
Condo vacation rentals in Stock Island
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Top-rated condo rentals in Stock Island
Guests agree: these condos are highly rated for location, cleanliness, and more.

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

Ocean Front Studio private Sandy Beach in Key West
Studio unit with fridge, microwave, settings for 2 and a king sized bed. Doors that open to a balcony overlooking the Atlantic Ocean. There is pool, hot tub, and a private sandy beach on the Atlantic ocean. 5 minutes walk to Duval street. The resort is located between the prestigious Casa Marina and the top restaurant on the island Louise Back Yard. There is free garage parking with the room. Washer, dryers and ice maker are available for guests. Powerful, but sometimes noisy air conditioning.

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.

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.

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage
Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip available on-site with commercial ice machine and fish cleaning station. Located in historic Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Seaport, Hemingway House, etc. On-site amenities: heated pool, boat slip, tiki bar & grills, parking, secure keyless entry, & building elevator. Large Park adjacent with tennis courts. 10min from airport (EYW).

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.

Condo de Paradise/Salt Water Pool/Boat Dock
This is one of the best kept secret locations. Can be a very romantic escape. This is a good place for honeymooners, guys or gals getaway, fishermen/fisherwomen weekend get away or family time. A private unit in paradise in a gated community. Only 10 miles to Duval Street and all that Key West has to offer. There is a dock that can be used to dock up to a 26 foot boat that can be launched at Geiger Key, a mile down the road and they will store your trailer.

Canal View Condo w/ Pool, Balcony & Bar
Celebrate the season in paradise at THE DAPPER DOLPHIN, an updated coastal-themed 1-bedroom, 1-bathroom condo, accommodating up to 4 guests. Featuring a complete kitchen, balcony, and access to resort amenities including a pool, Tiki Bar, restaurant, Marina, and more! Situated in the heart of Marathon, it offers proximity to the beach, restaurants, activities, and all the essentials for an unforgettable vacation experience right on-site!

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.

The Island Suite @ KW vacation
The Island Suite is part of a historic Key West property built around 1889. Suite #16 is located on the first floor at the rear of the 411 William Street building. The Island Suite has one of the premiere locations in Old Town, Key West with lively Duval Street just 3 blocks away and the neighborhood boasting some of the finest older homes in Key West.

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!

A Perfect Getaway
The perfect spot in the heart of Key West. Located in the exclusive Truman Annex’s gated community. Once you are in the Annex you are located near Fort Zachary Taylor National Beach and 2 blocks from Duval St. Everything is in walking distance.
Popular amenities for Stock Island condo rentals
Weekly condo rentals

Key West Paradise Poolside

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

Ocean Front Suite with Direct Beach Access

Bright Condo in Paradise

Casa Arosa

J Ferrara - Updated Studio, Pool, Walk To Duval St

Corner Unit 2BR | Deck | Pool | W/D

Charming Key West By the Sea
Pet-friendly condo rentals

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

Chagall’s Corner | Newly Remodeled!

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Free Parking, Pool, & Pet Friendly - The Trinidad

Dog Friendly 1BR | Pool | Easy Beach Access

Curaçao Key West 2BR Condo w/ Pool&Waterfront Dock

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access

La Maisonnette~ Gated Condominium 1 Block to Duval
Condo rentals with a pool

The Reef at Marathon private villa/ Marina incl

Old Town Oasis at The Annex

Rum Cay at Sunrise Suites

Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK

Heron Hideaway

Cozy apartment in Marathon Key

M18 - Spacious 3 bedroom, 2 bath Gulf side condo!

Serenity on Southard at The Annex
When is the best time to visit Stock Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R7,209 ZAR | R7,817 ZAR | R6,949 ZAR | R6,080 ZAR | R5,611 ZAR | R5,437 ZAR | R5,385 ZAR | R5,038 ZAR | R4,534 ZAR | R5,107 ZAR | R5,854 ZAR | R6,011 ZAR |
| Avg. temp | 21°C | 22°C | 24°C | 25°C | 27°C | 29°C | 30°C | 30°C | 29°C | 27°C | 25°C | 23°C |
Quick stats about condo rentals in Stock Island

Total vacation rentals
Explore 100 vacation rentals in Stock Island

Nightly prices starting at
Stock Island vacation rentals start at R1,563 ZAR per night before taxes and fees

Verified guest reviews
Over 5,310 verified reviews to help you choose

Family-friendly vacation rentals
90 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
90 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
100 of Stock Island vacation rentals include wi-fi access

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

4.8 Average rating
Stock Island stays are highly rated by guests—averaging 4.8 out of 5!
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