
Holiday rentals in Deer Key
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Top-rated holiday rentals in Deer Key
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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.
LocationValueKitchen
4.93 out of 5 average rating, 81 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.
FamilyLocationWalkability
4.73 out of 5 average rating, 26 reviews
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.
ValueFamilyDecor
4.98 out of 5 average rating, 129 reviews
Welcome to Paradise! Private Pool, SUPs, Kayak!
Paradise Awaits You!! With a Beautiful Private Pool, 40’ Dock, Kayaks, SUPs, & Bikes; Welcome to Paradise is the Perfect Place to Stay & Play in the Sun & on the Water! Our home w Breezy Palms is centrally located w Beaches, Boating, Fishing, Diving, Swimming, Dining & Refreshing Cocktails just minutes away! We are owners, Luis & Aysie. We put all our love of the Keys into our home, & we just know you will love it too. Message us or book instantly & start planning your trip to Paradise!
ValueLocationHospitality
4.86 out of 5 average rating, 36 reviews
Captain’s Quarters Ahoy Mateys! Florida, Keys
This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.
LocationFamilyDecor
4.93 out of 5 average rating, 153 reviews
Entire private two family water front home.
Forget your worries in this spacious and serene space. This is a great option for large multi-generational families that want to be in two separate areas of a full home. This is a full two family home with separate entrances. Enjoy 75 feet of waterfront with a concrete seawall, davits, a fish cleaning station, and direct ocean and bay access via nearby Vaca Cut. The home offers full privacy, a private heated and chilled pool in the heart of Key Colony Beach; the entire home is yours!
LocationFamilyPool
5.0 out of 5 average rating, 6 reviews
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.
ValueFamilyBeach
4.94 out of 5 average rating, 145 reviews
P01 - New 3 bed, 3 bath with private pool
This beautiful new home offers 3 bedrooms, 3 baths and a comfortable open floorplan. Additionally, this property boasts and abundance of fabulous outdoor living space and is ideally located minutes from Coco Plum Beach. - Maximum Occupancy: 6 guests (includes adults and children of any age) (*children of any age, including infants, count toward occupancy) - No day guests or visitors allowed above the advertised max. occupancy. - Parking: 3 vehicle max - 3 bedroom/3 bathroom
FamilyLocationQuiet
5.0 out of 5 average rating, 12 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
FamilyLocationBeach
5.0 out of 5 average rating, 6 reviews
Coco Plum Paradise - Marathon 5 BR 4 BA Waterfront
Entire Waterfront Home. 5 Bedroom, 4 Full Baths, Heated Pool and Spa, 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
LocationFamilyCheckout
4.93 out of 5 average rating, 46 reviews
Waterfront Pool Home w/ Private Dock, Tiki Hut & B
Captain’s Hideout, your 4BR waterfront escape in Marathon’s Little Venice, built for boaters, families, anglers, and easy Keys living with quick access near Vaca Cut to the Gulf. 🏊♂️ Private backyard pool ⛵ 28’ dock with fish cleaning table 🌴 Huge tiki hut hangout area 🍳 Outdoor kitchen + dining space 🧊 Commercial ice machine + bait freezer 🛏️ Ground-level comfort for 10 🐾 Pet & kid friendly with pack ’n play + highchair
ValueAccuracyComfort
5.0 out of 5 average rating, 4 reviews
4BR 3B, Heated Pool & Spa, 60' Dock
Enjoy breathtaking views of the Gulf and Ocean from the screened in patio of this beautiful 4 BEDROOM/3 BATH canal front home. Bring your boat to the 60' dock on a 200' wide canal just 10' away from the Ocean. Relax by the pool/spa area after a day of fishing. A pool heater is offered as an option for your convenience. Please inquire about water heater fee and operating instructions before booking. (VR Lic # PLR2020-00104)
FamilyLocationHot tub
4.95 out of 5 average rating, 108 reviewsPopular amenities for Deer Key holiday rentals
Other great holiday rentals in Deer Key

Tiny Home Aqua Lodges 2/1
FamilyValueHot tub
4.77 out of 5 average rating, 159 reviews
Best Location in Marathon & KCB!
FamilyLocationCleanliness
5.0 out of 5 average rating, 18 reviews
Direct Oceanfront Private Paradise - Pool/Spa/Dock
LocationFamilyKitchen
5.0 out of 5 average rating, 33 reviews
Castillo Del Mar- Ocean access from your backyard
FamilyLocationView
5.0 out of 5 average rating, 15 reviews
Tropical Keys Retreat | Pool | Hot Tub | Cinema
FamilyValueSleep quality
5.0 out of 5 average rating, 81 reviews
Gorgeous Ocean View Home!
ValueFamilyBeach
4.86 out of 5 average rating, 99 reviews
3/2 Home w Dock, lagoon, kayaks!
FamilyLocationAmenities
4.86 out of 5 average rating, 14 reviews
*NEW!*Life is a Marathon~VIEWS!~Pool~Dock~HotTub!
FamilyLocationBathroom
5.0 out of 5 average rating, 4 reviewsDestinations to explore
- Miami Holiday rentals
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- The Rain Barrel Village





