Best Vacation Homes in Florida Keys
10.0
Private Pool
Hot Tub
Fireplace/Heating
Pool
10.0- Fireplace/Heating
- Pool
Parking
Air Conditioner
10.0
Ocean View
Balcony/Terrace
View
Pet Friendly
8.6
Oceanfront- Hot Tub
- Pool
- Ocean View
10.0- Fireplace/Heating
- Pool
- View
- Parking
8.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Private Pool
- Oceanfront
- Hot Tub
- Pool
Florida Keys Luxury Rentals
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
- Fireplace/Heating
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- Breakfast
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
Florida Keys Pet Friendly Vacation Rentals
- Pet Friendly
- Air Conditioner
Internet
Child Friendly
10.0- Balcony/Terrace
- View
- Breakfast
- Pet Friendly
10.0- Private Pool
- Oceanfront
- Hot Tub
- Pool
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
10.0
Private Beach- Oceanfront
- Hot Tub
- Fireplace/Heating
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Private Pool
- Oceanfront
- Pool
- Ocean View
- Pool
- Balcony/Terrace
- Pet Friendly
Kitchen
Florida Keys Large Vacation Homes
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
10.0- Internet
- Child Friendly
Laundry
Security/Safety
9.6- Oceanfront
- Hot Tub
Spa- Fireplace/Heating
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
10.0- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
- Private Pool
- Oceanfront
- Pool
- Ocean View
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
Why Choose Rent By Owner for your Florida Keys Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Florida Keys Vacation Rentals
Where are the best neighborhoods to stay in Florida Keys?
When considering where to stay in the Florida Keys, you'll find a variety of neighborhoods that cater to different tastes and preferences. From the lively atmosphere of Key West to the tranquil beauty of Islamorada, each area offers unique experiences and access to stunning coastal views. Whether you're seeking vibrant nightlife, relaxed beachside living, or serene island landscapes, choosing the right neighborhood in the Florida Keys can enhance your vacation. With dependable vacation rentals available throughout these popular areas, you can enjoy a seamless and memorable stay tailored to your interests.
Key West Historic District
In this historic district, you can immerse yourself in the vibrant culture and rich history that define the area's unique charm. It's an ideal spot for travelers seeking authentic Florida Keys experiences with easy access to local attractions.
View 2074+ Rentals in Key West Historic DistrictOld Town
The heart of the region's lively atmosphere, Old Town offers charming streets and colorful architecture perfect for exploring on foot. Staying here places you close to the city's iconic sights and bustling local scene.
View 2045+ Rentals in Old TownSunset Key
This luxurious island retreat provides serene surroundings and stunning sunsets, making it a perfect choice for those seeking tranquil escapes within the Keys. Here, you can enjoy exclusive privacy while still being near regional attractions.
View 3712+ Rentals in Sunset KeyDowntown
Located at the core of the destination, downtown offers convenient access to shops, dining, and entertainment options. It’s an ideal base for experiencing the lively spirit of the Keys.
View 856+ Rentals in DowntownUptown - Upper Duval
This vibrant neighborhood features a mix of local eateries, boutique shopping, and nightlife, making it perfect for travelers who want to experience the energetic side of the area.
View 685+ Rentals in Uptown - Upper DuvalKey Largo Village
Set in the scenic Keys, this village provides a peaceful atmosphere combined with convenient access to marine activities and natural beauty, ideal for outdoor enthusiasts.
View 699+ Rentals in Key Largo VillageBahama Village
Known for its cultural diversity, Bahama Village invites visitors to enjoy a lively neighborhood with local businesses and a friendly community atmosphere.
View 70+ Rentals in Bahama VillageNew Town
Offering a more residential vibe, New Town is suited for travelers looking for comfortable accommodations away from the busy tourist areas, yet still close to the region's main attractions.
View 87+ Rentals in New TownBest Times to Visit Florida Keys
When should you plan your Vacation Rentals stay?
Choosing the right time to vacation here ensures you enjoy ideal weather and fewer crowds, making your stay in this destination truly memorable.
Peak Season Highlights
Winter (December to February)
During the winter months, this destination experiences its peak season, attracting visitors seeking warm weather and sunny skies. You'll enjoy the lively atmosphere and abundant outdoor activities.
Spring (March to May)
Spring marks another high-traffic period when travelers indulge in outdoor adventures and water sports under pleasant temperatures. The region's natural beauty shines during this vibrant season.
Off-Season Highlights
Summer (June to August)
In summer, the area sees a dip in visitor numbers despite warm weather, offering a more relaxed experience. It's an ideal time for those who prefer fewer crowds and are comfortable with higher humidity.
Fall (September to November)
Autumn is considered an off-peak period when the region sees fewer tourists. You'll find this season perfect for enjoying peaceful surroundings with mild temperatures and less busy beaches.
Weekly Weather Forecast for Florida Keys
How to Book Your Florida Keys Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Florida Keys
Common Vacation Rentals Amenities
What amenities can you expect?
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 access to private outdoor pools perfect for relaxing after a day of exploring the area.
- Take advantage of spacious patios or decks ideal for outdoor dining and entertaining guests.
- Benefit from direct access to sandy beaches or waterfront areas right at your doorstep.
