Best Vacation Homes in Old Town
10.0
Oceanfront
Pool
Ocean View
Balcony/Terrace
10.0- Pool
View
Breakfast
Parking
10.0- Ocean View
- Balcony/Terrace
- View
Pet Friendly
10.0
Private Pool
Fireplace/Heating- Pool
- Balcony/Terrace
10.0- Pet Friendly
Child Friendly
Security/Safety
10.0- Pool
- Balcony/Terrace
Kitchen- Parking
9.8- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
9.8- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
Old Town 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
- Kitchen
Spa- Pool
- Pet Friendly
- Parking
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
9.5- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
Old Town Pet Friendly Vacation Rentals
- Private Pool
- Oceanfront
- Pool
- Ocean View
10.0- Fireplace/Heating
- Pool
- View
- Pet Friendly
10.0- Pool
- Balcony/Terrace
- Pet Friendly
- Parking
- Oceanfront
- Ocean View
- View
- Pet Friendly
10.0- Fireplace/Heating
- Pool
- View
- Pet Friendly
10.0- Pet Friendly
- Kitchen
Air Conditioner
Internet
10.0- Pool
- Balcony/Terrace
- Pet Friendly
- Kitchen
10.0- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
Old Town Large Vacation Homes
10.0
Hot Tub- Pool
- Balcony/Terrace
- Kitchen
10.0- Fireplace/Heating
- Pool
- View
- Pet Friendly
7.4- Pool
- Ocean View
- Balcony/Terrace
- View
10.0- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
10.0- Fireplace/Heating
- Pool
- View
- Pet Friendly
10.0- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
10.0- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
10.0- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
Why Choose Rent By Owner for your Old Town Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Old Town Vacation Rentals
Where are the best neighborhoods to stay in Old Town?
When exploring Old Town in Key West, Florida, you’ll find a variety of neighborhoods that perfectly suit different travel styles. Each area offers its own unique charm and easy access to the vibrant local culture, colorful architecture, and historic landmarks. Whether you prefer strolling through lively streets filled with boutique shops or relaxing in quiet, picturesque surroundings, choosing the right neighborhood can enhance your stay. With a wide selection of trustworthy vacation rentals, you'll discover comfortable and conveniently located options that make experiencing the best of Key West effortless and enjoyable.
Key West Historic District
In this area, you can enjoy charming streets filled with historic architecture and vibrant local culture, making it an ideal spot for exploring authentic Key West experiences.
View 1443+ Rentals in Key West Historic DistrictDowntown
Here, you'll find a lively atmosphere with easy access to shops, dining, and entertainment, offering a convenient base for discovering the region's top attractions.
View 601+ Rentals in DowntownUptown - Upper Duval
This neighborhood offers a relaxed vibe with unique local spots, perfect for those seeking a quieter area while remaining close to the lively heart of the destination.
View 455+ Rentals in Uptown - Upper DuvalBahama Village
Known for its colorful culture and welcoming community, staying in Bahama Village immerses you in a vibrant neighborhood rich in Caribbean influence.
View 53+ Rentals in Bahama VillageHistoric Seaport
Staying near the harbor provides picturesque views and convenient access to waterfront activities, ideal for enjoying the area's maritime heritage.
View 224+ Rentals in Historic SeaportTruman Annex
This exclusive enclave boasts historic charm and proximity to key sites, offering a peaceful retreat within the lively island environment.
View 213+ Rentals in Truman AnnexMidtown
Midtown presents a more residential setting with local eateries and parks, suited for travelers wanting an authentic experience away from tourists.
View 4633+ Rentals in MidtownMeadows
Set in a tranquil part of the region, Meadows provides a serene atmosphere while still being close to the area's popular attractions.
View 82+ Rentals in MeadowsBest Times to Visit Old Town
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here can enhance your experience, whether you're seeking lively festivals or peaceful beaches in this charming destination.
Peak Season Highlights
Winter (December to February)
During the winter months, you can experience warm, pleasant weather perfect for exploring this tropical destination without the overwhelming heat.
Spring (March to May)
Springtime offers ideal conditions with lively atmosphere and plenty of sunshine, making it a popular period for visitors seeking vibrant local events and outdoor activities.
Off-Season Highlights
Summer (June to August)
In the summer, expect hotter and wetter weather, which can be a great time to find more affordable and less crowded vacation rentals here.
Fall (September to November)
Early fall features fewer tourists and cooler temperatures, providing a relaxed atmosphere for exploring this destination at your own pace.
Weekly Weather Forecast for Old Town
How to Book Your Old Town Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Old Town
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 a private outdoor patio or balcony to unwind in the warm Floridian sun.
- Take advantage of outdoor grilling areas for delicious meals in a scenic setting.
- Relax by a sparkling shared or private pool, perfect for cooling off after exploring the area.
- Make use of lush, landscaped gardens or courtyards that enhance your outdoor experience.
- Stay active with access to tennis courts or other sports facilities on-site.
- Benefit from convenient outdoor parking options close to your rental home.
- Relish the tropical vibes with outdoor seating areas designed for social gatherings or quiet mornings.
Top Attractions Around Old Town
What attractions are nearby?
