Vacation rentals with beach access in Stock Island

A modern living area features a spacious layout with a comfortable seating arrangement and a large flat-screen TV mounted on the light green wall. Natural light floods in through expansive glass doors, revealing views of the outdoors. A stylish kitchen island with sleek countertops complements the space.

4.95 out of 5 average rating, 166 reviews

Fully renovated 2/2 bath condo w/ shared pool!

**Brand New Listing** Welcome to Captains Choice - The NICEST Unit at Sunrise Suites Key West, unit 302. Tropical winds, sunset views and Key West charm await when you book your stay in this gorgeous completely renovated two bedroom, two bathroom condo "Captain's Choice". Highlights include: Smart TVs in each room Keurig New stainless Kitchen/appliances In-unit, full size washer/dryer Located near restaurants, a convenience store, & Smathers Beach End unit One parking space, free of charge

4.94 out of 5 average rating, 140 reviews

A serene waterfront view showcases clear turquoise waters under a bright blue sky. A boat can be seen cruising along the horizon, while a patio with seating is visible at the forefront, adjacent to a dock lined with black posts.

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.

4.97 out of 5 average rating, 273 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, renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, air fryer/oven tumbled marble 2 person shower, private front deck with seating for 4, 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

4.8 out of 5 average rating, 139 reviews

A serene waterfront view captures a light-colored building with turquoise accents, surrounded by lush palm trees. The calm water reflects the structure and sky, creating a tranquil atmosphere. Soft clouds float above, enhancing the peaceful setting of the marina.

Boat in Key West

A Great Escape! Private 2 Bed Rm Beautiful Marina

Our Marina has a pool and a small private beach overlooking the beautiful Keys water! More affordable than most places in Key West while able to reconnect with nature at this private getaway on the Great Escape. As you approach the boat, you feel your dream vacation has come true . One of a lifetime. Staying on a beautiful sportfisher yacht, laying in the waters of the calm keys and in the most beautiful peaceful marina, will definitely set you free from all your worries and stress.

The living area features a spacious sectional sofa facing a large window with multiple shutters, allowing natural light to fill the room. A modern coffee table is situated on a soft area rug, complemented by dining stools near the open kitchen with updated appliances.

4.87 out of 5 average rating, 115 reviews

Waterfront Sanctuary in the Keys!

Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property won’t disappoint! Fully stocked kitchen/bathrooms. Never ending activities for your group at the Venture Out Resort- a gated community with oversized pool, hot tub, pickle ball/tennis/basketball courts, fishing, lobstering, biking, kayaking, boating! Launch your boat from the private ramp and tie it up on our 35’ seawall! Situated between Key West & Marathon, this property is THE PLACE!

A spacious wooden deck features two light blue lounge chairs and a white umbrella, offering a relaxing spot to enjoy ocean views. The gentle waves of the Atlantic can be seen in the background, while the shore is lined with natural sand and small rocks.

4.97 out of 5 average rating, 107 reviews

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.

4.92 out of 5 average rating, 170 reviews

A serene pool area features a clear blue water swimming pool surrounded by lounge chairs and umbrellas. A lush landscape of palm trees and green foliage complements the setting, with a charming cottage visible in the background.

Townhouse in Key West

Poolside Cottage #411

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat 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, kayaks, paddle boards and golf carts can be rented locally

4.89 out of 5 average rating, 123 reviews

A cozy living space features a navy blue sofa adorned with nautical-themed throw pillows. A dining area with a glass table and chairs is visible in the background, alongside a decorative display of framed art and a potted plant. Natural light filters through the windows.

Houseboat in Marathon

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.

4.82 out of 5 average rating, 120 reviews

A private beach scene features four adirondack chairs in white and turquoise, positioned in soft, sandy areas under palm trees. The calm ocean extends to the horizon, with a distant dock visible on the water. Bright clouds hover in a blue sky.

