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The Hotel Fanatic - Vacation Rentals in Meadows

Harborside Motel & Marina in Key West From US $227
         

8.6 (1361 Reviews)
Hotel
Harborside Motel & Marina
  • Air Conditioner
  • Parking
  • Pool

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Luxury Places to Stay in Meadows

Over 143+ Luxury Places to Stay in or Near Meadows
Bayview North One in Key West From US $2,792
         

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New
House
Bayview North One
  • Parking
  • Pool
  • Wheelchair Accessible

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Meadows Manor | Elegant Oasis with Private Pool in Key West From US $2,100
         

9.6 (17 Reviews)
House
Meadows Manor | Elegant Oasis with Private Pool
  • Air Conditioner
  • Pool
  • TV

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Bayview Retreat in Key West From US $2,086
         

New
House
Bayview Retreat
  • Parking
  • Pet Friendly
  • Pool

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St Kitts - Downtown Waterfront Penthouse Pool Dock Parking in Key West From US $2,063
         

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8.1 (13 Reviews)
House
St Kitts - Downtown Waterfront Penthouse Pool Dock Parking
  • Air Conditioner
  • Parking
  • Pet Friendly

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St John - Downtown Waterfront Penthouse Pool Parking Dock in Key West From US $2,063
         

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9.3 (3 Reviews)
House
St John - Downtown Waterfront Penthouse Pool Parking Dock
  • Air Conditioner
  • Parking
  • Pet Friendly

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St Thomas - Waterfront Penthouse sleeps 16 w Pool & Boat Dock in Key West From US $2,063
         

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8.9 (12 Reviews)
House
St Thomas - Waterfront Penthouse sleeps 16 w Pool & Boat Dock
  • Air Conditioner
  • Parking
  • Pet Friendly

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Meadows Manor in Key West From US $1,986
         

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New
House
Meadows Manor
  • Security/Safety
  • Child Friendly

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Eisenhower Retreat in Key West From US $1,832
         

New
House
Eisenhower Retreat
  • Parking
  • Pet Friendly
  • Pool

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Top-Rated Vacation Rentals with a Pool in Meadows

Over 117+ Top-Rated Vacation Rentals with a Pool in or Near Meadows
Waterfront Dock Pool Key West Near Duval in Key West From US $524
         

10.0 (37 Reviews)
Condo
Waterfront Dock Pool Key West Near Duval
  • Air Conditioner
  • Parking
  • Pet Friendly

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Eliza Street Retreat, 2 bedroom, 2 bathrm, + loft, private pool, great location in Key West From US $307
         

10.0 (7 Reviews)
House
Eliza Street Retreat, 2 bedroom, 2 bathrm, + loft, private pool, great location
  • Air Conditioner
  • Parking
  • Pool

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Shady Palms | Historic Charm Private Pool & Effortless Island Style 2BD/2.5BA in Key West From US $437
         

10.0 (6 Reviews)
House
Shady Palms | Historic Charm Private Pool & Effortless Island Style 2BD/2.5BA
  • Air Conditioner
  • Parking
  • Pet Friendly

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Fabulous Home with Private Saltwater Pool, Central AC, & High-Speed WiFi in Key West From US $253
         

10.0 (6 Reviews)
House
Fabulous Home with Private Saltwater Pool, Central AC, & High-Speed WiFi
  • Air Conditioner
  • Parking
  • Pool

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The Margaret Suite in Key West From US $562
         

10.0 (4 Reviews)
Apartment
The Margaret Suite
  • Air Conditioner
  • Parking
  • Pool

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PINEAPPLE BREEZE ~ JUST RENOVATED Home in The Meadows with Pool! in Key West From US $344
         

10.0 (4 Reviews)
House
PINEAPPLE BREEZE ~ JUST RENOVATED Home in The Meadows with Pool!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Tropical Heron Hideaway w/Hot Tub + Pool in Key West From US $398
         

10.0 (3 Reviews)
Apartment
Tropical Heron Hideaway w/Hot Tub + Pool
  • Air Conditioner
  • Parking
  • Pool

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Turtle Nest Condo - Pool - 2nd Floor in Key West From US $405
         

