Meadows Holiday Rentals
- Key West
- ·
- The Meadows
- 0.07 mi to center
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
- Key West
- ·
- The Meadows
- 0.12 mi to center
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
- Key West
- ·
- The Meadows
- 0.12 mi to center
- Private Pool
- Hot Tub
- Pool
- Pet Friendly
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Key West
- ·
- The Meadows
- 0.13 mi to center
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
Luxury Holiday Rentals in Meadows
- Pool
- Balcony/Terrace
- Kitchen
- Parking
- Child Friendly
- Security/Safety
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
- Hot Tub
- Pool
- Balcony/Terrace
- View
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
- Balcony/Terrace
- View
- Breakfast
- Pet Friendly
- Pool
- Balcony/Terrace
- View
- Breakfast
Top-Rated Holiday Rentals with a Pool in Meadows
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
- Key West
- ·
- The Meadows
- 0.08 mi to center
- Private Pool
- Oceanfront
- Pool
- Ocean View
- Key West
- ·
- The Meadows
- 0.12 mi to center
- Oceanfront
- Hot Tub
- Pool
- Ocean View
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
- Key West
- ·
- The Meadows
- 0.13 mi to center
- Oceanfront
- Hot Tub
- Pool
- Ocean View
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
- Key West
- ·
- The Meadows
- 0.13 mi to center
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
Pet-Friendly Holiday Rentals in Meadows
- Hot Tub
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
- Key West
- ·
- The Meadows
- 0.11 mi to center
- Private Pool
- Pool
- Pet Friendly
- Kitchen
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Key West
- ·
- The Meadows
- 0.07 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Pool
- Key West
- ·
- The Meadows
- 0.11 mi to center
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
Large Holiday Rentals and Private Villas in Meadows
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
- Pool
- Balcony/Terrace
- View
- Air Conditioner
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
- Hot Tub
- Pool
- Balcony/Terrace
- View
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Private Pool
- Oceanfront
- Hot Tub
- Pool
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
Wheelchair Accessible Holiday Homes in Meadows
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
Meadows Private Villas and Holiday Homes Under $200
- Key West
- ·
- The Meadows
- 0.13 mi to center
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Air Conditioner
- Pool
- Kitchen
- Air Conditioner
- Internet
- Key West
- ·
- The Meadows
- 0.06 mi to center
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
- Key West
- ·
- The Meadows
- 0.12 mi to center
- Oceanfront
- Hot Tub
- Spa
- Pool
Instantly Bookable Holiday Homes in Meadows
- Key West
- ·
- The Meadows
- 0.11 mi to center
- Pool
- Balcony/Terrace
- Kitchen
- Parking
- Key West
- ·
- The Meadows
- 0.12 mi to center
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
- Fireplace/Heating
- Air Conditioner
- Internet
- Bedding/Linens
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Key West
- ·
- The Meadows
- 0.07 mi to center
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
Book a Last Minute Place to Stay in Meadows
About Casai's Private Villas and Holiday Rentals in Meadows
Discover more than 147 vacation rentals available in Meadows. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Meadows.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Meadows, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Meadows. On average, places to stay near Meadows offer 1138.25 ft², with nightly prices averaging US $793.
With Casai, finding and comparing holiday rentals in Meadows is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Top Accommodation Types in Meadows
| Type | Count |
|---|---|
| Vacation Homes | 93 |
| Holiday Apartments | 8 |
| Cottages | 1 |
Use these Quick Filters to Find a Holiday Rental in Meadows
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Meadows.
Weather in Meadows, FL
View the weather forecast for Meadows before booking your Meadows Vacation Rentals to confirm your best time to go.
Other Places to Stay in Meadows, FL
Frequently Asked Questions About Meadows?
What are the top holiday rentals in Meadows?
With numerous options available in Meadows, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Meadows:
- BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
- Waterfront 4 Bed, 4-Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED
- Old Town Key West | Waterfront 2BR | Pool
- ~ CASABLANCA GRANDE ~ Old Town quiet duplex with pool, hot tub, and parking!
- Waterfront 2BR | Pool + Dock | Key West
- Eliza Street Retreat, 2 bedroom, 2 bathrm, + loft, private pool, great location
- Shady Palms - Stay In Comfort - 2BD/2.5Bath - Private Pool
- PINEAPPLE BREEZE ~ JUST RENOVATED Home in The Meadows with Pool!
- Tropical Heron Hideaway w/Hot Tub + Pool
- Upper Bayview South
How many holiday rentals have private pools in Meadows?
Discover a selection of holiday rentals with private pools near Meadows with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Casa de Rosalie by AvantStay | Great Location w/Pool, BBQ & Outdoor Dining
- WANDERLUST ~ Stunning 3 Bed, 3 Bath Retreat in Peaceful Neighborhood w/Pool!
- BELLE MAISON ~ 5 BR/3 Ba Home w/Pool/Spa in The Meadows!
- Historic "Old Town" Charm
Which holiday homes in Meadows are best for families?
If you're searching for a family-friendly holiday home in Meadows, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Meadows:
- Bright and Comfortable 3 bedroom/2.5 bath Classic Conch in the Meadows
- Heron Hideaway
- The Palms Hotel
How many Casai.com holiday rentals are available in Meadows?
As of 2026, Casai boasts over 147 properties listed in the Meadows area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Meadows.
Nearby Neighborhood (3)
| Neighborhood | Property Count |
|---|---|
| Old Town Vacation Rentals in Key West, Florida | 2163 |
| The Meadows Vacation Rentals in Key West, Florida | 104 |
| White Street Gallery District Vacation Rentals in Key West, Florida | 4446 |





































































