Holiday rentals with a pool in Marathon

4.93 out of 5 average rating, 82 reviews

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.

ValueFamilyKitchen

4.73 out of 5 average rating, 26 reviews

Sunset Key Escape/Pool, Dock, Kayaks & Gulf Access

Welcome to Sunset Key Escape Your Private Waterfront Retreat in Marathon Bask in the beauty of the Florida Keys at Sunset Key Escape, a stylish and serene 3 bedrooms, 3 bathroom waterfront getaway designed for comfort, adventure, and unforgettable views. Whether you are unwinding poolside, launching a kayak at sunrise, enjoying dinner by the water under the stars, or challenging friends and family to a ping pong match, this home offers a true Keys escape surrounded by nature and coastal charm.

LocationFamilySleep quality

5.0 out of 5 average rating, 5 reviews

Searenity Vacation Rental! Pool, Tiki Hut, Dockage

Searenity is a newly updated ground level vacation rental! A direct shot to the Gulf in about two minutes and nestled in a nice quiet neighborhood on Dolphin Drive in Marathon, this home is in a great central location! There is plenty of dockage for your boat and a gorgeous tropical back yard with everything you need for the perfect Keys vacation - pool with jets, tiki hut, grill, outdoor refrigerator, fish cleaning station, two kayaks, two bikes, back porch, and plenty of outdoor furniture!

FamilyLocationHospitality

A sparkling in-ground pool is visible in the foreground, surrounded by a spacious patio. Lounge chairs are positioned along the deck, offering views of the lagoon. Lush palm trees provide shade, while a clear sky enhances the tranquil atmosphere of the waterfront setting.

4.99 out of 5 average rating, 179 reviews

Cancellation Deals: 10/24 - 10/31 & 11/28 - 12/05

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.

LocationFamilySleep quality

An inviting outdoor space features comfortable seating and a hot tub, surrounded by lush greenery. A large screen is set up for movie nights, and ambient lighting enhances the evening atmosphere as the sun sets.

5.0 out of 5 average rating, 81 reviews

Tropical Keys Retreat | Pool | Hot Tub | Cinema

Welcome to Paradise Palms: ⭑ 1750 sqft liveable space on 10,500 sqft estate ⭑ Private home, deck, patio & backyard, overlooking a beautiful scenic landscape ⭑ Crystal pool, hot tub, movie theater, remote workspace, game room with arcade & more ⭑ Secure parking for up to six vehicles, boat trailer parking, RV and EV charging ⭑ 10 min to sombrero beach & just minutes to all island attractions ⭑ Fully stocked kitchen ⭑ Extremely safe neighborhood License #VACA-24-20 License #VACA-24-32

ValueLocationAccess

5.0 out of 5 average rating, 6 reviews

Marathon Oceanfront 4BR Private Pool 60’ Boat Dock

Wake up to open-water views at your private oceanfront retreat in Marathon. Bring the boat, step into your private pool, Perfect for families and boating groups.Your private 60' dock offers direct water access, freshwater for rinsing gear and flushing engines, while parking accommodates up to 4 vehicles. • Direct oceanfront setting • Private swimming pool • Private 60' boat dock • Complimentary kayaks • Sleeps up to 10 • Parking for 4 vehicles • Wi-Fi + dedicated workspace

FamilyLocationCondition

4.86 out of 5 average rating, 620 reviews

Three modern Aqua Lodges are positioned on water, featuring white exteriors and blue roofs. Each lodge has a furnished deck with chairs, providing relaxed seating options. A smooth, concrete path runs alongside the lodges, leading to a marina setting with sailboats in the background.

Villa in Marathon

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!

FamilyLocationOutdoor spaces

The two-story home is complemented by lush palm trees and surrounded by water, reflecting the vibrant colors of the sunset. Lounge chairs are positioned on the patio, and lights from the home illuminate the water, creating a serene atmosphere.

4.96 out of 5 average rating, 56 reviews

🏝Beautiful🏖 Water🏊‍♀️ View🌅 Pool Gym🏋️ Room, Private⛵️ Dock⚓️

Over 100ft of water frontage, with expansive bay view of all the beautiful wildlife that Marathon has to offer! Pets are always welcome but you MUST‼️indicate how many guest and pets when you make the booking. If cleaning crew discover sign of pets, guest will be charge $350/entire stay due to the extra cleaning work from the cleaning crew. With an outdoor heated pool, paddle boards, and kayaks, you and your family will never need to leave the home for activities!

