Florida Keys Vacation Rentals

New Featured Properties

Victorian Dream — $$$$$ MM 90, 5 bedrooms, 5 baths, sleeps 10-12 (especially if there are children). This beautiful Bay Front Victorian home offers a great location for large families or corporate retreats. Exceptional water views; Warm and luxurious, romantic island-style décor; Exquisite finishes, wrap-around porches, several terraces including roof-top terrace with spectacular view. Wood floors, chef’s kitchen, marble baths, 3 jacuzzi-style tubs, 2 fireplaces. Enormous 5-room Master suite with office, bedroom, sitting room, bathroom and walk-in closet. 3 kitchens including a phenomenal outdoor kitchen and dining/living area overlooking the Bay. Heated Pool with pool slide. Children’s playground area with swings and slide. Putting green in back yard. Waterfront Gazebo; porches everywhere for viewing the best sunsets in the Keys. This is a beautiful home with so much charm. For the techno-buff, there are several flat-screen TV’s, even outside, all state-of-the-art electronics for your enjoyment. High Speed Internet, Wi-Fi. Satellite TV, dockage for jet skis and boats, outdoor lobster/bait tanks, and much, much more.

Fisherman's Cove — $$$ MM 104, 3 bedroom, 3 bath, bayfront resort with endless panoramic views of Florida Bay. This brand new establishment offers 6 spacious residences each with private balconies, luxurious island style furnishings, gourmet kitchens and wifi. Resort amenities include fitness center, heated pool, private owners terrace with hot tub, on-site waterfront dining and entertainment. This unique property offers island living with a Miami flair, all in one hot spot!

Caribbean Breeze — $$$ MM 89, 3 bedrooms, 3 baths, sleeps 8-10. Tropical oceanfront delight with sandy white beach, heated pool and 350' dock. Property is gated and fenced for privacy. Enclosed porch extends the length of the house and offers beautiful ocean views. Perfect environment for fun in the sun or watch the sunrise swaying in the hammock. High speed internet and pet friendly!

Key Lime House — $$ MM 86, 4 bedrooms, 3 baths, Sleeps 8-10. This beautiful canal front home comes complete with balconies off each bedroom, tiki hut, deep water dockage, bait freezer, fish cleaning station, sandy beach area and tidal pool. Kayak or swim right off the dock. This 3 story keys home is great for friends and families to enjoy the "keys" way of living, so bring your boat or rent one and fish, snorkel and sunbathe to your heart's content.

Grace Point — $$$ MM 74, 3 bedrooms, 2 baths, sleeps 8. This beautiful 3 story, canal front home with elevator has wonderful bay views. Deep water dockage with easy boat access to bay and ocean. 2nd story has large living/dining/kitchen area with screened in balcony. 3rd story has small game room and master bedroom with amazing views. Hot Tub on 3rd story balcony. Cozy gazebo out at the point of the property a perfect place to wind down at the end of day and watch the manatees swim by.

Sunset Dream — $$$ MM 83, 5 bedrooms, 3 baths, sleeps 10. Large, private bayfront property, located in the heart of Islamorada. This well-kept simple vacation home with pool, tiki hut and boat basin is bound to help you relax and unwind. Beautiful endless bay views and sunsets galore.

Oceanfront

Karapan — $$$$$ MM 81.5, 5 bedrooms, 5½ baths, sleeps 10-12. Spacious, private plantation-style estate home on 5 acres. Elevator. Heated pool and jacuzzi, sandy beach. Spectacular open-water sunrise views. New basketball court and tennis court, shared with Karapan 2. Caretaker resides on grounds to accommodate guest needs and to maximize security. High-speed internet. Conveniently located in the heart of Islamorada. May be combined with Karapan 2 for a perfect corporate retreat.

Karapan II — $$$$$ MM 81.5, 4 bedrooms, 4 full baths each one has a jacuzzi tub and large walk in shower, sleeps 8-10. Oceanfront brand new house, all one level, located next to the original on the same beautiful estate grounds. Spacious great room, large open kitchen equipped for gourmet cooking, grand master bedroom with sitting room, deep wrap around porches, pool with sloped entry and spa. Private, yet can be combined with Karapan I for a total of 9 bedrooms, 9 baths, two pools, tennis court, basketball court, all on 5 lush acres of the ultimate estate in Islamorada.

