Florida Keys - Key West Vacation Rentals, Condos & Resorts

 
Florida Keys Vacation Rentals
 
 
 Find the best deals for vacation rentals, villas, condos, hotels and resorts by vacation places to stay 
Vacation Rentals | Condo & Villa Rentals | Hotels & Suites | Beach Resorts | Guest House Rentals | Inns | Property Managers
Home > Florida Keys
 

Florida Keys Vacation Rental & Resort Directory

 
Action Keys Realty P.O. Box 421063, Summerland Key FL
Summerland Key

Summerland Key CARIBBEAN-STYLE COMFORT WITH SWIMMING POOL - 970 Caribbean Drive, East, Summerland Key

This spacious, Caribbean-style vacation home comes equipped with its own private swimming pool and great deep-water canal. We added terrific views to make this the perfect setting for your next vacation in Paradise! Ice machine, bait freezer, do
Big Pine Key

Big Pine Key AFFORDABLE COMFORT W/ EXCELLENT BOATING ACCESS - 29133 Mango Lane, Big Pine Key

Simple and sweet with no muss, no fuss. It's all right here - Gulf Side! This quaint two bedroom vacation home offers views, a deep-water boating and swimming canal and a protective seawall. This home offers 2 queen-size beds and an additional sle<
Cudjoe Key

Cudjoe Key COMFORTABLE HOME IN TROPICAL FLORIDA KEYS - 22952 Captain Kidd Lane, Cudjoe Key

Kick back and relax in this Island vacation home. Or, enjoy the spacious deck located off the kitchen area, and take in the warm tropical breezes, canal and spectacular sunset skies. Fish from the dock or take advantage of the convenient boating acce
Cudjoe Key

Cudjoe Key IMMACULATE HOME ON GREAT CANAL - 23017 Sailfish Lane, Cudjoe Key

Enjoy the rustle of swaying palms and the balmy tropical breezes from the screened and tiled balcony of this immaculate Island home. Home-away-from-home comforts include central air and a well equipped kitchen. The 30' dockage area provides qui
Summerland Key

Summerland Key SPACIOUS TROPICAL ESCAPE W/ ROOM FOR BOAT - 1069 Gulf Drive, Summerland Key

This Summerland Key vacation home is situated on a private, fully fenced lot, with a tastefully decorated interior with great features such as hardwood floors and a beautifully well equipped, custom kitchen. Spacious living and dining rooms provide
Summerland Key

Summerland Key OCEANFRONT 3 BEDROOM GORGEOUS HOME - 317 Sawyer Dr, Summerland Key

Escape from all your cares at this wonderful vacation rental on Cudjoe Key. Just the spot to unwind and let your hair down. There are 3 bedrooms and 3 baths plus a recreation room for the kids to get away. Open and airy living and kitchen area for fr
Cudjoe Key

Cudjoe Key CANALFRONT HOME W/ BREEZY DOCK - 22952 Hawkins, Cudjoe Key

This great vacation home is conveniently located on Cudjoe Key. The all tile kitchen is fully equipped and living & dining rooms provide ideal entertaining areas for friends and family. Enjoy warm, tropical breezes on the large wood dock, overlook
Cudjoe Key

Cudjoe Key TROPICAL PARADISE WITH CAPE COD STYLE - 125 Tortuga Lane, Cudjoe Key

From the private balcony located off the master bedroom living area, to airy and vaulted ceilings, this Cape Cod style home promises all the comforts of home, and so much more! The 40' dock and yard is landscaped with native foliage and offers
Cudjoe Key

Cudjoe Key TRIOPICAL PARADISE WITH TIKI HUT & POOL - 356 Sawyer, Cudjoe Key

This beautiful, vacation home is tropical, bright and confortable. You'll wish it was your own! Kitchen is fully equipped with all the luxuries of home (and more!). Tiki Hut and hammock dockside, overlook a great deepwater boating and swimming cana
Little Torch Key

Little Torch Key BEAUTIFUL GULF SIDE PARADISE - 263 Barry Avenue, Little Torch Key

Enjoy the ultimate in relaxation with this open-water home on Little Torch Key (gulf side) mile marker 29. This very private hideaway is painted in bright tropical colors to give you that old-island feel. This spacious 2,000 square foot home has ple
Big Pine Key

Big Pine Key MAGNIFICENT OPEN WATER VIEWS - 30843 Granada Avenue, Big Pine Key

Magnificent open water views in this beautiful 3 Bedroom, 2 bath home on Big Pine Key! This home boasts décor by an award winning Key West decorator. Includes fast access Internet for you to surf the internet quickly in addition to a large screen T
Ramrod Key

