Summerland Key vacation rentals

An outdoor patio area features white furniture with cushioned seating, providing a comfortable space for relaxation. The ocean view extends beyond the railing, with water reflecting shades of blue and green under a partly cloudy sky.

4.91 out of 5 average rating, 34 reviews

Rise And Shine On The Water

Spectacular sunrise view! Room to park one vehicle, but we do have a free overflow lot if needed. Community amenities include tennis, pickle ball, bocce ball, heated pool, hot tub, designated swim area, pool table, ping pong, & darts. We provide bedding, towels, pots & pans. TV in living room & one bedroom. We will also have boat bumpers installed all along the concrete dock that will accommodate a 40' boat. We offer 100% money back if your rental is in the projection cone of a named hurricane.

4.93 out of 5 average rating, 129 reviews

A clear view of the waterfront features a well-maintained seawall alongside tranquil blue waters. Palm trees line the shore, offering a tropical feel. The space is enhanced by direct access for boating activities, emphasizing the serene and inviting coastal environment.

Cottage in Cudjoe Key

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family-friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

Two white Adirondack chairs are positioned beside a small table on a paved area near the water. Each chair is complemented by a yellow pillow, creating a comfortable seating space for relaxation. A few personal items, including a bag and a cooler, are visible on the table.

4.92 out of 5 average rating, 53 reviews

Private Ocean Oasis by Key West, Florida

Beautiful stilted two bedroom/two bathroom vacation home awaits your arrival. Break taking views of the Atlantic Ocean are picture worthy. This home hosts a 36' seawall on a wide canal. Dock equipped with fishing cleaning station, cleats, swim ladder, outdoor shower and bait freezer. King-, queen-, full- and twin-size mattresses provide comfortable sleeping accommodations for all guests. Extensive indoor and outdoor furniture allow for all to relax, recharge and enjoy their time in paradise!!

4.75 out of 5 average rating, 8 reviews

The exterior of the home is illuminated by green lights, showcasing a raised structure surrounded by palm trees. Large glass doors are visible, along with a spacious deck that offers views of the water. A tranquil canal reflects the soft glow of the lights.

Home in Summerland Key

Sailfish Dream on Cudjoe Key-28 day minimum

Sailfish Dream is your keys getaway to indulge in the keys lifestyle. Located at MM 23. For boating enjoy deep channels, quick access to all waterways, Looe Key 20 min by boat. Explore islands bordering channel to Gulf. This 2nd floor home has lots of natural light, vaulted ceiling, plenty of parking, 75 ft of seawall, wrap around balcony, swim in canal, sleeps 6 people. This 2 bed/2 bath home is family friendly for wonderful memories to be made. We are working with a 28 day minimum.

4.8 out of 5 average rating, 15 reviews

A covered porch features a spacious deck overlooking a serene canal. Lush greenery and palm trees can be seen alongside the water, with boats docked nearby. The calming scene is paired with a clear blue sky, creating a tranquil setting for relaxation.

Home in Little Torch Key

Indulge yourself. It's heavenly in Little Torch

Welcome to our new 3 bedroom, 2 full bath home with a 60' dock on a gorgeous wide deep water canal. We are only 1,200' to the open waters of Pine Channel at the very southern end of Little Torch Key. Our home is thoroughly cleaned and sanitized before each visit. We have a guest friendly cancellation policy described in the additional house rules section. The living room, dining area and spacious kitchen open to a cozy rear porch and deck overlooking the serene canal. Enjoy ---....

Cottage in Little Torch Key

A wooden dock extends over tranquil waters, featuring two blue chairs positioned for scenic views. Sunlight reflects off the water's surface, while a clear blue sky and scattered clouds create a serene backdrop. The dock provides access to fishing and relaxation.

4.9 out of 5 average rating, 167 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. 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 dock and enjoy the underwater scenery!