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10.0 (2 Reviews)
Apartment
Turtle Nest Condo - Pool - 2nd Floor
  • Air Conditioner
  • Parking
  • Pool

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Pet-Friendly Vacation Rentals in Meadows

Over 57+ Pet-Friendly Vacation Rentals in or Near Meadows
Key West Downtown Waterfront, sleeps 8, Dock & Pool Pet-Friendly in Key West From US $785
         

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9.9 (16 Reviews)
House
Key West Downtown Waterfront, sleeps 8, Dock & Pool Pet-Friendly
  • Air Conditioner
  • Parking
  • Pet Friendly

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ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo with Private Hot Tub in The Meadows! in Key West From US $172
         

10.0 (1 Review)
House
ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo with Private Hot Tub in The Meadows!
  • Air Conditioner
  • Pet Friendly
  • TV

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Oversized home for the whole family w/private pool & dock in Key West From US $1,167
         

9.8 (147 Reviews)
House
Oversized home for the whole family w/private pool & dock
  • Air Conditioner
  • Parking
  • Pet Friendly

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~ CASABLANCA ~ Fabulous home w/private pool/parking, in a quiet location. in Key West From US $177
         

9.8 (125 Reviews)
House
~ CASABLANCA ~ Fabulous home w/private pool/parking, in a quiet location.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Luxury Waterfront Home with Private Pool and Dock! in Key West From US $973
         

9.8 (92 Reviews)
House
Luxury Waterfront Home with Private Pool and Dock!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Waterfront Condo | Pool, Dock, Parking, Sleeps 8 in Key West From US $393
         

9.8 (39 Reviews)
Condo
Waterfront Condo | Pool, Dock, Parking, Sleeps 8
  • Air Conditioner
  • Parking
  • Pet Friendly

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Waterfront Dock Pool Pet Friendly Near Duval St in Key West From US $694
         

9.8 (32 Reviews)
Condo
Waterfront Dock Pool Pet Friendly Near Duval St
  • Air Conditioner
  • Parking
  • Pet Friendly

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Waterfront Condo Dock Pool Near Duval St in Key West From US $711
         

9.8 (29 Reviews)
Condo
Waterfront Condo Dock Pool Near Duval St
  • Air Conditioner
  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in Meadows

Over 15+ Large Vacation Homes & Villas in or Near Meadows
Authors Key West Guesthouse in Key West From US $159
         

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8.8 (970 Reviews)
House
Authors Key West Guesthouse
  • Air Conditioner
  • Pool
  • View

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Conch style home in Oldtown with private pool AND dock! in Key West From US $904
         

9.8 (137 Reviews)
House
Conch style home in Oldtown with private pool AND dock!
  • Air Conditioner
  • Parking
  • Pool

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3-Story spacious conch style home w/private pool & dock! in Key West From US $1,095
         

9.8 (156 Reviews)
House
3-Story spacious conch style home w/private pool & dock!
  • Air Conditioner
  • Parking
  • Pool

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Waterfront Dock Pool Penthouse Near Duval St in Key West From US $934
         

9.6 (42 Reviews)
Condo
Waterfront Dock Pool Penthouse Near Duval St
  • Air Conditioner
  • Parking
  • Pet Friendly

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Penthouse Waterfront Dock Pool Condo Near Duval St in Key West From US $581
         

9.6 (38 Reviews)
Condo
Penthouse Waterfront Dock Pool Condo Near Duval St
  • Air Conditioner
  • Parking
  • Pet Friendly

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Waterfront Dock Pool Near Duval St Penthouse in Key West From US $581
         

9.6 (35 Reviews)
Condo
Waterfront Dock Pool Near Duval St Penthouse
  • Air Conditioner
  • Parking
  • Pet Friendly

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BELLE MAISON ~ 5 BR/3 Ba Home w/Pool/Spa in The Meadows! in Key West From US $1,301
         

New
House
BELLE MAISON ~ 5 BR/3 Ba Home w/Pool/Spa in The Meadows!
  • Air Conditioner
  • Pet Friendly
  • Pool

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Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool in Key West From US $625
         