Ramrod Key OPEN-WATER VIEWS & NEW SWIMMING POOL - 531 West Indies Drive, Ramrod Key

Sit back and relax in this delightful home, situated on the open water. The entire rear wall of this home is glass for endless views of the blue-green waters of the Florida Keys. Equipped with all the comforts of home plus a heated pool. The open por
Little Torch Key

Little Torch Key SPECTACULAR OCEAN VIEWS - 1381 state road 4-A, Little Torch Key

Set sail for a glorious Florida Keys vacation at the Blue Marlin. Spacious and comfortable for 6 people in this 3 bedroom, 2 bath, Little Torch Key home. Located down a private lane and overlooking the crystal blue waters of Pine Channel, gulf side.
Big Pine Key

Big Pine Key TROPICAL VACATIONS BEGIN AT ATLANTIS - 31120 Atlantis Road, Big Pine Key

Everyday is a great day at Atlantis. Beautiful Big Pine home located just minutes to Bogie Channel. This channel affords direct access to the Content Keys on the Gulf, for diving and snorkeling or quick access to the Atlantic for big sport fish. Just
Summerland Key

Summerland Key A PERFECT VACATION SPOT IN THE FLORIDA KEYS! - 860 Lagoon Drive, Summerland Key

Looking for that perfect vacation spot in the Keys? This is the one. Luxury waterfront accommodations await for the whole group. This stately home has all the best of everything. The large great room has lots of seating. 42” Flat screen Sony hi-d
Key West

Key West TROPICAL SECLUSION WITH A SWIMMINGPOOL & CANAL - 28 Boulder Drive, Key West

Tropical seclusion and privacy at its very best. Located just 15 miles from Key West. This luxury rental consists of 2 full suites. The first floor has a roomy living room, huge screen porch, queen sleeper sofa, bath and bedroom. The second floor h
Summerland Key

Summerland Key TROPICAL CANALFRONT GET-AWAY - 441 Coral Avenue, Summerland Key

The Coral House is a prime destination spot for a great Florida Keys vacation! Conveniently located on Ramrod Key, mile marker 27. Close to all the choice restaurants and services that the Florida Keys have to offer. This home is beautifully deco
Summerland Key

Summerland Key SUNNY & BREEZY CANALFRONT HOME - 957 Gulf Drive, Summerland Key

Sit back and relax in this clean, airy, and spacious vacation home. Located on a canal and equipped with all the comforts of home. The open porch catches the breeze and sun. This tropical setting will set your mind at ease.The canal provides qui
Big Pine Key

Big Pine Key FLORIDA KEYS GET-AWAY VACATION HOME - 30856 Minorca Drive, Big Pine Key

A get away to “Our Island Thing” will be unforgettable vacation for everyone. Huge 1900 sq ft house with lots of room for the whole family and kids. 2 level concrete home is roomy and airy upstairs with huge kitchen, living and dining area, master be
Summerland Key

Summerland Key TROPICAL PARADISE ON QUIET LANE - 491 Coral Avenue, Summerland Key

Key West / Big Pine Key / Marathon
Cudjoe Key

Cudjoe Key NEW CANALFRONT HOME W/ SCREENED PORCH - 22717 Blackbeard Lane, Cudjoe Key

This Cudjoe Key home is neat as a pin. Brand new in 2007 with all the comforts of home. Bright and shiny kitchen with everything you may need to create wonderful get togethers. The large comfortable living room has plenty of seating including recline
Big Pine Key

Big Pine Key GULF SIDE VACATION HOME! - 3818 Dyer Rd, Big Pine Key

Manatee Bay located in the Port Pine Height area is just the right spot to bring your family and friends for an unbelievable Keys vacation. Great Gulf-side boating is at your fingertips and just a short run out to the Atlantic to fish and dive all
Big Pine Key

Big Pine Key FLORIDA KEYS GETAWAY - 3848 Donna Road, Big Pine Key

Pack your floral shirts, swimming gear and sandals and come on down to Angelfish Cove. Fun is the order of the day. Enjoy the beautiful crystal clear swimming pool or jump in your boat to go explore some of the best fishing and diving the Florida Key
Summerland Key

Summerland Key A FISHERMAN'S DELIGHT - 4008 Dorn Rd, Summerland Key

Enjoy the ultimate peace and quiet offered on Big Torch Key. Located just 5 miles off the Overseas Highway. This pristine area is a true treasure of the lower Keys. This home is nicely remodeled and boasts large spacious room and comfortable furnishi
Cudjoe Key

