Waterfront vacation rentals in Summerland Key

4.94 out of 5 average rating, 165 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.

4.92 out of 5 average rating, 133 reviews

A covered Tiki Hut is featured at the waterfront, furnished with comfortable seating arrangements. Views of the water and dock are visible beyond the structure, framed by lush greenery and palm trees. The space is designed for relaxation and enjoyment of the serene surroundings.

Home in Key Colony Beach

Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

4.9 out of 5 average rating, 235 reviews

A motorboat is anchored on calm waters, featuring a spacious front deck. Two individuals are seated comfortably, enjoying the view. The boat's sleek design is complemented by a canopy overhead and small steps leading into the water, creating a relaxed atmosphere.

Boat in Key West

Stay on Roxie - free transport & snacks, BYOB.

Read our reviews and relax with last minute weather cancellation! 🌞 Shower, toilet and power to recharge phones, full cellular. Enjoy a peaceful night or two on the water! Free parking and one free round trip transport to/from Roxie per night stay! Roxie is anchored in ~3ft lagoon. We live on a boat a half-mile away if you need anything at all! Roxie has a Keurig, coffee pods, bread, peanut butter-jelly, and bottled waters. No cooking but you may bring to-go food, beer/booze/wine. 🛥️🌴🎣

4.96 out of 5 average rating, 181 reviews

A spacious outdoor porch features a round dining table surrounded by four chairs. A kayak is positioned nearby, and lush greenery and water views are visible in the background, enhancing the inviting outdoor space.

Villa in Duck Key

Beach House Getaway - Kayaks - 2BR 2.5BA Villas

Welcome to Beach House Getaway, a charming villa tucked away on the serene island of Duck Key and perfectly situated in the heart of the Florida Keys. Nestled between Key Largo and Key West, Duck Key serves as a peaceful yet convenient base for your island getaway. Its central location means you’re just a short drive from some of the most iconic destinations in the Keys, including the natural wonders of Bahia Honda State Park, the famous waters around Islamorada, and the lively Key West.

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.

4.93 out of 5 average rating, 119 reviews

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.

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, 142 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!

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.

4.84 out of 5 average rating, 118 reviews

Spanish Queen @Venture Out

Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

5 out of 5 average rating, 4 reviews

Home in Little Torch Key

Florida Keys Retreat

Apretreats home. Perfect for large boats or multiple watercrafts! Total 200 ft of dockage: 100ft of dock on the basin side! 18 ft deep! Another 100ft of dock on the canal side Large 5/4 home, where you can be together and have privacy at the same time Upstairs you have 3/2 2 king bedrooms 1 queen bedroom Downstairs you have 2 1/1 units, each with their own kitchenette, king bedroom Downstairs and futton/sleeper sofa Take a dip in the pool NOT PET FRIENDLY

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.

4.82 out of 5 average rating, 106 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, 107 reviews

A scenic waterfront area is depicted with vibrant green lounge chairs positioned on a sandy peninsula. Surrounding waters provide a tranquil blue hue. Wooden docks extend into the bay, complemented by lush palm trees and colorful buildings in the background.

Home in Summerland Key

Waterfront Anchor House with Boat Basin & Ramp!

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!

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, 130 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.

A vibrant sunset casts a warm glow over the outdoor area featuring a sheltered gazebo, surrounded by lush greenery and reflective water. Nearby, a modern living room is furnished with comfortable seating and a large screen, creating an inviting space for relaxation.

4.95 out of 5 average rating, 113 reviews

Coco Plum Waterfront Hideaway Home in Marathon

This Coco Plum home is the ultimate family getaway! With four bedrooms, two bathrooms, a modern living room with a 4K TV and surround sound, and an outdoor area that includes a fire pit, outdoor dining, and outdoor living space. The boat dock and breathtaking sunset views make this the perfect home for your fishing adventures. Beautiful Coco Plum beach is just a ten minute walk away. Make this home your next island adventure.

Popular amenities for Summerland Key waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

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.

4.91 out of 5 average rating, 163 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

5 out of 5 average rating, 20 reviews

An aerial view captures the layout of the Ocean Isles Fishing Village, showcasing multiple light blue condos with white roofs positioned along winding roads. The Atlantic Ocean glimmers in the background, surrounded by lush greenery and residential areas, illustrating the tranquil setting of the Florida Keys.

