Apartment holiday rentals in Stock Island

A charming entrance is framed by lush tropical plants and palm trees. The light green door complements the inviting beige exterior of the home. A cozy seating area is situated on the porch, and brick pathways lead through a landscaped yard filled with vibrant foliage.

4.94 out of 5 average rating, 109 reviews

Tropical Heron Hideaway w/ Hot Tub + Pool

Welcome to our unique and charming Airbnb. This cozy retreat offers the perfect blend of comfort and style, featuring a private porch where you can relax and enjoy the island breeze. Take a dip in the refreshing pool or unwind in the private hot jacuzzi after a day of exploring. Enjoy cooking a delicious meal on the grill, and experience a peaceful stay in a one-of-a-kind space. Whether you're here to relax or explore, our home provides everything you need for an unforgettable Key West getaway!

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, 200 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

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.

4.99 out of 5 average rating, 135 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.

A charming white wooden building features a wraparound porch with multiple chairs overlooking the street. The ground floor showcases a variety of colorful shop windows, while the upper level includes several dormer windows under a sloped roof. Lush greenery and palm trees are visible nearby.

4.79 out of 5 average rating, 100 reviews

Cuban Paradise @ Cuban Club

Built in 1917 as a “club” for Cuban cigar makers and their families as their home-away-from-home, this building soon became the center of social and community life for the Cuban population in Key West. After the original Cuban Club burned down in 1983, it was restored and converted to luxurious and spacious suites. Escape the stress and cares of your daily life with a vacation to the wonderful Cuban Paradise! This roomy two-bedroom condo has a private balcony to enjoy all the hustle and

Apartment in Summerland Key

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.

4.97 out of 5 average rating, 31 reviews

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!

A private balcony is shown, featuring colorful patio chairs and vibrant tropical plants. The space is framed by white railings and light blue shutters, creating a fresh and inviting setting for relaxation.

4.89 out of 5 average rating, 293 reviews

Tropical Old Town Bungalow

Great Location, Close to Duval & Beach Welcome to paradise! This Tropical Old Town Bungalow is located perfectly between Key West’s best beaches and the best restaurants and nightlife! The rental unit sits right between the White Street Art Gallery District and the Historic District, which features some of Key West’s most historic homes and properties. Whether you are walking, riding bikes or grabbing a quick cab, no destination is too far from this conveniently located rental.

A bright and airy living space features a large sectional sofa, a dining area with a light-colored table and chairs, and large glass doors leading to a balcony with water views. Light wood paneling and artwork enhance the overall ambiance.

4.88 out of 5 average rating, 266 reviews

Waterfront Dock Pool Condo Near Duval St Pet OK

Bring friends and family to this spacious 1,350 sq ft waterfront corner condo in historic downtown Key West. Enjoy a full kitchen, open living space, and a private balcony with marina and pool views. Dockage available with a fish cleaning station and commercial ice maker, perfect for boating and fishing. Located about 1 mile from Duval Street, the Historic Seaport, and Hemingway House. Amenities include a heated pool, tiki area, BBQ grills, parking, elevator, and secure entry.

A spacious living room is furnished with a soft blue sofa and matching armchair. Light wooden flooring complements the room's bright atmosphere, and a coffee table sits in the center. Large sliding glass doors lead to a patio area, allowing natural light to fill the space.

4.9 out of 5 average rating, 177 reviews

Tropical Escape at Sunrise

We thoroughly sanitize upon check-out. This luxurious condo features a wonderful tropical interior design. It includes 2 spacious BR's: king bed/ full bath, queen bed/ full bath). Our living room sofa bed accommodates 1 guest. A fully equipped kitchen. Patio overlooks pool. WiFi, basic cable, 3 TV's, A/C, washer-dryer, workout center, BBQ, tennis court, elevator, parking. Accommodates no more than 5 guests. Must be 25 and older.

A light-filled living area features a comfortable sofa paired with accent tables. Soft blue walls create a calming backdrop, while stylish decor elements, such as framed artwork and lamps, add character. A mirror reflects the space, enhancing its openness and inviting ambiance.

