Choose Key West Rentals for Restful and Relaxing Getaways

Planning a trip to Key West, Florida means that you’re well on your way to a sunny and tropical getaway from all of the stress of your life at home. Key West condos offer economical and convenient ways to take in all that this beautiful island has to offer, with easy access to both the beach and busy nightlife.

Key West Rentals Offer Easy Beach Access


No matter what you plan on doing during your stay, Key West vacation rentals can be found on the beach if you want to be able to simply wake up in the morning and walk directly out to the ocean. You may also find one of the Key West condo rentals on a private beach area so that you and your family can enjoy your stay away from the crowds.

Find Key West Vacation Rentals near Several Attractions and Activities


You should plan on several activities while staying at one of the Key West rentals, as you’ll have one less thing to worry about before heading out for a day on the town. Snorkeling, chartering a deep-sea fishing boat and even shopping for local novelties are some of the most common activities before retiring to one of the Key West vacation rentals. Consider a Key West rental on the golf course if you like to putt around on the green.

Stay for a Season at Key West Condo Rentals


If you’re planning on staying with a group, Key West condo rentals offer ideal solutions for several bedrooms and accommodations very near each other. Some Key West rentals can also be reserved for long-term stays if you want to get away from chilly winter weather for a season!

This island is known for its relaxed lifestyle, beauty and catering activities to tourists. There’s no doubt that you and your family will feel welcome at any of the Key West vacation rentals, and well-rested upon your return home. You’ll also like the convenient amenities of Key West condo rentals for entertaining your newfound friends you’re sure to meet in this tropical oasis! Search today!

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.


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Key West Vacation Rentals

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Vacation Destinations in Key West

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Casa Amor - 3BR Residence 2 Blocks from Duval Street

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 233509
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Key West house rental - Pool and Loggia
3 Bedrooms, Sleeps 8,
House, 2 Bathrooms, 1 Half Bath, near the ocean, town, pool
Rates - per property (USD)
$2,200 - $3,500/week
$4,800 - $8,800/month
Contact the Owner
Details and Availability

Henry's Penthouse on the Ocean in Key West (weekly / nightly rentals)

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 112032
compare
Key West condo rental - Ahhh - the pool (heated) with ocean in background
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, waterfront, tennis court
Rates - per property (USD)
$265/night
$1,670/week
Contact the Owner
Details and Availability

DIRECT OCEANFRONT FREE WIFI & HBO

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 149233
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Key West condo rental - This is the view from the master bedroom
3 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, 1 Half Bath, beach, pool
Rates - per property (USD)
$375/night
$2,350/week
Contact the Owner
Details and Availability

Beautiful Waterfront Single Family Home - 5 miles from Key West

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 322888
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Key West house rental - Front of house at sunset
3 Bedrooms, Sleeps 6,
House, 3 Bathrooms, near the ocean, waterfront, balcony
Rates - per property (USD)
$875 - $1,225/week
$3,000 - $5,000/month
Contact the Owner
Details and Availability

"TROPICAL JEWEL @ ELIZABETH": 2BR/2BA Meticulously Restored Conch Home at the Historic Seaport

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 7069257h
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Key West house rental - The back porch is the perfect place to spend the afternoon.
2 Bedrooms, Sleeps 6,
House, 2 Bathrooms, downtown, near the ocean
Rates - per house (USD)
$6,000 - $9,000/month
Contact the Owner
Details and Availability

"CASA FELIZ @ WHITE STREET" 3BR/3.5BA Lushly Decorated Private Home in Old Town, Large Private Pool

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 7062607h
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Key West house rental - A quiet enclave in Old Town. The perfect vacation.
3 Bedrooms, Sleeps 8,
House, 3 Bathrooms, 1 Half Bath, downtown, near the ocean
Rates - per house (USD)
$5,750 - $11,000/month
Contact the Owner
Details and Availability

"VILLA VENEZIA @ THE GULF": Luxurious & Sophisticated 2BR/2.5BA Oceanfront Villa in Truman Annex

