Holiday houses in Pelican Key

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Top-rated holiday rentals in Pelican Key

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
A plate of vibrant dragon fruit sits on an aqua blue chair on a waterfront patio. Two glasses filled with a refreshing beverage are placed nearby, while lush greenery and boats are visible in the background under a clear blue sky.
Holiday home in Key Largo
4.84 out of 5 average rating, 338 reviews

4. Tranquil Waterfront Stay in Key Largo

Enjoy water front living in Key Largo! Watch the boats go by with fresh catch served daily at the local restaurants. See manatees, nurse sharks and fish swim by the canal all day. Dock your boat at the Pilot House Marina just down the street. Our unit is Modern, Spacious and Spotless with Private Parking, Fast Wifi, Netflix, Cold AC, Plush Pillows and a Cozy bed. We are on a main canal to open ocean. Near Rodriguez Key, Mosquito Bank, Christ of the Abyss and many sunken shipwrecks for exploring.

Top Guest favourite
The eco-friendly two-story River Queen vessel is anchored in a calm harbor, showcasing a modern design. The structure features large windows and a rooftop terrace, with a wind turbine on the left. The surrounding landscape includes lush greenery, complementing the serene water view.
Boat in Tavernier
4.92 out of 5 average rating, 398 reviews

Island Sanctuary Islamorada

Stay aboard the eco-friendly two-story 63 ft River Queen with a 360 degree view with beautiful sunrises and sets, mored 1/8 mi offshore in a quite harbor close to shopping center, movie theater, hospital, bars & restaurants. A 10-foot dinghy with small outboard to come & go from shore "ONLY", nowhere else. I also offer Personal Training, deep tissue work & Life Coach sessions. I live on the vessel about a hundred yards from you so if there are any questions, etc. I will be there to assist you.

Guest favourite
An open living area features a stylish sectional sofa adorned with decorative pillows. A round wooden coffee table sits on a light area rug, and a ceiling fan gently rotates above. The dining area showcases a long table with elegant chairs, and artwork is displayed on the walls.
Home in Key Largo
5 out of 5 average rating, 35 reviews

NEW! CASA LARGO -Golf Cart, 2 Kings 3 Bath, Kayaks

NO RESORT, GUEST OR MANAGEMENT FEES WHEN BOOKING MY HOMES! Welcome to your Key Largo vacation rental. This oceanside villa is family friendly and packed with amenities. Guests enjoy pools, beach, three kids kayaks, pickleball, tennis courts, and a unique saltwater swimming lagoon that is perfect for a refreshing dip. Spend your days kayaking, fishing, boating, snorkeling or relax on the nearby beach and experience the best of the Florida Keys. 8 guests, mix of adults and children, max 7 adults.

Top Guest favourite
A serene waterfront scene captures a vibrant sunset reflecting off calm waters. Multiple boats are docked along the marina, with silhouettes of masts against the colorful sky, creating a peaceful atmosphere ideal for relaxation.
Home in Key Largo
4.98 out of 5 average rating, 250 reviews

Waterfront Sunsets, Great Price, Relaxing Spot!!!

Beautiful Waterfront, Modern Coastal Décor, Spacious !! Enjoy your vacation in this beautiful recently renovated home. Views from almost every window and door of the harbor. Walk to many local restaurants and bars for fresh local seafood and a cold draft beer!! 28 day rental. Enjoy sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

Guest favourite
A serene sunset view showcases a circle of white Adirondack chairs positioned around a fire pit. The calm waters reflect vibrant hues of orange and purple from the sky, creating a peaceful atmosphere.
Townhouse in Key Largo
4.87 out of 5 average rating, 175 reviews

Sunrise Escape - Ocean Front Villa - Sleeps 10

Wake up to the sunrise over the ocean and unwind with sunset views from your private jetty. This marina-front, ocean-view townhouse in Kawama Yacht Club puts you steps from kayaking, snorkeling, and the best of the Keys. Spacious, stylish, and designed for unforgettable family and friend getaways. Breathtaking sunrises from one of two private terraces, coffee in hand, overlooking the marina and the Atlantic Ocean. Located in an exclusive, quiet section of Kawama Yacht Club, this beautifully po

Guest favourite
A modern kitchen features white cabinetry and stainless steel appliances. A wooden cutting board is placed on the counter, complemented by cooking utensils. Soft lighting illuminates the space, enhancing the clean and functional design. A window with shutters allows natural light to enter.
Condo in Key Largo
4.91 out of 5 average rating, 161 reviews

Gorgeous lagoon-front 2BR Townhouse with 2 pools

Kawama Yacht Club is situated between an extension of John Pennekamp Coral Reef State Park and a salt-water, filtered, tidal snorkeling lagoon! Two pools, tennis courts, private beach, a waterfront (lagoon) will keep you busy on site, while the neighborhood offers boating, many great restaurants and you may even swim with dolphins just outside the gates to the community. The townhouse comes equipped with two bicycles and two kayaks. All brand new appliances throughout + extra lg washer/dryer.