Alligator Reef & Cottage — $$$$ MM 84, 4 bedrooms, 3 baths main house, plus 3 bedroom 2 bathroom cottage sleeps 12-14. Beautiful oceanfront estate. Heated pool. Fishing and observation pier, kayak, putting green, horseshoes.

Deep Blue View — $$$$ MM 87, 5 bedrooms, 3 baths, sleeps 10-12, Deep Blue has a unique projection room on the ground level of the home. This large, lovely decorated property boasts: Heated pool, Screened in porch with pool table, unobstructed ocean views. This private gated property will make your Keys vacation unforgetable. There is local marina dockage available.

Island Palms — $$$$ MM 82, 3 bedrooms, 2 baths, sleeps 6-8. Gorgeous oceanfront sandy beach, nearby marina dockage. Heated pool. Conveniently located in the heart of Islamorada. Two additional cabanas may also be reserved, adding up to 2 bedrooms and 2 baths.

Aguazul — $$$ MM 87, 4 bedrooms, 3 baths, sleeps 8-10. Captivating oceanfront home with heated pool and deepwater dock. Gated. Amenities include 2 kitchens. High-speed internet.

Coral Cove — $$$ MM 81, 3 bedroom, 3 bath, exquisite home in a quiet, gated, oceanfront community. This plantation style home has wrap around porches for enjoying the relaxing ocean breezes. High speed internet available and flat screen TV’s and DVD players in each bedroom. Pet friendly!

Deja Blue — $$$ MM 75 Ocean front in Lower Matecumbe, Islamorada. Recently renovated 2 bedrooms, 2 full baths, den with a queen futon. Charming seaside cottage with beautiful views, new gourmet kitchen, new marble baths, new 100 foot dock, even a Tiki Hut on the beach. Perfect Keys getaway for couples or your family. Pet friendly!

Gabriel's Haven — $$$ MM 65, 4 bedrooms plus den with sleeper sofa, 5 baths, sleeps 10-12. Gated. Distinguished, upscale, private estate. Oceanfront sandy beach, swim spa. High-speed internet.

Islamorada Beach House — $$$ MM 75, 2 bedrooms, 2 baths, sleeps 4-6, At Islamorada Beach House you will have breathtaking sunrises. Relax in the outdoor Jacuzzi, after a day on the pristine ocean. The upstairs of Islamorada Beach House has a loft with a pool table. This property is private and gated, with a beach area.

Mar Vista — $$$ MM 95, 3 bedrooms, 3 baths, sleeps 8. Deepwater dock, heated pool, and magnificent ocean view. Amenities include game room and den. Monthly Rental.

Ocean Terrace — $$$ MM 81, 3 bedrooms plus den bedroom, 3 baths, sleeps 8-10. Gated. Private. Oceanfront sandy beach perfect for bonefishing. Oversized outdoor jacuzzi, kayak. High-speed internet. Conveniently located in the heart of Islamorada.

Ocean's End — $$$ MM 75, 3 bedrooms, 2 baths, sleeps 6-8 This Key West Style, ocean front home offers a heated pool with openwater ocean views, privacy in quiet Lower Matacumbe. There is dockage at the nearby marina available. DSL is now available.

Sandbar Beach Estate — $$$ MM 65, 3 bedrooms, 3 baths, sleeps 6-8. Gated. Private. Picturesque white sandy beach offering open water views.

The Russell Estate — $$$ MM 83, 3 bedrooms, 2 baths, sleeps 7. Sandy beach, shallow-water dock to accommodate 21 foot vessel. Private. Superb oceanfront views. Two-person kayak, bicycles. High-speed internet.

Orange Blossom — $$ MM 92, 2 bedrooms, 2 baths upstairs with one additional bedroom and bath downstairs. Both have sleeper sofas. Sleeps 6 – 8. Beautiful ocean views and deep water dockage. Perfect for an offshore fishing retreat or kayakers haven. Enjoy kayaking out to the crystal clear waters surrounding Tavernier Key to experience the peaceful serenity of the keys. Monthly Rental.

Bayfront

Villa Montelepre — $$$$$ Elegant, luxurious and very private estate home in a class of its own. Oversized heated swimming pool with jacuzzi overlooking Florida Bay with an open-water sunset view. Deep-water dockage and davits accommodating boats up to 40 feet. Pick fruits from the private orchard within the grounds. Gated with full security system. Monthly Rental.