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 7070000h
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Key West cottage rental - The pool is just steps from the villa.
2 Bedrooms, Sleeps 6,
Cottage, 2 Bathrooms, 1 Half Bath, downtown, near the ocean
Rates - per cottage (USD)
$2,950 - $5,500/week
$7,700 - $12,000/month
Contact the Owner
Details and Availability

"PARADISE PERFECTED @ THE SANCTUARY": Elegantly Furnished 3BR/2.5BA Luxury Home with Private Pool

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 7048606h
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Key West house rental - The back yard is your little piece of paradise... perfected.
3 Bedrooms, Sleeps 8,
House, 2 Bathrooms, 1 Half Bath, near the ocean, terrace
Rates - per house (USD)
$4,800 - $8,800/month
Contact the Owner
Details and Availability

"HIDDEN TREASURE' @ CASA EAST": Luxury 3BR's, Baby Grand Piano, Huge Private Pool

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 7048504h
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Key West house rental - The Pool: big enough to swim laps, plenty of room to relax.
3 Bedrooms, Sleeps 6,
House, 3 Bathrooms, beach, near the ocean
Rates - per house (USD)
$5,500 - $9,500/month
Contact the Owner
Details and Availability

"NATALIE'S BAHAMA CONCH' @ THE SANCTUARY": Lavishly Furnished 3BR/2.5BA Home w/ Private Pool

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 7048559h
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Key West house rental - The spacious & private pool area is a quiet oasis.
3 Bedrooms, Sleeps 8,
House, 2 Bathrooms, 1 Half Bath, near the ocean, resort
Rates - per house (USD)
$4,800 - $9,250/month
Contact the Owner
Details and Availability

“ANGEL CONCH @ ANGELA STREET": Heavenly 3BR Private Home with Pool & Jacuzzi...

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 7048535h
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Key West house rental - The Hi-Def TV rises magically from the sideboard.
3 Bedrooms, Sleeps 6,
House, 3 Bathrooms, downtown, resort
Rates - per house (USD)
$5,250 - $9,500/month
Contact the Owner
Details and Availability

Sunrise Suites

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 7023700h
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Key West condo rental
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, pets considered
Rates - per condo (USD)
$150 - $250/night
$1,050 - $1,720/week
$4,500 - $7,125/month
Contact the Owner
Details and Availability

Pelican Landing Dominica Room

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 7067247h
compare
Key West condo rental
1 Bedroom, Sleeps 4,
Condo, 1 Bathroom, communal pool, air-conditioning
Rates - per condo (USD)
$198 - $218/night
$1,386 - $2,786/week
$5,940 - $8,940/month
Contact the Owner
Details and Availability

Truman Annex: Self Catering Beautiful ground floor condominium with large deck

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 136334
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Key West condo rental - Front view of property
2 Bedrooms, Sleeps 6,
Condo, 1 Bathroom, downtown, near the ocean, pool
Rates No rental rates available - please contact the owner
Contact the Owner
Details and Availability

Mar Y Sol

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 40007h
compare
Key West condo rental
3 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, 1 Half Bath, beach, private pool
Rates - per condo (USD)
$375 - $650/night
$2,350 - $4,188/week
Contact the Owner
Details and Availability

$750 Per Week Bargain Rates for Aug. & Sept.

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 184913
compare
Key West condo rental - Living Room
2 Bedrooms, Sleeps 6,
Condo, 1 Bathroom, beach, near the ocean, pool
Rates - per property (USD)
$135 - $275/night
$750 - $1,595/week
Contact the Owner
Details and Availability

Brucie's Pristine Pool Peek is Paradise in Truman Annex

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 290407
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Key West condo rental - You are a few steps from the Truman Annex pool.
1 Bedroom, Sleeps 2,
Condo, 1 Bathroom, near the ocean, town, pool
Rates - per property (USD)
$1,000 - $1,600/week
Contact the Owner
Details and Availability

