Best Vacation Homes in The Meadows
1224 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $1,547/Night
For 7 Nights US $10,826
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,259/Night
For 7 Nights US $8,814
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Pool
- Balcony/Terrace
- Breakfast
US $314/Night
For 7 Nights US $2,197
1300 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $822/Night
For 7 Nights US $5,757
1194.79 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- View
US $919/Night
For 7 Nights US $6,433
1224 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Pool
US $982/Night
For 7 Nights US $6,872
1020 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $300/Night
For 7 Nights US $2,103
1200 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $1,005/Night
For 7 Nights US $7,032
The Meadows Luxury Rentals
US $2,792/Night
For 7 Nights US $19,544
US $2,500/Night
For 7 Nights US $17,500
2444 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Balcony/Terrace
US $2,370/Night
For 7 Nights US $16,590
10 Guests
4 Bedrooms
4 Bathrooms
Free Cancellation
House
- Hot Tub
- Balcony/Terrace
- View
US $2,086/Night
For 7 Nights US $14,605
2002.09 ft²
16 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Pet Friendly
US $2,063/Night
For 7 Nights US $14,441
2002.09 ft²
16 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- View
US $2,063/Night
For 7 Nights US $14,441
2400.35 ft²
16 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- View
US $2,063/Night
For 7 Nights US $14,441
3605 ft²
12 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $1,872/Night
For 7 Nights US $13,104
The Meadows Pet Friendly Vacation Rentals
1283 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $474/Night
For 7 Nights US $3,319
1194.79 ft²
8 Guests
1 Bedroom
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- View
US $958/Night
For 7 Nights US $6,708
639 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Oceanfront
- Hot Tub
- Ocean View
US $176/Night
For 7 Nights US $1,235
1194.79 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- View
US $919/Night
For 7 Nights US $6,433
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Private Pool
- Pool
- Pet Friendly
US $631/Night
For 7 Nights US $4,415
1200 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $878/Night
For 7 Nights US $6,148
1142 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $360/Night
For 7 Nights US $2,521
612 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Private Pool
- Hot Tub
- Pool
US $577/Night
For 7 Nights US $4,038
The Meadows Large Vacation Homes
2898 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $1,705/Night
For 7 Nights US $11,938
2400.35 ft²
15 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- View
US $1,672/Night
For 7 Nights US $11,704
2898 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $1,336/Night
For 7 Nights US $9,355
266.61 ft²
34 Guests
16 Bedrooms
13 Bathrooms
House
- Pool
- Balcony/Terrace
- View
US $798/Night
For 7 Nights US $5,586
2829 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Pool
US $1,446/Night
For 7 Nights US $10,120
2400 ft²
16 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $1,865/Night
For 7 Nights US $13,057
2000 ft²
16 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $1,796/Night
For 7 Nights US $12,574
2000 ft²
16 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $1,836/Night
For 7 Nights US $12,852
Why Choose Rent By Owner for your The Meadows Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for The Meadows Vacation Rentals
Where are the best neighborhoods to stay in The Meadows?
When choosing where to stay in Key West, Florida, exploring neighborhoods like The Meadows offers a fantastic opportunity to experience the local charm and relaxed island lifestyle. Located in a peaceful part of the city, The Meadows provides convenient access to the vibrant attractions and stunning waterfronts of Key West, making it an ideal base for your tropical getaway. With a range of well-maintained vacation rentals in this area, you can enjoy a comfortable and authentic experience while staying close to the heart of the island’s unique character.
Key West Historic District
In this vibrant area, you can immerse yourself in the rich history and charming architecture that define the region's unique character. Staying nearby allows easy access to the historic charm that makes this destination truly special.
View 2409+ Rentals in Key West Historic DistrictOld Town
Nestled in the heart of the region, Old Town offers colorful streets and a lively atmosphere, perfect for exploring local culture and enjoying convenient access to popular attractions.
