Vacation in the Keys – the most complete vacation rentals in the Florida Keys

Our homes have the finest amenities, interior appointments, and private areas for your ultimate relaxation and comfort. From private, romantic homes to accommodations for events, groups or multiple families, we have the setting for the vacation of your dreams, whether you’re entertaining friends or family, or escaping from it all. We also have exceptional knowledge of each Key’s character and activities, as well as the resources to arrange the experience you seek. And our customer service is unsurpassed; we are personally available 24/7 to respond to your needs.

Vacation in the Keys – the most complete vacation rentals in the Florida Keys

We offer the most complete vacation rentals in the Florida Keys, with Luxury Estates of Key Largo and Luxury Homes in Marathon, and Luxury Villas of Key West. Our upscale, waterfront properties are among the most elite in the Keys. Feel free to call us directly at anytime should you have any questions. We look forward to seeing you here.

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Key Largo

Key Largo, the first and northernmost of the Florida Keys, is an hour’s drive from South Florida’s two major airports and a world away. Enjoy Key Largo’s ties to the sea, including scuba diving, snorkeling, underwater hotel, sport fishing, eco-tours, beaches, and dolphin encounter programs. Key Largo also offers nature trails and a center for wild birds.

Islamorada

This perfect family vacation destination offers something to do in, under, above or near the water 24 hours a day. The aqua blue waters surrounding the “village of isles” provide fantastic views from every bridge and waterfront restaurant and home.

Aquazul

AQUAZUL

4 bedrooms (possibly 5), 3 baths, sleeps 8-10; 3,000-sq.-ft. Heated oceanfront pool, dockage, fishing right from the 300-ft. pier. Private beach and shaded roof-top porch.

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LITTLE BAY

3 Properties; each sleep up to 6 people. Upper & Lower Duplexes; each 1,500 sq. ft. with 2 bedrooms, 2 baths, and a porch overlooking the Bay. The Cottage is a bright & airy 1,250-sq.-ft unit, 2 bedrooms, 2 baths.

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Fisherman's Dream | Islamorada Vacation Rental Property

FISHERMAN’S DREAM

3 bedroom, 2.5 bath. Sleeps 6. Immediate Ocean and Florida Bay access, best boating in the Keys. Two parking areas plus RV parking with 50 Amp outlet. Close to shopping, dining, movies, grocery stores, marinas, boat sales and services and so much more.

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ISLAND PALMS ESTATE

In the heart of Islamorada, 2 very private homes make up this impressive estate with lush landscaping, a sandy beach, and beautiful views. Walking distance to shops and restaurants. 10 bedrooms, 8 baths together or rented separately as two 5 bedroom homes each with its own entrance and pool.

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Island Palms North House Pool View

ISLAND PALMS NORTH

Two houses located on one beautiful estate, rented separately, 5 bedrooms, 3 baths, sleeps 10-12. Gorgeous oceanfront sandy beach, conveniently located in the heart of Islamorada. Additional cabana/lockout may also be reserved, adding 1 bedroom and 1 bath, for 2 more people.

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ISLAND PALMS SOUTH

In the heart of Islamorada, 2 very private homes with lush landscaping, a sandy beach, and beautiful views. Walking distance to shops and restaurants. 10 bedrooms, 8 baths together or rented separately as two 5 bedroom homes each with its own entrance and pool.

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Karapan | Islamorada | Vacation in the Keys Vacation Rentals

KARAPAN

5 bedrooms, 8.5 baths, sleeps 10-12. Spacious, private plantation-style estate home with elevator on 5 acres. Additional 1-bedroom apartment available to rent along with the main house; sleeps 2.

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VILLA BELLA

3 bedrooms, 3.5 baths, sleeps 7. Gated estate home featuring unique second-floor terrace. Private. Ample deep-water dock with easy access to both ocean and bay with drawbridge. Heated pool, Jacuzzi, superb open-water views. High-speed internet.

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LEILA’S BEACH HOUSE

3 bedrooms, 2 baths, sleeps 6-8. Heated pool, outdoor shower. Bone fishing right in front of house. Jacuzzi in master bath, steam shower. Sit-in kayak; 2 paddle boards; 16-ft. Catamaran ( upon request).

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Ocean Terrace | Islamorada | Vacation in the Keys Vacation Rentals

OCEAN TERRACE

3 bedrooms plus den bedroom, 3 baths, sleeps 6-8. Gated. Private, beautiful oceanfront home with sandy beach. Porch swing, Tiki hut, and pool overlooking the ocean. Close to shopping and restaurants.

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THE RUSSELL ESTATE

Homey, tranquil 2-acre oceanfront cottage with 3 bedrooms, 2 baths. Sleeps 7. Sandy beach, shallow-water dock to accommodate 21 foot vessel. Beautiful sunrises; 300 feet of sandy beach; ocean swimming, snorkeling and fly-fishing right off the property.

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Island Palms Treetop | Islamorada Vacation Rental Property

ISLAND PALMS TREETOP HOUSE

A beautiful tree top apartment which is available to rent with one or both of the houses in the compound.