Cudjoe Key FLORIDA KEYS FAMILY VACATION - , Cudjoe Key

This home is great for families! It has been recently updated with new tile throughout, new furnishings and bedding, and features 3 bedrooms and 2 bathrooms as well as a roomy loft area. You’ll enjoy an open living plan with a nice size full kitchen
Summerland Key

Summerland Key RAMROD KEY VACATION HOME - 27431 Barbados Lane, Summerland Key

Ready for some fun in the sun? This Ramrod Key vacation home is the perfect spot! This home is located at milemarker 27 in Breezeswpt Beach Estates. Spend some fun time at the Looe Key Reef Resort Tiki bar just a mile away where you can sip on s
Big Pine Key

Big Pine Key 2 BEDROOM BIG PINE KEY RENTAL - 1545 Fern Ave, Big Pine Key

Nice and comfortable 2 bedroom, 2 bathroom vacation home on Big Pine Key in the Eden Pines area. This vacation rental is neat and clean with a 40' wood boat dock and fish cleaning area to clean all that great, fresh fish you're gonna catch. Easy
Summerland Key

Summerland Key PLANTATION STYLE HOME - 841 Crane Blvd, Summerland Key

Welcome to Bow Channel Manor and step back in time to Old Florida! You'll find this plantation style home remeniscent of Florida past! Enjoy family-style vacationing on a private 4 acre parcel of land on Upper Sugarloaf Key. The grounds are lik
Summerland Key

Summerland Key 2 BEDROOM SUMMERLAND KEY HOME - 24317 Caribbean Drive W, Summerland Key

This lovely 2 bedroom, 2 bath residence is located on Summerland Key at mile marker 24 just north of Key West for sightseeing, great restaurants or just take in the color of the local history in our southernmost most city. The home is comfortably
Summerland Key

Summerland Key COTTAGE ON LITTLE TORCH KEY - 423 Barry Ave, Summerland Key

Delightful and comfortable Florida Conch-style Cottage on Little Torch Key. Enjoy the beautiful, open-water views over Pine Channel with incredible sunrises and moon rises. The interior of this home has been beautifully updated with new kitchen, i
Summerland Key

Summerland Key Vacation Home - 817 Bay Drive, Summerland Key

Casa Turquesa is the jewel of Summerland Key. Located directly on the beautiful crystal blue keys waters with deep water boat access for the avid angler and plenty of dockage for all the water toys. This stylish home is outfitted in Florida tropi
Cudjoe Key

Cudjoe Key Vacation Home - , Cudjoe Key

Detailed description coming soon... This is a monthly vacation rental!
Summerland Key

Summerland Key 3 BEDROOM LUXURY HOME - 1005 Flagship Drive Exn, Summerland Key

You will be absolutely delighted to vacation at this remarkable luxury vacation home on Summerland Key. This multimillion dollar home has only the best to offer. The kitchen is a chef‘s dream with top of the line stainless appliances, cook top, built
Summerland Key

Summerland Key 2 BEDROOM FLORIDA KEYS HOME - 162 Galleon Lane, Summerland Key

Pack your floral shirts, swimming gear and sandals and come on down to Angelfish Cove. Fun is the order of the day. Enjoy the beautiful crystal clear swimming pool or jump in your boat to go explore some of the best fishing and diving the Florida Key
Big Pine Key

Big Pine Key 2 BEDROOM HOME ON BIG PINE KEY - 30830 Watson Blvd, Big Pine Key

Truly remarkable Big Pine Key vacation home. Rare Duplex on over ½ acre in the Doctors Arm area. A huge boat basin and direct access to Bogie channel. Rent one or both sides for the best family vacation destination in the Keys. Fully fenced for pr
Big Pine Key

Big Pine Key 3 BEDROOM HOME ON BIG PINE KEY - 30830 Watson Blvd, Big Pine Key

Truly remarkable Big Pine Key vacation home. Rare Duplex on over ½ acre in the Doctors Arm area. A huge boat basin and direct access to Bogie channel. Rent one or both sides for the best family vacation destination in the Keys. Fully fenced for pr
Big Pine Key

Big Pine Key 5 BEDROOM FAMILY VACATION HOME - 30830 Watson Blvd, Big Pine Key

Truly remarkable Big Pine Key vacation home. Rare Duplex on over ½ acre in the Doctors Arm area. A huge boat basin and direct access to Bogie channel. Rent one or both sides for the best family vacation destination in the Keys. Fully fenced f
Cudjoe Key

