
Beachfront holiday rental in Stock Island
Find and book unique beachfront homes on Airbnb
Top-rated beachfront accommodation in Stock Island
Guests agree: These beachfront homes are highly rated for location, cleanliness and more.

Boaters delight! 1 min to open water, Dock & Beach
Inquire for monthly discounts. The happy house 339 at ghee mail. Quaint and charming home nestled in the Florida Keys. Secluded single family property with open water access. Private Dock, Beach, kayak launch area with kayaks and bikes available to use. Very private tranquil location. See manatees/fish swimming by. Enjoy endless sunsets from the front porch. Fantastic views from every room in the house. Beds: 1 King bed, 2 twins, 2 trundle Marathon Vacation Rental License#. VACA-22-375

Palm - Beach Houses Key West
If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we can’t wait to host you. Experience the charm of our recently renovated, one-of-a-kind two-bedroom beach bungalow, nestled right on the shore. Enjoy breathtaking ocean views from your private deck, relax on the sandy beach, and soak in the tropical ambiance. This family-friendly retreat offers the perfect setting to make you feel like you’re on your very own private island.

New Private 4/3 Single Family - Kayaks & Bicycles+
Blue Treasure at Sombrero Beach is a 2020 built single-family home in a private community within walking distance to the beautiful Sombrero beach and 5 minute boat ride to the ocean. This house is a private fully equipped 4/3 that has three king memory foam beds and one queen memory foam & queen sofa memory foam. All the rooms have a TV w/ cable & Netflix. We also have a separate downstairs area that we provide kayaks, paddle boards, and bicycles at no additional cost. License #:VACA-20-150

Oceanside home 111, dock,kayaks,bikes,pool,fishing
This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. This is #111 and I also rent adjacent homes 109 and 107 in case you need more than one. We are 40 feet from the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on the balconies or poolside, where you can sun, fish or boat from the docks. Key West is 17 miles away.

Family Suite at Sugarloaf Key Hotel (Pet Friendly)
Discover the perfect blend of comfort, relaxation and adventure at the Sugarloaf Key Hotel, nestled within the Sugarloaf Key / Key West KOA Resort campground. Newly built in 2023, this beautiful 6-person pet-friendly vacation suite offers everything you need for a great stay. Nestled amongst gorgeous tropical scenery, this resort includes robust amenities including resort-style pool and hot tub with an adjacent pub, quaint sand beach, marina, water rentals, café, camp store and more!

Beautiful Beachfront Villa w/ Pool/Tiki/Dock
Beautiful Beachfront home located directly across the street from famous Sombrero Beach, with heated pool & Tiki Bar. Large wrap around balconies provides stunning beach views, sunrises & sunsets for relaxation. It boasts open floor plan with a large entertainment area that includes a gorgeous Olhausen Pool table, large bedrooms & the master bath is also a steam room. A 45' dock & spacious yard is great for entertaining or barbecuing. Pool Heater is available for an additional fee.

SeaEsta! Bring your boat & 1 block to the beach!
Take a 1 Block walk to Sombrero Beach, dock your boat at this waterfront home or simply relax on the patio. 3 Bedrooms 3 baths. Large deck for cooking out. Direct access to the Atlantic. 65" TVs in all rooms. Enjoy your mornings by starting at our Coffee bar. Our home is fully furnished with all the essentials. We even include Kayaks, Bikes and Fishing Poles as well as Corn Hole and Giant Jenga. Boat Rental is offered at an additional cost. - VR License No: VACA -20-147

Houseboat Getaway In Marathon
Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.

P87 - Modern 4 bedroom, 4 bath home on open water
Stunning views with premier Sombrero Beach location sets this home apart from all others! This ocean front home is spectacular inside and out! With 4 bedrooms and 4 full bathrooms this home can easily accommodate large groups; perfect for families or business colleagues. Please note, due to the number of stairs throughout this home it is not suitable for guests who have difficulty navigating stairs. There is no roof top is access.

Key West Condo with Balcony Ocean View
Enjoy beautiful views of the Atlantic Ocean while enjoying a private balcony. Newly re-modeled kitchen. Air conditioning and ceiling fans located in every room. Amenities include pool, hot tub, and tennis courts. Just a few steps across the street in Smathers Beach which offers beach chairs, umbrellas, paddle boards, kayaks and sailboats available for rent. Two vehicles max. NO TRAILERS of any kind allowed to park on property.

