Holiday rentals with beach access in Stock Island

4.89 out of 5 average rating, 177 reviews

An American flag is displayed on a balcony, gently waving in the ocean breeze. The calm waters are reflected under a cloudy blue sky, creating a serene atmosphere. White railings and chairs frame the view, emphasizing the oceanfront location.

Cottage in Cudjoe Key

ATLANTIS...Ocean Front Cottage Retreat!

ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

ViewWalkabilityQuiet

A charming cottage features a covered deck with a dining table and chairs, positioned beside a pool. Lush palm trees and tropical plants surround the area, adding greenery. The pool water is clear and inviting, with a depth marking visible at the edge.

4.95 out of 5 average rating, 403 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.

ViewBeachWi-Fi

4.97 out of 5 average rating, 129 reviews

The living room features a light-colored couch and love seat, complemented by decorative pillows. A coffee table sits in the center, and a Smart TV is mounted on the wall. Natural light is provided by the sliding glass doors, leading to an outdoor space.

Cottage in Cudjoe Key

Beautiful Cottage & Amenities in Gated Community

Our comfortable, beautifully decorated two bedroom/two bathroom home with full sized kitchen is located in the Venture Out gated community. This is the perfect place if you are looking for peace in a quiet, family friendly, safe environment. Amenities include on-site convenience store, saltwater pool, spa, tennis courts, pickleball courts, a marina with marine fuel, double wide boat ramps, pool table, ping-pong, and much more, in a gated 24-hour security resort. All guests must be registered.

WalkabilityBeachAmenities

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, 210 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 & drip coffee New stainless appliances In-unit, full size washer/dryer Located near restaurants, a convenience store, Beach, beach towels One parking space, no charge

WalkabilityBeachAccuracy

4.81 out of 5 average rating, 114 reviews

A clear view of the sparkling waterway is framed by lush palm trees, with a blue boat docked on the left. The scene captures a seamless blend of greenery and water, while the surrounding landscape offers unobstructed access to open waterways.

Bungalow in Cudjoe Key

Cudjoe Key OCEANFRONT 2B/2B in gated community!!

Pets are not allowed. Sparkling clean and beautifully remodeled 2Bd/2Ba vacation home that features OPEN WATER views with great boating access to the ocean or gulf! This waterfront paradise features a 35' concrete seawall. There is a resort usage fee of $125 payable upon arrival to Venture Out. Pre-registration form of guests must be completed prior to stay or when checking in at the security gate. Check out my other property right next door! airbnb.com/h/islandtherapy46444432

BeachViewFamily

4.83 out of 5 average rating, 183 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.

WalkabilityBeachAccess

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.

4.89 out of 5 average rating, 157 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!

BeachViewShared spaces

4.92 out of 5 average rating, 235 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

ViewWalkabilityLocation

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.

4.87 out of 5 average rating, 134 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.

ViewWalkabilityComfort

A large heated Olympic-sized pool is set within a tropical landscape, surrounded by palm trees and lounging chairs. The inviting blue water reflects the sky and is complemented by the nearby resort building, which features multiple levels and balconies.

4.92 out of 5 average rating, 200 reviews

KW Luxury 2/2 Beachfront resort Tropical Oasis

1357 s f Lux beachfront resort condo w/ all the amenities - beachfront huge heated pool, 3 lighted tennis courts, 20 man hot tub, tropical gardens, beach, saunas, Gym, BBQ Grills everything to make your vacation spectacular! You must be at least 25 years old to rent this property. This is a no animal rental due to extreme allergies of the owner. 16% mgmt fee is Abnb fee.

ViewBeachCheck-in

A bright living area features a green sofa adorned with decorative cushions, flanked by two woven ottomans. Natural light filters through the white curtains, while a large television and colorful wall art enhance the space. Rattan accents and indoor plants bring a refreshing touch.

4.92 out of 5 average rating, 119 reviews

Betty's Place

Welcome to our charming 2-bedroom, 2-bathroom getaway, nestled in the tropical surroundings of Cudjoe Key, which is located 20 miles from Key West, the most southern point in the United States. This cozy retreat offers the perfect blend of comfort and convenience, ideal for couples, families or a group of friends looking to explore the beauty of the Florida Keys.

BeachWalkabilityAmenities

The outdoor swimming pool features a circular design surrounded by tropical palm trees and lounge chairs. Bright blue umbrellas provide shade for guests, while the clear blue sky enhances the vibrant atmosphere of the gated community.

4.94 out of 5 average rating, 155 reviews

Paradise found

Located on Stock Island this 3 bedroom home is only 8 minutes from Duval street. Walking distance to several great restaurants. Gated community with a gym and large resort style swimming pool. Queen bedroom on first floor with full bath. Second floor King room with private full bath. 3rd bedroom as two twin beds beds with private full bath.