Cudjoe Key NICE 2 BEDROOM CANALFRONT HOME - 22456 Lafitte Drive, Cudjoe Key

Lafitte Landing is the perfect destination for your Florida Keys vacation. Very nicely appointed 2 bedroom, 2 bathroom canal front home is very comfortable and spacious. This home offers a living-dining-kitchen great room floor plan with comfortable
Little Torch Key

Little Torch Key IDEAL FAMILY VACATION - 28537 John Silver Road, Little Torch Key

This beautiful custom home located in Jolly Rodger subdivision on Little Torch Key has the best of everything. Just furnished in 2012 with the finest tropical décor, flat screen TV’s, wireless internet and top of the line gourmet kitchen. The larg
Summerland Key

Summerland Key GREAT CANELFRONT VACATION HOME! - 25856 Anne Bonny Rd, Summerland Key

Welcome to Margarita Villa! Located in Jolly Roger Estates on Little Torch Key, where you’ll find some of the best deep water boating in the Lower Keys! Just imagine yourself gazing out at these spectacular ocean vistas! The entire water-side of t
Little Torch Key

Little Torch Key BEACHFRONT VACATION RENTAL HOME! - 529 Pirates Rd, Little Torch Key

Here is the hidden treasure you have been looking for. Pirates Pointe is a great get a way for you and the family. Located in the Jolly Rodger subdivision at mile marker 28 which boasts excellent deep draft boating. Dolphin Marina is located at th
Summerland  Key

Summerland  Key GREAT FLORIDA KEYS VACATION HOME!! - 24216 Caribbean Dr W, Summerland Key

Just imagine...Balmy southeast winds are blowing with a perfect Florida Keys sunset right in front of you, while relaxing in your comfy lawn chair with a frozen margarita. This could be you if you choose Ocean Breeze for your next Florida Keys advent
 
Compass Realty P.O. Box 344, Key West FL
Key West

Key West GORGEOUS 4BR 4BA HOME WITH POOL - 200 Front St, Key West

Luxury 4BR home in the heart of Old Towns Truman Annex. Fully appointed with gourmet kitchen and private pool.
Key West

Key West BEACHFRONT KEY WEST CONDO - 3841 North Roosevelt Boulevard, Key West

The Best of Key West gets even better! Beachside Resort & Conference Center is a seven acre luxury waterfront resort condominium with lush tropical gardens, large waterfront swimming pool, Jacuzzi, resting canopies, two bars and a fine restaurant. Yo
Key West

Key West PRIVATE ESTATE HOME - Admiral's Lane Truman Annex, Key West

This home has everything to offer from exotic furnishings and accessories to a 40 foot private pool! Located in the heart of Old Town within the Truman Annex this home is convieniently located within walking distance to all of the area attractions an
 
American Caribbean Real Estate Middle Key 57966 Morton St, Marathon FL
Marathon

Marathon COCO PLUM BEACHFRONT VILLAS - Coco Plum Drive 1C, Marathon

Beautiful waterfront townhome at Bonefish Yacht Club with boat slip included. Located on the Key Colony/Coco Plum Beach channel with great views of the waterway! Ocean access within minutes. Enjoy the views and the breezes from the balconies just
Marathon

Marathon GULF WATERFRONT RENTAL - FLORIDA KEYS - 5th Avenue Gulf, Marathon

Spacious canal front home just off the Gulf of Mexico. Bring your whole family. This home has four bedrooms, 2.5 baths, and comfortably furnished for your stay. Unwind on the wooden deck overlooking the water. There is 30 feet of dockage for your
Key Colony Beach

Key Colony Beach LUXURY WATERFRONT RENTAL - FLORIDA KEYS - 720 10th Street, Key Colony Beach

Higher end, immaculate, well-maintained, luxury one-half duplex on stilts. Beautifully decorated, roomy and spacious, with well-equipped kitchen. Includes 37.5 feet of dockage. Easy access to Atlantic and Gulf. Relax in the hot tub
Marathon

Marathon CANAL VIEW - FISHING IN MINUTES - 92nd St., Marathon

Quick ocean access and eastern open water view! Great for a family or two couples. Very comfortable, furnished two bedroom, 2 bathroom, stilted single family home on ocean side canal with 50 feet of dockage, control depth 4 feet. Direct access to
Marathon

Marathon Vacation Home - , Marathon

Rare, ground level, waterfront single family home on ocean side canal with dockage. Easy access to the Atlantic. Two bedrooms, two full baths, enclosed porch area can be used as third bedroom. Small screened porch facing canal. Central air condition
 
