Holiday rentals in Stock Island

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Stock Island

  • Total holiday rentals

    Explore 380 holiday rentals in Stock Island

  • Nightly prices starting at

    Stock Island holiday rentals start at €96 per night before taxes and fees

  • Verified guest reviews

    Over 15,600 verified reviews to help you choose

  • Family-friendly holiday rentals

    270 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 100 rentals that welcome pets

  • Holiday rentals with a pool

    330 properties feature pools

  • Rentals with dedicated workspaces

    220 properties have a dedicated workspace

  • Wifi availability

    360 of Stock Island holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Stock Island rentals

  • 4.7 Average rating

    Stock Island stays receive an average rating of 4.7 out of 5 from guests

Top-rated holiday rentals in Stock Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A well-maintained community pool is surrounded by lush tropical landscaping, featuring lounge chairs with blue umbrellas. The clear water reflects the bright blue sky and palm trees, creating a relaxing atmosphere for guests to enjoy.
Home in Key West
4.88 out of 5 average rating, 95 reviews

Key West Paradise

Bring the whole family or a great group of friends to this fantastic house w/lots of room for fun. 3 Bed (1 on main level, 2 up), 3 Full Baths (1 on main level, 2 up), sleeper sofa in living room and air mattress in closet, Steps to Community Pool, Sleeps up to 8. Nice Kitchen for your use. High speed internet. TV in the living room and in every bedroom. Enjoy the breeze from your nice size front porch, rear deck off living room, and balcony off upstairs bedroom. 8 minutes to Duval Street.

Top guest favourite
Boat in Key West
5 out of 5 average rating, 16 reviews

3BR In Resort Village, Pools, Free Kayak & Shuttle

Experience the ultimate KEY WEST VIBE aboard our 3BR/2BA sailboat Located at the luxury Perry Hotel, you’ll enjoy ice-cold AC, palm trees, and salty air. Free Perks: Kayak, pools, parking, and free shuttle to Old Town! Full Resort Access: 2 sparkling pools & hammock park, 2 restaurants, ice cream shop, private bathhouse & Views of million-dollar yachts Live the island life w full access to all resort amenities. Your tropical escape awaits! This memorable place is anything but ordinary.

Top guest favourite
A well-maintained two-story house features light-colored siding and contrasting blue shutters. A spacious, welcoming front porch is framed by tropical plants and neatly arranged landscaping. Steps lead up to the front door, providing easy access to the entrance.
Home in Key West
5 out of 5 average rating, 37 reviews

Casa Calypso 3bed3bath sleeps 8 beautiful decorate

Bring the whole family to this great place with lots of room for fun. Very clean, organized stand alone house with everything you will need to have a great stay! Fully stocked kitchen with a kuerig and drip coffee pot. Can have twin beds downstairs or convert into a king. Two king bedrooms upstairs. Each bedroom has its own bath! A queen sleeper couch in living room with a screen divider for privacy if needed. Steps away from the large heated community pool. Several nice restaurants around.

Top guest favourite
Aerial view showcasing a waterfront property bordered by vibrant green mangroves. The calm turquoise water reflects the blue sky dotted with white clouds. A marina with docked boats is visible nearby, creating a serene coastal landscape.
Apartment in Key West
4.99 out of 5 average rating, 136 reviews

Gorgeous Ocean View in Paradise, Close to Key West

This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the ocean and mangroves from your private balcony. Enjoy your privacy as you start your day, then venture out to explore all that Key West has to offer: water sports, quaint shops, delicious food, history all around you, and so much more! On property features: Pool, Hot Tub, Yellowfin Bar & Kitchen and Parking. Beach supplies included: Coolers, Snorkel Gear and Beach Towels.

Superhost
The exterior of the houseboat is showcased, featuring a spacious upper sun deck with white railings. A staircase leads from the deck down to the dock. The houseboat is moored in calm waters, surrounded by sailboats and a clear blue sky adorned with scattered clouds.
Houseboat in Stock Island
4.88 out of 5 average rating, 43 reviews

Stella on Stock Island

Perched on the shimmering waters, this 1 bedroom, 1 bath houseboat epitomizes cozy waterfront living. Step inside and you'll find yourself welcomed into an inviting living space. The living area transitions into a kitchen complete with essential appliances. Down the hall from the living area lies the bedroom offering a peaceful haven for rest and relaxation after a day spent exploring. An elegantly appointed bathroom awaits, featuring modern fixtures and amenities. Queen Bed & Sofa Bed

Guest favourite
Boat in Key West
4.83 out of 5 average rating, 24 reviews

43' Classic Yacht Views, Pools, Duval Shuttle

Create unforgettable Key West memories while staying on our long time charming liveaboard 43' Trawler. This 2 bedroom 1.5 Bath mini yacht will be the perfect home base for your adventures around town or to just sit and enjoy the incredible views and nature. Being at the award winning Perry Marina gives you all the amenities of a 5 star resort. 2 Pools, 3 Restaurants on site, free shuttle to town, hotel gym, laundry and all the charter and adventure options you could ever ask for.