LocationValueKitchen

5.0 out of 5 average rating, 24 reviews

P36 - Charming and immaculate 2 Bedroom, 2 bathroo

Charming and immaculate 2 Bedroom, 2 bathroom stilted, half duplex offering deep-water dockage and private pool. Located in fabulous Key Colony Beach. Key Colony Beach is a small, friendly, walkable island in the heart of Marathon, the Florida Keys. Located mere minutes from beaches, bike and running paths, golf courses, tennis courts, the Dolphin Research Center, Aquarium Encounters and the Turtle Hospital. - Maximum Occupancy: 6 - 4 adults max and 2 children)

LocationFamilyWalkability

The backyard features a pool surrounded by a marble deck, with lounge chairs and an umbrella for shade. A tiki hut with seating stands nearby, complemented by landscaped greenery and palm trees. The multi-level home is illuminated softly against the evening sky.

5.0 out of 5 average rating, 18 reviews

Luxury Oasis, Pool, Kayaks, Dock, Near Beach

Welcome to Casa De Cayo 🏆 Featured in Rolling Stone as one of the best Airbnbs for large groups Exactly what you want from the Florida Keys—just 1 mile from Sombrero Beach. This modern 3BR retreat shines outdoors with a pool, tiki hut kitchen, hammock, and 40’ deep-water dock (no lift use), plus kayaks & paddleboard for the perfect island stay.

LocationFamilyIndoor spaces

A resort-style pool is surrounded by lounge chairs, set on a brick patio with a view of palm trees and the ocean. The scene is bright and open, showing a clear sky with scattered clouds, enhancing the outdoor leisure space.

4.8 out of 5 average rating, 15 reviews

Oceanview Rooftop Retreat 3BR 3BA in Marathon FL

Welcome to Rooftop Bliss – the ultimate family getaway in Marathon, FL! This spacious 3BR/3BA villa is perfect for making memories together, with a private rooftop deck, resort-style pool, and a safe, gated community. Close to beaches, fishing spots, and fun island attractions, it's your home away from home in the Florida Keys.

ValueFamilyComfort

The exterior of the newly renovated home is showcased, featuring a large covered porch supported by white columns. Palm trees line the surroundings, and warm lighting illuminates the entrance, creating an inviting atmosphere against the twilight sky.

4.95 out of 5 average rating, 174 reviews

Marathon one-level home on the Marina - with slip!

***New Listing! Recently renovated with all new furnishings and appliances*** Beautiful oasis in the heart of the Florida Keys, Marathon is a fisherman's paradise. Coral Lagoon is the perfect destination for a relaxing family getaway and this home is all new with stylish interior and unbeatable location.

LocationFamilyAccess

Popular amenities for Marathon rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5.0 out of 5 average rating, 120 reviews

A private backyard features a heated pool surrounded by tropical landscaping. Lounge chairs are positioned on the wooden deck beside the pool. The two-story home includes large glass doors that open onto the deck, providing easy access to outdoor spaces.

Home in Duck Key

Private Pool Tropical Oasis - Centrally Located

FamilyLocationTV

5.0 out of 5 average rating, 10 reviews

A Paradise Point by Sombrero Beach

LocationHospitalityHot tub

4.86 out of 5 average rating, 36 reviews

A private inground pool is surrounded by palm trees under a clear blue sky. A colorful rubber duck floats on the water's surface. A hammock can be seen in the background, while a red umbrella provides shade over two seated chairs nearby, creating a serene outdoor setting.

Home in Key Colony Beach

Welcome to Paradise! Private Pool, SUPs, Kayak!

ValueLocationBeach

5.0 out of 5 average rating, 5 reviews

*NEW!*Life is a Marathon~VIEWS!~Pool~Dock~HotTub!

FamilyLocationAccuracy

5.0 out of 5 average rating, 6 reviews

Home in Key Colony Beach

Entire private two family water front home.

FamilyLocationAmenities

5.0 out of 5 average rating, 3 reviews

Emerald Palms ~ Waterfront ~ Pool ~ Dock ~ Games

FamilyLocationCondition

5.0 out of 5 average rating, 27 reviews

Villa Serenity At Sombrero Private Pool Spa Dock

FamilyLocationAccuracy

5.0 out of 5 average rating, 4 reviews

Sombrero Sanctuary~ Pool, Pet Friendly, Near Beach

FamilyLocationIndoor spaces

Apartment rentals with a pool

4.9 out of 5 average rating, 156 reviews

Apartment in Marathon

Mad Mahi | Housekeeping + Waterfront + Marina View

ValueFamilyPets

Apartment in Key Colony Beach

Amazing Ocean Front Views Key Colony Beach

LocationFamilyBathroom

4.97 out of 5 average rating, 286 reviews

Apartment in Key Colony Beach

The image captures a view of the Atlantic Ocean framed by lush palm trees. A pathway meanders alongside the vibrant green lawn, leading toward the beach. The clear blue sky is visible above, enhancing the calm and serene coastal atmosphere.

