Waterfront vacation rentals in Stock Island

4.95 out of 5 average rating, 182 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 MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

A serene view of a waterfront canal is captured from a covered porch. The calm water reflects the sky, with boats docked along the edges. Palm trees gently sway in the breeze, enhancing the coastal setting. Nearby structures suggest a vibrant community atmosphere.

4.81 out of 5 average rating, 324 reviews

SEPT/OCT. Save$Oceanfront 4 BIKE/2 Kayak KING Bed

*PERFECT LOCATION! * 35' Seawall *AWESOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. At MM# 23 only 25min to Key West. In a gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C *Fully equipped kitchen *Includes grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library. Too much to list! WE WILL NEED YOUR EMAIL WHEN YOU CONFIRM THE BOOKING IN ORDER TO SEND YOU THE REGISTRATION FORMS AND THE RULE PACKET.

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, 141 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.

4.83 out of 5 average rating, 186 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.

A refreshing pool area is surrounded by green palm trees and blue umbrellas. Lounge chairs are arranged neatly around the pool, while tables with chairs provide seating for guests. The clear blue sky enhances the inviting atmosphere of the community space.

4.85 out of 5 average rating, 149 reviews

Penthouse in Paradise

Coconut Mallory is a waterfront private community that provides resort amenities. Hop in one of the two on-site pools to cool down after soaking up the sun at Smathers Beach, Key West's largest public beach just 2 miles away. There is also a Jacuzzi and a picnic area with BBQs for guest use. This unit is a two bedroom two bath. It also features two off street parking spaces included. *The Master Tub is not to be used per the community as leaks have occurred in other units before.

Home in Upper Sugarloaf Key

The bungalow stands illuminated against a night sky, surrounded by swaying palm trees. Soft reflections shimmer on the water's surface, while the sandy beach extends along the shoreline. The structure features large windows, showcasing a welcoming interior visible from outdoors.

The Lighthouse - Beach Houses Key West

If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.

4.93 out of 5 average rating, 134 reviews

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.

4.89 out of 5 average rating, 288 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.

An aerial view showcases a coastal community with a spacious beach area, palm trees, and turquoise waters. The two-story unit features a large balcony above the entrance, with the surrounding buildings and lagoon clearly visible, highlighting the vibrant landscape of the area.

4.96 out of 5 average rating, 213 reviews

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

A heated pool is surrounded by a spacious deck, featuring lounge chairs and a dining table with blue chairs. Beyond the pool, a pathway leads to lush greenery and the ocean view under a partly cloudy sky.

4.83 out of 5 average rating, 112 reviews

Palm Breezes! Room for Everyone on the Ocean.

This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1.. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Grill, Jacuzzi. Full WiFi. TVs in every bedroom! Travel down our private dock way to the beautiful Cudjoe Bay, hop one of the many kayaks and take a healthy paddle with your friends/family or just enjoy the breathtaking ocean view while you sit on the porch.

4.95 out of 5 average rating, 116 reviews

Home in Summerland Key

Anchor House

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Haven House to reserve both homes if available). Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the point and enjoy the underwater scenery!

4.93 out of 5 average rating, 241 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

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.

4.88 out of 5 average rating, 136 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.

Popular amenities for Stock Island waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

A spacious outdoor patio is displayed, featuring a dining table surrounded by six chairs. The railing offers a view of Garrison Bight Marina, where boats are docked and palm trees sway. Sunlight casts patterned shadows across the patio floor.

4.89 out of 5 average rating, 105 reviews

Key West Condo 2B/2B with Pool & Boat FREE Slip

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, 201 reviews

KW Luxury 2/2 Beachfront resort Tropical Oasis

A lush garden expanse is depicted, featuring vibrant greenery and colorful flowers. Palm trees sway in the gentle breeze, while the ocean is visible in the background. A pool is nestled within the landscaped area, complemented by a shady outdoor dining space under a canopy.

5.0 out of 5 average rating, 4 reviews

Best Resort in Key West, 2BD/2BA

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

The exterior of a multi-level villa is shown, featuring a light-colored façade with green shutters and a metal roof. Lush palm trees surround the building, offering a tropical ambiance, while a glimpse of the ocean is visible in the background against a serene sky.

4.82 out of 5 average rating, 11 reviews

Hyatt Windward Pointe! Great Location!

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.

4.92 out of 5 average rating, 12 reviews

Henry's Penthouse On The Ocean

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.

Apartment in Big Pine Key

Hyatt Beach House, Key West - 2 bedroom suite

The kitchen features modern white cabinetry with a granite countertop. Appliances include a refrigerator, oven, microwave, and dishwasher. A coffee maker is also visible, along with a sink located beneath a window with patterned curtains. The backsplash is designed with light-colored tiles for an elegant touch.

New Deluxe Duplex Unit, 2 Queen Beds, Unit G-4

4.79 out of 5 average rating, 106 reviews

Waterfront house rentals

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.

4.88 out of 5 average rating, 162 reviews

Waterfront Sanctuary in the Keys!

An aerial view captures a vibrant community of stilt homes nestled along the coastline, with clear blue waters stretching in the background. Lush palm trees dot the landscape, while a distinctive red marker indicates a specific location within this scenic setting.

4.83 out of 5 average rating, 131 reviews

Spanish Queen @Venture Out

4.81 out of 5 average rating, 16 reviews

Home in Key West

KW CanalFront 3BR: Htd Pool, Boat Tie-Up, Pet OK

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, 30 reviews

Jan. Disc, Waterfront Retreat/Dock/Pool/golf cart,

4.94 out of 5 average rating, 18 reviews

Oceanfront 2BR in Venture Out - 35’ Dock + Pool

A two-story waterfront home is situated under a clear blue sky, surrounded by palm trees and lush greenery. The property features a bright white exterior with a balcony, along with a manicured yard of decorative rocks and native plants.

4.95 out of 5 average rating, 92 reviews

Keys Island Villa - Venture Out Home 354

4.97 out of 5 average rating, 60 reviews

Tiki Time in Cudjoe Key 136

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, 97 reviews

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

Waterfront condo rentals

A serene pool area is visible in the foreground, bordered by lush greenery and ocean views. Tall palm trees sway gently along the shoreline, where the calm water reflects the sky. A distant pier can be seen, enhancing the coastal atmosphere.

4.93 out of 5 average rating, 185 reviews

Beach Club Ocean Front 2BR Condo

4.74 out of 5 average rating, 443 reviews

A large outdoor pool is framed by lounge chairs in vibrant blue, surrounded by tropical palm trees. The sun casts a warm glow over the water, while boats are visible in the distance, enhancing the serene atmosphere.

Condo in Stock Island

Grand Marina Suite - Poolside & Waterfront Condo

4.97 out of 5 average rating, 29 reviews

The Lark's Landing at Sunrise Suites

A scenic view from the balcony showcases palm trees swaying gently near a sandy beach. The turquoise ocean blends into the blue sky, with wispy clouds visible. Sunlight reflects off the water, enhancing the tranquil atmosphere of the coastal landscape.

4.88 out of 5 average rating, 78 reviews

Somewhere on the beach

4.81 out of 5 average rating, 81 reviews

Casa Papa Del Mar Ocean Front 1800 Atlantic specta

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

4.76 out of 5 average rating, 34 reviews

Andy’s Attic | Budget-Friendly!