Last Updated January 5, 2021 1/5/2021

Top 15 Vacation Rentals for a Florida Keys Road Trip

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Considered a classic all-American road trip, a drive in the Florida Keys means exploring picture-perfect islands with coral reefs perfect for snorkeling, some of Florida’s top state and national parks and eating freshly-caught seafood at local restaurants. Starting in Key Largo, the most comprehensive Florida Keys road trip will take you to Tavernier, Islamorada, Long Key, Marathon, the Lower Keys and Key West. Along the way, make a pit stop and stay at one of these tropical-inspired Airbnbs and VRBO’s to enjoy perks such as beachfront access, outdoor pools and access to water-based adventures.

Ready to create your Florida Keys itinerary? Make sure to add outdoor activities in Key Largo, fishing excursions in Islamorada and paddling adventures in Marathon to your route. After you cross the famous Seven Mile Bridge and explore the Lower Keys, continue on U.S. 1 to Mile Marker 0 and embrace the anything-goes attitude and colorful attractions in Key West.

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Private, Oceanfront Beach Property – Key Largo Private, Oceanfront Beach Property – Key Largo
Credit: airbnb.com
Private, Oceanfront Beach Property – Key Largo

Private, Oceanfront Beach Property – Key Largo

Embrace the island lifestyle in the Florida Keys by staying at this beachfront property.  In addition to its beautiful oceanfront setting and captivating waterfront views, the apartment comes equipped with paddleboards, beach games and snorkel sets for two. Take in the island views from the spacious living room and full kitchen, then step outside on the patio for Atlantic Ocean views or head to the outdoor bar. The secluded Key Largo stay is only one hour from the Miami airport, and there’s no other oceanfront houses for miles.

Upscale Villa with Marina, Pools, Saltwater Lagoon & Kayaks – Key Largo Upscale Villa with Marina, Pools, Saltwater Lagoon & Kayaks – Key Largo
Credit: VRBO.com
Upscale Villa with Marina, Pools, Saltwater Lagoon & Kayaks – Key Largo

Upscale Villa with Marina, Pools, Saltwater Lagoon & Kayaks – Key Largo

Located in the heart of Key Largo, this sleek 3-bedroom villa offers a “summer cottage” feel. Along with new appliances and furniture, guests can take advantage of the free Wi-Fi, cable TV and gas grill on the balcony. You’ll have two kayaks and two bicycles to use at your leisure, with the home conveniently located in front of a saltwater lagoon and just steps from a family-friendly pool and playground. Housed in the Kawama Yacht Club, you’ll have access to on-site amenities such as a small sandy beach, tennis court and marina with a boat ramp.

Escape to the Seaside at Tiburon Cottage – Key Largo Escape to the Seaside at Tiburon Cottage – Key Largo
Credit: airbnb.com
Escape to the Seaside at Tiburon Cottage – Key Largo

Escape to the Seaside at Tiburon Cottage – Key Largo

This one-bedroom suite in Key Largo is perfect for budget-savvy travelers, featuring separate bedroom and living areas and a private entrance. In addition to a flat-screen TV, complimentary Wi-Fi and premium cable, the one-bedroom space is cozy and adorned with charming beach decor. Enjoy sitting by the dock, take a dip in the pool or bask in the sunshine in one of the lounge chairs, while restaurants are within walking distance.

Oceanfront Paradise with Private Beach, Pool & Kayaks – Tavernier Oceanfront Paradise with Private Beach, Pool & Kayaks – Tavernier
Credit: VRBO.com
Oceanfront Paradise with Private Beach, Pool & Kayaks – Tavernier

Oceanfront Paradise with Private Beach, Pool & Kayaks – Tavernier

This bright and cheery two-bedroom condo in Tavernier offers amazing panoramic views of the Atlantic Ocean. Take in the epic views as you enjoy dinner at the dining table, cheers with drinks on the small furnished balcony or grab a pick-me-up from the coffee hutch with Starbucks K-cups. Board games and an HD Smart TV provide entertainment, while some of the condo’s amenities include a community pool, resort beach, kids playground, BBQ grills and recreational area.

