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Featured Vacation Rental

Bayside And Beautiful
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Oasis of the Keys
The Keys are well-known for many things, including the variety of homes by the water. Oasis of the Keys is no ordinary water-front home though. This r......
Property Code: Oasis of the Keys
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 6
Location: Big Pine Key
Pets Allowed: No
Gardenia Place
.  Welcome to the Fabulous Florida Keys and Gardenia Place Situated at MM 30 in the popular Eden Pines subdivision in Big Pine Key where the......
Property Code: Gardenia Place
Bedrooms: 2 | Bathrooms: 1 | Max Occupancy: 4
Location: Big Pine Key
Pets Allowed: No
Kawama Yacht Club Tower 301
This beautiful 3rd floor condo has fabulous marina, pool and ocean views! Fully renovated with brand-new tiled floors throughout, all new interior doo......
Property Code: KT301 KL
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 6
Location: Key Largo
Pets Allowed: No
Your Oceanfront Resort Vacation Destination
Ocean Pointe ~ A private, gated resort located in the heart of the Upper Keys. Property features include a heated Olympic sized swimming pool, private......
Property Code: Ocean Pointe 4312
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 4
Location: Tavernier
Pets Allowed: No
Calypso Corner
This spacious, tropical home that sleeps 8, has a gorgeous dock and patio area, a fully equipped kitchen with an induction cooktop, stainless applianc......
Property Code: Calypso Corner
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 8
Location: Little Torch Key
Pets Allowed: Yes
Kawama Tower Unit 307
Very nicely furnished 3rd floor condo in Kawama Tower has 2 bedrooms & 2 full baths, fully-equipped kitchen & well-stocked linen closet (including poo......
Property Code: KT307 KL
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 6
Location: Key Largo
Pets Allowed: No
Positively Poolside
This fantastic 2 bedroom 2 1/2 bath townhome is in a guard gated community nestled among the fairways and greens of the coveted Key West Gol......
Property Code: Positively Poolside
Bedrooms: 2 | Bathrooms: 2.5 | Max Occupancy: 6
Location: Key West
Pets Allowed: No
Coastal Chic with Forever Ocean Views!
Property Code: Ocean Pointe 3312
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 4
Location: Tavernier
Pets Allowed: No
Lone Palm
Enjoy a quaintly appointed home in the Florida Keys fashion at Lone Palm!! This home has two bedrooms and one bathroom with an open concept kitchen......
Property Code: Lone Palm
Bedrooms: 2 | Bathrooms: 1 | Max Occupancy: 4
Location: Little Torch Key
Pets Allowed: No
Sunset Palms
Enjoy the quiet life here at Sunset Palms! This home has two bedrooms and two bathrooms with an open concept kitchen, dining and living room area. ......
Property Code: Sunset Palms
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 7
Location: Big Pine Key
Pets Allowed: Yes
Cudjoe`s Paradise Found
Canal Front 35 Seawall Simply elegant describes this 2 Bedroom with 2 Bath, canal front stilt home! This home features a 35 concrete seawall with acc......
Property Code: Cudjoe`s Paradise Found
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 6
Location: Cudjoe Key
Pets Allowed: No
Ocean Point 5301
Hello, Gorgeous! Pristine 2/2 Condo overlooking the Atlantic Ocean Ocean Pointe ~ A private, gated resort located in the heart of the Upper Keys. P......
Property Code: Ocean Pointe 5301
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 6
Location: Tavernier
Pets Allowed: No
Birdwell`s Nest
Located in a nice, quiet area of Big Pine Key this ground level 2 Bedroom / 2 Bath home is super clean and loaded with charm. You will be so comfortab......
Property Code: Birdwell`s Nest
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 6
Location: Big Pine Key
Pets Allowed: Yes
Blue Lagoon
Welcome to the Blue Lagoon . . .  a beautiful, warm and inviting two bedroom, 2 bath coastal chic home in the ever popular Port Pine Heights. &nb......
Property Code: Blue Lagoon
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 4
Location: Big Pine Key
Pets Allowed: No
Lower Matecumbe Retreat
Located in a quiet waterfront community in Lower Matecumbe, this charming  home has everything you need to start creating Florida Keys vacation m......
Property Code: Tollgate
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 4
Location: Lower Matecumbe Key
Pets Allowed: No
Caribbean Hideaway
At Caribbean Hideaway you will get all the Florida Keys has to offer. This 2 bedroom / 2 bathroom home is located on a canal with a beautiful concr......
Property Code: Caribbean Hideaway
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 6
Location: Big Pine Key
Pets Allowed: Yes
Kawama Yacht Club Tower 201
Gorgeous marina, pool & ocean views! This beautifully-renovated 2-bedroom/2-bath condo has it all. Kitchen features granite countertops & soli......
Property Code: KT201 KL
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 6
Location: Key Largo
Pets Allowed: No
Gigi`s Place
COMPLETELY RENOVATED after hurricane with completely new interior Keys decor and outdoor pool.  Entertain your family and friends at the outside ......
