
Vacation rentals in Monroe County
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Top-rated vacation rentals in Monroe County
Guests agree: these stays are highly rated for location, cleanliness, and more.

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!!!

Coconut Grove Stunning City View Suite Free Park
INCREDIBLE VALUE! First, a $30 gift card to our restaurant GreenStreet and a bottle of champagne will be awaiting you in your room! In Coconut Grove, this privately owned & renovated bright suite on the 15th floor of a luxurious waterfront property offers breathtaking city views, is fully equipped for 2 w/ a king size bed & full bath. Enjoy all the luxury amenities this property has to offer, pool & hot-tub with incredible bay views, penthouse gym, sauna, business center, 24-hr security, squash

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.

Turtle-By-The-Sea: the Best Deal in KCB!
A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

Guest Studio apt, Private entrance, Patio, Parking
Take it easy at this unique and tranquil getaway in our 1930's Spanish Villa in the center of Little Havana and Coral Gables in the heart of Shenandoah. Your Guest Suite is equipped with a private entrance, private garden, and parking. Casita Amorcita is designed to give you the feeling of 'home' and 'love,' with the guest experience in mind. All linens are 100% cotton. Here you will have all that you need to rest, recover, recharge, and enjoy. We look forward to welcoming you home.

Adorable private studio
Relaxing, private, peaceful and centrally-located studio. You do not share your space with anyone. Walking distance to restaurants, supermarket, bus stop, Gym and Florida International University. Conveniently close to Miami Airport, Kendall Regional Hospital, Dolphin Mall, TopGolf, Everglades Airboat Expeditions, City Place Doral with Fresh Market, shops, Movie Theaters, Comedy Club, live music and more. Eleven miles from Bayside and Wynwood Walls. The beach? A short 15-mile drive!

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.

Oceanfront Breeze, Stunning Views, Beach/Pool
Newly renovated ocean front condo with gorgeous, unobstructed views from every window. Beautiful studio condo on the 1st floor only steps away from the private beach and heated pool. Condo features a fresh, clean interior with brand furnishings, bathroom and kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

Quiet tropical Oasis setting with 1 bed and 1 bath
Tropical oasis centrally located between Miami Beach and Key Largo. Although you may never want to leave. The cozy casita with private bath and balcony is tucked away, surrounded by lush vegetation and sounds of the waterfall. Take a dip in the pool or grotto, relax with an afternoon cocktail under the tiki hut, or snooze in the hammock. During those cooler months soak in the hot tub. Enjoy the miles of nearby walking paths stretching from Coconut Grove to Black Point Marina.

Hidden Beach unit 1 The Perfect Place to stay
This place is extraordinary. There is nothing like it in Key West. Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

“Have Fun at Hacienda Paraíso” Suite 1 | pool |
Welcome to Room 1, the first addition at Hacienda Paraíso. This suite is conveniently located next to another Airbnb suite, providing flexibility for your stay. It features a private entrance, bathroom, kitchenette, and dining table, ensuring a comfortable and self-contained experience. Enjoy the convenience of hotel-like amenities paired with the added bonus of access to our stunning pool and lush yard, creating a truly relaxing retreat.

Villa Samsara - on a beautiful 5 acre farm
When you come and stay with us, it’s a deeply immersive experience with our horses. Often you will find them in your front door or window. There is something profoundly impactful about being around horses and sharing close-quarters with them. You are in their energy field, receiving all that they have to offer. Without even realizing it, your energies are being grounded and regulated through their presence.
Popular amenities for Monroe County vacation rentals
Other great vacation rentals in Monroe County

Waterfront with Boat Lift/Kayaks and Hot Tub

Florida Keys Oceanside Utopia

Kelly’s Kabin - Private FL Keys Cottage

Cottage 30 min from Key West, free parking, pool

Brand new efficiency Parking,independent entrance.

P36 - Charming and immaculate 2 Bedroom, 2 bathroo

The Roseate House at Grassy Key Lic. #VACA-25-222

Salty Mermaid Ocean Pointe 4406
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- The Turtle Hospital
- Coral Castle
- Calusa Beach & Loggerhead Beach
- History Of Diving Museum
- Sea Oats Beach
- Everglades Alligator Farm
- Conch Key
- Long Beach
- Theater of the Sea
- Schnebly Redland's Winery & Brewery
- Monkey Jungle
- Bahia Honda State Park
- Sunset Park
- Florida Keys Aquarium Encounters
- Key Largo Kampground And Marina
- Seven Mile Bridge
- Calusa Campground
- Robbies Marina Of Islamorada
- Dolphin Research Center
- Founder's Park
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