Andrews Inn 223 Eanes Lane, Key West FL
Key West

Key West BEST KEPT SECRET IN KEY WEST! - 223 Eanes Lane, Key West

To reach this charming bed and breakfast, you wander down a shaded lane steps from Duval Street. Andrews Inn immediately offers peace and tranquility as you enter through a garden gate to our secluded world. A shimmering pool is nestled in a lush t
 
Kon Tiki Resort 81200 Overseas Highway, Islamorada FL
Islamorada

Islamorada FLORIDA KEYS VACATION RESORT - 81200 Overseas Highway, Islamorada

For decades, generations of guests have made The Kon Tiki Resort in Islamorada the vacation destination of choice in which to share treasured moments and make lasting memories. Located in the Sports fishing Capital of the World, The Kon Tiki is centr
 
Rainbow Bend Resort 6600 O'Neil Rd, Sebring FL
Marathon

Marathon FREE USE OF MOTORBOATS WITH YOUR STAY! - 57784 Overseas Hwy, MM58, Marathon

Come to our Beach Resort for Boating, Fishing and more! Capture the spirit of the old Florida Keys. Unwind and enjoy a barefoot walk along a sandbar island, or sun yourself on the resort's private beach as you take in the view of beautiful subtropic
 
Historic Key West Inns 50629 Hwy 6, Glennwood Springs CO
Key West

Key West WELCOME TO HISTORICK KEY WEST INNS - 725 Truman Avenue, Key West

Historic Key West Inns are comprised of 6 unique and historic inns that are conveniently located next to all the Duval Street and Old Town action. Each inn has its own charm and accommodations to suit all your vacation needs. Every morning begins wit
 
Bud N' Mary's Fishing Marina P.O. Box 628, Islamorada Key FL
Islamorada

Islamorada FLORIDA KEYS FISHING PARADISE! - 79851 Overseas Highway, Islamorada

Bud N’ Mary’s is a world famous Islamorada Fishing marina, located in the heart of the beautiful Florida Keys. Call us today at 305-664-2461. Absorb the atmosphere of the Keys Alla Hemingway, Writer Zane Grey, and The Splinter, Ted Williams. Bu
 
Tarpon Flats Inn & Marina 1521 Alton Rd. #529, Miami Beach FL
Key Largo

Key Largo THE BEST INN - FLORIDA KEYS - 29 Shoreland Drive, Key Largo

Escape to Key Largo's ultimate weekend or vacation getaway ~ the best Inn in the Florida Keys. Located directly on the Atlantic Ocean, in unspoiled Largo Sound. Offering the best access to the finest of Florida Keys charter fishing, Everglades's ex
 
 
Owners / Managers
Do you have Florida Keys Vacation Rentals and would like to promote them in our vacation rental and resort directory to obtain more clients! Learn More...

Vacation Rentals

Toll Free: 888-855-8787
(Local: 727.738.1737)

 
Florida Keys Vacation Rentals Find Places To Stay
Lower Keys Big Pine & Lower Keys
Key Largo Key Largo
Marathon Marathon
Key West Key West
Islamorada Islamorada
Tavernier Tavernier

Last minute rentals Last Minute Rentals & Deals
 
Florida Keys Nightly & Daily Rentals
Weekly Rentals Weekly Vacation Rentals
Short Term Rentals Short Term Vacation Rentals
Long Term Rentals Long Term Rentals
 
Studio Studio 
1 Bedroom 1 Bedroom
2 Bedroom 2 Bedrooms
3 Bedroom 3 Bedrooms
4 Bedroom 4 Bedrooms
Large Villa 5+ Bedrooms
 
Pet Friendly Pet Friendly Vacation Rentals
Handicap Handicap/Wheelchair Access
Pool With Private Swimming Pool
Beachfront Waterfront or Near Beach
Luxury Luxury Vacation Rentals
Gay Friendly Gay Friendly Lodging
Hot Tub Homes With Jacuzzi/Spa
Golf Rentals Near Golf Course
 
Find a Property Manager for Vacation Homes
Property Manager - Do you need to find a Rental Management Company for your Florida Keys vacation rental home?
 
 Pets Allowed
Pet Friendly Vacation Rentals - Want to bring your family dog? Find a selection of vacation home rentals and villas for rent with pets allowed.
 
 Golfing
Golf Resorts & Rentals - Find a vacation rentals for year-round golfing at your favorite travel destination.
 
 Vacation Homes by Owner
Vacation Homes - Find short term Vacation Rentals, Villas, Condos and Cabins for rent at Rental Homes by Owner