Property Code: Gigi`s Place
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 8
Location: Little Torch Key
Pets Allowed: Yes
Kawama Tower Condo #401
This beautifully refurbished 4th floor condo has great marina and ocean views from the living room, master bedroom & balcony! Gorgeous wood floors......
Property Code: KT401 KL
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 6
Location: Key Largo
Pets Allowed: No
Nightly Rate Starting At: $150.00
Kawama Yacht Club Tower 403
Kawama Yacht Club - A private gated condominium community in the heart of Key Largo. This updated 2 bedroom, 2 bath condo has everything you’......
Property Code: KT403
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 6
Location: Key Largo
Pets Allowed: No
Nightly Rate Starting At: $145.00
Silver Shores Topaz
Property Code: Siver Shores S Topaz
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 6
Location: Key Largo
Pets Allowed: No
Nightly Rate Starting At: $92.85
Croton Lane Retreat
This comfortable home is located on a canal with 2 bedrooms (Queen beds) and 2 full bathrooms.  It has a beautiful screened-in porch with comfort......
Property Code: Croton Lane Retreat
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 6
Location: Big Pine Key
Pets Allowed: No
Big Pine Breeze
Charming and tastefully decorated 2/2 home with beautiful sunset views from the large walk-around deck on the upper level with a large screened deck o......
Property Code: Big Pine Breeze
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 8
Location: Big Pine Key
Pets Allowed: No
Cullums Key West
Located just minutes from the city that never sleeps! . . .  Key West with all the restaurants, history and night life you ca......
Property Code: Cullums Key West
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 6
Location: Geiger Key
Pets Allowed: Yes
Port Royal Retreat
WELCOME TO CUDJOE KEY AND PORT ROYAL RETREAT!   This charming coastal chic home looks like a Chip and Joanna Gaines (HGTV) redo!  Nice&n......
Property Code: Port Royal Retreat
Bedrooms: 2 | Bathrooms: 1 | Max Occupancy: 4
Location: Cudjoe Key
Pets Allowed: No
Three Little Birds
Welcome to Three Little Birds....  This 2 bedroom/2 bath canal front home is located deep within the National Key Deer Refuge.  Peace and tr......
Property Code: Three Little Birds
Bedrooms: 2 | Bathrooms: 2 | Max Occupancy: 6
Location: Big Pine Key
Pets Allowed: No
Gasparilla Villa
Welcome to the Fabulous Florida Keys and Gasparilla Villa.    Located just 23 miles from the ever popular Key West with all th......
Property Code: Gasparilla Villa
Bedrooms: 3 | Bathrooms: 2 | Max Occupancy: 6
Location: Cudjoe Key
Pets Allowed: Yes
58 Palms
You won’t want to be rescued from this island oasis. You will enjoy the peace and quiet, relaxing by the pool, or taking your boat out for the 3......
Property Code: 58 Palms
Bedrooms: 3 | Bathrooms: 2 | Max Occupancy: 9
Location: Big Pine Key
Pets Allowed: No
Bayview Isle
Luxury Home in Premier Islamorada Neighborhood.  Unique Islamorada Waterfront Home in Desirable Venetian Shores! This home features a beauti......
Property Code: Bayview Isle
Bedrooms: 3 | Bathrooms: 3 | Max Occupancy: 8
Location: Islamorada
Pets Allowed: Yes
Canalside Retreat in Popular Plantation Key Colony
Canalside Retreat in the Colony! This three bedroom, two bath home is the perfect Keys getaway. A great Upper Keys location in the popluar neighbor......
Property Code: Plantation Key Colony-G
Bedrooms: 3 | Bathrooms: 2 | Max Occupancy: 6
Location: Plantation Key
Pets Allowed: Yes
March Special**$5,500.** 31ft boat slip and pet friendly..ask for details
Property Code: Ocean Harbour P42
Bedrooms: 3 | Bathrooms: 2 | Max Occupancy: 6
Location: Plantation Key
Pets Allowed: Yes
Ocean Harbour K31
Property Code: Ocean Harbour K31
Bedrooms: 3 | Bathrooms: 2 | Max Occupancy: 6
Location: Islamorada
Pets Allowed: No
Sunset Serenade
Enjoy the quiet life here at Sunset Serenade This home has three bedrooms and two bathrooms with an open concept kitchen, dining and living room ar......
Property Code: Sunset Serenade
Bedrooms: 3 | Bathrooms: 2 | Max Occupancy: 6
Pets Allowed: Yes
Plumeria Paradise
This gorgeous Key Haven waterfront home has maximized outdoor living space to make the most of Keys living. Picturesque outdoor covered "living r......
Property Code: Plumeria Paradise
Bedrooms: 3 | Bathrooms: 4 | Max Occupancy: 10
Location: Key West
Pets Allowed: No
Blue Mangrove House
Welcome home to your perfect island getaway at this spacious canalfront home on the water in Breezeswept Beach Estates! This home features everything ......
Property Code: Blue Mangrove House
Bedrooms: 3 | Bathrooms: 2 | Max Occupancy: 8
Location: Ramrod Key
Pets Allowed: No
Sugarloaf Shores
Stunning open water views at this drop dead gorgeous Sugarloaf Shores home.  Hawaiian style architecture boasts wrap around balconies with 2 sepa......
