
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.

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
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
4.87 out of 5 average rating, 181 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, 281 reviews
Cottage By The Sea
Cottage By The Sea...! If you love turtles.This is the spot for you.I have a 150 pound giant sulcata tortoise in the front yard.And then I have four other little turtles that live in an enclosement , also in the front yard and a giant snapping turtle in my koi pond Our 2 bedroom Guest House is located on the Oceanside of Key Largo in a quaint and quiet neighborhood, with a huge yard surrounded by exotic flowers and trees. It is walking distance to a famous local's Tiki Bar and Restaurant
4.9 out of 5 average rating, 421 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!
4.91 out of 5 average rating, 207 reviews
Largo Getaway: 3 King Suites + In-Law Space
🔑 Managed by KEYLARGOTRAVELS See our profile for all listings. VIRTUAL TOUR: YouTube @Keylargotravels, go to Shorts it is called Mariners 🛏 SLEEPING Bedroom 1 – First Floor In-Law Suite: King bed, en-suite full bathroom with shower, plus a full-size sleeper sofa in the living area Bedroom 2 – Third Floor Master: King bed, en-suite full bathroom, plus a twin floor mattress available if needed Bedroom 3 – Third Floor Guest Suite: King bed plus twin bunk beds, en-suite full bathroom
4.93 out of 5 average rating, 100 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, 235 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, 220 reviews
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, 102 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
Waterfront Home 3/2.5,HotTub,2Sup,4Kayaks,Golf Car
Key Largo Waterfront House! 3BR/2.5BA remodeled high tech home + game room, dock, 4 kayaks, 2 paddle boards & golf cart included. Rent our 22’ boat or jet skis right from the backyard! Walk/golf cart to John Pennekamp Park. Kick back in the hot tub, hammock, or game room. Spot manatees while snorkeling, fire up the grill, and enjoy island vibes.—your ultimate Key Largo adventure awaits! Search Sunkissed Vacation Rental Monroe County Short Term Rental Permit #25300040
4.86 out of 5 average rating, 101 reviewsPopular amenities for holiday rentals near Theater of the Sea
Condo rentals with Wi-Fi

Sunshine Paradise Key Largo Ocean Pointe 4402
4.94 out of 5 average rating, 112 reviews
Your Happy Place - Oceanfront
4.95 out of 5 average rating, 151 reviews
Tiki Time! Ocean Pointe Top Floor King 1 Br/1Ba
4.96 out of 5 average rating, 252 reviews
Lux Suite Open Ocean Views- 2 Balconies+Pool & Bar
4.9 out of 5 average rating, 168 reviews
Ocean Views at Ocean Pointe
4.99 out of 5 average rating, 225 reviews
Best View Ocean Pointe Pool Beach King Bed, Gated
4.97 out of 5 average rating, 233 reviews
Gorgeous lagoon-front 2BR Townhouse with 2 pools
4.91 out of 5 average rating, 171 reviews
BEAUTIFULLY DESIGNED OCEANFRONT CONDO
4.93 out of 5 average rating, 172 reviewsFamily-friendly house rentals

Captain’s Quarters Ahoy Mateys! Florida, Keys
4.93 out of 5 average rating, 153 reviews
4BR 3B, Heated Pool & Spa, 60' Dock
4.95 out of 5 average rating, 108 reviews
The Paradise 2
4.9 out of 5 average rating, 174 reviews
Private Pool Tropical Oasis - Centrally Located
5.0 out of 5 average rating, 119 reviews
OceanView 2/2.5 w Beach Pool & Marina Islamorada
5.0 out of 5 average rating, 21 reviews
TheSandbar: Partial Ocean view,Pool,Free Dockage
5.0 out of 5 average rating, 27 reviews
Exceptional vaca in Angler's Reef Islamorada
5.0 out of 5 average rating, 28 reviews
Life On A Rock Luxury Home in Downtown Islamorada
5.0 out of 5 average rating, 8 reviewsApartment rentals with air conditioning

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
4.96 out of 5 average rating, 295 reviews
Ocean View 2br/2ba w/pool, bar, gym + dockage 28ft
4.99 out of 5 average rating, 106 reviews
Little Peace of Haven
4.9 out of 5 average rating, 124 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
6. Key Largo Waterfront Studio | Dock, Snorkel
4.89 out of 5 average rating, 299 reviews
Beachside Unit 22 - Private Beach on Atlantic
4.86 out of 5 average rating, 153 reviews
Keys Sunset Sanctuary
5.0 out of 5 average rating, 20 reviewsOther great holiday rentals near Theater of the Sea

NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
4.97 out of 5 average rating, 35 reviews
Closest Oceanfront Home - 3 Stories and Boat Dock
5.0 out of 5 average rating, 23 reviews
Perfect escape to the ocean
4.79 out of 5 average rating, 67 reviews
Off-Grid Islamorada Houseboat
5.0 out of 5 average rating, 9 reviews
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
4.96 out of 5 average rating, 79 reviews
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
5.0 out of 5 average rating, 6 reviews
Has canal ocean sbigdavechartersandtours.comm-1m
4.99 out of 5 average rating, 69 reviews
The Nest Villa & Marina in the heart of Islamorada
4.9 out of 5 average rating, 20 reviewsDestinations to explore
- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Biscayne National Park
- Schnebly Redland's Winery & Brewery
- Homestead-Miami Speedway
- 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
- Harry Harris Beach and Park
- Dolphin Research Center
- Monkey Jungle
- Founder's Park
- History Of Diving Museum
- Homestead Bayfront Park
- Calusa Campground
- Conch Key





