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Places to stay near Theater of the Sea

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Top-rated holiday rentals near Theater of the Sea

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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

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.

4.92 out of 5 average rating, 401 reviews
Guest favourite
A comfortable living area is highlighted by a light-colored sofa with textured cushions, accompanied by a woven coffee table. Natural light enters through multiple windows, revealing touches of coastal decor and a glimpse of a bedroom in the adjacent space.
Cottage in Islamorada

Islamorada bungalow 2 bed & pool

Welcome to paradise! Completely remodeled and immaculately maintained, Bungalow Blue is nestled away in the quiet quaint Shady Palms community of 7 cottages in Islamorada, MM 76. Ideally situated next to the community heated pool, down the street from private boat ramp. If you're looking to relax and unwind while also being close to all that Islamorada has to offer, this is the place for you. Enjoy the FL Keys lifestyle in your private backyard, take a bike ride to World Famous Robbie's Marina

4.95 out of 5 average rating, 105 reviews
Guest favourite
A serene pool area is surrounded by lush tropical landscaping and palm trees. Lounge chairs are positioned around the pool, along with blue umbrellas providing shade. The clear water sparkles under the bright sun, creating an inviting space for relaxation.
Cottage in Islamorada

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.

4.96 out of 5 average rating, 151 reviews
Top Guest favourite
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.
Condo in Tavernier

Toes in the Sand - 2 Bedroom Condo Sleeps 4

Two bedrooms and two full bathrooms on the 4th floor with ocean views. Amenities include a huge heated pool and hot tub with a bar, a beach cafe serving food and drinks, a private Key's beach, viewing pier, rentable boat slips & boat trailer storage, tennis, pickleball courts, basketball, children's swings, and BBQ areas, and gated entry with 24-hour security! Just remember that you're on "Island Time," mon, relax and enjoy! Perfectly located between Key Largo and Islamorada, close to Penneka

4.86 out of 5 average rating, 271 reviews
Guest favourite
Houseboat in Islamorada Tavernier

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 💫

4.9 out of 5 average rating, 278 reviews
Top Guest favourite
Townhouse in Islamorada

Closest Oceanfront Home - 3 Stories and Boat Dock

Welcome to Paradise Palms, the crown jewel of oceanfront living in Islamorada. This gated, three-story retreat is one of the closest homes to the water, offering unobstructed panoramic views, rare third-floor balcony access, and boat dockage. Thoughtfully designed with modern coastal elegance, enjoy two oceanfront balconies, luxury amenities, and unforgettable sunrises and sunsets. Your comfort and satisfaction are our top priorities. Let us help you turn your vacation dreams into reality.

5.0 out of 5 average rating, 23 reviews
Guest favourite
A private beach area is revealed, featuring rows of blue lounge chairs set on soft, sandy ground. Lush greenery borders the beach, while a wooden pier extends into the calm, turquoise water. A thatched gazebo provides shade, and scattered palm trees complete the coastal scene.
Condo in Tavernier

Your Happy Place - Oceanfront

Experience the ultimate coastal getaway at Ocean Point in the Florida Keys. Nestled along the Atlantic Ocean, our 2 bed/2 bath condo offers unrivaled ocean views from the moment you step inside.  Indulge in the array of amenities available at our property including a private beach, pier, marina, snorkeling, family pool and a full service restaurant. Our condo comfortably sleeps 6-7 guests. Equipped with full kitchen and washer/dryer, we provide all the conveniences for a seamless stay. 

4.95 out of 5 average rating, 151 reviews
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

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.

4.97 out of 5 average rating, 231 reviews
Top Guest favourite
The living area features a comfortable light blue sofa and a glass-top coffee table, complemented by tropical-themed decor. A ceiling fan circulates air above, while a kitchen bar with high chairs is visible in the background. Natural light enters through multiple windows, enhancing the welcoming atmosphere.
Home in Islamorada

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.

4.97 out of 5 average rating, 219 reviews
Superhost
A bright living area features a comfortable gray sofa, decorative chairs, and a coffee table on a patterned rug. Natural light floods the space through large windows, creating a relaxed atmosphere. A wall-mounted TV and a small desk can also be seen, along with coastal decor.
Apartment in Tavernier

When Paradise is Key: Tropical Oceanfront Condo

🚨*PRICE YOU SEE IS ALL IN! Includes Airbnb fees and taxes!*🚨 🚨09.09.26 - 10.14.26 Elevator will be out of service due to installation of a new elevator 🚨 ☀️ Discover the ultimate beachfront getaway in our top floor, two-bedroom, two-bathroom condo, perfectly designed to offer an unforgettable escape. Nestled right on the oceanfront, this retreat comfortably accommodates up to six guests, making it ideal for families, friends, or couples seeking a serene coastal experience. ⛱️