Property Code: Sugarloaf Shore
Bedrooms: 3 | Bathrooms: 3 | Max Occupancy: 8
Location: Sugarloaf Key
Pets Allowed: No
Nightly Rate Starting At: $334.00
Aqua Paradise Dream
At Aqua Paradise Dream you will get all the Florida Keys has to offer. This 3 bedroom / 2 bathroom home is located on a canal with a beautiful 60 f......
Property Code: Aqua Paradise Dream
Bedrooms: 3 | Bathrooms: 2 | Max Occupancy: 9
Location: Big Pine Key
Pets Allowed: No
Piece of Paradise
Enjoy a Piece of Paradise in this beautifully decorated home on Summerland Key. Everything is immaculate here. Located on a beautiful, crystal clear b......
Property Code: Piece of Paradise
Bedrooms: 3 | Bathrooms: 3 | Max Occupancy: 6
Location: Summerland Key
Pets Allowed: No
Lazy Flip Flop
Kick back at the Lazy Flip Flop! This beautiful three bedroom two bath home is neat and cozy. Bring your friends or family for a vacation and brin......
Property Code: Lazy Flip Flop
Bedrooms: 3 | Bathrooms: 2 | Max Occupancy: 8
Location: Big Pine Key
Pets Allowed: Yes
Keys Living
Florida Keys Living, the way it should be!! Located in Doctor`s Arm, a very nice and quiet neighborhood. This 3 Bedroom / 2 Bathroom home that sleeps......
Property Code: Keys Living
Bedrooms: 3 | Bathrooms: 2 | Max Occupancy: 8
Location: Big Pine Key
Pets Allowed: Yes
Garden Sanctuary
Gorgeous, beautifully furnished 3 bedroom 2.5 bath home plus den in the Sanctuary at Key West Golf Club! Quiet cul-de-sac location, large private yard......
Property Code: Garden Sanctuary
Bedrooms: 3 | Bathrooms: 2.5 | Max Occupancy: 6
Location: Key West
Pets Allowed: No
The View
The View is a large home with sunset & open water views, boating and a pool... This comfortable home has an open floor plan with spectacular vi......
Property Code: The View
Bedrooms: 3 | Bathrooms: 2.5 | Max Occupancy: 8
Location: Cudjoe Key
Pets Allowed: Yes
Sunset View
Bring the whole family to this spacious 3 bedroom, 3 bath pool home that sleeps 10. Wide open spaces are found here with the vaulted ceilings and open......
Property Code: Sunset View
Bedrooms: 3 | Bathrooms: 3 | Max Occupancy: 10
Location: Big Pine Key
Pets Allowed: Yes
St. Somewhere
Enjoy a quaintly appointed home in the Florida Keys fashion at St. Somewhere, Parrothead Paradise!! This home has three bedrooms and two full sized......
Property Code: St. Somewhere
Bedrooms: 3 | Bathrooms: 2 | Max Occupancy: 6
Location: Little Torch Key
Pets Allowed: Yes
Annies Place
You won’t want to be rescued from this island oasis. You will enjoy the peace and quiet, relaxing by the pool, or taking your boat out for the 3......
Property Code: Annies Place
Bedrooms: 3 | Bathrooms: 2 | Max Occupancy: 6
Location: Big Pine Key
Pets Allowed: Yes
Casa Brisa
At Casa Brisa Enjoy the Breeze of the Florida Keys!! This 3 bedroom / 2 bathroom home is located on a canal with a beautiful dock and boat lift in ......
Property Code: Casa Brisa
Bedrooms: 3 | Bathrooms: 2 | Max Occupancy: 8
Location: Ramrod Key
Pets Allowed: No
Newfound Paradise
Enjoy all the best Big Pine Key Paradise views from Newfound Paradise’s complete wraparound deck, with two screen rooms overlooking the open wat......
Property Code: Newfound Paradise
Bedrooms: 3 | Bathrooms: 2 | Max Occupancy: 8
Location: Big Pine Key
Pets Allowed: No
Tropical Oasis
This "Tropical Oasis" is light and bright with an open floor plan, spacious pool, and lush landscaping for you and your guests on a memorabl......
Property Code: Tropical Oasis
Bedrooms: 3 | Bathrooms: 2.5 | Max Occupancy: 8
Location: Key West
Pets Allowed: No
Island View
Enjoy the quiet life here at Island View This home has three bedrooms and two bathrooms with an open concept kitchen, dining and living room a......
Property Code: Island View
Bedrooms: 3 | Bathrooms: 2 | Max Occupancy: 8
Pets Allowed: Yes
My Kind of Paradise
Come enjoy all the Florida Keys has to offer.  This home is spacious inside and outside with a pool and tiki hut in the tropical backyard. Locate......
Property Code: My Kind of Paradise
Bedrooms: 3 | Bathrooms: 2 | Max Occupancy: 6
Location: Big Pine Key
Pets Allowed: No
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