Blue Palms Retreat
This 3 bedroom/2 bath oceanfront home with amazing views on Cudjoe Key private heated salt water swimming pool, shaded hang out area, ping pong table, corn hole game. The pier, gazebo, kayaks and kayak launch area is shared with one other home, Latitudes. You can dock your 24' boat at the pier. The water is shallow getting out to the channel with about a 2' draft.

Hyatt Beach House-Quiet Key West Spot!
Located 2.7 miles from Smathers Beach and 3.8 miles from the Ernest Hemingway Home & Museum, this quiet piece of Key West is the best location for relaxation. The property is on a corner of the island featuring its own private beach and water access. Other activities in the area include scuba diving, snorkeling, parasailing, fishing, dolphin watching, and boating.
Popular amenities for Stock Island beachfront rentals
Pet-friendly beachfront home rentals

Beach Home and Boater’s Paradise Sombrero

Adventurers escape breathtaking off-grid houseboat

Powell Family Resort

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS

RV In The Keys | Tropical Retreat

Key West Luxury Houseboat at Yacht Club Resort

Family Retreat

Calypso Cottage
Beachfront home rentals with a pool

Marathon Beachfront | 2 Queens + Veranda

Marathon Oceanfront | 2 King Beds + Balcony

Marathon Beachfront Suite | 1BR Veranda +Luxe Bath

Marathon Beachfront | King Bed + Veranda

Marathon Beachfront | 2BR, Veranda + 2 Luxe Baths

WATERFRONT GALLEON BEACH & MARINA, 2BR+Amenities

Marathon Beachfront Suite | 1BR Veranda +Luxe Bath

Marathon Beachfront | ADA 2 Queens + Veranda
Private beachfront home rentals

The Galleon Resort in beautiful Key West-2 bedroom

Ocean Dream – Your Private Beach + Pool (M#31)

Hyatt Windward Pointe Resort: Beachfront Condo

(# 6)Waterfront Beautiful 4 Bed 3 Bath Pool Home

Oceanfront Key West Condo

Private Beach House Resort Oasis, 2-Bedroom Suite

Oceanside home 107,dock,kayaks,bikes,pool,fishing,

ATLANTIS...Ocean Front Cottage Retreat!
Quick stats about beachfront rentals in Stock Island

Total holiday rentals
Explore 10 holiday rentals in Stock Island

Nightly prices starting at
Stock Island holiday rentals start at $663 NZD per night before taxes and fees

Verified guest reviews
Over 430 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Holiday rentals with a pool
10 properties feature pools

Wi-Fi availability
10 of Stock Island holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Stock Island rentals

4.9 Average rating
Stock Island stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Havana Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Four Corners Holiday rentals
- Key West Holiday rentals
- Rentals with a fire pit Stock Island
- Apartment rentals Stock Island
- Waterfront rentals Stock Island
- Rentals with a washing machine and dryer Stock Island
- Rentals with a hot tub Stock Island
- Rentals with beach access Stock Island
- Hotel rooms Stock Island
- Boat rentals Stock Island
- Rentals with a patio Stock Island
- Rentals with an EV charger Stock Island
- Rentals with a kayak Stock Island
- Rentals with pools Stock Island
- Family-friendly rentals Stock Island
- Fitness-friendly rentals Stock Island
- Condo rentals Stock Island
- Pet-friendly rentals Stock Island
- Rentals with outdoor seating Stock Island
- House rentals Stock Island
- Beachfront rentals Monroe County
- Beachfront rentals Florida
- Beachfront rentals United States
- Sombrero Beach
- Smathers Beach
- Long Beach
- Bahia Honda State Park
- Fort Zachary Taylor Historic State Park
- Ernest Hemingway Home & Museum
- Sunset Park
- Seven Mile Bridge
- Key West Lighthouse Museum
- Florida Keys Aquarium Encounters
- Key West Butterfly & Nature Conservatory
- Southernmost Point
- The Turtle Hospital
- Boyd's Key West Campground
- Calusa Beach & Loggerhead Beach
- Boca Grande Key