Beachside Unit 33-Private Tropical Beach Plus Pool

ValueLocationIndoor spaces

4.88 out of 5 average rating, 168 reviews

4.97 out of 5 average rating, 120 reviews

A light-filled living area is visible, featuring a comfortable seating arrangement and a mounted television. A dining table occupies the foreground, adorned with a bowl of oranges. The walls are painted in soft blue, providing a relaxed atmosphere, with a ceiling fan overhead.

Apartment in Marathon

Slip, Private Ramp, Pool, Trailer Parking, Freezer

FamilyValueParking

4.99 out of 5 average rating, 113 reviews

A light-filled living room reveals ocean views through sliding glass doors. A spacious white couch and armchair offer comfort, while a wooden coffee table rests on a patterned rug. Decorative elements include natural wall art and a bright indoor plant, enhancing the coastal ambiance.

Apartment in Tavernier

Tequila Sunrise

ValueFamilyAccess

4.97 out of 5 average rating, 234 reviews

Apartment in Tavernier

Best View Ocean Pointe Pool Beach King Bed, Gated

FamilyValueNearby

4.86 out of 5 average rating, 271 reviews

A thatched-roof gazebo provides a sheltered seating area with wooden adirondack chairs. The serene ocean glimmers in the distance, while green navigation markers are visible on the water's surface. The structure features a wooden railing surrounding the space, enhancing the coastal atmosphere.

Apartment in Tavernier

Toes in the Sand - 2 Bedroom Condo Sleeps 4

LocationFamilyWalkability

4.92 out of 5 average rating, 154 reviews

Apartment in Key Largo

Ocean Shores Villa 2 with pool and boat slip

ValueFamilyOutdoor spaces

Other holiday rentals with a pool

Townhouse in Key Colony Beach

A serene outdoor space features two wooden lounge chairs positioned on a grassy area beside calm waters. A small table is placed nearby, and a private dock extends towards the water, flanked by lush greenery in the background under a bright blue sky.

Castillo Del Mar- Ocean access from your backyard

FamilyLocationAccuracy

5.0 out of 5 average rating, 15 reviews

5.0 out of 5 average rating, 18 reviews

An oceanfront heated pool is presented, with clear water reflecting the sky. Surrounding palm trees harmonize with the serene coastal backdrop, and lounge chairs offer seating options. The pool area is enclosed by a fence, providing a defined relaxing space with views of the ocean.

Flat in Marathon

OCEAN community, perfect condo

LocationHospitalityWalkability

4.88 out of 5 average rating, 26 reviews

A private hot tub sits on the rooftop terrace, surrounded by a white railing. Lush greenery fills the foreground, while a view of the Gulf coast extends towards the horizon under a clear blue sky.

Villa in Marathon

Florida Keys Wellness Gem Tranquility & Activity

LocationFamilyAccuracy

4.96 out of 5 average rating, 24 reviews

New oceanfront 5BR home w/pool, slip, and beach

LocationFamilyPool

A spacious pool area is framed by tropical landscaping, showcasing a large, clear swimming pool. Sun loungers are arranged around the pool, providing places to relax. A tiki hut offers shaded seating options, enhancing the outdoor living experience with serene water views.

4.82 out of 5 average rating, 51 reviews

Waterfront Keys Home | Pool, Hot Tub & 35’ Dock

FamilyLocationAccuracy

A tranquil canal scene is depicted, lined with palm trees and private docks. Water reflects the clear blue sky, creating a serene atmosphere. Boats are moored along the canal, showcasing direct access to Gulf and Ocean waters.

5.0 out of 5 average rating, 54 reviews

Yellowtail Getaway with Boat Dock and Pool 2

ValueFamilyBiking

The image captures a sparkling private pool overlooking the water, with a sandy beach and a wooden dock in the distance. A yellow kayak is positioned nearby, and several lounge chairs are arranged by the pool, inviting relaxation under the tropical sky.

4.92 out of 5 average rating, 49 reviews

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish

ValueLocationGetting around

A private pool with crystal-clear water reflects sunlight, featuring a large inflatable flamingo floating serenely. The surrounding area is bright and spacious, with a view of a light-colored house and tropical greenery in the background.