
Home rentals with a pool near Sombrero Beach
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool near Sombrero Beach
Guests agree: these stays are highly rated for location, cleanliness and more.

Sea Ray Cove w/ 80' Dock, Pool, Beach & Tiki Hut
2025 - New concrete dock, fenders & fish filet table. 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.

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!

Sombrero Beach Getaway
Spend your days boating, fishing, and swimming in the South Florida sunshine when you escape to this waterfront home in Marathon! Scenically, this home features a 90 -foot dock (with a filet cleaning table and water), a private heated outdoor pool, and a patio where you can grill your fresh catch each evening. We are located just minutes away from restaurants, bars and entertainment. Key West is less than an hour from the property. We can provide help with Golf Cart and Boat rentals.

Waterfront Oasis3/2 Direct Ocean
Welcome to our stunning vacation rental property located on the waters of the ocean, where you can enjoy the ultimate tropical getaway. Our property boasts of an exceptional location, featuring a private dock that provides direct access to the ocean. This beautifully furnished property has three spacious and comfortable bedrooms that can accommodate up to eight guests, making it perfect for families or friends. The two modern bathrooms are fully equipped with all the necessary amenities

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.

Sombrero Beach Home w/ Heated Pool, Kayaks & More
3 bed/2.5 bath home a block from Sombrero Beach - walk to beach, avoid parking fee! 3 bedrooms (2 ensuite): 1 king, 1 queen, 2 XL twins. Cook's kitchen, open plan living/dining room. Enjoy heated pool, incredible outdoor shower, chaise lounges, gas grill, outdoor dining, hammock, and sunsets over the ocean from our dock. House comes with beach chairs, sand toys, pool floaties, kids books and games. Strong Wifi, cable & streaming TV. 2 kayaks for your use. NO DOCKING FOR BOATS.

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!

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

Villa Mars In Marathon
Enjoy your Florida Keys Vacation at the NEWLY LISTED Villa Mars! This recently renovated two bedroom, two bathroom single level home is the perfect place for your tropical getaway! Centrally located on 29th Street in The City of Marathon, you will be right in the middle of all the action and attractions with most being within walking/biking distance. The home comes fully stocked with everything youll need to be comfortable during your stay!

P87 - Modern 4 bedroom, 4 bath home on open water
Stunning views with premier Sombrero Beach location sets this home apart from all others! This ocean front home is spectacular inside and out! With 4 bedrooms and 4 full bathrooms this home can easily accommodate large groups; perfect for families or business colleagues. Please note, due to the number of stairs throughout this home it is not suitable for guests who have difficulty navigating stairs. There is no roof top is access.

Paradise in Key Colony Beach + Cabana Club
Beautiful two bedroom, two bathroom property in the prestigious Key Colony Beach neighborhood. This property is a ten minute walk from Sunset Beach, two minute walk from restaurants and bars in KCB and across the street from a golf course, tennis court and playground. Dockage for boats up to 50ft and beautiful water views. Key Colony Beach Cabana Club is included with your stay. You'll feel completely relaxed in this tropical oasis.

Sombrero Sunset-Marathon 7BR 6BA Waterfront Pool
Make memories of a lifetime in Sombrero Beach, Martathon in the Florida Keys. 7 bedrooms (6 King Beds), 6 full baths, 80' dock, private pool, fenced yard, parking for 6 vehicles plus two boat trailers. Only minutes from the Atlantic Ocean and Gulf of Mexico. Enjoy world class fishing and diving. Sombrero Beach is stunning and only a mile away. Beautiful neighborhood with golf course views from the front.
Popular amenities for rentals with a pool near Sombrero Beach
House rentals with a pool

Beach House in Marathon with Amazing Backyard!

Heated&Cooled PrivatePool/CabanaClub/Bikes/PaddleB

Tropical Keys Retreat | Pool | Hot Tub | Cinema

Waterfront 2-bedroom Home w/Pool and Spa

Oceanfront with Pool near Sombrero Beach

Lagoona-Matata

Sombrero Beach Beauty~ 50` Dock Private Pool Home!

Conch Cottage
Apartment rentals with a pool

Beachside Unit 14 - Brand New Kitchen and Bathroom

Marathon 2BR Waterfront property on Resort

Private Beach in Marathons Key Colony Beach

King Suite | Heated Pool | Marathon Keys | Sleep 4

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

Paradise found! Sea-Esta Condo beach and pool.

Ocean Isles Mackeral Row VACA-23-137

*NEW* Private Beach, pool & fully loaded kitchen
Other holiday rentals with a pool

Salty Kisses Beach House

Waterfront Private Home w/Pool-Family&Pet Friendly

Twin Dolphin Marathon Deep Water Canal, 100’ Yard!

Castillo Del Mar- Ocean access from your backyard

Luxury Boating Paradise+Pool+Sailing Kayaks

Get Hooked private pool & dock

Villa 7205 on Duck Key- Boat Slip Available

Dockside Paradise | Brand New, Large Dock, Private
Quick stats about rentals with a pool near Sombrero Beach

Total holiday rentals
Explore 110 holiday rentals in Sombrero Beach

Nightly prices starting at
Sombrero Beach holiday rentals start at €104 per night before taxes and fees

Verified guest reviews
Over 1,680 verified reviews to help you choose

Family-friendly holiday rentals
110 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
110 of Sombrero Beach holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Sombrero Beach rentals

4.8 Average rating
Sombrero Beach stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Family-friendly rentals Sombrero Beach
- Beachfront rentals Sombrero Beach
- Rentals with outdoor seating Sombrero Beach
- Apartment rentals Sombrero Beach
- Pet-friendly rentals Sombrero Beach
- Rentals with beach access Sombrero Beach
- Rentals with a patio Sombrero Beach
- House rentals Sombrero Beach
- Rentals with a hot tub Sombrero Beach
- Villa rentals Sombrero Beach
- Rentals with a washing machine and dryer Sombrero Beach
- Rentals with a kayak Sombrero Beach
- Waterfront rentals Sombrero Beach
- Rentals with pools Marathon
- Rentals with pools Monroe County
- Rentals with pools Florida
- Rentals with pools United States
- Everglades National Park
- Smathers Beach
- Ernest Hemingway Home & Museum
- Robbies Marina Of Islamorada
- Seven Mile Bridge
- Theater of the Sea
- Bahia Honda State Park
- The Turtle Hospital
- Fort Zachary Taylor Historic State Park
- Florida Keys Aquarium Encounters
- Conch Key
- Dolphin Research Center
- Founder's Park
- Key West Butterfly & Nature Conservatory
- Southernmost Point
- Harry Harris Beach and Park
- History Of Diving Museum
- Key West Lighthouse Museum
- The Rain Barrel Village
- Mel Fisher Maritime Museum
- Truman Little White House
- Curry Hammock State Park
- Key West Aquarium