While staying here, you'll have the opportunity to explore a variety of nearby activities in the area, from vibrant dining and unique shopping experiences to scenic waterfront walks and cultural attractions that showcase the charm of this destination.
Family Activities
- Visit the Key West Aquarium: Discover marine life through interactive exhibits that are perfect for engaging children and adults alike in this family-friendly attraction.
- Explore Mallory Square Sunset Celebration: Enjoy captivating street performers and a breathtaking sunset view, creating memorable moments for your family in this vibrant part of town.
- Tour the Historic Lighthouse and Keeper's Quarters: Climb to the top for panoramic views and learn about the area's maritime history in this iconic landmark.
- Relax at Fort Zachary Taylor Beach: Spend a fun-filled day swimming and picnicking at one of the region’s most scenic beaches, ideal for families seeking a relaxed outdoor experience.
Adult Activities
- Sipping cocktails on historic Duval Street: You can enjoy lively nightlife and unique local bars in the heart of Old Town, offering a true taste of the area's vibrant culture.
- Exploring the Ernest Hemingway Home and Museum: Visiting this famous author’s residence gives you insight into the region's literary history and charming architecture.
- Taking a sunset cruise from the nearby harbor: Experience breathtaking views of the coastline and the setting sun while relaxing aboard a boat in this seaside destination.
- Strolling through the colorful streets of Old Town: Discover boutique shops, art galleries, and historic landmarks that showcase the region’s distinctive charm and character.
Other Places to Stay in Old Town, FL
Key West Wildlife Center
Studios of Key West
Key West Burlesque Theater
Higgs Beach
Key West Garden Club
Key West
Key West Historic District
Duval Street
Downtown
Uptown - Upper Duval
Truman Annex
Bahama Village
Old Town Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Cuisine: Savor the authentic flavors by dining at local eateries to get a true taste of this destination's vibrant culinary scene.
- Stroll Through Historic Districts: Take leisurely walks around the area’s historic streets to discover charming architecture and hidden gems unique to here.
- Plan Water-Based Activities: Make the most of your stay by engaging in water sports or harbor cruises offered nearby, highlighting the region’s stunning coastline.
- Visit Notable Landmarks: Allocate time to explore prominent sites that capture the essence of this destination’s rich history and culture.
Transportation Options
- Walking: Exploring on foot allows you to fully immerse yourself in the charming streets and vibrant atmosphere of this destination's historic district.
- Bicycle Rentals: Biking offers an eco-friendly and convenient way to navigate through the area while enjoying the scenic waterfront views and local attractions.
- Taxi Services: Taxi options provide quick and comfortable transportation, giving you easy access to popular sites within the region.
- Rental Cars: Renting a car grants flexibility for exploring beyond the immediate vicinity, perfect for those seeking to discover more of this destination at their own pace.
Local Customs Options
- Conch Republic Independence Day: Celebrated on April 23rd, this unique local custom honors the area's history with vibrant parades and festivities that you can experience during your stay.
- Fresh Seafood Dining Etiquette: Emphasizing the region's maritime roots, dining here often involves enjoying freshly caught seafood in a relaxed, informal setting that embodies the island's laid-back vibe.
- Sunset Celebrations at Mallory Square: Every evening, locals and visitors gather to watch the sunset while enjoying street performers and local artisans, creating a lively atmosphere that captures the area's spirit.
- Respect for Marine Environment: Preserving the region’s natural beauty is essential, so you'll find that eco-friendly practices and respectful interactions with marine life are deeply ingrained in local customs.
Frequently Asked Questions About Old Town?
1. What are the top vacation rentals in Old Town?
There are a lot of options in Old Town. If you plan on staying in the Old Town area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Old Town:
- Almond Tree Inn Hotel - Adults Only
- Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
- Bright & Modern Condo—7 MinWalk to the Beach! Pool, Bikes & 2 Furnished Porches!
- Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- Casa Calypso- Beautiful Tropical 3 KING Beds, 3 baths - 2 miles to beach
- Hidden away near the Southernmost Point, Louisa's Hideaway is it!
- ~ CLOUD 9 ~ It's heaven on earth in this 3B/3BA lavish home with pool/parking
- Boli Townhouse - Luxury WEEKLY Rental in gated Truman Annex-Saturday to Saturday
- MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
- Everything Key West has to offer @ Mango Cottage
2. How many vacation rentals have private pools in Old Town?
There are 603 vacation rentals with private pools near Old Town. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Old Town are best for families?
If you are looking for a family-friendly vacation home in Old Town, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Old Town:
4. How many Rentbyowner vacation rentals are available in Old Town?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 3628 in the Old Town 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 Old Town.
5. What is the cancellation policy for vacation rentals in Old Town, Key West?
6. How do I find out about the amenities included in a vacation rental in this area?
7. Are there any house rules I should be aware of when staying here?
8. What is the check-in and check-out process for vacation rentals in this destination?
9. How can I ensure my reservation is secure when booking a vacation rental in this region?
Old Town Top Rated Vacation Rentals
10.0- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
10.0- Private Pool
- Oceanfront
- Pool
- Ocean View
10.0- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
