
Beachfront holiday rentals in Vaca Key
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Top-rated beachfront rentals in Vaca Key
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Villa 5027 on Duck Key BOAT SLIP available
Boat slip available for an additional $100 per night. Ask about availability. This villa boasts breathtaking sunsets and is just minutes from watersports, charter fishing, waterfront restaurants, and local attractions, all while being surrounded by one of Duck Key’s most exclusive island neighborhoods with lush tropical landscaping. Duck Key is perfect for families or a serene couples retreat. Dine while watching spectacular sunsets from the rear deck, or explore the Middle Keys. No smoking/Pet
4.88 out of 5 average rating, 120 reviews
*NEW* Private Beach, pool & fully loaded kitchen
Escape to paradise in our luxurious, beautifully furnished beachfront oasis in the heart of Key Colony Beach, Florida. This stunning two-bedroom, two-bath condo offers the ultimate Florida Keys getaway, featuring private beach access, a community pool with tiki huts, BBQ grills, lounge areas and beautiful ocean views. Perfect for families, couples, and small groups, this relaxing coastal retreat combines comfort, privacy, and an unbeatable beachfront location just steps from the sand and water
4.93 out of 5 average rating, 42 reviews
Amazing Ocean Front Views Key Colony Beach
Everything is brand new in this gorgeous condo with amazing oceanfront views. #40 has two queen beds, well equipped kitchen with full-size appliances and everything you need to cook & serve meals. Fast, reliable WiFi, large SmartTV. Super cold new A/C unit Enjoy stunning views of sunrise from your private balcony & sunsets next door at Sunset Park. Heated pool, beach BBQs & tiki huts for guest use We are centrally located to awesome Keys adventures just a few miles drive from the condo.
4.97 out of 5 average rating, 286 reviews
Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!
Experience the relaxing setting of this 4BR 4.5Bath home, ideally situated in the picturesque waterfront neighborhood of Marathon, FL. Discover the area's scenic beauty and a diverse selection of water activities, attractions, and landmarks. After a day of exploring, return to our home for a rejuvenating stay. ✔ 4 Comfy BRs ✔ Open Design Living ✔ Full Kitchen ✔ Balcony ✔ Backyard (Pool, Games, BBQ, Lounges, Dining) ✔ 73-Foot Dock ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below!
5.0 out of 5 average rating, 60 reviews
Grouper Getaway @ Ocean Isles Fishing Village
Escape to paradise at the Grouper Getaway located at Ocean Isles Fishing Village in Marathon Key, FL. This beautiful brand new fully furnished 1 bed/2 bath studio townhouse, offers a central location and an array of luxurious amenities for a truly unforgettable vacation. Steps away from the the Atlantic Ocean, enjoy the largest pool in Marathon with clear views of the VACA Cut boat traffic and the Sombrero Light House. Enjoy fishing, paddle boarding, kayaking, tiki huts, beach, and grills.
4.99 out of 5 average rating, 76 reviews
Paradise found! Sea-Esta Condo beach and pool.
Sea-Esta is located on the Atlantic Ocean with a private white sandy beach. If the ocean isn’t calling you, Sea-Esta by the heated pool to cool off and work on your tan. Or, Sea-Esta in your master bedroom with its king-size bed and ocean views from its small deck. Sea-Esta under the shade of the lush landscaping that Sea Isle has to offer. Walking distance to Sunset Park, 3 par golf course, pickleball, tennis, bocce ball, and playground. Safe bike/walking paths throughout Key Colony.
4.96 out of 5 average rating, 52 reviews
Beachside Unit 33-Private Tropical Beach Plus Pool
Unit 33 Details: Second Floor, Walk-in shower, Two Queen Beds, Maximum Occupancy 4 Guests (0-2 years old count as a guest). 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.”
4.88 out of 5 average rating, 168 reviews
Waterfront Villa & Sunset Views
Come and relax on your own veranda that overlooks the turquoise waters of the beautiful Duck Key. The outdoor living space is quiet and serene, making it a perfect place to unwind. Families and honeymooners alike can enjoy this island oasis. Centrally located at Mile Marker 61, Duck Key is just a short drive to Key West. Explore everything the Florida Keys have to offer or stay local to enjoy world-renowned restaurants, fishing, snorkeling, and diving. The opportunities are endless.
4.85 out of 5 average rating, 113 reviews
Vibrant Beachfront Villa
Welcome to Beachfront Villa that has recently been renovated. The 2 bedroom 1.5 bath luxury villa is located in the popular area of Duck key alongside of Hawks Cay Resort. Duck Key marina is located across the street where you can dock your boat or charter a boat for the day. Enjoy stunning sunset views from the back porch. Kitchen includes all amenities including silverware ,plates , cups , and pots. Linens and towels provided. *** Pets welcome with host approval and pet fee. ****
4.81 out of 5 average rating, 238 reviews
360 DEGREE WATERVIEW HOUSEBOAT
IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.
4.93 out of 5 average rating, 394 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
5.0 out of 5 average rating, 12 reviews
Houseboat Getaway In Marathon
Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.
4.87 out of 5 average rating, 142 reviewsPopular amenities for beachfront rentals in Vaca Key
Pet-friendly beachfront home rentals