Villa Soleil-Enjoy America's Caribbean with Style and Comfort

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 141421
compare
Key West townhome rental - Sunny Living Room
2 Bedrooms, Sleeps 6,
Townhome, 2 Bathrooms, 1 Half Bath, near the ocean, town, garden
Rates - per property (USD)
$1,500 - $2,500/week
Contact the Owner
Details and Availability

Havana Lane

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 20875h
compare
Key West house rental
2 Bedrooms, Sleeps 4,
House, 2 Bathrooms, satellite or cable
Rates - per house (USD)
$310 - $530/night
$2,100 - $3,710/week
Contact the Owner
Details and Availability

Surf Side

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 40052h
compare
Key West condo rental
3 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, private pool
Rates - per condo (USD)
$375 - $650/night
$2,350 - $4,188/week
Contact the Owner
Details and Availability

Coconut Cabana

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 20886h
compare
Key West house rental
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, beach
Rates - per house (USD)
$340 - $630/night
$2,310 - $4,410/week
Contact the Owner
Details and Availability

Louisa House

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 20885h
compare
Key West house rental
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, 1 Half Bath, beach, satellite or cable
Rates - per house (USD)
$470 - $800/night
$3,150 - $5,600/week
Contact the Owner
Details and Availability

Casa Caracol-Beautiful New Cottage Just Blocks from Duval Street

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 277296
compare
Key West house rental - Front Porch
2 Bedrooms, Sleeps 6,
House, 2 Bathrooms, beach, downtown, daily maid service
Rates - per property (USD)
$388 - $458/night
Contact the Owner
Details and Availability

Spacious Ocean Front Resort - 3 Bedroom Condo

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 232367
compare
Key West condo rental - View of pool & part of complex
3 Bedrooms, Sleeps 8,
Condo, 3 Bathrooms, beach, sauna
Rates - per property (USD)
$400 - $500/night
$2,400 - $3,150/week
Accepts Online Payments
Contact the Owner
Details and Availability

Duval St. 6 bedroom Compound w/ 2 Private Heated Pools, Parking & Huge Roof Deck

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 228157
compare
Key West villa rental - Guest house living room & pool
6 Bedrooms, Sleeps 14,
Villa, 7 Bathrooms, downtown, near the ocean, pool
Rates - per property (USD)
$8,400/week
Contact the Owner
Details and Availability

Beach Club #303

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 20894h
compare
Key West condo rental
2 Bedrooms, Sleeps 4,
Condo, 2 Bathrooms, beach, communal pool
Rates - per condo (USD)
$1,750 - $3,430/week
Contact the Owner
Details and Availability

Colony Poolside

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 76142h
compare
Key West bungalow rental
1 Bedroom, Sleeps 2,
Bungalow, 1 Bathroom, communal pool, satellite or cable
Rates - per bungalow (USD)
$160 - $320/night
$1,050 - $2,240/week
Contact the Owner
Details and Availability

Vista Fresco

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 7013304h
compare
Key West condo rental
2 Bedrooms, Sleeps 4,
Condo, 2 Bathrooms, beach, communal pool
Rates - per condo (USD)
$240 - $380/night
$1,540 - $2,660/week
Contact the Owner
Details and Availability

Old Town Key West 2 bedroom Cottage with Private Pool

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 7069978h
compare
Key West cottage rental - Casa Manana Front view
2 Bedrooms, Sleeps 6,
Cottage, 2 Bathrooms, downtown, private pool
Rates - per cottage (USD)
$3,500 - $7,000/month
Contact the Owner
Details and Availability

"CASA BLANCA 1888 @ WHITE STREET": Large 4BR/3BA Historic Private Home in Old Town with Large Pool

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 7048550h
compare
Key West house rental - Out back is a big courtyard with a really big pool.
4 Bedrooms, Sleeps 10,
House, 3 Bathrooms, downtown, resort
Rates - per house (USD)
$6,600 - $12,000/month
Contact the Owner
Details and Availability
1 2 3 4 5 Last