House holiday rentals in Summerland Key

Horizon

Horizon is a bright beautiful upscale home, custom designed to take full advantage of its unique ocean location. Every room, has a wide sliding glass door to oceanfront balconies. Every bedroom has a private bath. Pool with Spa, Observation Platform for those sunrises on open water, ping pong, corn toss, kayaks and paddle boards, multiple dining areas, WIFI, quality appliances, comfy cotton bedding, crib, high chair multiple TV's poolside loungers, rocking chairs & bird watching. ++++

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!!

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.

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.

Yellow Home - Receive $500 towards a Boat Rental!

Receive a $400 gift certificate towards a boat rental. When you reserve a week for any of the dates and house below. When you book a full week at one of our vacation rental homes staying between the dates of September 1st through Dec 20, 2025. Please reach out before booking for boat availability. Beautiful 3 bedroom 2 bath home nestled off of US 1. Kayaks included with the rental. Private heated pool and deck with a view of the Atlantic Ocean. Boat dockage available with parking.

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!

The Tarpon Retreat

Enjoy a quiet and serene space with phenomenal water access to Bogie Channel, the Back Country, and amazing Gulf, Atlantic fishing and local beaches. Our cathedral ceiling with open concept living, 60-foot concrete dock, and Lower-level enclosure for fishing gear make this the perfect place to relax. Put in kayaks or your paddle boards right from the shoreline. Canal close to Old Wooden Bridge Marina with boat launch and fuel. Boats up to 30’ can be tied up at the house.

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.

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!