
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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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
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
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
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
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.
4.91 out of 5 average rating, 169 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.
4.97 out of 5 average rating, 35 reviews
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
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
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
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
Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath
Turtle lovers rejoyce! Enjoy this Two Bedroom/Two Bath Condo with the perfect blend of style, comfort and convenience. Featuring a spacious living room and a fully stocked Kitchen. The Master bedroom features a King size bed and ensuite master bathroom. The guest bedroom features a Queen bed with a unattached bathroom. Both bathrooms feature a walk-in shower. The balcony offers views of the nature preserve and peek-a-boo views of the Atlantic Ocean!
4.94 out of 5 average rating, 158 reviews
Fishing Getaway | Dock, Pool & Sunrise
Wake up to breathtaking oceanfront sunrises in the Sportfishing Capital of the World. This luxury 3BR, 3BA townhome in Islamorada features a private dock, waterfront resort-style pool, and a quiet gated community just minutes from the Keys’ best fishing, marinas, restaurants, and attractions. Pet-friendly and fully equipped, it’s the perfect escape for anglers, families, couples, and extended stays.
5.0 out of 5 average rating, 13 reviewsPopular amenities for holiday rentals near Theater of the Sea
Condo rentals with Wi-Fi

Ocean Views at Ocean Pointe
4.99 out of 5 average rating, 224 reviews
Lux Suite Open Ocean Views- 2 Balconies+Pool & Bar
4.91 out of 5 average rating, 166 reviews
Your Happy Place - Oceanfront
4.95 out of 5 average rating, 151 reviews
BEAUTIFULLY DESIGNED OCEANFRONT CONDO
4.93 out of 5 average rating, 171 reviews
Best View Ocean Pointe Pool Beach King Bed, Gated
4.97 out of 5 average rating, 232 reviews
SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
4.9 out of 5 average rating, 337 reviews
Blue Haven Key Largo | Ocean Pointe 1315
4.92 out of 5 average rating, 127 reviews
Tiki Time! Ocean Pointe Top Floor King 1 Br/1Ba
4.96 out of 5 average rating, 251 reviewsFamily-friendly house rentals

Banana Cabana
4.85 out of 5 average rating, 133 reviews
The Paradise 2
4.9 out of 5 average rating, 173 reviews
Great key Largo home with water front and pool
4.91 out of 5 average rating, 113 reviews
Key Largo Waterfront: Tiki, Dock, Kayak & Pool
4.97 out of 5 average rating, 188 reviews
Tiny Home on Waterfront | Bay Views | Deck | Pool
4.91 out of 5 average rating, 205 reviews
Angler's Eden
4.97 out of 5 average rating, 114 reviews
Captain’s Quarters Ahoy Mateys! Florida, Keys
4.93 out of 5 average rating, 151 reviews
4BR 3B, Heated Pool & Spa, 60' Dock
4.95 out of 5 average rating, 108 reviewsApartment rentals with air conditioning

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
4.96 out of 5 average rating, 295 reviews
When Paradise is Key: Tropical Oceanfront Condo
4.88 out of 5 average rating, 101 reviews
Little Peace of Haven
4.9 out of 5 average rating, 124 reviews
Ocean View 2br/2ba w/pool, bar, gym + dockage 28ft
4.99 out of 5 average rating, 104 reviews
5. Key Largo Waterfront Studio | Kayak & Reef
4.84 out of 5 average rating, 276 reviews
A Piece of Paradise in KL, Florida
4.8 out of 5 average rating, 180 reviews
Cozy Keys Efficiency 8a
4.86 out of 5 average rating, 117 reviews
Beachside Unit 22 - Private Beach on Atlantic
4.86 out of 5 average rating, 153 reviewsOther great holiday rentals near Theater of the Sea

Off-Grid Islamorada Houseboat
5.0 out of 5 average rating, 9 reviews
Perfect escape to the ocean
4.79 out of 5 average rating, 67 reviews
The Nest Villa & Marina in the heart of Islamorada
4.89 out of 5 average rating, 18 reviews
Off The Charts-Waterfront Tiki Bar & Private Dock
5.0 out of 5 average rating, 15 reviews
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
4.96 out of 5 average rating, 79 reviews
Waterfront Cottage Walk to World Famous Lorelei
4.97 out of 5 average rating, 71 reviews
El Encanto | Private pool and tropical tiki
5.0 out of 5 average rating, 22 reviews
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
5.0 out of 5 average rating, 4 reviewsDestinations to explore
- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Biscayne National Park
- Homestead-Miami Speedway
- Schnebly Redland's Winery & Brewery
- Coral Castle
- Bahia Honda State Park
- Seven Mile Bridge
- Robbies Marina Of Islamorada
- Everglades Alligator Farm
- Key Largo Kampground And Marina
- Ernest F. Coe Visitor Center
- Florida Keys Aquarium Encounters
- Deering Estate
- Dolphin Research Center
- Harry Harris Beach and Park
- Founder's Park
- Monkey Jungle
- History Of Diving Museum
- Homestead Bayfront Park
- Calusa Campground
- Conch Key