Island Getaway – Tavernier Island Getaway – Tavernier
Credit: airbnb.com
Island Getaway – Tavernier

Island Getaway – Tavernier

Catering to couples, this Tavernier Airbnb is just a few streets away from water access and within easy access of many Upper Keys activities. In addition to a fully-equipped kitchen, the newly built apartment also has a spacious living room and a king-size bed. Nature lovers will enjoy the complimentary kayak usage, as well as the beach towels, beach chairs, snorkel gear and cooler for guests.

Oceanfront Condo with Amazing Ocean & Marina Views – Tavernier Oceanfront Condo with Amazing Ocean & Marina Views – Tavernier
Credit: VRBO.com
Oceanfront Condo with Amazing Ocean & Marina Views – Tavernier

Oceanfront Condo with Amazing Ocean & Marina Views – Tavernier

Boasting gorgeous marina and Atlantic Ocean views, this beautiful VRBO sleeps up to six guests. Set in Ocean Pointe resort, amenities include an outdoor pool, BBQ area, a beach area with lounge chairs and beachside volleyball. There’s also a marina and fishing pier to explore, while the condo itself has convenient perks such as a balcony with ocean views and a fully-equipped kitchen.

The Island Dog, 2 Bedroom Conch House – Islamorada The Island Dog, 2 Bedroom Conch House – Islamorada
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The Island Dog, 2 Bedroom Conch House – Islamorada

The Island Dog, 2 Bedroom Conch House – Islamorada

Traveling down to Islamorada, this charming two-bedroom conch house has a full kitchen with new appliances, 3 flat-screen Smart TVs and a dining room with a high-top bar table. Its colorful decor is sure to put you in a good mood, while the shared pool is great for cooling off. Outdoors, there’s a private community boat ramp and private ocean channel, within a short drive from the famous Robbie’s where you can hand-feed tarpon.

Atlantic Ocean Beachfront Duplex With Private Dock and Beach – Long Key Atlantic Ocean Beachfront Duplex With Private Dock and Beach – Long Key
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Atlantic Ocean Beachfront Duplex With Private Dock and Beach – Long Key

Atlantic Ocean Beachfront Duplex With Private Dock and Beach – Long Key

Located on one of the only private beaches in the Florida Keys, this beachfront two-bedroom home sits at the southern tip of Long Key. It features a fully-equipped kitchen, patio and beach furniture, as well as a BBQ grill, tiki hut and kayaks. In addition to beautiful Atlantic Ocean views, the property is just a short walk from Long Key State Park where you can go birdwatching, hiking, canoeing and snorkeling. Diving and fishing are also popular in this area.

House with Heated Pool and Spa & Boat Dock – Marathon House with Heated Pool and Spa & Boat Dock
Credit: VRBO.com
House with Heated Pool and Spa & Boat Dock

House with Heated Pool and Spa & Boat Dock – Marathon

Bring the whole family to this bright 3-bedroom house in Marathon, which offers direct access to the ocean, 37 feet of dockage and a sparkling outdoor pool surrounded by sun loungers, a hot tub and a tiki bar. Cool off with its central A/C, then take advantage of the BBQ grill, premium cable TV, high-speed Wi-Fi and outdoor picnic table with its own TV. Love fishing? Not only does it have a fish cleaning station, but there’s also an industrial ice maker at your disposal and is located just minutes from a reef and off-shore fishing spots. Outdoor enthusiasts will also enjoy the snorkeling and scuba diving available nearby.