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Marathon

Vaca Cove

4 LARGE Bedrooms 3 FULL bathrooms with LARGE RESORT size EXCLUSIVE POOL for VACA COVE. This resort also has over 250’ of DEEP WATER wave protected dockage with water and electric on the dock. All Homes are Waterfront with water views overlooking our State Protected Bonefish Bay. You and your family will have your own private stay in one of the most beautiful waterfront resorts on Marathon.

UNIT A – SHORE THANG

Introducing our “SHORE THANG” (Unit A) home, with breath taking views of Bonefish Bay waters and the Florida Keys eco-system at your front door you will feel you’re part of nature itself.

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UNIT B – SEA FOREVER

Introducing our “SEA FOREVER” (Unit B) home, with breath taking views of Bonefish Bay waters and the Florida Keys eco-system at your front door you will feel you’re part of nature itself.

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UNIT C – REEL PARADISE

Introducing our “REEL PARADISE” home, with breath taking views of Bonefish Bay waters and the Florida Keys eco-system at your front door you will feel you’re part of nature itself.

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UNIT D – BIKINI HOUSE

Introducing our “BIKINI HOUSE” (unit D) home, with breath taking views of Bonefish Bay waters and the Florida Keys eco-system at your front door you will feel you’re part of nature itself.

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UNIT E – ENDLESS SUMMER

Introducing our “ENDLESS SUMMER” (Unit E) home, with breath taking views of Bonefish Bay waters and the Florida Keys eco-system at your front door you will feel you’re part of nature itself.

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UNIT F – ISLAND TIME

Introducing our “ISLAND TIME” (unit F) home, with breath taking views of Bonefish Bay waters and the Florida Keys eco-system at your front door you will feel you’re part of nature itself.

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UNIT G – BEACH DAZE

Introducing our “BEACH DAZE” (unit G) home, with breath taking views of Bonefish Bay waters and the Florida Keys eco-system at your front door you will feel you’re part of nature itself.

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Cudjoe Key

SANDS

Private home in gated community with pool, boat dock, kayaks, and bikes. 18 miles to Key West. The 1200 square foot home boasts two master suites, each with a queen bed, each with separate private full baths, 32” HDTVs, as well as accommodations on other floors. Fish or kayak right off the end of the dock Looe Key and American Shoal Reef are only a short boat ride away, where you’ll find the most beautiful snorkeling and diving reefs in the Keys and excellent fishing. Close to very good restaurants, a gym/wellness center, and Cudjoe Garden’s Marina, a full service marina. The only 18-hole miniature golf course in the keys is located five miles away. Bahia Honda State Park and the Dolphin Research Center, which offers dolphin encounters, are other area attractions.

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Key West

Key West is known as the “Southernmost City,” represented by a concrete replica of a buoy at the corner of South and Whitehead Street, claimed to be the southernmost point in the contiguous 48 states. Key West’s whimsical atmosphere, light-hearted lifestyle, history, restaurants, shops, and sights give Key West it’s well-deserved reputation for fun, relaxing, and memorable vacations.

Windsor Gardens

Elegant 3 bedroom 3 and 1/2 bath. Old Town Elegance and modern sophistication in this newly complete townhome conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beautiful villas that boast over 1700 sq ft. on two levels.

Each has its own private garden with heat optional swimming pool. The open living /dining area features comfortable sofas & chairs, and a dining table to seat six. Just off the living room is your complete and fully-equipped modern kitchen with top of the line appliances and a center island/bar. Sliding doors open from the living area to a deck and the pool edged by variety of tropical plants.

Windsor III | Key West | Vacation in the Keys Vacation Rentals

WINDSOR GARDENS III

Email or call +1 (305) 735-3636 for booking info.

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Windsor III | Key West | Vacation in the Keys Vacation Rentals

WINDSOR GARDENS IV

Email or call +1 (305) 735-3636 for booking info.

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Windsor III | Key West | Vacation in the Keys Vacation Rentals

WINDSOR GARDENS V

Email or call +1 (305) 735-3636 for booking info.

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KEYS GETAWAY

This 2-bedroom, 2-bath, 750-sq.-ft. single-family property sleeps 6.  Boat dockage includes a 35′ seawall located on 60′ wide canal with quick access to the ocean and gulf.  Dock is equipped with dock posts, cleats, swim ladder and fish cleaning table with a patio table, chairs and two lounge chairs to relax by the water’s edge.

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WHITE STREET HIDEAWAY

Fantastic 4 bedroom, 3 bathroom abode in the heart of Key West has a crystal-clear pool with waterfall. 6′ high private wall gateway. Beautiful beaches, great restaurants, and wonderful shopping are all nearby.

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Want to Know More?

Just give us a call
+1 (305) 735-3636

Just give us a call
+1 (305) 735-3636

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    Vacation in the Keys – where past guests become new friends.

    Vacation in the Keys owners, Mike and Suzy Hood, take your vacation personally. Their expertise in the Florida Keys, sport fishing and recreation, property management, and customer service help create your perfect vacation.

    Mike
    +1 (305) 735-3636 o
    +1 (717) 339-8953 m
    Suzy
    +1 (305) 735-8456 o
    +1 (443) 605-9387 m