour Islamorada Oceanfront Views 3/2.5 UPDATED condo DOCK
Islamorada
Image gallery for Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach

Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
Islamorada
Image gallery for Canal Front Beautifully Renovated Home w/ Great Deck, Private Boat Ramp + WI-FI

Canal Front Beautifully Renovated Home w/ Great Deck, Private Boat Ramp + WI-FI
Tavernier
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value
Your guide to a long term stay in Islamorada
Islamorada, known as the "Village of Islands," offers a stunning backdrop for travelers looking to enjoy a long-term stay. Whether you're contemplating a month-long escape, an extended family vacation, or searching for short-term rentals to live in, you'll find a variety of furnished rentals that cater to your needs. With beautiful beaches, vibrant marine life, and a relaxed atmosphere, Islamorada is perfect for those seeking a longer getaway.
Save on long term rentals in Islamorada
For families planning to settle into Islamorada for an extended stay, long-term rentals provide both comfort and convenience. Monthly rentals offer the flexibility to explore the area while enjoying the privacy of a home away from home. Discover discounted monthly rentals in Islamorada designed for long-term living. Plus, with a free cancellation policy, you can book with confidence, knowing that you have options should your plans change.
Vacation Rentals with good WiFi
Are you a digital nomad seeking a perfect spot for remote work? Islamorada is an excellent choice for those looking to blend productivity with relaxation. Many vacation rentals feature reliable WiFi, allowing you to stay connected while enjoying the island's beauty. Check out long-term rentals with great WiFi in Islamorada for a seamless workation experience.
Pet-friendly accommodations in Islamorada
If you're traveling with furry friends, Islamorada offers a range of pet-friendly vacation rentals that make extended stays enjoyable for everyone. With spacious yards and nearby parks, you can ensure your pets have a great time too. Search for Islamorada long-term rentals that welcome pets for a stress-free getaway.
Vacation rentals in Islamorada with great kitchens
Experience the joy of cooking your favorite meals during your monthly stay in Islamorada. A rental with a well-equipped kitchen allows you to prepare fresh seafood caught right from the Keys. Discover furnished rentals with kitchens in Islamorada that provide all the comforts of home.
No need to worry about parking
Long-term travelers often face parking challenges, but Islamorada has a variety of furnished rentals with secure parking options. Whether you're planning weekend excursions or daily commutes, finding monthly rentals with parking in Islamorada ensures that you can come and go with ease throughout your stay.
Accessible vacation rentals in Islamorada
For travelers seeking wheelchair-accessible accommodations, Islamorada caters to all guests with a selection of inclusive vacation homes. These rentals are designed for comfort and ease, providing a welcoming environment for long-term stays. Browse Islamorada's wheelchair-accessible rentals to ensure an enjoyable and seamless experience for everyone.
Islamorada accommodations with a pool
If you’re looking to cool off during your stay in the Florida Keys, consider renting a furnished property with a pool. Relaxation is just a splash away, making it the perfect addition to your month-long vacation. Explore rentals with a pool in Islamorada and create unforgettable memories in a tropical paradise.