Vacation rentals with beach access in Summerland Key

4.89 out of 5 average rating, 178 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!

4.97 out of 5 average rating, 131 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.

4.93 out of 5 average rating, 154 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.

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, 212 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

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

4.97 out of 5 average rating, 37 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)

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!

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!

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!

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, 137 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.

4.94 out of 5 average rating, 122 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.

4.93 out of 5 average rating, 101 reviews

A cozy sleeping area featuring a quilted bedspread in various patterns. A kitchenette with modern appliances is visible, complemented by cabinetry. Two refrigerators are nestled in the corner, and a large mirror reflects the space. Ambient lighting and decorative touches add character.

Houseboat in Marathon

b watervibe

Enjoy the sounds of nature when you stay in this unique place. It's something different to enjoy with your partner of a romantic and fun moment and thus relax and forget about the everyday life. You can enjoy fishing, kayaking, adventure, and other local activities. A great camping experience for guests who like something fun and different. Try it and you'll tell me. It offers a space for 2 people.

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, 122 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.

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,

Step into your private oasis! This stunning home features a sprawling outdoor space, perfect for boating, fishing or relaxing under the stars. Complete with a beautiful landscaped butterfly garden, park benches and tables. This property is one of a kind compared to space and privacy. Perfect for relaxation and rejuvenation.

Popular amenities for Summerland Key beach access rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

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.

4.9 out of 5 average rating, 168 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

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 lively street scene showcases a classic two-story building featuring blue shutters and a prominent sign for Venter Surf & Sport. People are seen browsing the shop, while bicycles are parked along the curb, indicating a vibrant, active atmosphere in the heart of Duval Street.

4.91 out of 5 average rating, 903 reviews

Duval Balcony Spanky's Retreat

4.92 out of 5 average rating, 284 reviews

Sunset Suite-Historic 2 BR, K/Q, Sleeps 4, Spa!

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.

Beachside Unit 22 - Private Beach on Atlantic

4.86 out of 5 average rating, 153 reviews

5.0 out of 5 average rating, 26 reviews

Apartment in Marathon

Marina View Villa | Dockfront, Pool & Tiki Bar

4.93 out of 5 average rating, 14 reviews

Oceanview condo w/pool, jacuzzi and tennis court

Apartment in Key Colony Beach

The room features two spacious beds with light-colored bedding, complemented by decorative pillows. A ceiling fan is present above, while large windows with shutters allow natural light. Colorful artwork depicting flamingos adorns the walls beside bedside tables and lamps.

2 Bdrm Oceanfront Complex Private Beach & Pool

4.93 out of 5 average rating, 41 reviews

House rentals with beach access

4.95 out of 5 average rating, 108 reviews

4BR 3B, Heated Pool & Spa, 60' Dock

4.85 out of 5 average rating, 189 reviews

The image captures a private dock setup with several tall pilings along the water's edge. Two adirondack chairs are placed on a grassy area, and a palm tree provides partial shade. The serene bay views and clear blue sky enhance the tranquil atmosphere of the outdoor space.

Home in Key Colony Beach

Waterview from three sides, Cabana Club, 30' Docks

4.78 out of 5 average rating, 9 reviews

Home in Summerland Key

Family Retreat

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, 91 reviews

Cozy 2 br/2 bath home in Cudjoe

A colorful array of lounge chairs in yellow, green, and blue is positioned by a shared pool area. A thatched-roof cabana is visible, providing shaded seating near the water's edge. The lush surroundings and bright blue sky complement the inviting atmosphere.

4.94 out of 5 average rating, 33 reviews

Oceanside home 109, dock,kayaks,bikes,pool,fishing

5.0 out of 5 average rating, 10 reviews

A Paradise Point by Sombrero Beach

4.86 out of 5 average rating, 7 reviews

Salty Dog Shack #335 - Ocean Views! Kayaks & Bikes

The backyard features a pool surrounded by a marble deck, with lounge chairs and an umbrella for shade. A tiki hut with seating stands nearby, complemented by landscaped greenery and palm trees. The multi-level home is illuminated softly against the evening sky.

5.0 out of 5 average rating, 18 reviews

Luxury Oasis, Pool, Kayaks, Dock, Near Beach

Condo rentals with beach access

Condo in Key Colony Beach

Sunrise View Condo - Key Colony - Private Beach

4.93 out of 5 average rating, 102 reviews

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

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, 315 reviews

Affordable Beachfront Luxury Condo Sleeps 6

4.88 out of 5 average rating, 112 reviews

A modern kitchen features stainless steel appliances and white cabinetry, complemented by a light countertop. A dining area and living space are visible in the background, along with a staircase leading to the upper level. Large sliding doors provide access to an outdoor view.

Condo in Duck Key

Villa 5087 on Duck Key BOAT SLIP available

The balcony offers stunning views of the turquoise waters and sandy beach, framed by palm trees. A resort-style pool can be seen nearby, and the expansive outdoor space invites relaxation under the sun, enhancing the beachside atmosphere.

4.95 out of 5 average rating, 43 reviews

Windswept Palms at The Beach

Condo in Key Colony Beach

A bright living area features a spacious sectional sofa and reclining chair, complemented by a large area rug with a wave pattern. A smart TV is mounted on the wall, and glass doors lead to a balcony with coastal views, framed by light blue curtains.

The Turquoise Turtle-Beach/Pool

4.89 out of 5 average rating, 9 reviews

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

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.