Apartment in Marathon

Oceanfront Getaway in Marathon! VACA-23-267

Apartment in Key Colony Beach

A shaded tiki hut with a thatched roof stands on the sandy shore, overlooking the calm, blue waters of the Atlantic Ocean. Two palm trees frame the structure, creating a serene beach environment, with gentle waves lapping at the rocks in the background.

4.86 out of 5 average rating, 137 reviews

Beachside Unit 22 - Private Beach on Atlantic

5 out of 5 average rating, 9 reviews

Apartment in Marathon

Villa 4204 on Duck Key - Boat Slip available

5 out of 5 average rating, 11 reviews

Apartment in Marathon

New! Waterfront Views | Pool & Tiki Bar

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.

4.87 out of 5 average rating, 75 reviews

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

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

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.

4.9 out of 5 average rating, 10 reviews

Henry's Penthouse On The Ocean

Waterfront house rentals

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.

4.93 out of 5 average rating, 28 reviews

Pelican's Roost, Waterfront comfort at Venture Out

5 out of 5 average rating, 20 reviews

Waterfront 2-bedroom Home w/Pool and Spa

5 out of 5 average rating, 32 reviews

An aerial view captures the beach house surrounded by lush greenery and neighboring properties along the waterway. A spacious dock extends into the canal, providing easy access to the ocean, while the large rooflines emphasize the coastal architecture.

Home in Key Colony Beach

Easy Ocean Access 30' Dock House Pool Cabana Club

A serene patio area showcases a private pool with illuminated edges, creating a calming ambiance. Outdoor furniture is arranged on a synthetic grass surface, framed by lush greenery and a tranquil water view, as the sky transitions to sunset hues in the background.

4.96 out of 5 average rating, 28 reviews

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

The exterior of a yellow house is shown with multiple windows providing natural light. A bike stands parked on the gravel beside a garden featuring tropical plants. Stairs lead to the entrance, and the surrounding area is landscaped with pebbles.

4.85 out of 5 average rating, 26 reviews

Fisherman's Paradise Cudjoe Key

A private wooden dock extends over calm waters, featuring a boat with a blue canopy and a small table with colorful umbrellas nearby. Palm trees line the waterfront, and a series of pastel-colored homes are visible across the canal, creating a serene setting.

5 out of 5 average rating, 124 reviews

Waterfront Oceanside, 60 Ft Dock, As seen on HGTV

A charming oceanfront house is set against the backdrop of the tranquil Atlantic Ocean. Lush greenery surrounds the property, while a vibrant blue pool is visible beneath the spacious overhang. The home features a light-colored exterior and a green metal roof, harmonizing with the coastal environment.

5 out of 5 average rating, 8 reviews

Amazing Oceanfront Home

4.78 out of 5 average rating, 9 reviews

*NEW!*Paradise Point~VIEWS!~Open Water~Dock~Pool!

Waterfront condo rentals

A spacious outdoor patio is viewed, featuring a dark wooden table and black wicker chairs. A decorative rope centerpiece is placed on the table. The horizon displays a vivid sunset with shades of orange, pink, and purple, casting a serene reflection over the calm water.

4.97 out of 5 average rating, 93 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

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

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

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, 256 reviews

Waterfront 2BR Condo | Pool | Key West

Condo in Key Colony Beach

An expansive view of a private beach is captured, showcasing gentle ocean waves lapping at the shore. Lounge chairs are arranged on a green lawn, offering relaxation options while a solitary figure strolls along the sandy beach. Palm trees frame the scene under a partly cloudy sky.

5 out of 5 average rating, 24 reviews

Private Beach in Marathons Key Colony Beach

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, 105 reviews

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

4.97 out of 5 average rating, 116 reviews

A light-filled living area is visible, featuring a comfortable seating arrangement and a mounted television. A dining table occupies the foreground, adorned with a bowl of oranges. The walls are painted in soft blue, providing a relaxed atmosphere, with a ceiling fan overhead.

Condo in Marathon

Slip, Ramp, Pool, Trailer Parking, Bait Freezer