View 2371+ Rentals in Old TownMeadows
This tranquil neighborhood provides a peaceful retreat while still being close to key points of interest, making it an ideal choice for those seeking relaxation amidst the area's natural beauty.
View 100+ Rentals in MeadowsWhite St. Gallery
Located within walking distance of the White Street Gallery District, this neighborhood offers a blend of artistic ambiance and easy access to local galleries, enhancing your cultural experience.
View 24+ Rentals in White St. GalleryBest Times to Visit The Meadows
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit here can enhance your experience, so consider planning your trip during the region's most favorable seasons for pleasant weather and enjoyable outdoor activities.
Peak Season Highlights
Winter (December to February)
During the winter months, you can experience the warm and inviting climate that makes this destination a popular choice for escaping colder weather elsewhere.
Average Temperature Daytime: 75°F - Nighttime: 65°F
Spring (March to May)
Springtime draws visitors seeking pleasant weather and vibrant scenery, making it an ideal season for enjoying the area's outdoor activities and exploring comfortably.
Average Temperature Daytime: 78°F - Nighttime: 70°F
Off-Season Highlights
Summer (June to August)
The summer period sees slightly fewer visitors, providing a quieter atmosphere while still offering warm temperatures perfect for beach days and relaxation.
Average Temperature Daytime: 88°F - Nighttime: 80°F
Fall (September to November)
Fall offers a more tranquil setting, with fewer crowds and mild weather, making it a great time to enjoy peaceful getaways along the coast.
Average Temperature Daytime: 85°F - Nighttime: 75°F
Weekly Weather Forecast for The Meadows
How to Book Your The Meadows Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in The Meadows
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor pool to relax after exploring the local scenery.
- Take advantage of spacious patios or decks for dining and entertaining outdoors.
- Benefit from lush, landscaped gardens that provide privacy and natural beauty.
- Make use of outdoor grills or barbecue setups for casual meals with family and friends.
- Relax in comfortable lounge areas designed for enjoying the warm Florida sun.
- Utilize outdoor showers or hammocks to unwind in a tranquil setting.
- Explore nearby walking paths or bike-friendly loops for outdoor recreation in the area.
Top Attractions Around The Meadows
What attractions are nearby?
When staying here, you'll have the opportunity to explore nearby beaches, charming local shops, and vibrant dining options that make this destination a perfect base for enjoying all that the region has to offer.
Family Activities
- Key West Butterfly & Nature Conservatory: Discover a magical world of butterflies and tropical birds that enchant children and adults alike, making it a memorable family outing here.
- Fort Zachary Taylor Historic State Park: Enjoy a relaxing day at this scenic park with shaded picnic areas, sandy beaches, and opportunities for swimming and exploring historic forts.
- The Key West Aquarium: Experience interactive exhibits and marine animal encounters that engage young explorers in the region's vibrant aquatic life.
- Smathers Beach: Spend your day lounging on the soft sands or trying water activities at this popular beach destination close to the area’s vacation rentals.
Adult Activities
- Explore the vibrant local art scene: Discover unique galleries and street art that reflect the creative spirit of this island destination.
- Enjoy water-based activities: Embark on snorkeling, kayaking, or paddleboarding adventures in the crystal-clear waters surrounding the area.
- Visit historic sites and landmarks: Immerse yourself in the region’s rich history by touring notable museums and preserved architecture.
- Savor fresh seafood at waterfront restaurants: Indulge in delicious coastal cuisine while enjoying scenic views that highlight the area's nautical charm.
Other Places to Stay in The Meadows, FL
The Unitarian Universalist Fellowship of Key West
Meadows
The Meadows Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Flavors: Take advantage of the area's renowned dining options to experience authentic Key West cuisine during your stay.
- Visit Nearby Beaches: Make time to relax at the beautiful beaches close to your vacation rentals, soaking in the sunshine and tranquil ocean views.
- Discover Unique Local Events: Check out community events and festivals that highlight the vibrant culture and lively spirit here in this destination.