4.88 out of 5 average rating, 101 reviews
Top Guest favourite
A solar and wind powered houseboat is moored on calm waters, featuring bright yellow shutters and a roof deck. Wind turbines and an American flag adorn the top, contrasting with the soothing blue sky and fluffy clouds in the background.
Boat in Islamorada

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, 391 reviews
Top Guest favourite
Condo in Tavernier

Turtle Nest 1 Private beach,Pool, 2bed 2bath

Ocean Pointe Suite is located on the Atlantic. Featuring ocean views from living room, master bedroom and balconies. King bed in master bedroom, Queen bed in guest bedroom, pull out queen sofa, 2 bathrooms, Smart TV's with cable WIFI. Completely stocked kitchen with all appliances. Amenities include heated swimming pool, private beach, marina with boat launch & dockage for extra fee book through marine info in pictures. Tennis courts, gazebo, located on 60 tropical acres.

4.91 out of 5 average rating, 141 reviews

Popular amenities for holiday rentals near Theater of the Sea

KitchenWifiPoolFree parking on premisesAir conditioning

Condo rentals with Wi-Fi

Top Guest favourite
A clear view of the ocean is captured from the balcony, showcasing the shimmering water beneath a bright blue sky. Lush greenery lines the foreground, while a dock extends into the sea. The scene conveys a serene coastal atmosphere.
Condo in Tavernier

Ocean Views at Ocean Pointe

4.99 out of 5 average rating, 224 reviews
Guest favourite
A spacious living area features light blue walls and coastal decor. A comfortable sofa is positioned against the wall, accompanied by a patterned throw pillow. A coffee table is centrally placed, while a bar seating area with stools offers additional gathering space. Natural light fills the room.
Condo in Tavernier

Light, Bright & Nautical Condo at Ocean Pointe

4.93 out of 5 average rating, 121 reviews
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

Gorgeous lagoon-front 2BR Townhouse with 2 pools

4.91 out of 5 average rating, 169 reviews
Guest favourite
A well-lit living area showcases a comfortable sectional sofa and a wooden dining table with light-colored chairs. A decorative bowl of lemons sits at the center of the table, while large windows offer views of the surrounding landscape and allow natural light to fill the space.
Condo in Tavernier

BEAUTIFULLY DESIGNED OCEANFRONT CONDO

4.93 out of 5 average rating, 171 reviews
Top Guest favourite
Condo in Tavernier

Best View Ocean Pointe Pool Beach King Bed, Gated

4.97 out of 5 average rating, 232 reviews
Guest favourite
A private beach area is visible, featuring soft white sand and arranged lounge chairs facing the calm ocean. Lush greenery lines the shore, with a small tree providing shade. In the background, a wooden pier extends into the water under a partly cloudy sky.
Condo in Tavernier

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

4.9 out of 5 average rating, 337 reviews
Top Guest favourite
A light-filled living space features a turquoise sofa with yellow accent pillows, paired with a round glass dining table. Rattan chairs complement the decor, which includes a vibrant tropical wall mural and a circular mirror. Modern appliances are visible in the kitchen area.
Condo in Tavernier

Tiki Time! Ocean Pointe Top Floor King 1 Br/1Ba

4.96 out of 5 average rating, 251 reviews
Top Guest favourite
Condo in Key Largo

Ocean Shores Villa 2 with pool and boat slip

4.92 out of 5 average rating, 149 reviews

Family-friendly house rentals

Guest favourite
A sandy beach area is framed by smooth rocks leading to clear blue waters. Two kayaks, one yellow and one green, are positioned along the shoreline. In the distance, several boats are visible on the water, under a partly cloudy blue sky.
Home in Key Largo

Banana Cabana

4.85 out of 5 average rating, 133 reviews
Guest favourite
A collage showcases four images: A serene sunrise over water, a cozy bedroom with a flat-screen TV, an open-concept living area with a kitchen and dining space, and a tranquil view of the evening sun reflected on the bay, complete with a kayak along the shoreline.
Home in Key Largo

Tiny Home on Waterfront | Bay Views | Deck | Pool

4.91 out of 5 average rating, 205 reviews
Superhost
Home in Key Largo

NEW! Casa Palma - Golf Cart, 2 King, Pool, Kayaks

4.89 out of 5 average rating, 114 reviews
Top Guest favourite
Home in Key Largo

Key Largo Waterfront: Tiki, Dock, Kayak & Pool

4.97 out of 5 average rating, 188 reviews
Guest favourite
Home in Marathon

4BR 3B, Heated Pool & Spa, 60' Dock

4.95 out of 5 average rating, 108 reviews
Top Guest favourite
An inviting outdoor area features a clear swimming pool surrounded by a paved patio. The two-story structure above includes spacious balconies with multiple seating options. Sunlight brightens the scene, and lush greenery is visible in the background, enhancing the tranquil environment.
Home in Marathon

