Pet-friendly holiday rentals in Marathon

Oceanfront Rooftop Views w/ 75ft of Dockage

Welcome aboard Captains Rooftop, Your 4BR Rooftop Deck Hot Tub Oasis on a direct ocean access canal with 75ft of dockage. This three story stilted rooftop home provides a unique unforgettable Florida Keys experience for your entire family. 🏊‍♂️ 2 Luxury jet Hot Tubs (One on the roof, one in the backyard) ⛵ Private 75ft dock surrounded by a mangrove jungle 🕹️ Foosball Table 🍳 Rooftop patio with BBQ grill & open ocean view dining 💻 High-speed Wi-Fi for streaming & remote work 🛏️ Comfortable

Waterfront Private Home w/Pool-Family&Pet Friendly

Welcome to Casa Pina! Located right in the heart of Marathon. Enjoy your trip to the keys in this stunning custom canal-front, 3 bed/3 bath private house comfortably accommodating 8 ppl, with soaring 25 ft wood ceilings, wonderful kitchen and living area, private pool, large yard, 40 ft dock, kayaks, paddle boards, grill. Plus a huge screened in Patio and game room with a pool table. Driveway with Ample parking, enough for four cars+. This house has everything you need for your FL Keys getaway!

Waterfront House with 37 ft Dock & Cabana Club

Right in the middle of the action between Miami and Key West. This 2/2 house has been nicely renovated and furnished with new stainless kitchen appliances and a gorgeous granite countertop. Comfortable outside/inside living space perfect for a getaway in paradise. Walk out to the porch and backyard, and you will be engulfed by the beauty of the sunset views while lying on the cozy hammock. It features lots of outdoor entertaining: fishing, paddling, BBQ or just plain hanging out in the shade.

Oceanview Marathon - Screened Porch, Theater & Bar

2020 New Construction Private, well-appointed 2 bed 2 bath home boasts: +5-Star OCEANVIEWS +Screened Porch with Ocean views to enjoy your morning coffee +Outdoor Theater +Bar and Adirondack chair conversation nook +Jumbo Nest Chairs over lush beach sand +Loungers +Full Kitchen +Grill Relax or adventure awaits - Minutes from the Keys' best public sandy beaches (Sombrero and Bahai Honda State Park), Theater of the Sea, Marathon Aquarium, Dolphin Research Ctr, Turtle Hospital and 7-Mile Bridge!

Beautiful Waterfront book now 2026 filling up fast

This property is like having your own private resort. We are on the Gulf of Mexico with a Million-dollar waterfront view & sunsets. 4BR + bonus room w/queen bed & futon. 2 full bathrooms 4 TVs. Pool, Private Dock. Watch the Dolphins daily. We a located next to the World-Famous Dolphin Research Center. House has wrapped around deck plenty of seating inside/out. Large private yard with plenty of room for all your needs. Walking distance to restaurant, marina. Kayaks/Paddleboards mostly available.

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.

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!

Waterfront Duck Key Villa - Sleeps 8 (7058)

BEST VIEW IN DUCK KEY!!!! Waterfront Villa at the heart of the Florida Keys - Duck Key Florida. Beautiful location with easy access to both the Atlantic Ocean and the Gulf of Mexico. Come check us out and see for yourself what the exclusive Duck Key area has to offer. DOCK INCLUDED-35 Foot. Conveniently behind the village! The Village at Hawks Cay Villas by KeysCaribbean are not affiliated with the Hawks Cay Resort; our guests do not have access to hotel amenities.

Waterfront Cozy Modern Retreat w/Deep Canal

Welcome to our beautiful waterfront home in Marathon! Our smoke-free property is modern, clean and features a 37ft long concrete dock, perfect for boating and fishing enthusiasts. With easy access to the movie theater, Sombrero Beach, Turtle Hospital, Publix, Walgreens, and delicious restaurants, you'll have everything you need right at your fingertips. We can't wait for you to experience the peacefulness and convenience of our lovely home.

Waterfront, Pool, Dock, Kayaks & Stunning Views

Welcome to Hook, Wine & Sinker, a beautifully designed 3-bedroom, 2-bathroom ground-level waterfront, pet-friendly home where comfort meets convenience in the heart of the Florida Keys. Overlooking the peaceful waters of Boot Key Harbor, this spacious getaway is perfect for families or small groups, with a maximum occupancy of 8 guests. Sleeping arrangements include 2 king bedrooms and 1 bedroom with 2 twin beds — there is no pullout couch.

Premium Floating Bungalow by Stay Ombi

Welcome to Stay Ombi, a fully off-grid escape on the gentle waters of Buttonwood Sound in the Florida Keys. Ombi offers three bungalows, crafted to immerse you in nature - without compromising on comfort. Guests are transported to the bungalow by boat (10-minute trip), which will be pre-stocked with all of your requested comforts. Our concierge team will work with you upon booking to plan one of the most unique experiences in the Keys.

A Paradise Point by Sombrero Beach

Modern Tropical Paradise | Marathon, FL Stylish home in exclusive Flamingo Isle, minutes from Sombrero Beach, marinas, fishing piers, indoor surf-style shop, and the Florida Keys Country Club. 3 bed | 2 bath + den Downstairs full bath with handicap-accessible walk-in shower Living room + playroom (pool table, games) Outdoor: Heated pool , Jacuzzi, BBQ, tiki hut Corner lot with parking for boat trailer & RV (full hook-ups)