4.99 out of 5 average rating, 81 reviews

EYW Getaway

Relax with the whole family at this peaceful place to stay. Our two-bedroom two-bathroom condo with complete kitchen is located at Sunrise Suites Resort. Amenities include shared heated pool, hot tub, tennis court and a basic gym. Our condo is located 1mile from the airport, 1.5 miles from the beach and 3.5 miles from downtown Duval St.

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, 314 reviews

Affordable Beachfront Luxury Condo Sleeps 6

My place sits on Smather's beach! Close to downtown and the airport. You’ll love the condo because of the location, the large indoor space, it's quiet, the pool, and has all the comforts of home. My condo is good for couples, solo adventurers, business travelers, families (with kids), and big groups. It’s spacious - and very clean!

4.87 out of 5 average rating, 137 reviews

Moonlight Paradise Upgraded Family oasis Tropical

Moonlight is a totally renovated condo that is located at 1800 Atlantic Blvd on the beach, with sunset views right from your own private balcony. Beautiful tropical decor. No attention to detail has been spared. Stainless Appliances & luxurious finishes.

New place to stay

Seas the Breeze – Poolside Condo Near the Beach

🌴 Seas the Breeze – Poolside Condo Near the Beach Relax in this poolside island retreat on the quiet side of Key West. This 2BR condo offers a peaceful setting with a heated pool, hot tub, and tennis courts, and just minutes from the beach.

Popular amenities for Stock Island apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

A serene waterfront view reveals gentle waves lapping against a sandy shoreline. Beach chairs are arranged near the water, providing a relaxing spot to enjoy the scenery. Lush palm trees frame the tranquil setting, enhancing the sense of peacefulness.

4.95 out of 5 average rating, 44 reviews

Condo de Paradise/Salt Water Pool/Boat Dock

5 out of 5 average rating, 24 reviews

Spacious unit + pool+ Kitchen. Desirable Resort

An ocean view is captured from the private balcony, showcasing lush palm trees and other tropical vegetation. The calm waters of the Atlantic are visible in the distance under a sky filled with soft clouds, creating a serene coastal atmosphere.

4.62 out of 5 average rating, 13 reviews

Magical Sunrises on the Atlantic, Upgraded Condo &

An open-concept living area offers a view of comfortable seating arrangements and natural light. The kitchen features a marble countertop and modern appliances. A balcony is visible through sliding glass doors, surrounding greenery enhancing the serene environment.

4.89 out of 5 average rating, 64 reviews

Key Lime Paradise 2bed 2bath Sleeps 6 Pool Hot tub

5 out of 5 average rating, 10 reviews

An aerial view captures the expansive outdoor pool surrounded by lounge chairs, with vibrant palm trees framing the scene. The tiki bar and grill overlook the calm lagoon waters, while boats can be seen in the distance, enhancing the coastal atmosphere.

Apartment in Marathon

Marathon 2BR Waterfront property on Resort

A view from a private balcony showcases the resort pool, surrounded by palm trees and a sun terrace. Lounge chairs are arranged neatly around the pool, while shaded seating areas provide options for relaxation. The bright blue sky enhances the atmosphere of leisure.

4.76 out of 5 average rating, 285 reviews

Pool View Suite | Beachside Resort

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, 21 reviews

Hyatt Beach House-Quiet Key West Spot!

A serene courtyard is surrounded by lush tropical landscaping, featuring a sparkling pool at its center. Comfortable loungers are positioned around the pool area, providing a space for relaxation. The backdrop includes a charming two-story building, enhancing the inviting atmosphere of this private retreat.

4.97 out of 5 average rating, 70 reviews

Coral Palms 1BR/King/Queen, Pool, block to Duval

Pet-friendly apartment rentals

4.81 out of 5 average rating, 300 reviews

Steps to Duval! Old Town. 3 blks to South Beach

A bright living area features a plush blue sofa adorned with colorful throw pillows. A coffee table sits in front of the sofa, surrounded by light wood accents. Large glass doors lead to a private balcony, inviting natural light and views of greenery.