New
House
Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool
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  • Parking
  • Pool

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Wheelchair Accessible Vacation Homes in Meadows

Over 20+ Wheelchair Accessible Vacation Homes in or Near Meadows
Bermuda Retreat-waterfront 2BR 2BA condo w/pool & boat slip in Key West From US $495
         

9.0 (108 Reviews)
Condo
Bermuda Retreat-waterfront 2BR 2BA condo w/pool & boat slip
  • Air Conditioner
  • Parking
  • Pool

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4-Bed, 4.5 Bath Condo & Bayfront Suites-non waterfront CLEANING FEE INCLUDED in Key West From US $746
         

9.8 (135 Reviews)
Condo
4-Bed, 4.5 Bath Condo & Bayfront Suites-non waterfront CLEANING FEE INCLUDED
  • Air Conditioner
  • Parking
  • Pool

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Waterfront 4-Bed, 4-Bath Condo at Bayfront Suites - CLEANING FEE INCLUDED in Key West From US $739
         

9.8 (111 Reviews)
Condo
Waterfront 4-Bed, 4-Bath Condo at Bayfront Suites - CLEANING FEE INCLUDED
  • Air Conditioner
  • Parking
  • Pool

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Waterfront 4 Bed, 4-Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED in Key West From US $906
         

9.8 (84 Reviews)
Condo
Waterfront 4 Bed, 4-Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED
  • Air Conditioner
  • Parking
  • Pool

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4-Bed 4.5 Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED Non-Waterfront in Key West From US $885
         

9.6 (101 Reviews)
Condo
4-Bed 4.5 Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED Non-Waterfront
  • Air Conditioner
  • Parking
  • Pool

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Waterfront 3-Bedroom Condo at Bayfront Suites & Marina- CLEANING FEE INCLUDED in Key West From US $720
         

9.6 (97 Reviews)
Condo
Waterfront 3-Bedroom Condo at Bayfront Suites & Marina- CLEANING FEE INCLUDED
  • Air Conditioner
  • Parking
  • Pool

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3-Bedroom 3-Bath Condo at Bayfront Suites & Marina - CLEANING FEE INCLUDED in Key West From US $724
         

9.6 (84 Reviews)
Condo
3-Bedroom 3-Bath Condo at Bayfront Suites & Marina - CLEANING FEE INCLUDED
  • Air Conditioner
  • Parking
  • Pool

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3 Bed 3 Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED (Non-Waterfront) in Key West From US $728
         

9.6 (80 Reviews)
Condo
3 Bed 3 Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED (Non-Waterfront)
  • Air Conditioner
  • Parking
  • Pool

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Meadows Vacation Rentals and Airbnb Places to Stay Under $200

Over 10+ Meadows Vacation Rentals and Airbnb Places to Stay Under $200
NEWTON'S NEST ~ Adult Only, 1st Floor 1 Bedroom, 1 Bath Condo w/Shared Pool! in Key West From US $163
         

10.0 (1 Review)
Condo
NEWTON'S NEST ~ Adult Only, 1st Floor 1 Bedroom, 1 Bath Condo w/Shared Pool!
  • Air Conditioner
  • Pool
  • TV

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Authors of Key West Guest House in Key West From US $134
         

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9.2 (1047 Reviews)
Bed & Breakfast
Authors of Key West Guest House
  • Air Conditioner
  • Pool
  • TV

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~ CASABLANCA TOO ~Chicly updated home with hot tub in a quiet location. in Key West From US $174
         

9.6 (117 Reviews)
House
~ CASABLANCA TOO ~Chicly updated home with hot tub in a quiet location.
  • Air Conditioner
  • Parking
  • Pet Friendly

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CABIN FEVER ~ First Floor 1 Bedroom, 1 Bathroom with Full Kitchen and Pool! in Key West From US $164
         

8.8 (3 Reviews)
Condo
CABIN FEVER ~ First Floor 1 Bedroom, 1 Bathroom with Full Kitchen and Pool!
  • Air Conditioner
  • Pool
  • TV

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The Fleming Suite | 1 bedroom condo w/shared pool in Key West From US $151
         