Home in Sugarloaf Key

The Guest House - Sugarloaf Beach Key West

One of a kind beach house with a private sandy beach, dock and boat dockage . Featuring a tropical ambiance and a family friendly setting that will make you feel like you are in your own private island. Ocean views. natural Florida Keys private beach, great for swimming, snorkeling, kayaking, paddle boarding or just reading a book by a palm tree * "Dock is currently undergoing maintenance, dockage will not be available until further notice"

A comfortable outdoor seating area is showcased, with bright blue cushions arranged around a dark table. The view overlooks crystal-clear waters, and decorative lanterns provide soft lighting. A potted flower adds a touch of color beside the seating, enhancing the peaceful ambiance by the water.

4.91 out of 5 average rating, 116 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

The expansive outdoor pool is framed by palm trees and surrounded by lounge chairs with blue umbrellas. The area is well-lit and features a shaded pavilion. The surrounding building showcases tropical landscaping, providing a relaxing atmosphere for guests.

4.9 out of 5 average rating, 152 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

Welcome to our Key West Condo. This spacious well appointed 2 bedroom, 2 bath condo sleeps 6 and is next to the best beach on Key West. This condo is the perfect alternative to staying in a hotel. It gives you a true island experience. Great for Couples and Families We have a Website specific to our Condo where we offer special pricing, discounts and additional pictures Search-keywestbeachsidecondo

A clear, inviting outdoor pool is surrounded by lush tropical landscaping. Palm trees are scattered around, softening the edges of the pool area. A multi-story building with a light-colored exterior provides a backdrop, featuring several balconies with white railings.

5 out of 5 average rating, 9 reviews

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 beach access rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

A serene waterfront view displays a three-story building with white structures mirrored by the calm water. Lush greenery surrounds the property, and a small boat glides across the water, enhancing the tranquil atmosphere.

Hyatt waterfront 2 BR-sleeps 6

A light-filled living area features a comfortable gray sofa and two accent chairs, arranged around a coffee table. A media console with a television is placed against the wall. Large sliding glass doors lead to a private screened-in porch, with views of palm trees.

4.67 out of 5 average rating, 3 reviews

Welcome to Your Tropical Key West Island Getaway

A modern kitchen is displayed, featuring dark blue cabinetry and stainless steel appliances. A sleek countertop hosts a sink and modern stove, while a microwave is mounted above. Natural light enters from a nearby window, enhancing the kitchen's functional layout.

5 out of 5 average rating, 3 reviews

Rare Beach Front Resort Key West- 2BD/2BA

An inviting outdoor lagoon pool is surrounded by lush tropical landscaping and tall palm trees. A spacious deck with sun loungers provides ample space for relaxation. The pool area is well-maintained, showcasing clear blue water under bright skies.

2 BR @ Hyatt Beach House Resort

A spacious pool area features a large swimming pool surrounded by lounge chairs and vibrant blue umbrellas. Lush palm trees provide shade, and ocean views are visible in the background, enhancing the tranquil atmosphere of the outdoor space.

4.88 out of 5 average rating, 8 reviews

Henry's Penthouse On The Ocean

A spacious living area is furnished with a comfortable sofa and armchair, complemented by a wooden coffee table. A large entertainment center features a television, while soft lighting enhances the room's ambiance. The space is adorned with tasteful decor and tiled flooring.

The Galleon Resort - Key West

A private balcony features a round table surrounded by four chairs, providing a comfortable space to enjoy the ocean view. Lush greenery and palm trees are visible in the background, with the tranquil ocean further enhancing the outdoor setting.

5 out of 5 average rating, 3 reviews

Oceanview condo w/pool, jacuzzi

A vibrant sunset casts warm hues over the beach, where two figures stand with arms outstretched, silhouetted against the colorful sky. The calm ocean reflects the golden light, with a sailboat visible in the distance and grasses framing the foreground.

4.7 out of 5 average rating, 132 reviews

Heart of Old Town Key West

House rentals with beach access

A serene waterfront scene captures the reflection of clouds and colorful sunset hues on the calm water. Flanking the canal are inviting homes characterized by palm trees, with docks indicating easy access for boating enthusiasts. The peaceful setting suggests a tranquil atmosphere.

4.92 out of 5 average rating, 25 reviews

Pelican's Roost, Waterfront comfort at Venture Out

4.8 out of 5 average rating, 70 reviews

An aerial view of the cottage surrounded by lush greenery and the calm waters of a mangrove area. The property features a spacious driveway leading to the home, with natural landscapes extending towards the Gulf of Mexico in the background.

