
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/ Pool, Beach, 80' Dock & 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!

Boater’s Paradise 3br/2.5ba at Coral Lagoon
*PLEASE NOTE* Villa slips/canal are under construction until Dec 2025. Please inquire before booking. Spectacular PET FRIENDLY 3 bed/2.5 bath 1350sf villa in beautiful Coral Lagoon, complete with a 40 foot wet slip and all the amenities! Spread out and enjoy the spacious, clean interior with free high speed wifi. Step outside to your boat and enjoy all the Gulf and Atlantic have to offer - both easily accessible in minutes. Relax with a drink at the pool after a long day of fun in the sun.

Oceanfront Sunrise Condo Private Beach Heated Pool
Impeccable condo directly on the ocean with water views from every window. Located in Key Colony Beach (middle Keys) with heated pool and private beach. Unit #20 is a studio condo with a classic Keys interior: newly renovated bathroom and crisp white kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Enjoy the private back balcony and private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

Waterfront Home 37.5-ft dock, Cabana Club Included
Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

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 and a paddle-board. 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.

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!

Oceanfront with Pool near Sombrero Beach
<b>Welcome to Seascape Point!</b><br /><br /> Perfectly situated at the end of a quiet block, this stunning fully-renovated house is the perfect place to relax and unwind in between your sightseeing or fishing excursions. The house sits on an oversized lot that juts into the ocean to offer amazing water views from every angle. Its incredible location next to a nature preserve provides you with unparalleled privacy plus daily sightings of exotic, tropical birds.

Beachside Unit 33-Private Tropical Beach Plus Pool
Unit 33 Details: Second Floor, Walk-in shower, Two Queen Beds, Maximum Occupancy 4 Guests, No elevator on site and Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”

Anglers Terrace, Condé 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

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. *Please note, we have been notified that construction will be starting on the lot next door to this home.

Waterfront Condo w/ Pool, Tiki Bar & Marina
Welcome to THE MAD MAHI – your ultimate waterfront getaway! This stunning 1-bedroom condo (sleeps 4) in Marathon is the perfect spot for a relaxing retreat. Enjoy the season while relaxing with a full kitchen, private balcony, resort pool, Tiki Bar, restaurant, & Marina with boat ramp, trailer parking, boat and slips. Located between Key Largo & Key West, with shops and dining just a walk or bike ride away.
Popular amenities for rentals with a pool near Sombrero Beach
House rentals with a pool

Brand New Luxury Oceanfront Home w/ Pool, 38' Slip

Sombrero Beach Getaway

Luxe Super Snapper-Heated Pool, Tiki, Dock, Lanai

Steps to Sombrero Beach | Dock + Pool + Dogs OK

The Roseate House at Grassy Key

Waterfront 2-bedroom Home w/Pool and Spa

Searenity Vacation Rental! Pool, Tiki Hut, Dockage

Luxury Boating Paradise+Pool+Sailing Kayaks
Condo rentals with a pool

"O" Fish Ally Paradise @Ocean Isle Fishing Village

Oceanside Spacious Studio Escape

Private Beach in Marathons Key Colony Beach

2-story condo w/ panoramic bay views and balconies

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

Paradise found! Sea-Esta Condo beach and pool.

Studio with Balcony, Kitchen, Open Living Space

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

Sombrero beach vacation paradise, great location

Marathon Keys Getaway • Pool • Hot Tub • NearBeach

Discount - Jan 31! 3 Bed/3 BA Cabana Club Access!

Casa Chiquita Waterfront Canal Home

Grand Blue/Mingolf/Dock/HtdPool/ArcadeMachines/BBQ

“La casa azul” step 3’ to a private pool

Bohemian Beach Bungalow

Sea Haven~ Waterfront Pool Home, 35' Dock
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 $185 AUD per night before taxes and fees

Verified guest reviews
Over 1,590 verified reviews to help you choose

Family-friendly holiday rentals
110 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
110 of Sombrero Beach holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
- Rentals with beach access Sombrero Beach
- Waterfront rentals Sombrero Beach
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- Rentals with pools Marathon
- Rentals with pools Monroe County
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- Everglades National Park
- Smathers Beach
- Cocoa Plum Beach
- Calusa Beach & Loggerhead Beach
- Theater of the Sea
- Conch Key
- Sea Oats Beach
- Long Key State Park
- Horseshoe Beach
- Windley Key Fossil Reef Geological State Park
- EAA Air Museum
- Sandspur Beach
- Bahia Honda State Park
- Long Beach
- Keys' Meads
- Sugarloaf Beach
- Cook Island




