Ole' Olivia

4 Bedrooms 3 Bathrooms Sleeps 8 Key West 2300 sq. ft. Pet Friendly

Ole Olivia is a beautiful four-bedroom home with a heated pool and high ceilings located in the heart of Key West on Olivia Street. This monthly rental is close to everything. There is one off-street parking.

Primary Bedroom

1 King

Second Bedroom

1 Queen

Third Bedroom

1 Queen

Fourth Bedroom

2 Twin

You will be delighted with this wonderful home with recent renovations, perfectly placed pool, and plenty of outdoor living space located on Olivia Street. This home is situated in the heart of Old Town, just 2 blocks to world famous Duval Street. Finely detailed with unparalleled amenities, this is the perfect vacation spot for the any guest who wants to enjoy Key West at its finest.

This two-story home features high ceilings and hardwood floors. The entire house is artfully decorated. The large kitchen includes granite countertops, fine designer cabinets, stainless appliances, and everything you need to cook, prepare, and serve your favorite Key West meal. Multiple sets of French doors open to your private heated pool, spa, and tropical gardens.

The primary bedroom with a king bed, antique furniture, and flat screen TV has French Doors overlooking your scenic backyard and pool. The bathrooms are spacious and elegant and include walk in showers and a large tub perfect for soaking away the day's sun filled adventures.

The tropical gardens features a heated private pool and outdoor tables/chairs. The backyard is the perfect place to enjoy your afternoon cocktail while grilling on the gas BBQ grill the perfect day's catch of fresh fish!

Off-street parking for two vehicles, and the front porch is perfect for enjoying the lazy days of Key West.

This is a monthly rental and only rents from the first of the month to the end of the month. We cannot split months.

Tourist Attractions

  • Health Beauty Spa
  • Marinas, Boat Rentals & Excursions
  • Museums
  • Key West Aquarium
  • Public Parks & Beaches
  • Key West Historic Seaport
  • Key West Tropical Forest & Tropical Garden
  • Southernmost Point Buoy
  • Dry Tortugas National Park & Fort Jefferson
  • Fort Zachary Taylor State Park & Beach
  • Sunset Celebration at Mallory Square
  • History Tours - Motorized, Walking & Biking
  • The Florida Reef - N. America’s only living coral barrier reef
  • Key West Marine Park stretching from Higgs Beach to South Beach
  • The Key West Butterfly & Nature Conservatory
  • Food Tours
  • Ghost Tours
  • Pub Crawls
  • Your reservation guest portal will provide details

Accommodation Essentials

  • Hair Dryer
  • Hangers
  • Kitchen
  • Wireless Internet
  • Air Conditioning
  • Bed Linens
  • Cable
  • Towels
  • Hot Water
  • Dryer
  • Essentials
  • Living Room
  • Parking
  • Lock on Bedroom Door
  • Private Entrance
  • Private Living Room
  • Washer

Leisure

  • Dolphin Watching
  • Dining Out
  • Live Theater, Concerts & Entertainment
  • Your reservation guest portal will provide details
  • Paint & Sip Art Classes
  • Bird Watching
  • Boating
  • Eco Tourism
  • Shopping

Kitchen

  • Stove
  • Coffee Maker - Drip
  • Dishes & Silverware
  • Microwave
  • Refrigerator
  • Toaster
  • Cooking Basics
  • Dishwasher
  • Oven
  • Dishes & utensils for kids
  • Kitchen Island
  • Dining table
  • Coffee Maker - Kcup
  • Coffee Maker - Kcup and Drip
  • Blender

Sports

  • Banana Boat Riding & Water Tubing
  • Wind Surfing
  • Ocean Waterpark & Challenge Course
  • Kayaking
  • Kite Boarding
  • Pickleball
  • Tennis
  • Golfing
  • Scuba Diving
  • Skydiving
  • Your reservation guest portal will provide details
  • Paddle Boarding
  • Cycling
  • DeepSea Fishing
  • Fishing - Backcountry
  • Jet Skiing
  • Para-sailing
  • Fishing - Pier
  • Sailing
  • Snorkeling
  • Swimming

Local

  • Banks
  • Grocery Stores
  • Fitness Centers
  • Hospital
  • Laundromats

Home Safety

  • Fire Extinguisher
  • Smoke Detector

Outdoor

  • BBQ Area
  • Garden or Backyard
  • Patio or Balcony
  • Grill
  • Fenced Yard

Special

  • Beach Essentials

Entertainment

  • DVD Player
  • Television

Facility

  • Free Parking
  • Pool

Location

  • Historic District

Pool

  • Heated Pool
  • Private Pool
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$322
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$305
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$302
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$321
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$310
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$304
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$310
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$320
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$329
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$332
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$318
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$312
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$311
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$317
     
October 2026
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$330
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$338
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$340
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$327
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$320
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$320
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$326
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$337
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$347
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$349
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$335
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$328
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$328
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$334
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$345
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$361
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$383
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$378
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$367
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$367
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$378
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$398
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$413
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$407
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$350
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$342
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$341
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$348
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$360
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$369
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$375
November 2026
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$362
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$310
         
December 2026
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$387
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January 2027
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$634
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$621
           
February 2027
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$677
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March 2027
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$682
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$708
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$722
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$738
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$737
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$736
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$736
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$735
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$734
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$733
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$733
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$732
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$728
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$724
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$721
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$716
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$711
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$707
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$662
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$636
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$628
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$636
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$663
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$666
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$663
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$651
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$646
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$621
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$621
     
April 2027
S M T W T F S
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$621
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$621
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$621
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$595
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$575
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$567
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$590
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$600
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$598
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$572
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$554
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$552
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$564
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$570
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$582
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$578
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$546
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$533
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$522
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$530
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$531
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$544
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$538
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$507
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$494
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$483
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$487
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$510
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$515
 

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