Marchettiville — $$$$ MM 76, 5 bedrooms, 3 baths. 200 feet of bay front with beach, pool, and dockage on Lower Matecumbe in Islamorada. Beautiful property on a double lot with panoramic views of Florida Bay. Spacious home recently remodeled with large great room upstairs and separate living room on pool level. Marble floors and bathrooms with body sprayers in showers. Bedrooms are carpeted. Large Tiki hut with bar, screened in porch with TV upstairs, covered patio poolside. 60 inch widescreen hi-def TV with surround sound in Great Room, 40 inch downstairs. This house has all the amenities for a great family vacation.

Nautica — $$$$ MM 83, 4 bedrooms, 4 baths, sleeps 10 — Nautica, located in the heart of Islamorada, has everything to make your Keys vacation perfect. Built in 2007, this location offers 4 bedrooms 4 baths, with a sofa sleeper in the den/game room, a large heated bay front pool, deep water protected dockage that can accommodate up to 30’+ boat, high speed Internet, and fax. Enjoy the beautiful Keys sunset while relaxing in the pool or BBQ'ing your catch of the day. Natutica is perfect for your next Keys vacation.

Snook House — $$$$ MM 75, Brand new model home with 4 bedrooms, 4½ baths, gourmet kitchen, private pool and spa. Located in a gated compound of 12 homes on the bay with a stunning private beach, community dock, and tennis courts.

Casa Tranquilla — $$$ MM 82, 3 bedrooms, 3 baths, plus separate 1 bedroom 1 bath cottage complete with full kitchen. 2 acre retreat on Florida Bay. Spectacular sunset views over open water. Deep-water protected dockage, oversized pool. High-speed internet. Conveniently located in the heart of Islamorada.

Layton Estate — $$$ MM 69, 3 bedrooms, 3 baths, sleeps 6-8. Wonderful sunset views over open water. Dock, swimming pool, charming large gazebo.

Osprey Bay — $$$ MM 82, 4 bedrooms, 3 baths, sleeps 8-10. Outstanding sunset views over open water. Private with dock, heated pool, jacuzzi. Conveniently located in the heart of Islamorada

Tarpon House — $$$ MM 76, 4 bedrooms, 4½ baths. This gorgeous home is in the premier gated community of Bonefish Bay, an enclave of 12 Key West-style homes with all the amenities of a large resort. White sand beach, tennis court, boat ramp & dockage with beautifully manicured grounds. Tarpon House has its own hot tub & heated pool and has been professionally decorated. Dockage & use of boat ramp is included.

Little Bay — $$ MM 82, At popular Little Bay you have your choice of 3 cottages. One has 1 bedroom and 1 bath, two others have 2 bedrooms and 1 bath. This beautiful bay front property with private boat basin is perfect for couples traveling together who would like more privacy. Gated and private in the heart of Islamorada.

Paradise South — $$ MM 82, 3 bedrooms, 1.5 baths, sleeps 6, beautiful sunsets, private protected boat basin, outdoor shower, in the heart of Islamorada. DSL available. Pet friendly!

Canals, Lagoons, and Waterways

Villa Grandeur — $$$$$ This is an elegantly modern home, great for large families. This home offers 5 bedrooms, 5 bathrooms, upscale finishes throughout, a sparkling pool and hot tub, and parking for up to a 65 foot boat. This home is three houses from the ocean and has great ocean views from the porches and sundeck. Monthly rentals.

Villa Bella — $$$$$ MM 86, 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.

Ct. Contessa I — $$$ MM 74, 4 bedrooms, 3 baths, sleeps 8-10. Three-story canalfront retreat on a corner lot, landscaped for privacy. Elevator. Rooftop sundeck with panoramic views of bay and ocean. Ample deep-water dock with easy access to both bay and ocean. Heated pool, jacuzzi. High-speed internet. Nearby sandy beach on Florida Bay for the exclusive use of this neighborhood. May be combined with Court Contessa II for an outstanding corporate retreat.

Ct. Contessa II — $$$ MM 74, 3 bedrooms, 3 baths, sleeps 6-8. Terrific deep-water dock offering easy access to both bay and ocean. Nearby sandy beach on Florida Bay for the exclusive use of this neighborhood. Can be combined with Court Contessa I for an ideal corporate retreat.

Angler's Lure — $$ MM 100, 2 bedrooms, loft, 2 baths, sleeps 6. This stunning yet affordable vacation town home is located in the heart of Key Largo. Relax by the pool walk to one of the best Keys restaurants. High speed internet access. Don’t miss the opportunity to stay in paradise. Monthly Rental.

