Vacation rentals in Rockland Key

4.91 out of 5 average rating, 285 reviews

A spacious porch is shown with a wooden deck and white railing. A ceiling fan is present above, offering a cooling feature. Nearby, a small table and chairs create a seating area surrounded by lush green vegetation, providing a private outdoor space for relaxation.

Townhouse in Key West

Comfortable, clean,beautiful home Summer Special

Introducing a brand new property hosted by AirBnb Superhost Roy Svenningsen. This home was fully renovated in January 2019. It features all new furnishings, stainless steel appliances, new flooring, marble countertops, and top quality mattresses. I look forward to hosting you in this beautiful family oriented gated community situated across from the Key West Golf Course and only 3 miles from Duval St. The home comes with parking for 2 cars. I am always available to answer any questions. Roy

4.93 out of 5 average rating, 129 reviews

Cottage in Cudjoe Key

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family-friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

Houseboat in Stock Island

A clear swimming pool reflects the blue sky, surrounded by lounge chairs and umbrellas. Palm trees provide shade along the edge, complementing the vibrant greenery. In the background, modern multi-story buildings showcase balconies, offering a relaxed atmosphere by the water.

4.96 out of 5 average rating, 23 reviews

The Writer's Block- Key West

Discover tranquility aboard this unique floating haven. It's a sleek modern retreat for those who crave space to read, write or find inspiration far from the stresses of the modern world --yet it's steps away from upscale restaurants, two fabulous pools, a gym and so much more. From a king bed to a full-sized shower and kitchenette, you'll enjoy the comforts of home while living directly on the water. Features a large private deck with panoramic views of the marina and its glorious sunsets.

4.8 out of 5 average rating, 270 reviews

A modern houseboat is anchored on calm waters during sunset. The structure features large windows and a spacious front deck with a grill station. The warm glow of the setting sun illuminates the exterior, reflecting off the water, creating a serene atmosphere.

Boat in Marathon

Paradise awaits on this cozy houseboat!

Our vision is for you to kick back, relax, and find your home away from home! Wether you want to celebrate with your loved one or retreat by yourself this floating home offers comfortable space for 2 adults. Located near the 7 mile bridge in Marathon Florida on the Atlantic Ocean nestled in a quiet, reserved mangrove area. This spot is fantastic because you have unparalleled access to out of this world sunset/sunrise views. Kayak through the mangrove and explore the surrounding areas.

4.97 out of 5 average rating, 259 reviews

Home in Key West

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, newly renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, tumbled marble 2 person shower, private front deck with seating for 4 and 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

A serene private pool area is surrounded by lush tropical landscaping. Lounge chairs are arranged along the water's edge, inviting relaxation. A rock feature complements the pool, enhancing the natural ambiance created by palm trees and various greenery.

4.88 out of 5 average rating, 1,501 reviews

At Mine | Lovely Suite steps from Duval Street

Beautifully renovated boutique hotel suite steps from Duval Street. Located on a quiet street, it offers a private pool and peaceful stay for vacationers and business travelers. The unit includes a comfy Queen bed, mini fridge, microwave, iron & board, hangers, TV, and AC. Enjoy Key West's warm weather year-round. This special place is close to everything, making it easy to plan your trip. Just a heads-up: Key West’s famous roosters love to strut and crow—part of the island charm!

4.97 out of 5 average rating, 100 reviews

A wooden pier extends into calm waters, leading towards a beach with soft golden sand. In the background, a multi-story building is nestled among palm trees, set against a sky with scattered clouds and a single bird in flight.

Condo in Key West

Hidden Beach unit 1 The Perfect Place to stay

This place is extraordinary. There is nothing like it in Key West. Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

4.86 out of 5 average rating, 185 reviews

A waterfront bar and grill setting features a wooden deck lined with colorful adirondack chairs. Palm trees provide greenery and shade. The entrance reveals diners inside, enjoying the relaxed atmosphere, with boats docked nearby reflecting in the calm water.

Townhouse in Key West

Poolside Cottage #412

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of KW. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the seaport and world famous Duval Street! Bikes, golf carts, kayaks, stand-up paddleboards and other watercraft can all be rented locally!

5 out of 5 average rating, 10 reviews

A serene outdoor area is highlighted by a clear blue salt-water pool surrounded by lounge chairs. Palms sway gently in the breeze, and a dining table sits nearby. The water view invites a sense of tranquility, complemented by landscaped greenery along the perimeter.

Townhouse in Key West

Exceptional Water View With Boat Dock!

This is the best kept secret. 10 miles from Duval St. for the night life, but a total private oasis if you are looking for a true get away. This is an end unit with a water view from every window in a gated community with a salt water pool. Wake up to an ocean view and have cocktails on the patio. This is a brand unit that has recently been completely renovated.

A charming entrance is revealed by a white picket fence, leading to a lush, landscaped pathway bordered by tropical greenery. A spacious patio area with dining furniture is visible under a large awning, while the upper balcony invites relaxation among the palm trees.

4.96 out of 5 average rating, 280 reviews

Poolside Truman Annex 2 Bed | Conch Life Condo

Cozy condo in the Truman Annex to fully experience the conch life. It is close to Fort Zachery Beach and State Park, Hemingway House, Mallory Square, and Duval Street. Location is perfect due to Island proximity to any event and occasion. My place is a great getaway for couples, solo adventurers, business travelers, and families (with kids).