Top Guest favourite
Holiday home in Key Largo
4.95 out of 5 average rating, 154 reviews

Ocean Shores Villa 3 with pool and boat slip

This centrally located boater's paradise is the perfect place to relax. Walk to restaurants, cook in kitchen or grill downstairs. With only 4 units in the building the guests have half an acre of waterfront entertainment (boat slip, Kayaks, Bikes, Hammock and Pool). 32ft Dock Slip and Trailer Parking are included in the rental. Relaxing Balcony that looks down the Ocean Canal is the perfect place to have your morning coffee. Conveniently located near Sandbars, State parks and many attractions.

Top Guest favourite
A sunset view is captured from a covered outdoor seating area, showcasing a tranquil waterway. Silhouettes of kayaks and a table are visible, while the setting sun creates a warm glow across the horizon. Natural textures are evident in the thatched roof above.
Tiny home in Key Largo
4.97 out of 5 average rating, 212 reviews

My Little Oasis2 Waterfront Retreat, Key Largo

Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

Top Guest favourite
An aerial view of a blue, two-story house surrounded by greenery. The backyard features a swimming pool, red umbrellas, and seating areas. A patio leads to the pool, and the front yard is landscaped with grass. The neighborhood shows a quiet street with nearby houses.
Home in Key Largo
4.99 out of 5 average rating, 150 reviews

Luxury Heated Pool/Jacuzzi, Games & Nice Backyard.

✨Bring the whole family to this great located house with a nice pool with spa, combo game table and lots of room for fun, and enjoy the beach, restaurants and entertainments around the area. ✨5BRs with smart TVs and comfortable mattresses and pillows. 3BR upstairs/2BR downstairs. ✨3 bathrooms, 1BR downstairs/2BR upstairs. ✨2 kitchens fully equipped with everything you may need. ✨Nice and quite neighborhood. ✨Sunsets are amazing at The Florida Keys. ✨Guest are always our priority.

Guest favourite
Home in Key Largo
4.91 out of 5 average rating, 46 reviews

Remodeled July 2025 2/2 Townhouse

🌴 Coastal Getaway ✔2 STORY BRAND NEW SPACIOUS TOWNHOME ✔BOAT SLIP AVAILABLE AT ADDITIONAL COST OF $4.25/ft/day ✔NO SLIP? NO PROBLEM....RAMP AVAILABLE AT NO ADDITIONAL COST FREE TRAILER STORAGE YOU MUST SHOW PROOF IF LIABILITY INS PRIOR TO ARRIVING, FIRST COME FIRST SERVE, THE DEVELOPEMENT RESERVES THE RIGHT TO TURN YOU AWAY IF BOAT PARKING IS FULL. ALSO YOU CAN ONLY DROP AND RETURN WITH HIGH TIDE. YOU MUST BE MINDFUL OF THE TIDES. ✔TENNIS & PICKLE BALL WITH LIGHTS

Superhost
A charming floating bungalow rests on calm waters, surrounded by an expansive horizon. Its thatched roof and large windows reflect a serene setting, while the gentle ripples of the water enhance the peaceful atmosphere.
Houseboat in Buttonwood Sound
4.91 out of 5 average rating, 34 reviews

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.

Guest favourite
The exterior of a charming lakefront retreat is displayed, featuring a private heated pool, green turf, and white Adirondack chairs arranged on a sandy area by the water's edge. A covered balcony offers shaded seating, with colorful twilight skies creating a serene backdrop.
Home in Key Largo
4.96 out of 5 average rating, 68 reviews

Lakefront pool house, jacuzzi Beachfront

Serene Lakefront Retreat – Your Perfect Getaway! Escape to paradise in this beautiful lakefront home , offering breathtaking water views, and a relaxing atmosphere. Nestled in a tranquil neighborhood, this home is perfect for families, couples, or friends looking to unwind and enjoy Florida’s natural beauty. Whether you're seeking a peaceful retreat or an adventure-filled getaway, this lake house provides the best of both worlds.

Popular amenities for Pelican Key holiday rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Pelican Key