Cheap Florida Keys Vacation Rentals – VRBO

We know how important it is to vacation in comfort while also finding cheap Florida Keys vacation rentals and accommodations, so we’ve compiled some of the best and cheapest VRBO vacation rentals throughout the Florida Keys to make it easier for you when booking your next trip! All of the homes we found have at least 2 bedrooms and 2 bathrooms and some are even pet-friendly, which you’ll see listed below.

From Key Largo to Key West, we’re sure you’ll find something cheap from our list that you love for your next vacation to the Florida Keys!

Check out a few of our favorite homes from each region in the Keys, below, and we’ve also made it easy for you to search and view all of the homes available for rent in each location, here:

Cheap VRBO Rentals in Key Largo

Key Largo offers a ton of fun activities and stunning scenery. Many tourists flock here for its amazing diving and snorkeling at John Pennekamp State Park and delicious seafood fisheries. Many find that hotels can be restricting, especially if you’re traveling with a large family and even your pets. These cheap VRBO home rentals are perfect for your next vacation if you’re looking for more space and privacy.

Key Breeze Waterfront Home offers stunning water views and plenty of space indoors and out.

Key Breeze Retreat is a 2 bedroom, 2 bathroom, 2nd story elevated home with an open floor plan with sliding doors and bay windows allowing you to enjoy the water view from the living room, kitchen, and dining room! This open floor plan connects to the next living area, and our favorite part of the home, a 32’ by 12’ covered deck that overlooks the 70’ foot canal!

This home is also dog friendly! You’re allowed 1 dog that’s less than 50lbs. Right now there’s availability for August/September and again in November. Running $157 per night on average, you can’t beat that price.

This Luxury House on the Ocean is perfect for large families and is updated with amazing, modern amenities. This house is pet-friendly, allowing up to 2 dogs under 50 lbs each and even comes with an extra large hot tub. With 5 bedrooms and 3 full baths this home offers the space you’re looking for on your next vacation.

Enjoy a paradise on the water with a perfect view and location. Bring your boat and enjoy fishing. Rodriguez keys is near and waiting for our guests.

And check out that awesome water view from the deck! This home is averaging $264 per night and has availability as early as this August – important to note: there’s a 28 night minimum rental so it’s best and cheapest to rent this with a large group and split the cost multiple ways to save money.

Cheap VRBO Rentals in Islamorada

Islamorada is the perfect spot to vacation in the Florida Keys. The amazing turquoise water and eclectic local shops, restaurants, and breweries make this town great for tourists. We’ve rounded up a few cheap options for your next vacation to this island paradise.

The Keys Kottage is an adorable and quirky villa home that’s set amongst lush palm trees and gardens. For $235 per night on average this quaint home is a great choice.

The Kottage is a “conch-style” cottage which was just completely remodeled and renovated and is completely new, from the tile floors to the new tongue-and-groove ceiling.

The property is directly on Florida Bay on Upper Matecumbe Key, and the Kottage is approximately 100 feet from the water.

This 2 bedroom, 2 bathroom home comfortably sleeps 6 people and offers the privacy you can only get with a single-family vacation home rental. It’s also pet-friendly, allowing 1 dog up to 20 lbs.

Enjoy a breezy afternoon on the patio relaxing with drinks or head down to the water for an amazing view! The Keys Kottage looks perfect for your next secluded Islamorada getaway and is one of the most charming and Cheap Florida Keys vacation rentals in our list.

If you’re looking for a larger home right on the water we found a great option in the heart of Islamorada! This waterfront home on a quiet/private road has a boat dock and lots of space inside and out for multiple families. This home has 3 bedroom and 3 full baths and comfortably sleeps 6. Here, you’ll be in the heart of Islamorada and all it’s awesome attractions.

We are walking distance to Robbie’s Marina, home to a large resident population of tarpon that you can watch and feed. They also have boat rentals and tours, and a wonderful restaurant. We are also very close to Bud and Mary’s Marina, World Wide Sportsman, Sandy Cove, and Calusa Cove Marinas, and more. There are many restaurants close by to visit by boat, car or bike.

Check out the availability as early at August, with various weekends available through September and October as well, averaging only about $300 per night depending on the dates!

Cheap VRBO Rentals in the Lower Keys

The Lower Keys offers a slower pace and total relaxation. You can get away from it all in one of these homes we’ve handpicked for you.

Walk to the famous Sombrero Beach from this spectacular waterfront home with dock and private pool. This one is perfect for an intimate family vacation or a couples retreat, with 2 bedrooms and 2 full baths.

Your home away from home on Marathon features a private boat dock, pool, and pool table – and you’re walking distance to Sombrero Beach. Start your day on your wraparound deck, iced coffee in hand, enjoying that lovely water view. Take your time – you’re in the Keys, so there’s no rush.

Averaging $289 per night, this island getaway is totally doable on a budget and worth every penny for it’s stunning accommodations and excellent location. Check out their availability for November and book your private Keys vacation now.

If you’re looking for cheap Florida Keys vacation rentals homes with amazing open water views, this home on Little Torch Key delivers! You can watch the sunrise from your private dock while sipping your morning coffee and truly enjoy your private Keys vacation. Centrally located close to Bahia Honda State Park and just 25 mins from Key West, this home has a secluded feel yet is close to all the best attractions in the Keys.

Enjoy this Open Water 2 bedroom 1 bath home. Walk into your open floor plan with views from every direction. Enjoy the sun rise on your large lovely open porch. Jump in your boat because you have the best access to both the Gulf and Ocean side.

This home is on our cheap list as it runs about $211 per night on average. Important to note that there is a 28 night rental minimum so it’s best to split with another couple to maximize savings. We loved this home too much to not include it on the list!

Cheap VRBO Rentals in the Key West

Key West is easily the priciest out of all the Florida Keys, but we were able to find some cheap options we think you’ll love. Key West is the perfect destination for a couples retreat or even a family-friendly getaway since there’s so much to do.

Stay in one of the best locations in Key West, the Truman Annex close to Fort Zachary Taylor State Park and in the heart of Old Town! This beautiful townhome offers modern upgrades with quintessential Florida Keys charm. With 2 bedrooms, 2.5 bathrooms and 3 floors, this home has enough space for the whole family to stay comfortably. And at $342 per night this is really cheap for Key West. We are seriously considering booking a week in August ourselves it looks so nice!

Truman Annex is a six block gated community right at the entrance to Ft. Zachary Beach, 2 blocks from Duval Street, and right next to the nightly Sunset Festival at Mallory Square. While a parking spot is provided…a car is not needed as you can walk to everything!

Since we love Old Town and the charm of the Truman Annex so much, here’s another cheap option for you! The President’s Lane Jewel is a perfectly located, 2 bedroom, 3 bath, end-unit townhome within walking distance of all the exciting attractions of Old Town. We’ll never recommend staying anywhere else on the island, pay the extra to be in the heart of it all and never have to use your car.

This President’s Lane jewel, is perfectly located on a corner lot. Multiple upgrades and special features make this a rare offering in the coveted Truman Annex neighborhood.

At only $307 per night this cheap option is perfect for a week-long trip with friends or family. Check out their availability for December, a great (and cooler) time to visit the island. The Holiday lights throughout the town and Historic Seaport are worth the trip during the months of November and December. Personally, this is our favorite time to visit Key West.

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