5 out of 5 average rating, 32 reviews

A serene beach scene features a sailboat anchored near the shore, with gentle waves lapping at the sand. Palm trees sway in the breeze, while a clear blue sky provides a vibrant backdrop to the peaceful setting.

Condo in Key West

EYW Getaway

Relax with the whole family at this peaceful place to stay. Our two-bedroom two-bathroom condo with complete kitchen is located at Sunrise Suites Resort. Amenities include shared heated pool, hot tub, tennis court and a basic gym. Our condo is located 1mile from the airport, 1.5 miles from the beach and 3.5 miles from downtown Duval St.

4.87 out of 5 average rating, 246 reviews

A tranquil beachfront scene showcases a sandy shore lined with palm trees. Calm waters reflect the sky, dotted with fluffy clouds. In the distance, a marina displays boats alongside wooden docks, while cozy thatched-roof structures provide shaded seating.

Houseboat in Key West

Key West Luxury Houseboat at Yacht Club Resort

2x Queen Bedrooms 2x Ensuite Full Bath Queen Sleeper Sofa and 1/2 Bath PANORAMIC Ocean Views 200+ FIVE STAR Reviews- FIVE YEARS SuperHost Rated ~ SUN DECKS on All Levels, HUGE SKY Deck Rooftop Ocean-View Living Room ~ Floor-to-Ceiling Windows ~ 50 inch TV ~ Granite Countertops Throughout ~Full Kitchen, Full Size Appliances ~

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Other great vacation rentals in Rockland Key

4.86 out of 5 average rating, 22 reviews

A white wooden sign displays the words 'Garden House' surrounded by lush green foliage. Tropical plants and palm leaves frame the sign, creating a serene and inviting atmosphere in the outdoor setting.

Private room in Key West

Garden House Queen Room

RussRating, 5 stars3 weeks ago

Amazing stay and even better than expected. The room was quaint and everything we needed. Close enough to walk everywhere. The amenities were great. I had forgotten there’s a little pool and that was a great treat after a long day in the sun. We’re already looking to book again!

A modern countertop is highlighted by a bronze faucet, complemented by clear glass jars filled with yellow bath sponges. The backsplash features a subtle blue herringbone pattern, adding a refreshing touch to the serene bathroom environment.

4.82 out of 5 average rating, 67 reviews

Blue Room at the Grand Maloney

DiegoRating, 5 stars1 week ago

Phenomenal place, the location was a big plus! you can walk everywhere. looking forward to staying again

A bright living space features large windows with light-filtering shutters, offering a view of the outside. A spacious day bed is positioned near the windows, complemented by a rustic dining table and chairs. The adjacent kitchen includes modern appliances, enhancing the open layout.

Home in Summerland Key

4.82 out of 5 average rating, 57 reviews

Kelly’s Kabin - Private FL Keys Cottage

LadyRating, 5 stars2 weeks ago

The cabin was cozy and super cute. It was impeccably clean. I only stayed one night but wish I stayed longer. She had all the necessary amenities. I didn’t get to use the patio since I mostly stayed out on the boat but wish I had more time to do so. Kristin had board games, shampoo, conditioner, body wash, blow dryer, washer, dryer and everything you would want in an AirBNB. There are plenty of restaurants nearby and the supermarket wasn’t too far. I felt safe in the neighborhood. I hope to come back and stay here again!

Private room in Big Pine Key

A serene outdoor area features two kayaks, one blue and one white, resting on a sandy surface next to a calm waterway surrounded by lush greenery. Comfortable seating is arranged nearby, creating a relaxing space for guests to enjoy the natural surroundings.

4.97 out of 5 average rating, 36 reviews

Sweet Spot - Kayak and SUP launch

JuleeRating, 5 stars1 month ago

We had a wonderful time. I took my daughter down to the Keys because well she’s 17 and growing up too fast so we got some us time. Our love for the ocean is deep. Staying here was perfect to get to Key West to do some adventures and was so peaceful to hangout and chill. Once you walk into the Airbnb it smelled so good and was very clean. Our room and bathroom was perfect. The Big Pine Rooster was our favorite place to eat. The breakfast and dinner was amazing and my daughter said they had great key Lime pie. We used the kayaks and just wished we would have been able to go out into the ocean instead of having to stay in the “slipway area” would have been amazing. Lili the owners sister was there and was great. She made sure the house always smelled great and made sure we were doing good and comfortable. She gave us a couple free passes for put out golf and unfortunately we couldn’t use them. Overall it was such a great stay and would recommend to everyone!

A spacious shared balcony is highlighted by a light blue ceiling and white railings. Several white chairs are arranged along the length, offering views of lush palm trees and rooftops of nearby structures. Natural light illuminates the area, enhancing the relaxing atmosphere.

5 out of 5 average rating, 7 reviews

Duval Corner - Pet friendly with Balcony

JulianRating, 5 stars2 weeks ago

Beautiful little apartment right on Duval Street. Really was a small slice of paradise.

4.88 out of 5 average rating, 354 reviews

A balcony is presented with several beige chairs arranged around a small table. A potted orchid adds a splash of color. The space features wooden flooring and is bordered by white railings and dark shutters, providing a cozy outdoor seating area.

Private room in Key West

Mallory House Room #1

LindsayRating, 5 stars2 weeks ago

We had a great stay. It's on the quieter side of town with so many great restaurants. Easy to walk to other popular spots as well. David also helped check us in and found us free parking which we very much appreciated. Thank you for a wonderful stay!