Waterfront holiday rentals near Sombrero Beach

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

Wake up to breathtaking water views at our 4-bedroom, 3-bathroom villa. Enjoy the 1800 sq ft layout, fully equipped kitchen w/stainless steel appliances, and granite countertops. Sleeps 10 with memory foam beds. Outside, relax by your private heated pool (winter) and tiki-shaded area. Fish from the 32' dock or use the BBQ gas grill. Includes 2 kayaks, 2 paddleboards, and 4 adult bikes for a 5-minute ride to Sombrero Beach. Exterior cameras for security. Vacation License #VACA-22-40. Book now!

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.

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

Oct. Cancellation Deals: 10/17 thru 10/31

2026 - New eco-friendly pool resurface completed This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

Sombrero Sanctuary~ Pool, Pet Friendly, Near Beach

Escape to your own slice of paradise in this Marathon, FL vacation rental, ideally located just seconds away from Sombrero Beach. This beautifully appointed 4-bedroom, 2-bath canal-front home offers the perfect blend of comfort, privacy, and upscale amenities. Equipped with a private heated pool (heated on request), private fishing dock, and lush tropical landscaping for added privacy, this home is ideal for families and fishing enthusiasts looking for the ultimate Florida Keys getaway.

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

Beautiful Beachfront home located directly across the street from famous Sombrero Beach, with heated pool & Tiki Bar. Large wrap around balconies provides stunning beach views, sunrises & sunsets for relaxation. It boasts open floor plan with a large entertainment area that includes a gorgeous Olhausen Pool table, large bedrooms & the master bath is also a steam room. A 45' dock & spacious yard is great for entertaining or barbecuing. Pool Heater is available for an additional fee.

Dog-Friendly • Pool & Boat Dock • Sombrero Beach

"We were welcomed by a manatee in the channel when we arrived." That's what guests keep saying about 61 Sombrero, our dog-friendly single-level home at the end of a quiet Marathon canal, a five-minute walk from Sombrero Beach. Cast off from the dock at sunrise, watch manatees drift past over coffee, then bike to Publix or back to the sand. Two kings, a queen on the quiet side, and a daybed-and-trundle room for the kids. Heated saltwater pool, gas grill, fenced yard, no pet fees.

SeaEsta! Bring your boat & 1 block to the beach!

Take a 1 Block walk to Sombrero Beach, dock your boat at this waterfront home or simply relax on the patio. 3 Bedrooms 3 baths. Large deck for cooking out. Direct access to the Atlantic. 65" TVs in all rooms. Enjoy your mornings by starting at our Coffee bar. Our home is fully furnished with all the essentials. We even include Kayaks, Bikes and Fishing Poles as well as Corn Hole and Giant Jenga. Boat Rental is offered at an additional cost. - VR License No: VACA -20-147

P82 - Sombrero Beach - 4 bedroom pool home with do

Sombrero Beach Sea-clusion awaits our guests! Get ready to create great vacation memories! This spacious 4-bedroom, 3 and a half-bath home is located one half block from the coveted sandy Sombrero Beach. Enjoy afternoons in the crystal clear oversized pool or bring your boat for fishing and snorkeling trips off our plentiful coral reefs. Construction has started on the lot next door to this home. We do not have a timeline for the ending of this construction.

Tiki Hut w/TV, Pool, Kayak, Paddleboards, Bikes!

This newly renovated tastefully decorated 3 bedroom, 3 bath home (pull-out couch) has a peek-a-boo view of the ocean and is seconds to open water in your boat! It has an open floor plan and is ground level with plenty of natural light and a fully fenced yard! Available for guest use are 4 bikes, 3 kayaks, and a paddleboard! It has a large pool with plenty of room for everyone to swim and play. The house legally sleeps 8 people, including infants and children.

Angler's Eden

Amazing get-away in the beautiful Florida Keys! This property (constructed in 2018) is a haven for families seeking to escape to paradise year-round. Situated on a deep water canal with ocean access and enough dock space to park your boat for the week. A floating dock is also provided with kayaks. Enjoy the large pool or ping pong table, or lounging in the sun! Beautiful Sombrero Beach is within walking distance (approx 1.5 miles) via a paved bike path.

Angler’s Terrace Conde Nast Traveler’s Best Airbnb

As published in Condé Nast Traveler, this is one of the best Airbnb's in Florida. Newly Built two story Tropical Oasis with pool has been thought-out meticulously. An open, very light & spacious floor plan, carefully appointed furnishings, and great location provide the perfect surroundings. Decorated with a Zen sensibility, It’s outdoor Patio deck and Rooftop Terrace extends your living space into the private quiet ocean setting with panoramic views