Vacation rentals in Rockland Key

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Top-rated vacation rentals in Rockland Key

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Guest favorite

Home in Key West

4.94 out of 5 average rating, 271 reviews

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Jul 31 – Aug 7

ﺩ.ﺇ1,861 per night

Guest favorite

Apartment in Key West

4.98 out of 5 average rating, 449 reviews

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval

1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs, DVD players & BlueTooth stereo system with CD player & radio.

Apr 9 – 16

ﺩ.ﺇ1,247 per night

Guest favorite

Guest suite in Marathon

4.98 out of 5 average rating, 184 reviews

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

Aug 2 – 9

ﺩ.ﺇ798 per night

Superhost

Tiny home in Big Pine Key

4.8 out of 5 average rating, 88 reviews

Breezy pines 28 foot 5th wheel trailer .

Central air,queen size bed in the bedroom,queen size futon in the living room, tv,stove,refrigerator,propane grill,wifi,and an outdoor dining table.Owner uses the outdoor storage shed for fishing purposes.Newly renovated vinyl floor.New carpet in the bedroom.New toilet installed.The water pressure has been fixed and is now perfect.One cup k cup machine.Mile marker 30.Take the north entrance.Take your first left.Take your second right.Bare right and lot 54 is the first trailer on the left.

Jul 26 – Aug 2

ﺩ.ﺇ398 per night

Superhost

Houseboat in Key West

4.81 out of 5 average rating, 253 reviews

Key West Houseboat Paradise

56 foot houseboat (1987), Fully Rebuilt in 2022. On a old 15 slip dock on Stock Island, 15 min drive to Key West. Big living room, Full Kitchen, Queen Bdrm + sofa bed. The dock is very local, 'old Key West' sort of vibe with mostly older live-aboard boats. The property has an fairly industrial feel to it with a 2-bay local garage/taxi company on site so Shore Side is nuthin' fancy but the back deck looks out on mangrove islands dotting Boca Chica Channel with two 12' Sea Kayaks ready to go.

Dec 12 – 19

ﺩ.ﺇ1,429 per night

Guest favorite

Cottage in Little Torch Key

4.91 out of 5 average rating, 145 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

Nov 19 – 26

ﺩ.ﺇ1,952 per night

Guest favorite

Guesthouse in Key West

4.93 out of 5 average rating, 527 reviews

Old Town - Room Opens to Pool and Garden

Located in the heart of Old Town, we are three blocks from Duval Street, a 10-minute walk to Higgs Beach, and around the corner from the best, least-expensive meal in town--El Siboney Cuban Restaurant. We suggest bicycling around Key West. Rentals from We-Cycle Bike Shop can be delivered to our door. Two blocks away, The Duval Loop offers free air-conditioned bus service 7 a.m. until midnight. We also offer a link with recommendations for excursions, tours, & restaurants.

Jun 8 – 15

ﺩ.ﺇ1,240 per night

Guest favorite

Condo in Key West

4.99 out of 5 average rating, 84 reviews

Hidden Beach Duplex, Best Place in Key West

Go to sleep and wake up smiling listening to the waves. 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. This is an extraordinary condo on an extraordinary property. This is nicest unit of 3 for rent at Hidden Beach. If you are discerning, this really is best place place to stay in Key West.

Oct 4 – 11

ﺩ.ﺇ2,357 per night

Guest favorite

Cabin in Marathon

4.9 out of 5 average rating, 21 reviews

New Cabins at Bonefish Bay

Make some memories at this unique and family-friendly place. Bring the family or just a romantic get away to enjoy the Keys. These new cabins have all your needs. Full bathroom and kitchen. Cozy but spacious. We also have boat ramp and dock space so you can bring your boats and water toys. We are located in the middle of the Florida Keys and easy access to all attractions and restaurants. We do have a big pool, bikes, and kayaks for our guests to use during their stay.

Sep 5 – 12

ﺩ.ﺇ611 per night

Guest favorite

Apartment in Key West

4.92 out of 5 average rating, 1032 reviews

At Mine | Lovely Suite steps from Duval Street

Beautifully renovated boutique hotel suite steps from Duval Street. This property is situated on a quiet street and offers a private pool and peaceful accommodation for vacationers and business travelers. The unit features a comfortable Queen-sized bed, Mini Fridge, a microwave, Iron and iron board, hangers, TV, and AC. Indulge in Key West's warm weather year-round. This special place is close to everything, making it easy to plan your visit.

Sep 24 – Oct 1

ﺩ.ﺇ955 per night

Guest favorite

Camper/RV in Big Pine Key

4.93 out of 5 average rating, 40 reviews

Having fun in the lower Keys

Enjoy the lovely setting of this romantic spot in nature. Big Pine Key is in the center of the lower Keys just 35 miles from Key West making it convenient to all the tourism and night life adventure the Keys have to offer while simultaneously being far enough away to allow for an off the beaten path relaxing experience. I have left several destinations for diving , fishing and/or great spots to just relax and take in the sun.

Aug 27 – Sep 3

ﺩ.ﺇ443 per night

Superhost

Home in Upper Sugarloaf Key

4.87 out of 5 average rating, 45 reviews

Bungalows at Sugarloaf Beach - The Lighthouse

Our amazing Lighthouse is a 2 bed 1 bath Loft Bungalow sitting just a few feet from our private beach. The master bedroom loft is accessed by a spiral stair, and has a beautiful bird’s eye view of the Atlantic Ocean. Our cozy nautical inspired living room leads outside to an exterior deck facing the beach perfect for peaceful mornings relaxing and sipping your coffee or cocktails.

Feb 18 – 25

ﺩ.ﺇ3,390 per night