Casa Mariposa: Easy Walk to Sombrero Beach – Marathon Casa Mariposa: Easy Walk to Sombrero Beach – Marathon
Credit: airbnb.com
Casa Mariposa: Easy Walk to Sombrero Beach – Marathon

Casa Mariposa: Easy Walk to Sombrero Beach – Marathon

Just one-minute drive from the beach, this Marathon Airbnb offers a private suite in a ground-level home. In addition to a saltwater lap pool surrounded by palm trees and red-leaved bananas, the one-bedroom space has a private entrance and king-size bed. Your room opens directly to the spacious patio and pool area, while in-room perks include a mini-fridge, coffee maker and selection of coffee, tea and bottled water. When you’re ready to explore, launch a kayak from Sombrero Beach.

Beachfront Condo with Ocean Views – Marathon Beachfront Condo with Ocean Views – Marathon
Credit: airbnb.com
Beachfront Condo with Ocean Views – Marathon

Beachfront Condo with Ocean Views – Marathon

This beachfront condo offers everything you need for a memorable Florida Keys getaway, including panoramic ocean views, beach access and an outdoor pool. The beautifully decorated 2-bedroom space boasts a private balcony with endless water views, a full kitchen, spacious living room and washer/dryer. It’s set directly on the beach, with beach chairs, umbrellas and towels provided for you. You’ll also have access to a shared pool and tennis court, while local restaurants are a short drive away.

Ocean Paradise with Bikes & Kayaks – Cudjoe Key Ocean Paradise with Bikes & Kayaks – Cudjoe Key
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Ocean Paradise with Bikes & Kayaks – Cudjoe Key

Ocean Paradise with Bikes & Kayaks – Cudjoe Key

Escape to Cudjoe Key and stay at this stunning two-bedroom waterfront house set on a canal, which features water views from every room. Sleeping up to six guests, it comes with a fully equipped kitchen, a grill and outdoor patio furniture. You’ll also have access to bikes and two-person kayaks, as well as shared amenities such as a pool, hot tub, marina, boat ramp, games room and playground.

Bella Vita, 1 Bedroom Condo Steps From Duval – Key West Bella Vita, 1 Bedroom Condo Steps From Duval – Key West
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Bella Vita, 1 Bedroom Condo Steps From Duval – Key West

Bella Vita, 1 Bedroom Condo Steps From Duval – Key West

Embrace the funky vibes of Key West in this bright and colorful Airbnb, which is located in Old Town less than a 1/2 block from Duval St. Kick back on the chairs found on the wrap-around porch, relax on the plush leather sofa in the living room or whip up a meal in the galley kitchen with bar seating. Rent a bike or scooter to explore the area around this popular Florida Keys Airbnb, as it’s set just a few blocks from the Southernmost Point, Hemingway House and other top Key West attractions.

Studio Suite with Shared Hot Tubs, Patio, Steps from Beach – Key West Studio Suite with Shared Hot Tubs, Patio, Steps from Beach – Key West
Credit: airbnb.com
Studio Suite with Shared Hot Tubs, Patio, Steps from Beach – Key West

Studio Suite with Shared Hot Tubs, Patio, Steps from Beach – Key West

Ideal for couples or small families, this charming Airbnb in Key West offers shared hot tub access and a large patio space. Tucked underneath a canopy of tropical trees, the suite is just a couple blocks from a beautiful beach in Key West, as well as restaurants and shops that line Duval St. The Pelican Suite features a kitchenette, cable TV and free Wi-Fi, while dogs are also welcome for an additional nightly fee.

Steps Off Duval, Private Deck, Free Breakfast & Happy Hour – Key West Steps Off Duval, Private Deck, Free Breakfast & Happy Hour – Key West
Credit: airbnb.com
Steps Off Duval, Private Deck, Free Breakfast & Happy Hour – Key West

Steps Off Duval, Private Deck, Free Breakfast & Happy Hour – Key West

One of the few rooms at Andrews Inn bed and breakfast, this beautifully decorated room comes with a few perks. In addition to a queen-size bed and sleeper sofa, the room comes with access to a breakfast with bottomless mimosas, free afternoon happy hour and an outdoor pool surrounded by plush sun loungers. Known for offering superb hospitality, the Airbnb also offers a prime location in Key West, sat adjacent to the Hemingway Estate.

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