Angler's Eden

4.97 out of 5 average rating, 114 reviews
Guest favourite
A waterfront patio is shown with comfortable seating, overlooking a calm body of water. The sun sets in the distance, casting warm light over the scene. Tropical vegetation can be seen, adding to the serene atmosphere.
Home in Key Largo

The Paradise 2

4.9 out of 5 average rating, 173 reviews
Top Guest favourite
A covered Tiki Hut is featured at the waterfront, furnished with comfortable seating arrangements. Views of the water and dock are visible beyond the structure, framed by lush greenery and palm trees. The space is designed for relaxation and enjoyment of the serene surroundings.
Home in Key Colony Beach

Captain’s Quarters Ahoy Mateys! Florida, Keys

4.93 out of 5 average rating, 151 reviews

Apartment rentals with air conditioning

Guest favourite
Apartment in Tavernier

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

4.97 out of 5 average rating, 220 reviews
Guest favourite
A dining area is presented with a round white table surrounded by four black and white patterned chairs. A light-colored runner with subtle stripes lays across the table, complemented by a decorative pineapple centerpiece. Natural light filters through the nearby window, enhancing the space.
Apartment in Key Largo

Little Peace of Haven

4.9 out of 5 average rating, 124 reviews
Guest favourite
Apartment in Key Largo

5. Key Largo Waterfront Studio | Kayak & Reef

4.84 out of 5 average rating, 276 reviews
Guest favourite
Apartment in Key Largo

A Piece of Paradise in KL, Florida

4.8 out of 5 average rating, 180 reviews
Guest favourite
A shaded tiki hut with a thatched roof stands on the sandy shore, overlooking the calm, blue waters of the Atlantic Ocean. Two palm trees frame the structure, creating a serene beach environment, with gentle waves lapping at the rocks in the background.
Apartment in Key Colony Beach

Beachside Unit 22 - Private Beach on Atlantic

4.86 out of 5 average rating, 153 reviews
Guest favourite
A welcoming entrance features a door labeled '8A' and is flanked by two red chairs with blue and white striped cushions. A small table rests between them, surrounded by potted plants. A window offers a glimpse of natural light within the unit.
Apartment in Marathon

Cozy Keys Efficiency 8a

4.86 out of 5 average rating, 117 reviews
Top Guest favourite
Apartment in Tavernier

Keys Sunset Sanctuary

5.0 out of 5 average rating, 19 reviews
Top Guest favourite
A serene beachfront area is depicted, featuring rows of blue sun loungers arranged on soft white sand. Lush greenery and palm trees border the beach, while the tranquil turquoise waters stretch towards the horizon. A wooden pier extends into the water, enhancing the coastal view.
Apartment in Tavernier

Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis

5.0 out of 5 average rating, 97 reviews

Other great holiday rentals near Theater of the Sea

Guest favourite
Houseboat in Islamorada

Off-Grid Islamorada Houseboat

5.0 out of 5 average rating, 9 reviews
Guest favourite
A floating home is anchored in clear waters, surrounded by lush greenery. The structure is highlighted by solar panels on the roof and a spacious white deck, featuring railings that outline the edges. Bright blue skies and distant mangroves create a serene backdrop.
Houseboat in Islamorada

Perfect escape to the ocean

4.79 out of 5 average rating, 67 reviews
Top Guest favourite
Home in Islamorada

Off The Charts-Waterfront Tiki Bar & Private Dock

5.0 out of 5 average rating, 15 reviews
Guest favourite
Villa in Islamorada

The Nest Villa & Marina in the heart of Islamorada

4.89 out of 5 average rating, 18 reviews
Guest favourite
A bright bedroom features a spacious bed with a white duvet cover and decorative teal throw. Art depicting fish adorns the walls. Natural light enters through the window, complemented by a stylish lamp. A wooden dresser occupies one corner, enhancing the room's coastal theme.
Bungalow in Islamorada

Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s

4.96 out of 5 average rating, 79 reviews
Top Guest favourite
The exterior of the cottage features a vibrant mural adorned with large floral designs, complemented by a light blue roof and shutters. Surrounded by lush greenery, the property sits on a textured gravel area under a clear blue sky.
Cottage in Islamorada

Waterfront Cottage Walk to World Famous Lorelei

4.97 out of 5 average rating, 71 reviews
Top Guest favourite
Home in Key Largo

El Encanto | Private pool and tropical tiki

5.0 out of 5 average rating, 22 reviews
Guest favourite
A houseboat is docked alongside a concrete walkway, with the river water reflecting the sunny blue sky. The boat features a shaded deck on top and a screened-in porch in the front, providing a comfortable outdoor space. Lush greenery is visible along the shore.
Houseboat in Key Largo

Key Largo's Best Kept Secret!

4.9 out of 5 average rating, 70 reviews