Top guest favourite
Home in Summerland Key
4.97 out of 5 average rating, 30 reviews

Starlight Serenity - Hideaway with Stunning Views

Escape to paradise at this serene 1-bedroom, 1-bath home in beautiful Sugarloaf Key sleeping up to four guests. Enjoy breathtaking views from the expansive wrap-around balcony, perfect for sunrise coffee or sunset cocktails. The spacious outdoor area is ideal for dining, lounging, and soaking in the tropical ambiance. Whether you're relaxing indoors or savoring the outdoors, this home offers the perfect blend of comfort and tranquility. Book your next getaway for 3 nights or more!

Superhost
A refreshing pool area is surrounded by green palm trees and blue umbrellas. Lounge chairs are arranged neatly around the pool, while tables with chairs provide seating for guests. The clear blue sky enhances the inviting atmosphere of the community space.
Flat in Key West
4.84 out of 5 average rating, 140 reviews

Penthouse in Paradise

Coconut Mallory is a waterfront private community that provides resort amenities. Hop in one of the two on-site pools to cool down after soaking up the sun at Smathers Beach, Key West's largest public beach just 2 miles away. There is also a Jacuzzi and a picnic area with BBQs for guest use. This unit is a two bedroom two bath. It also features two off street parking spaces included. *The Master Tub is not to be used per the community as leaks have occurred in other units before.

Top guest favourite
A spacious swimming pool is surrounded by lush tropical greenery and lined with lounge chairs. Tiki-style huts provide shaded areas for relaxation, while the pool's clear blue water reflects the vibrant sky, creating a serene and inviting environment.
Home in Key West
5 out of 5 average rating, 41 reviews

Funky Chicken Cottage with Shared Pool in Paradise

Funky Chicken Cottage is a charming and eclectic vacation rental located in Key West, just a short drive away from the main island on Stock Island, Florida. This 3 bedroom, 3 bathroom property is the perfect blend of comfort and style, with unique Martha DePoo art and Cuban art. The highlight of this property is the beautiful pool area, gated community. The property also features two parking spaces under the house, making it convenient for guests who are driving to the island.

Guest favourite
An open-concept living area features wraparound seating in dark leather surrounding a polished wooden dining table. Abundant natural light filters through panoramic windows, reflecting off the rich wooden flooring. Tropical-themed wall decor and greenery enhance the inviting aesthetic. A well-equipped kitchen is visible in the background.
Boat in Key West
4.92 out of 5 average rating, 49 reviews

Sailboat Retreat | Resort Amenities

Step aboard The Dream, your own sailboat in Key West, Florida! This is not your typical Airbnb — it's a floating escape on a beautiful 1-bedroom, 2-bathroom 42 foot sailboat docked at the exclusive Perry Hotel & Marina (just minutes from downtown!) Enjoy a queen bed in the spacious Captain’s suite, 2 full-sized paddle boards, snorkel gear, private Wi-Fi, and more. With tropical vibes and the comforts of home, this is where island adventure meets peaceful retreat.

Top guest favourite
A sleek black camper with metallic accents is positioned on a gravel area. Two comfortable chairs are placed on a patterned outdoor rug, surrounded by palm trees and a white fence. An extendable awning provides shade beside the entry door.
Camper van/Motorhome in Stock Island
4.92 out of 5 average rating, 91 reviews

Rooster Camper at Leo's

Our charming Rooster Camper in Stock Island is the perfect spot for your Key West getaway. Fully furnished, it offers a comfortable bed and a kitchenette with essential amenities for a relaxing stay. Located just two blocks from the entrance to Key West, you can easily bike, scooter, or take a golf cart into town. This camper is set inside Leo’s RV Park, and guests can enjoy shared amenities during their stay. For the comfort of all guests, pets are not allowed.

Top guest favourite
Houseboat in Key West
5 out of 5 average rating, 15 reviews

Strictly Pleasure | Unique Yacht Stay in the Keys

Staying aboard Strictly Pleasure offers a truly unique Keys experience. Enjoy life on the water with beautiful marina views, sunsets from the bow, and the charm of staying on a classic yacht. Located at Perry Marina, guests have access to pools, waterfront restaurants, and the trolley to downtown Key West. It’s the perfect mix of relaxation, location, and a one-of-a-kind stay you won’t find in a typical hotel.

Popular amenities for Stock Island holiday rentals

When is the best time to visit Stock Island?

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Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Stock Island?

    Four-legged friends are welcome in Stock Island. Choose from more than 100 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Stock Island?

    Yes! Work meets play with ease at over 220 vacation rentals in Stock Island featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly house rentals in Stock Island?

    Stock Island has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in boat rentals in Stock Island?

    Experience the best of Stock Island with our boat rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there Stock Island apartment rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 60 apartment rentals with pools in Stock Island, available on Airbnb. Make a splash and soak up the sun in style!

  • Do condo rentals in Stock Island have air conditioning?

    Absolutely! We offer over 100 condo rentals with air conditioning in Stock Island. Enjoy a tailored experience with all the comforts you desire.

  • Do houseboat rentals in Stock Island have wifi?

    Absolutely! We offer over 10 houseboat rentals with wifi in Stock Island. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Stock Island have a bbq area?

    Absolutely! We offer over 20 house rentals with a bbq area in Stock Island. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Stock Island have a gym?

    Absolutely! We offer over 50 condo rentals with a gym in Stock Island. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Condo Rentals in Stock Island?

    Enhance your stay in our Condo Rentals with the most popular amenities: over 50 homes with a gym, over 100 homes with air conditioning, over 10 homes with a bbq area, over 100 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Stock Island