Condominiums and Townhomes

Bay Harbor Units

These beautifully appointed upscale condos are unique bayside units that offer an oceanview. Located in the Keys where the Atlantic and Gulf are just yards apart, Bay Harbor offers open balconies, dockage, access to the complex with jacuzzi, pool, tennis and much more. Just 5 miles south of Islamorada, so convenient for shopping and restaurants. Stainless steel appliances, granite counter tops, upscale furnishings and high end electronics make these spectacular units desirable yet affordable. Each of the Bay Harbor units has elevator access in the building.

Bay Harbor #215 — $$-$$$ Beautifully appointed two bedroom two bath condominium with Jacuzzi tub and water view. Complex has luxury pool and hot tub, fitness center, clubhouse and more. Located near restaurants and shopping. Beach across the street.

Bay Harbor #301 — $$-$$$ This 3 Bedroom 3 Bath condominium offers beautiful, upscale furnishings, Jacuzzi-style hot tub and amazing water views. New Victorian inspired condominium complex is located across the street from Anne’s Beach and offers a gorgeous pool and hot tub, fitness center and clubhouse. The location of this property is near lots of shopping and restaurants.

Bay Harbor #311 — $$-$$$ Beautifully Appointed 2 Bedroom 2 bath Condominium with a water view. Modern island-style décor and Jacuzzi-style tub in Master Bath. New Victorian-style condominium complex offers breathtaking pool/hot tub area, fitness center and clubhouse.

Bay Harbor #314 — $$-$$$ This incredible 4 Bedroom, 4½ Bath penthouse condominium is a breathtaking work of art. Immaculately designed, with highest end, designer furnishings, incredible views of the ocean and lagoon, jacuzzi-style tubs and chef's kitchen. This condominium can also be connected to aonther next-door unit to create a 7 Bedroom, 7 Bath unit. Great for large parties, weddings or vacations in the islands. This new Victorian/Island-inspired complex is across the street from beach and offers gorgeous pool, hot tub, fitness center, clubhouse and is located near shopping and restaurants.

Bay Harbor #316 — $$-$$$ This 3 Bedroom, 3 Bath condominium is perfect for a Keys getaway. Great island style décor, media room, views of ocean and lagoon, jacuzzi-style tub, upscale kitchen and ability to adjoin the condominium next door to create a 7 Bedroom, 7 Bath dwelling fit for a king. This Victorian/Island styled new condominium complex offers a gorgeous pool/hot tub area, fitness center, clubhouse and is located near restaurants and shopping.

Key Largo Mariner's Club

This resort offers a wide array of amenities: tennis & basketball courts, BBQ's with the family in this beautiful sandy hammock area overlooking the marina. State of the art club house, fitness center, heated pool and coral waterfall grotto. Enjoy the newly completed ocean side pool, featuring a zero entrance and waterfall with stunning views of the Atlantic Ocean. Lookout pier. Causal dining & tiki bar directly on the Atlantic Ocean with nightly entertainment.

For off-season rates and specials, please call us at (305) 664-0547 and ask for Robert.

Ocean View Villa #121 — $$$ Largest floor plan in Mariners Club. Lots of room in this 3 bedroom 3 bath with 2800 square feet, overlooking marina and ocean. Large eat-in kitchen, separate living room and den. Marble floors and granite counters. A luxurious place to enjoy your vacation.

Ocean Front Townhouse #411 — $$$ 3 bedroom, 3 bath townhouse. Direct ocean front. Incredible views. Tropical décor and family friendly. Screened-in ocean front patio with spiral staircase to breathtaking beach-style lagoon pool (largest in the Keys!). Large master suite has vaulted ceilings and full length windows with a panoramic direct ocean front view of sailboats anchored offshore. Marble master bath with sunken jacuzzi and skylights. Second bedroom has bunk beds with trundle. Third bedroom, on main floor, has daybed that converts to king. It's all here for a wonderful family vacation. This unit also has a garage.

Hammock View #709 — $$ This beautiful townhouse has 2 bedrooms, 2½ baths upstairs with spacious queen bedroom and separate living area and queen size sleeper sofa downstairs. It is surrounded with natural subtropical views, quiet gated community, tennis courts, 2 pools, marina and more.

More information:

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