Home in Summerland Key

Kelly’s Kabin - Private FL Keys Cottage

A well-lit dining area features a round wooden table surrounded by six woven chairs. A decorative centerpiece is placed on the table. Adjacent, a cozy living space is visible, showcasing a sectional sofa, a ceiling fan, and large windows allowing natural light.

4.86 out of 5 average rating, 64 reviews

Cozy 2 br/2 bath home in Cudjoe

5 out of 5 average rating, 4 reviews

A charming cottage is surrounded by lush tropical greenery, with a welcoming front porch featuring two oversized rocking chairs. The light pink exterior contrasts with the vibrant foliage, and the entrance is framed by tall palm leaves, creating a serene and inviting atmosphere.

Home in Key West

Poolside Cottage at Simonton Court - Adults Only

Two pelicans are perched on a wooden dock, surrounded by rippling water. The dock is supported by green posts, providing a serene setting in a tropical landscape. Subtle foliage in the foreground enhances the natural ambiance of the scene.

5 out of 5 average rating, 18 reviews

Oceanside home 111, dock,kayaks,bikes,pool,fishing

Aerial view of the Venture Out community showcases a large swimming pool adjacent to the sandy beach. Palm trees surround the area, with calm turquoise waters extending into the distance. Amenities include a tiki structure and a spacious lounging area, ideal for relaxation and outdoor activities.

4.78 out of 5 average rating, 45 reviews

Waterfront FL Keys Cottage @ Venture Out

5 out of 5 average rating, 12 reviews

An outdoor lanai features a round glass table surrounded by four green cushioned chairs. A ceiling fan is mounted above, and a tree partially shades the area, providing a serene setting for relaxation.

Home in Key West

Roost Haven w/ free private parking spot

A boat is docked at a private marina, showcasing a spacious outdoor area. A fish cleaning station is visible nearby, along with a hose and power source. Colorful buildings line the waterfront, and clear blue skies reflect over the water.

5 out of 5 average rating, 6 reviews

35’ dock/Completely Remodeled VO 366

Condo rentals with beach access

4.82 out of 5 average rating, 289 reviews

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

5 out of 5 average rating, 6 reviews

Southard Quarter at Truman Annex | Walk to Duval

A clear view of a swimming pool is framed by palm trees and greenery. Lounge chairs are positioned alongside the pool, and the ocean can be seen in the distance. The scene conveys a relaxed outdoor atmosphere, inviting guests to enjoy the coastal surroundings.

5 out of 5 average rating, 4 reviews

Key West 2 BR Deluxe, Beach Front, sleeps: 6

A spacious living area features large glass doors that allow natural light to fill the room, offering views of the surrounding landscape. Comfortable blue sofas are arranged around a central coffee table on tiled flooring, complemented by a stylish armchair. Decor elements include framed pictures and modern lamps.

4.59 out of 5 average rating, 150 reviews

Colorful 2BR Oceanfront 4th-Floor | Balcony

An aerial view showcases the resort's central pool surrounded by palm trees and landscaped gardens. The inviting pool area is complemented by a spacious pavilion with a metal roof, providing a gathering space. The background features the resort's accommodations and the lush natural environment.

Condo in Summerland Key

5 out of 5 average rating, 6 reviews

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

An Olympic size pool is highlighted in the image, surrounded by palm trees and lounge chairs. The building in the background offers several balconies, and a well-maintained garden area is visible, enhancing the outdoor setting next to the beach.

4.78 out of 5 average rating, 300 reviews

Affordable Beachfront Luxury Condo Sleeps 6

The entrance of a resort is captured, featuring tall palm trees swaying gently in the breeze. A clear sky with soft sunlight peeks through the trees, illuminating the path lined with greenery. A white picket fence borders the area, adding to the welcoming ambiance.

4.81 out of 5 average rating, 47 reviews

Casa Arosa

A living room is presented with a combination of modern and inviting elements. A flat-screen TV is mounted on the wall, complemented by two seating areas featuring comfortable sofas and chairs. Natural light filters through the balcony doors, enhancing the space's brightness.