Make a Florida Keys vacation rental your headquarters for fun in the sun!

The Florida Keys, a 120-mile long chain of islands off the southern coast of Florida, offers the ultimate laid-back island vacation.

Guests of Florida Keys vacation rentals will find more a multitude game fish in the beautiful clear waters of the Keys, including snapper, grouper, sailfish, marlin and tarpon. Charter boats and experienced guides are available to help visitors land that big catch.

The Florida Keys is America’s premier destination for diving and snorkeling. North America’s only living-coral barrier reef runs the length of the Keys, about five miles offshore. The reef is protected by the Florida Keys National Marine Sanctuary and teems with colorful marine life. A number of local dive operators offer snorkeling and diving trips, equipment and instruction.

Key West, the southernmost town in the U.S., is a feast for the senses. The palm-lined streets are filled with tin-roofed conch houses, gingerbread cottages, tropical gardens, sidewalk cafes, open-air bars, eclectic shops and a variety of entertainment. Each evening at sunset, a crowd gathers at Mallory Dock for an impromptu celebration, featuring music and entertainment by street performers. Guests of Key West vacation rentals can also visit Ernest Hemingway’s home and the John Audubon House.

The Lower Keys is a quiet region with small resorts, wilderness areas and some great beaches. Bahia Hondo State Park, at mile marker 37, boasts beautiful white sand beaches. Veterans Memorial Park, on Little Duck Key at mile marker 40, is pet- and family-friendly. Guests of Lower Keys vacation rentals can snorkel or dive on the Looe Key coral reef, or catch a glimpse of the tiny Key Deer at National Key Deer Refuge.

Visitors to Marathon, midway down the Keys, will find a variety of marine activities available in Boot Key Harbor. Most waters are open to fishing, but some have been set aside for diving and snorkeling. Guests of Marathon vacation rentals can visit the museum and nature center at Crane Point Hammock, a 64-acre preserve.

Islamadora is a prime sport fishing spot for guests of Islamorada vacation rentals. Visitors can explore the nature trails at Long Key State Recreation Area and Windley Key Quarry Fossil Reef State Geologic Site. Windley Key’s Theater of the Sea features shows starring dolphins and other sea creatures.

Key Largo, the northernmost island in the Florida Keys, is just an hour’s drive south of Miami. Guests of Key Largo vacation rentals can enjoy fishing and diving here, and the nearby Everglades are a great destination for birding and kayaking.

Reserve your Florida Keys vacation rental now for a memorable vacation!

Expand your search for Florida vacation rentals to include Miami vacation rentals and Ft. Lauderdale rentals in South Florida, Destin vacation rentals and Siesta Key rentals on the Gulf Coast, or Orlando vacation home rentals near Disney.

Vacation Rentals in the Florida Keys

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'CONCH CASA GRANDE' @ Truman Annex: 11' Ceilings, Private Pool & 6 Master Suites

— Property 177191
Florida Keys house rental - Conch Casa Grande: NOT your everyday 'conch home'.
7 Bedrooms, Sleeps 12,
House, 7 Bathrooms, downtown, near the ocean, balcony
Rates - per property (USD)
$7,000 - $15,000/week
$21,500 - $38,000/month
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'HIDDEN TREASURE' @ Casa East: Luxury 3BR's, Baby Grand Piano, Huge Private Pool

— Property 177317
Florida Keys house rental - The Living Room: big, breezy & comfortable...
3 Bedrooms, Sleeps 6,
House, 3 Bathrooms, beach, near the ocean, pool
Rates - per property (USD)
$8,900 - $11,000/month
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“FALLING WATER” @ Old Town: Breathtaking 5BR Private Compound with Private Pool

— Property 180171
Florida Keys house rental - The convertible sectional makes a fifth bedroom.
5 Bedrooms, Sleeps 12,
House, 4 Bathrooms, 1 Half Bath, downtown, near the ocean, pool
Rates - per property (USD)
$17,000 - $33,000/month
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'OLD TOWN OASIS' @ Truman Annex: Spacious 2 BR Oceanfront Condo

— Property 181289
Florida Keys condo rental - The Living Room- 10 ft ceilings & 50' high-def TV.
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, downtown, waterfront, balcony
Rates - per property (USD)
$2,400 - $3,950/week
$8,000 - $9,900/month
Calendar Updated Nov 20 2009

Property Review

The property at Truman Annex was exactly what we were looking for in a vacation property. The condo is in a great location, clean, bright, and well-maintained. The property manager was friendly...
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'COLORFUL CONCH' @ the Sanctuary: Decorator Home with 4BR/3BA & Private Pool

— Property 189356
Florida Keys house rental - Meticulously furnished to a very high standard...
4 Bedrooms, Sleeps 6,
House, 3 Bathrooms, beach, resort
Rates - per property (USD)
$8,000 - $11,000/month
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'SOUTHERN STAR' @ William Street: Luxurious 3BR/3BA Historic Old Town Home

— Property 193075
Florida Keys house rental - A very private yard & a gorgeous pool....
3 Bedrooms, Sleeps 6,
House, 3 Bathrooms, village, waterfront, pool
Rates - per property (USD)
$7,700 - $11,000/month
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Oceanside Retreat in the Florida Keys (Marathon Mm 50)

