Holiday rentals with a pool in Marathon

Beach House, Private Pool, Dock, Gulf View Sunsets

You don’t come to the islands to stay in a town—you come to slow down. Welcome to our tropical keys beach home, tucked away from the traffic and noise of US Hwy #1. Sway with the palms on the wraparound deck, soak in wide-open panoramic bay views, and catch fiery sunsets right off your dock. Fire up the BBQ, brew a Keurig, float in the private pool, or cast a line from the 300’ private pier/dock. Easy going island living with ocean / gulf breezes, comfy beds, quality linens, Wi-Fi, and cable TV.

*NEW!*Paradise Point~VIEWS!~Open Water~Dock~Pool!

✨ Welcome to Paradise Point! 🌊⛵ Indescribable Views! This stunning sanctuary offers Water Frontage on 3 sides giving over 180° of unparalleled Atlantic Ocean Views, Direct Ocean Access from your Private Dock, perfect for boating or fishing right from the backyard🎣🐟 After a day on the water, unwind in your Heated Pool, take in the breathtaking views, & fire up the grill for a sunset BBQ to remember! 🌅 Whether you're looking for relaxation, luxury, or adventure, Paradise Point has it all! 🌴☀️

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.

Castillo Del Mar- Ocean access from your backyard

Welcome to PARADISE! — perfect for salty families, fishing lovers and beach goers • Prime Location – In Key Colony Beach with access to Cabana Club pool & private beach • Walk to Dining – Steps from Sparky’s Landing & Island Company • Boater’s Paradise – Backyard dockage for boats up to 30 ft • Spacious Kitchen – Family-style layout with 4-person bar top • Boho Dining Room – Perfect for cozy dinners and entertaining • Amenities include washer + dryer, fully stocked kitchen, Cozy Tv Room

Amazing Oceanfront Home

Mesmerizing views, directly on the Atlantic Ocean! Sleeps 10 with 4 bedrooms and 3 bathrooms. We have a 28 foot pool (heat, for an extra charge) with a view you will not forget. We have Paddle boards, Kayaks, bikes, snorkel gear, etc. We also have a game room with a ping pong table, big screen TV, card table, and a piano. We have a very nice Kid's Park (just down the street). I do Last Minute Deals, just contact me! We require a standard signed rental agreement in order to rent the house.

Coco Plum Paradise - Marathon 5 BR 4 BA Waterfront

Entire Waterfront Home. 5 Bedroom, 4 Full Baths, Heated Pool with attached Soaking Tub, Tiki Hut with bar and seating, Ample Parking, Big Fenced Yard, First and Second Floor Covered Balconies, 110' waterfront with 80' Dock, 5 Minute Walk to Beach, 10 Minutes to ValHala Sand Bar, on a 200' Wide Canal. Licensed to sleep up to 12 guests; 5 King Beds, 1 Pullout Sofa Bed. Outdoor 4 lounge chairs, 12 adirondack chairs. Fully stocked kitchen. Beautiful location. License No. VACA-22-157

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. 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.

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.

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)

Oceanfront mermaid house pool and dock

Perfect spot for a laid back Keys vacation. We are the last house in the canal overlooking the Atlantic. Ocean views with a pool, , ice maker, grill, tiki bar. Fully remodeled in 2019, our home has been completely renovated with all brand new appliances and kitchen, brand new furniture throughout. fish cleaning table. Come sit by the tiki bar and cool off in the pool after a long day on the water.

Waterfront Pool Home w/ 30’ Dock, Kayaks & Outdoor

Captain's Cove, your 4BR waterfront escape in Marathon, set on a quiet canal with direct ocean access. Designed for unforgettable Keys living for families and boaters alike. 🏊‍♂️ Private backyard pool ⛵ 30’ boat dock + 4 kayaks 🍳 Covered outdoor kitchen & BBQ 🚿 Spa-style rain & jet showers w/ luxury toiletries 🛏️ Ground-level comfort for 8 🐾 Pet & kid friendly