4.96 out of 5 average rating, 25 reviews

The Butterfly Nest | Newly Updated w/ Shared Pool

4.87 out of 5 average rating, 284 reviews

Waterfront Condo | Pool, Dock, Parking, Sleeps 8

4.73 out of 5 average rating, 173 reviews

Walkable 1BR | Deck | Pool | Dog Friendly

An outdoor tiki bar with a thatched roof is situated next to a heated pool. Surrounding palm trees add a tropical touch. A table with four chairs is positioned on the deck, providing a space for relaxation and enjoyment of the waterfront view.

4.87 out of 5 average rating, 52 reviews

Waterfront Dock Pool Downtown Near Duval Pet

The living area features a light, airy ambiance with natural wood tones and comfortable furnishings. A spacious sofa is complemented by two armchairs, all arranged around a central coffee table on a textured area rug. Natural light filters through the woven shades of the windows, enhancing the serene atmosphere.

4.8 out of 5 average rating, 46 reviews

La Maisonnette~ Gated Condominium 1 Block to Duval

A spacious balcony view reveals a heated pool surrounded by lounge chairs. Tiki huts are visible nearby, alongside the boat slips and palm trees, set against a clear blue sky, showcasing a relaxing outdoor space for guests.

4.87 out of 5 average rating, 202 reviews

Waterfront Condo + Dock Pool Downtown Near Duval

A serene waterfront scene is captured at sunset, featuring palm trees, boat docks, and a gently reflecting harbor. A large boat is tied up alongside the dock, with colorful lights and silhouettes of the surrounding structures visible in the background.

4.91 out of 5 average rating, 269 reviews

Waterfront Condo Dock Pool Downtown Near Duval

Apartment rentals with a pool

4.56 out of 5 average rating, 9 reviews

Southard Quarter at Truman Annex | Walk to Duval

A private balcony features a round table set with soft blue plates and glasses of juice. Comfortable chairs surround the table, with a bowl of fresh fruit placed in the center. Lush greenery and partial ocean views contribute to a serene outdoor setting.

4.85 out of 5 average rating, 160 reviews

Anchor Drop modern elegance upgrades throughout vi

An inviting infinity pool reflects the bright blue sky and palm trees, creating a serene atmosphere. The ocean is visible beyond the pool, enhancing the tropical setting. The gentle waves and lush greenery contribute to a relaxing environment.

5 out of 5 average rating, 14 reviews

Key West at Hyatt Windward Pointe

A spacious balcony features two comfortable blue chairs and a small table. The view overlooks lush gardens and the Atlantic Ocean, framed by palm trees. Large sliding glass doors allow access to the interior, while the cloudy sky creates a serene ambiance.

4.89 out of 5 average rating, 106 reviews

Key Wes't Best- Upgraded condo 5 mins to Smathers

4.92 out of 5 average rating, 139 reviews

Orchid Bay Condo + Pool • Old Town • Walk to Duval

A cozy King bedroom features a vibrant red bedspread, complemented by decorative pillows. Soft lighting from a bedside lamp creates a calming ambiance. A full-length mirror reflects the room's decor, while a doorway leads to an adjoining bathroom.

4.65 out of 5 average rating, 264 reviews

Sunrise Suites Resort Key West, FL U #111 2bdr2bth

A view from the balcony showcases a serene ocean scene with gentle waves lapping against the shore. Palm trees sway in the breeze, enhancing the tropical atmosphere. The white railing offers a clear line of sight to the pier extending into the water.

5 out of 5 average rating, 3 reviews

Fabulous Coconut Beach Key West

A scenic view of the Atlantic Ocean is captured, with glistening waters and a partly cloudy sky. Lush palm trees line the shore, and a pool area is visible in the foreground, framed by the adjacent condominium structures, enhancing the serene coastal atmosphere.