— Property 264471
Florida Keys house rental - Canal View - Rear of House
2 Bedrooms, Sleeps 6,
House, 1 Bathroom, near the ocean, waterfront, balcony
Rates - per property (USD)
$950 - $1,100/week
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“SOUTHWINDS” @ Key West Beach Club: 2 BR Beachfront Condo, Panoramic Ocean Views

— Property 204250
Florida Keys condo rental - Your balcony view speaks for itself...
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, waterfront, pool
Rates - per property (USD)
$5,500 - $9,900/month
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'SIMPLY IRRESISTIBLE' @ The Pool: 2BR 2.5BA Luxurious Poolside Townhome

— Property 206279
Florida Keys townhome rental - The Living Room: Simple elegance & a high-def TV.
2 Bedrooms, Sleeps 6,
Townhome, 2 Bathrooms, 1 Half Bath, near the ocean, resort, pool
Rates - per property (USD)
$3,600 - $5,000/month
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'SOUTHERNMOST BELLE' @ The Annex: 7 Bedrooms, Huge Porches & Large Private Pool

— Property 225064
Florida Keys house rental - A very private yard & a gorgeous pool....
7 Bedrooms, Sleeps 14,
House, 5 Bathrooms, downtown, resort, pool
Rates - per property (USD)
$6,500 - $14,000/week
$20,000 - $35,000/month
Calendar Updated Nov 20 2009

Property Review

We have been renting in Key West for ten years now, and this year was our first time renting "Southernmost Belle". We have already reserved the house for next year, and now wouldn't think of...
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'GEORGIA PEACH' in Old Town: 4BR Luxury Home @ the Meadows

— Property 225229
Florida Keys house rental - 'Georgia Peach', on a quiet street in the Meadows
4 Bedrooms, Sleeps 10,
House, 4 Bathrooms, 1 Half Bath, downtown, resort, pool
Rates - per property (USD)
$7,000 - $11,000/month
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'TURTLE CAY SPA' @ the Sanctuary: Walled Yard & 2 Master Suites

— Property 226088
Florida Keys house rental - Living room: large & airy with overhead fans
2 Bedrooms, Sleeps 6,
House, 2 Bathrooms, near the ocean, resort, pool
Rates - per property (USD)
$5,000 - $6,200/month
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“PENNY'S POMPEI” @ Key West Golf Club: Elegant 2BR/1.5BA Townhome

— Property 229104
Florida Keys house rental - The community pool: just across the street...
2 Bedrooms, Sleeps 6,
House, 1 Bathroom, 1 Half Bath, near the ocean, resort, pool
Rates - per property (USD)
$3,100 - $4,500/month
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'TOP 'O THE COPA' @ Duval: Gorgeous Old Town Penthouse, Available Nightly

— Property 229160
Florida Keys condo rental - A fifteen foot ceiling & lots of light...
1 Bedroom, Sleeps 4,
Condo, 1 Bathroom, 1 Half Bath, downtown, village, terrace
Rates - per property (USD)
$375 - $400/night
$1,675 - $2,400/week
$5,500 - $6,600/month
Calendar Updated Nov 20 2009

Property Review

We loved the location as we could walk to both the gulf or the ocean from this central location. We were not bothered by any late night noise which you might think would be the case on Duval...
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'WATER'S EDGE' @ Gulfview Pointe: Luxurious 4BR Home on Florida Bay

— Property 230758
Florida Keys house rental - Water's Edge: on a quiet lane set in the mangroves
4 Bedrooms, Sleeps 10,
House, 2 Bathrooms, 1 Half Bath, near the ocean, waterfront, pool
Rates - per property (USD)
$6,600 - $14,000/month
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“SOUTHERNMOST ARTS & CRAFTS”, 2BR/2BA Private Home @ South Street

— Property 238081
Florida Keys house rental - The Pool Area is truly an oasis
2 Bedrooms, Sleeps 6,
House, 2 Bathrooms, downtown, near the ocean, pool
Rates - per property (USD)
$7,900 - $8,800/month
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“CASA BLANCA 1888' @ White Street: Private Home in Old Town, 4BR & Large Pool

— Property 238180
Florida Keys house rental - The Master Suite has a balcony with a view...
4 Bedrooms, Sleeps 10,
House, 3 Bathrooms, downtown, resort, pool
Rates - per property (USD)
$7,000 - $12,000/month
Calendar Updated Nov 20 2009

Property Review

We frequent key west at least 5 times a year this was the best place we have ever stayed. The home was immaculate the pool was so refreshing on a hot afternoon. Bruce was great checked with us to...
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“HEAVENLY ZEN @ GRINNELL”: 4BR Private Home @ The Historic Seaport

— Property 238200
Florida Keys house rental - The courtyard is a peaceful oasis...
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, downtown, resort, pool
Rates - per property (USD)
$7,700 - $11,000/month
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New Key West Condo 2/BR - 2.5/BA