- Plan Outdoor Activities: Enjoy outdoor adventures like fishing, boating, or exploring scenic trails to fully immerse yourself in the region's natural beauty.
Transportation Options
- Car Rentals: Renting a car is one of the most flexible ways to explore the region and enjoy your stay here at your own pace.
- Public Transit: The local bus system offers affordable and reliable transportation options to key destinations around the area.
- Bike Rentals: Biking is a popular choice for getting around here, providing an eco-friendly way to experience the scenery up close.
- Taxi and Rideshare Services: Taxis and rideshare apps like Uber or Lyft provide convenient door-to-door service throughout this destination.
Local Customs Options
- Respect for Waterfront Heritage: Locals in this area honor a long-standing tradition of fishing and maritime activities that are central to their way of life.
- Celebration of Art and Music: The community embraces vibrant art festivals and live music events, reflecting the region’s rich cultural heritage and laid-back vibe.
- Eco-Friendly Practices: Sustainability is important here, with many residents supporting eco-conscious initiatives to preserve the area's natural beauty.
- Balancing Relaxation and Festivity: Visitors often partake in a relaxed pace of life while enjoying lively local events, making it ideal for those seeking both tranquility and community spirit.
The Meadows Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in The Meadows?
There are a lot of options in The Meadows. If you plan on staying in the 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 The Meadows:
- BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
- Old Town "Eleuthera" 2BR Waterfront Corner Condo
- The Palms -3 bedroom 2 bath home in The Meadows w/pool oasis & guest cottage
- ~ CASABLANCA GRANDE ~ Old Town quiet duplex with pool, hot tub, and parking!
- Eliza Street Retreat, 2 bedroom, 2 bathrm, + loft, private pool, great location
- "Dominica" Key West 2BR Dock, Pool, Pet-Friendly
- Welcome to the Shady Palms - Private Pool - 2 Bdrm, 2.5 baths
- Fabulous Home with Private Saltwater Pool, Central AC, & High-Speed WiFi
- PINEAPPLE BREEZE ~ JUST RENOVATED Home in The Meadows with Pool!
- Heron Hideaway
2. How many vacation rentals have private pools in The Meadows?
There are 32 vacation rentals with private pools near The Meadows. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in The Meadows are best for families?
If you are looking for a family-friendly vacation home in The Meadows, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in The Meadows:
4. How many Rentbyowner vacation rentals are available in The Meadows?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 145 in the The Meadows area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in The Meadows.
5. What is the cancellation policy for booking a vacation rental here?
Cancellation policies vary depending on the individual property listing. You should review the specific property's cancellation terms on its page or contact the host directly to understand the conditions and any potential fees.
6. Are there any specific check-in and check-out times I should be aware of?
Check-in and check-out times are set by each property owner. Details are typically listed in the booking description, so it's recommended to confirm these times during your reservation process or by reaching out to the host.
7. How do I ensure the property has the amenities I need for my stay?
Each property listing includes a detailed list of available amenities. For any special requirements, you can contact the host beforehand to confirm that the property meets your needs.
8. Is there a secure way to pay for my booking?
Payments are processed through a secure platform integrated into the booking website. It’s best to use this system to protect your financial information and ensure a smooth transaction.
9. What should I do if I encounter an issue during my stay or need assistance?
In case of any problems, you should contact the property host directly first. If you require further support, the booking platform offers customer service to assist with resolving issues related to your reservation or stay.
The Meadows Top Rated Vacation Rentals
965 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Balcony/Terrace
US $311/Night
For 7 Nights US $2,180
1642 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $219/Night
For 7 Nights US $1,533
1596 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Pool
US $409/Night
For 7 Nights US $2,866
US $513/Night
For 7 Nights US $3,588
455 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $494/Night
For 7 Nights US $3,455
1800 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $927/Night
For 7 Nights US $6,487
500 ft²
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
US $457/Night
For 7 Nights US $3,199
1014 ft²
9 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Balcony/Terrace
US $349/Night
For 7 Nights US $2,446
