Kid-friendly vacation rentals in Key West

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Key West

Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.

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Guest favourite

Apartment in Key West

4.98 out of 5 average rating, 451 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. 28 – May 5

$510 CAD per night

Guest favourite

Guest suite in Marathon

4.98 out of 5 average rating, 186 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. 4 – 11

$349 CAD per night

Superhost

Vacation home in Key West

4.87 out of 5 average rating, 230 reviews

Historic Cigar House. 3rd floor Suite W/Kitchen

This unit is located in the historic "Cigar House" of the Island City House Hotel. Unit 12 is on the 3rd floor and is one of the most requested units in the entire hotel. Your private balcony overlooks the pool. Only 3 blocks from Duval street so close everything, yet quiet enough for a good nights sleep. You will have your own private entrance and use of all the hotel amenities. The space is a private 1BR with a kitchen and NEW sleeper sofa (12/23). In Old Town, walk to everything.

Apr. 25 – May 2

$598 CAD per night

Guest favourite

Home in Key West

4.97 out of 5 average rating, 206 reviews

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.

Apr. 9 – 16

$895 CAD per night

Guest favourite

Boat in Islamorada

4.9 out of 5 average rating, 171 reviews

HOUSEBOAT 2BD, PRIVATE KEYS COTTAGE LOGGERHEAD

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! Unfortunately, we do not have spare slips for private boats at this time. A 5% lodging tax will be charged on arrival.

Oct. 1 – 8

$327 CAD per night

Superhost

Houseboat in Key West

4.84 out of 5 average rating, 177 reviews

Happys Houseboat

This beautiful houseboat is nestled in a calm protected bay, it has hot water, a fridge and Air Conditioning! This boat was featured in Old Dominion‘s music video “I was on a boat that day”. Beautiful sites all around to wake up on the water and sunsets and stars to experiences as you relax on the top deck in the evening. Included in the rental is use of a skiff to get to and from land and and a seventh generation local captain to assist in check in and give a tour of the Houseboat.

Jul. 5 – 12

$593 CAD per night

Guest favourite

Guesthouse in Key West

4.93 out of 5 average rating, 528 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.

May 26 – Jun. 2

$507 CAD per night

Guest favourite

Condo in Key West

4.89 out of 5 average rating, 148 reviews

Large waterfront 2/2 end unit with boat slip

Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip available on-site with commercial ice machine and fish cleaning station. Located in historic Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Seaport, Hemingway House, etc. On-site amenities: heated pool, tiki bar & grills, bike rentals, parking, secure keyless entry, & private elevator. Large park adjacent with tennis courts. 10min from airport (EYW).

Apr. 10 – 17

$1,141 CAD per night

Superhost

Apartment in Key West

4.88 out of 5 average rating, 930 reviews

At Mine | Key West 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.

Nov. 23 – 30

$461 CAD per night

Guest favourite

Apartment in Key West

4.97 out of 5 average rating, 237 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).

Oct. 2 – 9

$536 CAD per night

Guest favourite

Houseboat in Key West

4.91 out of 5 average rating, 193 reviews

Key West Luxury Houseboat

EXPANSIVE OCEAN VIEW. 2 Queen Bdrms with Large Ensuite Baths on 1st level. Ocean view 2nd Level Living Room and Full Kitchen with half bath. Spacious fore and aft decks. 15 min from downtown KEY WEST. Located at Stock Island Yacht Club. Panoramic Views from 3rd level sun deck POOL, PRIVATE BEACH, Gym.

Mar. 3 – 10

$1,058 CAD per night

Guest favourite

Guest suite in Marathon

5.0 out of 5 average rating, 162 reviews

Dolphin Drive

Spacious, fun unit with private entrance and large living room with kitchen, bedroom and bathroom (Sleeps up to 4). Game room/living room includes billiards, ping pong and darts. Room for your boat trailer and vehicle in long, private driveway. 2/10 of a mile from the public boat ramp.

Jun. 21 – 28

$270 CAD per night