— Property 246336
Florida Keys condo rental - Waterside View of Condos and Clubhouse
2 Bedrooms, Sleeps 4,
Condo, 2 Bathrooms, 1 Half Bath, beach, near the ocean, pool
Rates - per property (USD)
$1,500 - $2,000/week
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“NOONA'S MANSION-by-the-SEA”: Oceanfront 6BR/5.5BA @ Truman Annex, Private Pool

— Property 254512
Florida Keys house rental - A gorgeous home in a quiet cul-de-sac
6 Bedrooms, Sleeps 14,
House, 5 Bathrooms, 1 Half Bath, pool, garden
Rates - per property (USD)
$7,700 - $16,000/week
$22,500 - $40,000/month
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'NATALIE'S BAHAMA CONCH': Lavish 3BR/2.5BA Home w/ Private Pool @ the Sanctuary

— Property 254555
Florida Keys house rental - The spacious pool area...
3 Bedrooms, Sleeps 7,
House, 2 Bathrooms, 1 Half Bath, near the ocean, resort, pool
Rates - per property (USD)
$7,000 - $9,900/month
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Bayfront Paradise Heated Pool Home on the Bay in Islamorada

— Property 243094
Florida Keys house rental
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, beach, waterfront, pool
Rates - per property (USD)
$1,800 - $2,200/week
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Tarpon Cove: Best Islamorada Vacation Rental

— Property 153876
Florida Keys house rental - Exterior
3 Bedrooms, Sleeps 6,
House, beach, waterfront, air-conditioning
Rates - per property (USD)
$1,700 - $1,900/week
$6,000/month
Accepts Online Payments
Calendar Updated Nov 20 2009

Property Review

Just wanted to tell you how very much we enjoyed our stay at your rental. The layout of the home is very spacious and yet so very cozy. It really was so relaxing and fun staying there. The...
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'AZURE MORNING' @ Kings Pointe: Luxurious 3 Bedroom Condo on the Atlantic

— Property 202314
Florida Keys condo rental - The view from your spacious balcony...
3 Bedrooms, Sleeps 8,
Condo, near the ocean, waterfront, pool
Rates - per property (USD)
$1,600 - $3,300/week
$4,800 - $7,700/month
Calendar Updated Nov 20 2009

Property Review

The location was just outside of Key West, which was perfect as it was close enough to enjoy down town, but away enough for peaceful evenings. My husband like the location because it was very...
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Oceanfront (Gulf) Condo, Fabulous Views, Heated Pool & Dock

— Property 113802
Florida Keys condo rental - View From Corner of Lower Deck, Left
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, 1 Half Bath, near the ocean, waterfront, pool
Rates - per property (USD)
$986 - $1,586/week
$4,444 - $6,044/month
Calendar Updated Nov 20 2009

Property Review

This experience was amazing for us. The condo made our experience the best because it was so clean and comfy. It was a nice place to know we could come back to after exploring all that the keys...
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“NINA'S PENTHOUSE on the BEACH” 3BR/3BA 2-Story Condo @ The Key West Beach Club

— Property 238333
Florida Keys condo rental - You'll be able to watch both sunrises & sunsets.
3 Bedrooms, Sleeps 8,
Condo, 3 Bathrooms, beach, resort, pool
Rates - per property (USD)
$7,700 - $12,000/month
Calendar Updated Nov 20 2009

Property Review

You can't go wrong with Nina's penthouse, especially if you can enjoy the 3 full bedrooms and baths, two of which are well situated for privacy. The third bedroom is actually a suite with TV and...
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OceanFRONT home new 2008, panoramic ocean views, pool, beach, WIFI - see Reviews

— Property 186650
Florida Keys house rental - View of Atlantic from deck of this oceanfront home
3 Bedrooms, Sleeps 8,
House, 2 Bathrooms, 1 Half Bath, beach, waterfront, pool
Rates - per property (USD)
$1,990 - $3,050/week
Calendar Updated Nov 20 2009

Property Review

Dear Pat & Steve, We had a great week! The lobstering was great and the fishing was fun! We took home fresh lobster, tuna, and dolphin. Your views from the home were beautiful & we loved...
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Key Lime Calypso

— Property 20880h
Florida Keys house rental
1 Bedroom, Sleeps 2,
House, 1 Bathroom, clothes dryer, deck wood
Rates - per house (USD)
$220 - $370/night
$1,470 - $2,590/week
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Villa Tropicale

— Property 56462h
Florida Keys house rental
4 Bedrooms, Sleeps 8,
House, 4 Bathrooms, adventure, air-conditioning
Rates - per house (USD)
$710 - $1,220/night
$4,830 - $8,540/week
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Florida Keys - 8 bedroom 6 baths - up to 16 guests!

— Property 160769
Florida Keys house rental - waterfront home
8 Bedrooms, Sleeps 16,
House, 6 Bathrooms, near the ocean, waterfront, air-conditioning
Rates - per property (USD)
$4,990/week
Calendar Updated Nov 20 2009

Property Review

We had a wonderful time at the two 4 bedroom houses in Marathon---the setting was beautiful, the houses were spacious and perfect for our family reunion, and the weather was unbelievably good....