4.91 out of 5 average rating, 317 reviews

Three colorful Adirondack chairs, yellow, turquoise, and green, are positioned on a sandy beach facing a calm blue ocean. A rocky shore and sparse greenery surround the seating area, while fluffy white clouds drift in a bright sky, enhancing the serene water view.

Villa in Marathon

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

A spacious balcony is shown with a sectional seating area facing the water, complemented by a white table. A chaise lounge is positioned nearby, offering ample space to relax. The view includes palm trees and distant boats under a clear blue sky.

4.97 out of 5 average rating, 159 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 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.

4.83 out of 5 average rating, 264 reviews

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!

*PERFECT LOCATION! * 35' Seawall *AWWSOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. Located in the lower Florida Keys at MM# 23 only 25minutes to Key West. Located in the gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C & heat *Fully equipped kitchen *Brand New Amenities including grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library, etc. Too much to list!

Top guest favorite

A view from the balcony captures neighboring houses and a landscaped area, with palm trees visible below. The calm waters of the Atlantic ocean stretch in the background under a clear, blue sky. The white railing frames the scenic vista.

4.93 out of 5 average rating, 177 reviews

106 Newly Renovated House with Oceanview and Pool

"This three-story home overlooks the Atlantic ocean in a gated community of only 10 other homes. Just south enough to enjoy the bluest water in the keys and only 20 minutes away from Key West! This pristine home sleeps 6 comfortably and makes a great destination to exploring all the wonders the FL Keys. Come enjoy the pool, fishing, boating, diving or just relax with the ocean breeze. This location has all the best of the Keys."

A light-filled living area features comfortable seating arranged around a central coffee table. Large sliding glass doors offer unobstructed views of the turquoise waters outside. Decorative elements include wall art and potted plants, enhancing the space's tranquil ambiance.

4.9 out of 5 average rating, 107 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 wooden dock extends into the water, featuring thatched-roof huts providing shaded seating areas. The clear blue water reflects the bright sky, scattered with fluffy clouds. A few palm trees gently sway in the breeze, enhancing the serene waterfront setting.

4.87 out of 5 average rating, 104 reviews

Island Oasis ~ YOUR Paradise Awaits!

Enjoy our little peace of paradise! Come and make memories at this laid back and family-friendly waterfront home. Located in a gated community, just 20 miles from Key West, this cottage is the perfect place if you want to relax and re-energize after a day of adventures and activities during your time in the Florida Keys!

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Summerland Key vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Summerland Key

An inviting outdoor recreation area is showcased, featuring a blue ping pong table and a foosball table, surrounded by seating options. In the background, a pool area is visible with sun loungers under shaded umbrellas, complemented by greenery and palm trees.

5 out of 5 average rating, 36 reviews

Waterfront Escape -VACA-23-408

5 out of 5 average rating, 9 reviews

A balcony area is visible, featuring a view of lush greenery and a pool in the background. A comfortable seating arrangement is positioned on the wooden deck, while light filters through the leaves, creating a serene atmosphere.

Apartment in Key West

Casa Caribe 2bed2bath sleeps 6 beautiful decorated

4.93 out of 5 average rating, 60 reviews

Home in Key West

Gone Coastal 2

A comfortable seating area is visible, featuring a wicker chair with a blue cushion and a glass-top table. Beyond the glass doors, a view of the ocean, palm trees, and an American flag is presented against a bright sky.

5 out of 5 average rating, 3 reviews

Waterfront Oasis3/2 Direct Ocean

Top guest favorite

A shaded tiki area features comfortable seating arranged around a low table, ideal for relaxation. The private heated pool can be seen in the background, accompanied by colorful loungers and umbrellas, creating a welcoming outdoor space for leisure and socializing.

Villa in Marathon

4.95 out of 5 average rating, 138 reviews

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

A comfortable chair is positioned on a balcony, offering a view of the ocean and palm trees. Soft white clouds float in a bright blue sky. A person is seen holding a book, enjoying the tranquil atmosphere.

4.91 out of 5 average rating, 179 reviews

Beachfront Villa - Florida Keys