Vacation rentals in Summerland Key

A serene view overlooks the water at sunrise, with soft pastels reflecting on the surface. A white patio table and chairs are positioned under the covered porch, inviting relaxation. The horizon features gentle clouds and distant islands, creating a peaceful atmosphere.

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

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.

4.93 out of 5 average rating, 54 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!!

A serene waterfront scene features a pier with thatched roof structures surrounded by calm blue waters. The sky is partly cloudy, showcasing a blend of whites and blues. Buoys are placed in the water, adding a touch of color to the landscape.

4.84 out of 5 average rating, 45 reviews

Relaxing Home in the Keys

This 2 bedroom, one bath home is located in Venture Out on Cudjoe Key, FL. 23 miles outside Key West!. Venture Out is a gated community that features, community pool, hot tub, tennis courts, basketball court, a private ramp, unit is 85 yards from ramp, easy for lunching kayaks. There is a dishwasher, grill, TV and free WIFI. The unit includes 2 adult bikes, 2 person Kayak and Paddle board at no extra chargeATTENTION: The community charges a non-refundable security/registration upon arrival.

4.78 out of 5 average rating, 9 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.

4.81 out of 5 average rating, 113 reviews

A view from a covered balcony overlooks a private sandy beach with gentle waves lapping at the shore. Palm trees line the beach, providing shade. A long dock extends into the turquoise ocean, enhancing the tranquil coastal atmosphere.

Home in Sugarloaf Key

The Guest House - Sugarloaf Beach Key West

If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we can’t wait to host you. One of a kind beach house with a private sandy beach, dock and boat dockage . Featuring a tropical ambiance and a family friendly setting that will make you feel like you are in your own private island. Ocean views. natural Florida Keys private beach, great for swimming, snorkeling, kayaking, paddle boarding or just reading a book by a palm tree.

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 long wooden dock extends into clear blue water, flanked by palm trees and lush greenery. Two turquoise chairs are positioned at the dock’s end, providing an ideal spot for relaxation and enjoying scenic water views under a bright sky dotted with clouds.

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!

An aerial view showcases the expansive resort area featuring a large swimming pool surrounded by lounge chairs. The vibrant blue water extends beyond the pool, with palm trees swaying gently in the breeze. Nearby, a shaded pavilion offers a gathering space with pathways leading toward additional amenities.

4.86 out of 5 average rating, 98 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!

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.

An outdoor patio is seen overlooking crystal-clear waters, featuring a charcoal grill and a view of the expansive ocean. Potted plants with vibrant flowers enhance the area, while a railing provides safety along the water's edge, inviting relaxation and enjoyment.

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 serene outdoor space features a hammock nestled between lush tropical foliage, with smooth pebbles laid on the ground. Steps lead up to a painted white railing that complements the natural surroundings. The area is enclosed by a white fence, creating a cozy atmosphere.

4.89 out of 5 average rating, 237 reviews

101- Newly Renovated Oceanside House with Pool

This home is on the Atlantic side of US 1. It is part of Sunrise Beach Resort, a gated community built in 2007 with only 10 other homes. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on one of two balconies, dock or poolside, where you can soak up the sun steps from the house. Breathtaking southwest views of the blue-green ocean and sunsets can be seen from the pool and dock.

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Popular amenities for Summerland Key vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Summerland Key

A private outdoor area features a swimming pool surrounded by lounge chairs. A tiki hut with dining furniture provides shade and views of the water. Palm trees complement the serene setting against a backdrop of blue skies and calm waters.

Home in Key West

5 out of 5 average rating, 4 reviews

Beautiful quiet neighborhood. Sunsets! Huge Pool!

A bright living space features large windows with light-filtering shutters, offering a view of the outside. A spacious day bed is positioned near the windows, complemented by a rustic dining table and chairs. The adjacent kitchen includes modern appliances, enhancing the open layout.

Home in Summerland Key

4.82 out of 5 average rating, 57 reviews

Kelly’s Kabin - Private FL Keys Cottage

An aerial view captures a community featuring a sandy beach area and a large pool surrounded by lounge chairs. The vibrant turquoise waters are visible, along with palm trees swaying gently in the breeze. Residences and boats can be seen along the canal and waterfront.

4.95 out of 5 average rating, 20 reviews

Sea Turtle Cove

A serene sunset is depicted over the water, with soft rays illuminating the sky and reflecting on the surface. Silhouettes of palm trees are visible in the foreground, complementing the tranquil atmosphere created by the fading light.

4.63 out of 5 average rating, 166 reviews

Ocean Front Home in Great Location

A shaded outdoor area features a hammock positioned between two columns, inviting relaxation. The stone flooring spans the space, leading to a tranquil pool with open water views visible beyond. Palm trees sway gently in the background, enhancing the peaceful ambiance.

Home in Summerland Key

5 out of 5 average rating, 4 reviews

A month in paradise pool home.

A golf cart is parked on a pebbled surface, featuring two cushioned seats in brown. The vehicle is equipped with a side platform for storage. Surrounding palm trees and vehicles can be seen in the background, adding to the outdoor ambiance.

4.79 out of 5 average rating, 19 reviews

Tropical Island Getaway

A concrete dock extends toward the turquoise waters, flanked by lush greenery. A fish cleaning station is positioned on the dock, and several birds are seen flying above against a clear blue sky.

5 out of 5 average rating, 3 reviews

Blue Heaven Waterfront Home