Places to stay near Theater of the Sea

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Top-rated holiday rentals near Theater of the Sea

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

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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.

Top guest favourite
Home in Islamorada
5 out of 5 average rating, 15 reviews

OceanView 2/2.5 w Beach Pool & Marina Islamorada

Everything you need for your Islamorada vacation is here including 2 gorgeous private beaches, kayaks, paddle boards, heated resort style pool, porch seating with ocean view, and 2 balconies. Located in the middle row of Anglers Reef, this home accommodates up to 6. Boat slip can be reserved for additional fee, if available. REELaxation is our only vacation rental and with an extensive background in customer service, extraordinary guest service and helping to make lifetime memories are our goal.

Guest favourite
A serene pool area is surrounded by lush tropical plants and swaying palm trees under a clear blue sky. A large blue umbrella provides shade over a lounging area, enhancing the inviting atmosphere of the outdoor space.
Cottage in Islamorada
4.96 out of 5 average rating, 142 reviews

Charming 2BR cottage in prime keys location w/pool

Your slice of Islamorada awaits at Key Lime Cottage! Step inside this 2-bedroom retreat and you’ll instantly feel at home. Tucked in a quiet neighborhood yet right in the heart of the Florida Keys, it’s the perfect blend of relaxation and convenience. Enjoy a full kitchen, access to a beautiful pool shared with just six homes, outdoor seating with a grill and fire pit and paddle boards. Whether you’re here to unwind, explore, or fish, everything you need for a perfect Keys getaway is right here.

Guest favourite
A charming tiny home is situated on the water, surrounded by lush palm trees. The dock features seating areas and a tiki-style shelter, with boats gently bobbing in the bay. Bright blue skies frame the scene, highlighting the serene waterfront atmosphere.
Home in Key Largo
4.91 out of 5 average rating, 197 reviews

Tiny Home on Waterfront | Bay Views | Deck | Pool

Down by the waters of Manatee Bay, you’ll find this idyllic tiny home for 6. With a full kitchen, three comfy beds,and access to a community pool, this is a prime location to enjoy the best of Key Largo. Sit on the deck and dip your toes in the water or explore the bay using the available kayaks and paddle boards. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

Guest favourite
Houseboat in Islamorada Tavernier
4.9 out of 5 average rating, 267 reviews

Baycation Houseboat * Florida Keys Waterfront Stay

Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers the perfect blend of comfort, adventure and true waterfront living. Wake up to breathtaking sunrises, sip your morning coffee as the marine life glide by, and fall asleep to the gentle sway of the water. Whether you’re celebrating something special or simply craving a one-of-a-kind getaway, this houseboat is the ideal home base for both keys adventures and peaceful retreats đŸ’«

Top guest favourite
A Tiki Hut provides shaded outdoor seating, featuring a dining table with chairs overlooking the bay. Sunning loungers are positioned nearby on a paved deck, with boats docked along the waterfront in the background, surrounded by palm trees and calm water.
Home in Key Colony Beach
4.93 out of 5 average rating, 137 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.

Top guest favourite
Apartment in Tavernier
4.96 out of 5 average rating, 223 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

***IMPORTANT*** The pictures you see here are of OUR unit. What you see is what YOU GET. No surprise when you arrive at Ocean Pointe. NO bait and switch. We own in the Prominent Building #3 just steps from the Pool & Jacuzzi. Wireless Internet Netflix & Cable TV, XBOX ONE. ***Most of our guests (99%) claim this is the cleanest Airbnb they have ever stayed in.*** You will get a TRUE UNIMPEDED OCEAN VIEW in our unit. Read our reviews, our past guests tell it all. ⭐ 5 STAR ⭐ Get what you pay for.

Top guest favourite
Four blue Adirondack chairs are arranged on a sandy terrace overlooking the ocean. The clear water extends toward a distant pier, and two kayakers can be seen paddling nearby under a bright blue sky dotted with white clouds.
Townhouse in Islamorada
4.97 out of 5 average rating, 30 reviews

NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom

🌊Welcome to The Seascape🌊 Experience waterfront living at its finest at The Seascape, a modern, newly constructed retreat nestled directly on the ocean where every morning begins in color, and every evening ends in calm. Here, the ocean isn’t just a view. It’s a presence. Come make memories at Islamorada's famous sandbar, legendary fishery, or gather on sunlit shores to relax and revel in life’s simplest joys with stunning views, direct water access, and a stylish escape from the everyday.

Top guest favourite
A spacious outdoor porch features a round dining table surrounded by four chairs. A kayak is positioned nearby, and lush greenery and water views are visible in the background, enhancing the inviting outdoor space.
Villa in Duck Key
4.96 out of 5 average rating, 184 reviews

Beach House Getaway - Free Kayaks 2/2.5

Welcome to Beach House Getaway, a charming villa tucked away on the serene island of Duck Key and perfectly situated in the heart of the Florida Keys. Nestled between Key Largo and Key West, Duck Key serves as a peaceful yet convenient base for your island getaway. Its central location means you’re just a short drive from some of the most iconic destinations in the Keys, including the natural wonders of Bahia Honda State Park, the famous waters around Islamorada, and the lively Key West.

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, 207 reviews

Oasis2 in Key Largo With a million dollar view

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
A vibrant garden area is surrounded by tall palm trees, featuring colorful tables in yellow, red, and blue, arranged around a sunshade awning. Lush greenery creates a serene ambiance, with pathways and cozy seating inviting relaxation and social gatherings.
Home in Islamorada
4.97 out of 5 average rating, 211 reviews

Flakey's

Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.

Guest favourite
An aerial view of a tranquil pool surrounded by lush greenery, featuring a spa area and two red umbrellas shading lounge chairs. A patio with a seating arrangement is visible alongside the pool, creating an inviting outdoor space.
Home in Key Largo
4.99 out of 5 average rating, 147 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.

Popular amenities for holiday rentals near Theater of the Sea

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Islamorada
  6. Theater of the Sea