Boaters delight! 1 min to open water, Dock & Beach
4.92 out of 5 average rating, 24 reviews
SeaEsta! Bring your boat & 1 block to the beach!
4.88 out of 5 average rating, 16 reviews
New Private 4/3 Single Family - Kayaks & Bicycles+
4.94 out of 5 average rating, 94 reviews
NEW-Luxury Waterfront Island Home-BEACH, Pool Dock
5.0 out of 5 average rating, 5 reviews
Beach Home and Boater’s Paradise Sombrero
4.5 out of 5 average rating, 8 reviews
Coco Plum Beach Paradise w Heated Pool & Boat Slip
5.0 out of 5 average rating, 6 reviews
Grassy Key Ocean Front Beach House
5.0 out of 5 average rating, 10 reviews
Spectacular 2BR Oceanfront Dog Friendly | Dock
4.71 out of 5 average rating, 17 reviewsBeachfront home rentals with a pool

Private Beach in Marathons Key Colony Beach
5.0 out of 5 average rating, 29 reviews
Canal/Dock - Cabana Club - Pickleball - Remodeled
4.98 out of 5 average rating, 48 reviews
2 Bdrm Oceanfront Complex Private Beach & Pool
4.93 out of 5 average rating, 41 reviews
Beachfront Villa w/ Pier & Pool
4.72 out of 5 average rating, 152 reviews
Beachfront Condo on Coco Plum Beach w/heated pool
4.9 out of 5 average rating, 10 reviews
Key Colony Beach oceanview condo, beach + pool
5.0 out of 5 average rating, 4 reviews
Sandy Beach Just Steps Away
4.6 out of 5 average rating, 5 reviews
3 Bedroom Private Oceanfront House - Sol
4.55 out of 5 average rating, 29 reviewsPrivate beachfront home rentals

1-bedroom suite - Full Kitchen, Dockage, Boat Ramp
4.96 out of 5 average rating, 53 reviews
Paradise awaits.
5.0 out of 5 average rating, 4 reviews
Exquisite Oceanfront Paradise - Key Colony Beach
4.92 out of 5 average rating, 232 reviews
Coastal Key Colony Beach Condo, Oceanfront Complex
4.92 out of 5 average rating, 358 reviews
Oceanfront Sunrise Condo Private Beach Heated Pool
4.97 out of 5 average rating, 235 reviews
Beachside Unit 22 - Private Beach on Atlantic
4.86 out of 5 average rating, 153 reviews
Exquisite Luxury Oceanfront Complex Key Colony
4.92 out of 5 average rating, 265 reviews
Bright Cheery Condo, Ocean Views in Key Colony
4.97 out of 5 average rating, 335 reviewsDestinations to explore
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- Beachfront rentals Monroe County
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Bahia Honda State Park
- Seven Mile Bridge
- Robbies Marina Of Islamorada
- Key Largo Kampground And Marina
- Theater of the Sea
- Ernest F. Coe Visitor Center
- Florida Keys Aquarium Encounters
- Harry Harris Beach and Park
- Dolphin Research Center
- Founder's Park
- History Of Diving Museum
- Calusa Campground
- Conch Key
- Curry Hammock State Park
- The Rain Barrel Village





