
Luxury rentals in Monroe County
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Top-rated luxury holiday rentals in Monroe County
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Dreamvilla in Pinecrest by Jatina Group
Towering palms and animal-shaped hedges greet you at this Miami escape. Sliding glass doors create an effortless transition from the sleek interior to the sprawling terrace. Work up a sweat in the in-house gym before plunging into the pool. At night, the bubbling hot tub transforms with a variety of vivid hues. There is a golf course nearby as well as plenty of parks and scenic beaches to wander. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower, Walk-in closet, Television, Safe, Terrace • Bedroom 2: Queen size bed, Ensuite bathroom with stand-alone shower, Television, Safe, Terrace • Bedroom 3: 2 Queen size beds, Ensuite bathroom with stand-alone shower, Television, Safe • Bedroom 4: 2 Queen size beds, Ensuite bathroom with stand-alone shower, Television, Safe • Bedroom 5: Queen size bed, Ensuite bathroom with stand-alone shower, Television, Safe • Bedroom 6: Twin size bed, Ensuite bathroom with stand-alone shower, Television OUTDOOR FEATURES • Terrace

New Waterfront Luxe: Pool-Spa-Dock-Beach-Gulf View
The Gulfside Retreat is the perfect tropical luxury location to unwind in the sun, enjoy endless activities, and stay a while. This 4-bedroom, 5-bathroom 1.5 acre Gulf-front home offers the ideal private resort experience. Our home features an open layout with massive outdoor space and amazing Gulf views. You will have your own private beach, boat dockage, protected lagoon, and a long private pier to enjoy the gulf breezes. Plus, easy access to the oceanside in minutes by boat via the Vaca Cut.

Private Beach, Pickleball Court and Tiki Bar
Hidden in the heart of Islamorada, this oceanfront villa offers an unmatched privilege of a secluded private beach—an experience few can claim. Expansive terraces stretch across both levels, framing ocean views. This haven's open design and spacious rooms blend seamlessly with serene surroundings. A lush tropical yard meets the oceanfront, where swaying palms and vibrant greenery create a private oasis, crafting a retreat as rare as it is extraordinary. Enhanced cleaning practices implemented.

House of the Royal Palms in Old Town
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ** Last Key Realty requires a credit card on file for all reservations. ** Key West is known for having amazing properties, but one home stands tall above the rest with its six majestic Royal Palm trees. HOUSE OF THE ROYAL PALMS features a spacious exterior that will make even the most high-end influencer envious. You’ll be spoiled with multiple seating areas, an oversized covered porch,

Peninsula Villa | Boat Dock | Heated Pool | Sunset
This grand peninsula retreat, embraced by the Ocean and lush mangroves offering utmost privacy, has been designed for ultimate vacationing. Nestled along the tranquil shores of Florida Bay, its array of indoor & outdoor living and lounge areas, heated pool with a tiki bar, expansive sandy playgrounds, dock with ocean-access canal, gazebo boasting sunset views make this magical oasis ideal for serene escapes or vibrant family gatherings. Enhanced cleaning practices implemented.

The Starboard House at Solaire Lunara Bay
Explore a stunning new build with eight generous bedrooms and a private pool. This exceptional home offers top-tier amenities, including free gym access and expansive living areas perfect for unwinding and entertaining. With its modern design and upscale finishes, this property is ideal for those who appreciate comfort and style. Experience a new standard of living that seamlessly blends elegance and convenience in this remarkable residence. Get ready to elevate your lifestyle.

2-Story 3BD Brickell Penthouse | Heated Pool | Gym
This incredible penthouse offers the premium amenities and service of a luxury hotel, combined with the space and value of a vacation rental. Enjoy sweeping views of Brickell and Biscayne Bay from the top 2 floors of the building. The first floor has floor-to-ceiling windows, flooding the space with natural light, along with a balcony and the 1st bedroom. The second floor has 2 bedrooms as well as a dedicated work space. The property is located in the heart of Brickell.

Maya's Secret Treasure at Duval - Unique Condo
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ** Last Key Realty requires a credit card on file for all reservations. ** Walking along Duval Street dreaming of the ideal Key West vacation destination, scanning the rooftops for possibilities, at first you’ll miss this hidden gem completely…but once you discover MAYA’S SECRET TREASURE, you will know you have found the ultimate home base to enjoy Key West.

Maison Residences, 8 Bedroom oceanfront w Pool
Escape to a laid-back paradise at this 8-bedroom Islamorada residence, where two sprawling units are rented as one. The terrace boasts ocean views while soaring windows drench the interior in ribbons of natural light. Tropical palms sway in the balmy breeze as you stroll to the beach. Take a dip in the pool, try snorkeling through the coral reefs, or grab a bite to eat at a local restaurant. Copyright © Island Villa Rentals of Islamorada. All rights reserved.

The Rigby House - Pool, One block from Duval St
Escape to paradise with this stunning 6-bedroom, 6.5 bathroom home nestled in the heart of historic Key West. Walking distance to everything, this home is ideal for families or large groups, this spacious retreat offers the perfect blend of modern amenities and tropical charm. Enjoy your own oasis with a sparkling private pool, surrounded by ample lounging space. Perfect for refreshing dips under the sun or evening cocktails under the stars.

Dream Villa in Coral Gables by Jatina Group
This unique villa showcases Miami modern and Caribbean flair featuring 5 en-suite bedrooms and six baths surrounded by lush tropical rectangular grounds canopied by majestic trees. 5 Bedrooms 6 Bathrooms 5,000 Interior Sq Ft Resort Style Pool & Jacuzzi Pool table / Ping-Pong / Game Room The entertainment continues inside in the Game Room where you can have your hand at billiards, ping-pong, arcades or just lounge and watch the fun ensue.

4 Bedroom Oceanfront Accessible Villa – Capacity 8
Enjoy abundant space with spectacular Atlantic Ocean views, and embrace the surrounding natural haven with indoor-outdoor living. At 3,100 SF each, the Villas include 3 in-suite king-bed bedrooms and 1 twin room, a full kitchen, dining room, laundry room, waterfront balconies, a 2-car garage and elevator. *A 5% Monroe county tourism tax will be collected at check in, as Airbnb does not include this tax in there bookings*
Popular amenities for Monroe County luxury holiday rentals
Other great luxury holiday rentals in Monroe County

LUXE Certified - Vizcaya Retreat - Prime Location!

House of the Royal Palms in Old Town

New Waterfront Luxe: Pool-Spa-Dock-Beach-Gulf View

Peninsula Villa | Boat Dock | Heated Pool | Sunset

Maya's Secret Treasure at Duval - Unique Condo

Private Beach, Pickleball Court and Tiki Bar

Plantation Tropicale at Casa East

The Starboard House at Solaire Lunara Bay
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