- Utilize outdoor grilling stations to prepare fresh seafood and local specialties with ease.
- Relax in shaded lanai areas designed for lounging and soaking up the sunshine.
- Make use of outdoor showers, especially useful after swimming in nearby waters.
- Experience well-maintained gardens or lush landscaping that enhance the outdoor ambiance of your stay.
Top Attractions Around Florida Keys
What attractions are nearby?
In this vibrant destination, you can enjoy a variety of water-based activities, explore scenic fishing spots, or simply relax on pristine beaches just moments from your Florida Keys vacation rentals.
Family Activities
- Snorkeling and Diving Tours: Explore the vibrant coral reefs and marine life that make this destination a premier spot for family-friendly underwater adventures.
- Visit the Dolphin Research Center: Engage with friendly dolphins and learn about marine conservation efforts in a hands-on, educational environment suitable for all ages.
- Key West Butterfly & Nature Conservatory: Wander through lush gardens filled with colorful butterflies and exotic birds, creating a magical experience for families visiting here.
- Fort Zachary Taylor Historic State Park: Enjoy a day of picnicking, swimming, and exploring historic fortifications while soaking up the scenic coastal views that define the area.
Adult Activities
- Snorkeling and Scuba Diving: Explore vibrant coral reefs and diverse marine life right in the waters surrounding this destination, offering unforgettable underwater experiences.
- Deep-Sea Fishing: Enjoy a thrilling day on the water with expert charters, targeting species like sailfish and tarpon that are abundant here.
- Island Hopping: Discover secluded islands and pristine beaches by boat, providing a perfect escape into the natural beauty of this region.
- Sunset Cruises: Unwind while watching breathtaking sunsets over the horizon on a leisurely cruise along the coast, ideal for relaxing evenings here.
Other Places to Stay in Florida Keys, FL
Florida Keys Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Water Activities: Book your snorkeling, fishing, or boating excursions early to secure the best spots and enjoy this destination's vibrant marine life.
- Choose a Prime Location: Select a vacation rental close to key beaches and dining options to maximize relaxation and convenience during your stay here.
- Explore Local Cuisine: Take the opportunity to indulge in fresh seafood and regional specialties at local eateries, adding authentic flavors to your visit.
- Respect the Natural Environment: Follow eco-friendly practices to preserve the area's unique ecosystems for future travelers seeking natural beauty and tranquility.
Transportation Options
- Rental Car Services: Renting a vehicle gives you the flexibility to explore the scenic byways and tranquil islands of this destination at your own pace.
- Public Transportation: The local bus system offers an economical way to navigate the area, connecting key spots without the hassle of parking.
- Taxicabs and Rideshare Apps: Convenient for quick trips within this region, allowing you to avoid driving while enjoying the sights around here.
- Maritime Transport: Water taxis and ferry services provide an authentic way to experience the area’s coastal charm and island-hopping adventures.
Local Customs Options
- Conch Shelling and Craftsmanship: Locally, you'll find that collecting conch shells and creating handcrafted jewelry from them is a cherished tradition here in the Keys.
- Fisherman's Etiquette: Respect for the region’s fishing culture is important, with anglers often observing specific methods and seasons that support sustainable practices.
- Hibiscus and Tropical Decor: Bright, tropical floral designs are commonly used in local homes and establishments, reflecting the area's vibrant natural surroundings.
- Seafood Tradition: Sharing fresh seafood, especially stone crabs and key lime dishes, is an integral part of social gatherings along this coastal destination.
Florida Keys Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Florida Keys?
There are a lot of options in Florida Keys. If you plan on staying in the Florida Keys area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Florida Keys:
- Almond Tree Inn Hotel - Adults Only
- Casa Cay West Beautiful Tropical 3 bedrooms 2 KING suites - 2 miles to beach
- Oceanfront Key Largo Paradise~Private Beach~Pool~Tennis~Marina~Cafe/Bar
- Summer Fun Awaits! Clean and Cozy w TOP FLOOR VIEWS.Your Home Away From Home!
- Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
- Key Lime Kottage- Waterfront Home on Gulf of Mexico w/Private Pool, Dock & More
- 🌴 Coco Plum Paradise 🌴 Private Bayfront Home Pool Hot Tub Dock View
- Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
- "Your own private resort" - Mockingbird Pointe - Waterfront, pool and dockage
- Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath
2. How many vacation rentals have private pools in Florida Keys?
There are 3115 vacation rentals with private pools near Florida Keys. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Florida Keys are best for families?
If you are looking for a family-friendly vacation home in Florida Keys, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Florida Keys:
4. How many Rentbyowner vacation rentals are available in Florida Keys?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 14798 in the Florida Keys 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 Florida Keys.
5. What is the cancellation policy for properties in the Florida Keys?
6. Are there any additional fees I should be aware of when booking a vacation rental here?
7. How do I know if a vacation rental in this region is suitable for my needs?
8. What safety measures are implemented in vacation rentals in this area?
9. How can I ensure my stay complies with local regulations in this destination?
Florida Keys Top Rated Vacation Rentals
10.0- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
10.0- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
10.0- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
10.0- Private Pool
- Hot Tub
- Pool
- Ocean View
10.0- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
10.0- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