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Popular amenities for Stock Island Accommodation with Beach Access

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

4.92 out of 5 average rating, 13 reviews

Oceanview condo w/pool, jacuzzi and tennis court

BeachViewAccuracy

The modern building is designed with balconies overlooking a serene pool area. A turquoise pool is bordered by lounge chairs and palm trees, creating a refreshing outdoor space. The backdrop features a clear sky and a sandy waterfront, enhancing the tranquil ambiance.

4.93 out of 5 average rating, 41 reviews

Oceanfront Condo in Key West, FL

BeachViewSleep quality

The resort pool is surrounded by palm trees and lush greenery, creating a serene atmosphere. Several lounge chairs are arranged neatly along the pool's edge, inviting relaxation under the clear blue sky. Breezy shades from umbrellas offer spots for comfortable seating.

Hyatt Beach House, Key West - 2 bedroom suite

CheckoutHospitalityCheck-in

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

HospitalityCheck-inLocation

4.6 out of 5 average rating, 10 reviews

Key West Condo 2nd Floor 2BDR beach, pool, balcony

WalkabilityBeachHospitality

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.

4.69 out of 5 average rating, 169 reviews

Heart of Old Town Key West

WalkabilityBeachBathroom

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.

4.91 out of 5 average rating, 11 reviews

Welcome to Your Tropical Key West Island Getaway

AmenitiesPoolValue

Fantasy Fest Week! Hyatt Windward Pointe.

Holiday House Rentals with beach access

A spacious heated pool is set amidst lush tropical landscaping, featuring palm trees and vibrant greenery. Several lounge chairs line the pool area, and a thatched-roof hut provides additional shade. The scene is enhanced by bright blue skies with scattered clouds.

4.74 out of 5 average rating, 143 reviews

Luxury Home- Parking, Bikes, WI-FI, Big Pool.

WalkabilityViewPool

Adirondack chairs are positioned on a coastal patio, providing views of the water and distant shoreline. Gentle waves reflect the sky, dotted with clouds. A palm tree sways lightly nearby, enhancing the serene environment by the water's edge.

4.97 out of 5 average rating, 92 reviews

Ocean's Edge VO Pad Boards, Kayak, Bikes-30 min KW

ViewBeachCheck-in

A charming waterfront villa is framed by lush palm trees, featuring a spacious sandy area with vibrant landscaping. A boat is docked nearby, with soft clouds drifting across the blue sky, contributing to a serene outdoor environment.

4.97 out of 5 average rating, 29 reviews

Aug. Discount, Waterfront Retreat/Pool/golf cart

ViewWalkabilityCheck-in

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.

4.97 out of 5 average rating, 33 reviews

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

ViewBeachLayout

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.

4.89 out of 5 average rating, 35 reviews

Pelican's Roost, Waterfront comfort at Venture Out

WalkabilityViewKitchen

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.

4.88 out of 5 average rating, 90 reviews

Cozy 2 br/2 bath home in Cudjoe

ViewBeachCleanliness

A charming cottage entrance is framed by lush tropical vegetation, including palm leaves and colorful plants. A small heated jacuzzi is visible beside the brick pathway leading to a light blue door with white trim. Two rocking chairs sit on the welcoming porch.

4.78 out of 5 average rating, 68 reviews

Historic Key West - Cigar House - Sleeps 4

WalkabilityBeachParks

5.0 out of 5 average rating, 8 reviews

Bahari House | Bahari House - Close to the Bars

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Holiday condos with beach access

4.97 out of 5 average rating, 36 reviews

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

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

BeachViewAir conditioning

A hand holds a tall, fluted glass filled with a yellow beverage against a backdrop of palm trees and the Atlantic Ocean. The clear blue sky complements the tranquil scene, with greenery visible in the foreground and a beach path in the distance.

5.0 out of 5 average rating, 46 reviews

Key West Condo with Balcony Ocean View

BeachWalkabilityBathroom

A spacious living area is furnished with two blue sofas adorned with decorative pillows. A mounted mirror reflects natural light from large sliding glass doors that lead to a balcony with outdoor seating. Wood-like flooring adds warmth to the inviting space.

4.83 out of 5 average rating, 24 reviews

Charming Key West By the Sea

BeachViewGetting around

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.

5.0 out of 5 average rating, 22 reviews

Hyatt Beach House-Quiet Key West Spot!

WalkabilityViewKitchen

4.85 out of 5 average rating, 40 reviews

Henry's Piece of Paradise On The Ocean In Key West

WalkabilityViewHospitality

A balcony is seen featuring a dining table set for four, with place settings and seaside views. Two chaise lounges are positioned nearby, ideal for relaxing. Lush greenery and ocean views are visible beyond the railing, creating a serene outdoor space.

4.74 out of 5 average rating, 47 reviews

Shang-Ri-La at The Beach

BeachViewAccuracy

A community pool is framed by a white railing, inviting relaxation. The surrounding area features palm trees and tropical foliage, while a yellow building with green shutters looms in the background. The pool depth is marked, and a set of stairs leads into the water.

4.67 out of 5 average rating, 33 reviews

Key West Sunrise Condo - Special Summer Rates

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