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
LEAVE A REVIEW

We are sorry, there are no reviews for this unit. Be the first to leave a review!

Available
Unavailable
Check-In Only
Check-Out Only


August 2025
S M T W T F S
          01 02
03 04 05 06 07 08 09
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31            
September 2025
S M T W T F S
  01 02 03 04 05 06
07 08 09 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30
$302
       
October 2025
S M T W T F S
      01
$285
02
$295
03
$340
04
$347
05
$303
06
$303
07
$305
08
$312
09
$326
10
$374
11
$384
12
$344
13
$347
14
$351
15
$359
16
$374
17
$422
18
$432
19
$391
20
$392
21
$394
22
$400
23
$412
24
$457
25
$464
26
$420
27
$417
28
$415
29
$416
30
$425
31
$466
 
November 2025
S M T W T F S
            01
$441
02
$396
03
$390
04
$385
05
$384
06
$390
07
$426
08
$507
09
$455
10
$398
11
$374
12
$365
13
$370
14
$407
15
$407
16
$361
17
$354
18
$349
19
$347
20
$354
21
$390
22
$392
23
$346
24
$360
25
$366
26
$368
27
$370
28
$420
29
$411
30
$339
           
December 2025
S M T W T F S
  01
$450
02 03 04 05 06
07 08 09 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30 31
$450
     
January 2026
S M T W T F S
        01
$772
02 03
04 05 06 07 08 09 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
$689
February 2026
S M T W T F S
01
$629
02 03 04 05 06 07
08 09 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
March 2026
S M T W T F S
01 02 03 04 05 06 07
08 09 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30 31
$562
       
April 2026
S M T W T F S
      01
$560
02
$568
03
$623
04
$625
05
$560
06
$551
07
$545
08
$545
09
$555
10
$611
11
$615
12
$550
13
$543
14
$537
15
$537
16
$548
17
$603
18
$606
19
$540
20
$532
21
$525
22
$523
23
$531
24
$585
25
$585
26
$518
27
$507
28
$498
29
$494
30
$501
   
May 2026
S M T W T F S
          01
$350
02
$350
03
$350
04
$350
05
$350
06
$350
07
$350
08
$350
09
$350
10
$350
11
$350
12
$350
13
$
14
$
15
$
16
$
17
$
18
$
19
$
20
$
21
$
22
$
23
$
24
$
25
$
26
$
27
$
28
$
29
$
30
$
31
$
           
June 2026
S M T W T F S
  01
$
02
$
03
$
04
$
05
$
06
$
07
$
08
$
09
$
10
$
11
$
12
$
13
$
14
$
15
$
16
$
17
$
18
$
19
$
20
$
21
$
22
$
23
$
24
$
25
$
26
$
27
$
28
$
29
$
30
$
       
July 2026
S M T W T F S
      01
$
02
$
03
$
04
$
05
$
06
$
07
$
08
$
09
$
10
$
11
$
12
$
13
$
14
$
15
$
16
$
17
$
18
$
19
$
20
$
21
$
22
$
23
$
24
$
25
$
26
$
27
$
28
$
29
$
30
$
31
$
 
August 2026
S M T W T F S
            01
$
02
$
03
$
04
$
05
$
06
$
07
$
08
$
09
$
10
$
11
$
12
$
13
$
14
$
15
$
16
$
17
$
18
$
19
$
20
$
21
$
22
$
23
$
24
$
25
$
26
$
27
$
28
$
29
$
30
$
31
$
         

Book Now

Detailed Quote
Add to Favorites
Inquire
Share
Print