7.6 (4 Reviews)
Condo
The Fleming Suite | 1 bedroom condo w/shared pool
  • Air Conditioner
  • Pool
  • TV

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Large 1 bedroom condo in the historic area of Key West! in Key West From US $191
         

New
Condo
Large 1 bedroom condo in the historic area of Key West!
  • Air Conditioner
  • TV
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The Sea Glass Cottage in Historic Key West in Key West From US $190
         

New
House
The Sea Glass Cottage in Historic Key West
  • Air Conditioner
  • Parking
  • Pet Friendly

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Tropical Escape with Central Locale, Private Hot Tub, WiFi, and Shared Pool in Key West From US $165
         

9.2 (131 Reviews)
Condo
Tropical Escape with Central Locale, Private Hot Tub, WiFi, and Shared Pool
  • Air Conditioner
  • Pool
  • TV

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Instantly Bookable Vacation Homes in Meadows

Over 47+ Instantly Bookable Vacation Homes in or Near Meadows
The Crystalmarine Suite – Rustic Luxury on the Sea in Key West From US $507
         

10.0 (3 Reviews)
Boat Rental
The Crystalmarine Suite – Rustic Luxury on the Sea
  • Air Conditioner
  • Parking
  • TV

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New Listing! Truman Show - Private, heated pool and chef's kitchen in Key West From US $887
         

10.0 (1 Review)
House
New Listing! Truman Show - Private, heated pool and chef's kitchen
  • Air Conditioner
  • Parking
  • Pool

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SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/Pool! in Key West From US $328
         

9.8 (9 Reviews)
House
SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/Pool!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Waterfront 4-Bed 3-Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED in Key West From US $857
         

9.6 (67 Reviews)
Condo
Waterfront 4-Bed 3-Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED
  • Air Conditioner
  • Parking
  • Pool

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Waterfront Dock Pool Condo Near Duval St Pet OK in Key West From US $577
         

9.6 (45 Reviews)
Condo
Waterfront Dock Pool Condo Near Duval St Pet OK
  • Air Conditioner
  • Parking
  • Pet Friendly

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Waterfront Condo Dock Pool Downtown Near Duval in Key West From US $656
         

9.6 (29 Reviews)
Condo
Waterfront Condo Dock Pool Downtown Near Duval
  • Air Conditioner
  • Parking
  • Pet Friendly

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Casa de Rosalie by AvantStay | Great Location w/Pool, BBQ & Outdoor Dining in Key West From US $297
         

9.6 (4 Reviews)
House
Casa de Rosalie by AvantStay | Great Location w/Pool, BBQ & Outdoor Dining
  • Air Conditioner
  • Parking
  • Pet Friendly

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Antigua Retreat- 2BR 2BA waterfront condo w/pool & boat slip in Key West From US $626
         

9.4 (152 Reviews)
Condo
Antigua Retreat- 2BR 2BA waterfront condo w/pool & boat slip
  • Air Conditioner
  • Parking
  • Pool

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About Meadows Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Thehotelfanatic Meadows, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Meadows. Places to stay near Meadows are 275.25 ft² on average, with prices averaging US $227 a night.

Thehotelfanatic makes it easy and safe to find and compare vacation rentals in Meadows with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Meadows

Type Count
Hotels 1

Use these Quick Filters to Find a Vacation Rental in Meadows

★ Pro Tip: Thehotelfanatic makes it easy to compare the best listings on Thehotelfanatic homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Thehotelfanatic homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Meadows.

Weather in Meadows

View the weather forecast for Meadows before booking your Meadows Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Other Places to Stay Near Meadows, FL


The Unitarian Universalist Fellowship of Key West 4,261 Properties The Meadows 103 Properties

Complexes around Meadows, FL


Bayfront Suites Marina 8 Properties Downtown Waterfront Dock 5 Properties Paradise Place 3 Properties Casablanca 2 Properties Town Introductory Rates 1 Properties

Meadows Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Meadows?

There are a lot of options in Meadows. If you plan on staying in the Meadows area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Meadows:

How many vacation rentals are available in Meadows?

Currently, the total number of properties listed in 2026 is over 1 in the Meadows area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Meadows.