Best Vacation Homes in Observation Tower
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
Why Choose Rent By Owner for your Observation Tower Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Observation Tower Vacation Rentals
Where are the best neighborhoods to stay in Observation Tower?
When selecting a neighborhood to stay in Observation Tower, Key West, Florida, you’ll find yourself immersed in a vibrant area that offers easy access to the island’s rich history and scenic beauty. This prime location provides a perfect balance of lively local culture and relaxed coastal charm, making it an ideal choice for your next getaway. By booking a vacation rental here, you’ll enjoy the convenience of nearby attractions and the comfort of a trustworthy, dependable accommodation experience tailored to your needs.
Key West Historic District
In the heart of the region, the Key West Historic District offers a charming blend of historic architecture and vibrant local culture, making it an ideal area to explore authentic Key West experiences. Staying nearby allows you to immerse yourself in the area's rich history while enjoying easy access to renowned attractions and scenic views.
View 2937+ Rentals in Key West Historic DistrictOld Town
Here, within Old Town, you'll find picturesque streets filled with colorful homes and lively entertainment options that capture the spirit of this destination. Opting for accommodations in this neighborhood means being close to the most popular dining, shopping, and nightlife spots in the region.
View 2855+ Rentals in Old TownSunset Key
For a tranquil retreat, Sunset Key provides exclusive access to pristine beaches and stunning sunset views, perfect for relaxing after a day of exploring. Choosing a stay in this area ensures you experience the serene beauty that makes this part of the region truly special.
View 3214+ Rentals in Sunset KeyDowntown
The Downtown neighborhood offers a lively atmosphere with an array of shops, eateries, and cultural sites that showcase the local flavor. Staying here provides convenient access to the region's vibrant scene, ideal for those seeking an energetic and central location.
View 1274+ Rentals in DowntownUptown - Upper Duval
Uptown and Upper Duval feature a mix of historic charm and modern amenities, making it a great choice for travelers looking for both comfort and accessibility. From this area, you can easily reach key attractions and enjoy the laid-back pace of the region.
View 890+ Rentals in Uptown - Upper DuvalBahama Village
Known for its lively Caribbean-inspired culture, Bahama Village offers vibrant streetscapes and unique local shops, providing an authentic taste of the region’s diverse heritage. Staying within this neighborhood immerses you in a colorful community rich in tradition and character.
View 107+ Rentals in Bahama VillageHistoric Seaport
Situated along the waterfront, the Historic Seaport is perfect for those interested in maritime history and scenic harbor views. Choosing accommodations here allows you to enjoy the region’s nautical charm and easy access to boat tours and waterfront activities.
View 461+ Rentals in Historic SeaportNew Town
This area provides a more residential feel with spacious homes and local businesses, making it a quieter option for visitors seeking relaxation. Its proximity to essential services and transportation links makes it a practical base for exploring the region.
View 125+ Rentals in New TownBest Times to Visit Observation Tower
When should you plan your Vacation Rentals stay?
To make the most of your stay, consider visiting during the shoulder seasons when the area offers pleasant weather and fewer crowds, ensuring an enjoyable experience in this popular vacation destination.
Peak Season Highlights
Spring (March to May)
During spring, this destination experiences warm weather and lively city events, making it an ideal time to explore the region's attractions.
Winter (December to February)
Winter months see pleasant temperatures with less humidity, providing a comfortable setting for sightseeing and outdoor activities.
Off-Season Highlights
Summer (June to August)
Summertime can bring higher humidity and afternoon thunderstorms, but it also offers fewer crowds for a more relaxed visit.
Fall (September to November)
Autumn experiences slightly cooler weather and lower visitor numbers, making it a quieter period to enjoy the area’s scenic views.
Weekly Weather Forecast for Observation Tower
How to Book Your Observation Tower Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Observation Tower
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 outdoor lounging areas with comfortable furniture to relax and soak up the sunny Florida weather.
- Take advantage of private or shared outdoor pools, perfect for a refreshing swim after exploring the region.
- Benefit from well-maintained barbecue grills to host delightful outdoor meals with family and friends.
- Make use of scenic outdoor dining spaces that offer beautiful views of the surrounding area.
- Explore lush landscaped gardens or tropical courtyards designed for peaceful strolls and relaxation.
- Utilize outdoor showers for rinsing off after beach visits or water-based activities at nearby beaches.
- Access designated parking or garage facilities to conveniently park your vehicle during your stay here.
Top Attractions Around Observation Tower
What attractions are nearby?
From here, you can explore a variety of local activities that showcase the vibrant culture and scenic beauty of this destination, providing memorable experiences just moments from your rental.
Family Activities
- Explore the Key West Maritime Museum: Dive into the area's rich maritime history through engaging exhibits and interactive displays suitable for all ages.
- Visit the Key West Butterfly and Nature Conservatory: Experience a vibrant sanctuary where your family can marvel at hundreds of butterfly species and exotic birds fluttering freely in a lush setting.
- Enjoy Water Activities at the Local Beaches: Take advantage of the region's calm waters with swimming, snorkeling, or relaxing on the sandy shores just minutes from Observation Tower.
- Discover Historic Old Town:** Stroll through the charming streets lined with colorful architecture, unique shops, and family-friendly cafes that capture the essence of this destination.
Adult Activities
- Sunset Viewing: Experience breathtaking sunsets over the Gulf of Mexico from the observation tower, creating unforgettable memories during your stay.
- Bird Watching: Enjoy observing local bird species in their natural habitat while taking in panoramic views of the region's diverse ecosystem.
- Photography Excursions: Capture stunning photos from unique vantage points that highlight the area's vibrant wildlife and scenic landscapes.
- Historical Tours: Learn about the region's maritime history through guided tours or informational displays located near the observation tower.
Observation Tower Travel Tips
How Can You Make the Most of Your Stay?
- Visit During Sunset:** Make time to enjoy the breathtaking sunset views from this destination to experience the area's natural beauty at its finest.
- Explore Local Cuisine:** Take advantage of nearby eateries to savor authentic regional flavors and enrich your stay in this vibrant coastal region.
- Plan Indoor Activities:** Keep a flexible itinerary by including indoor options for relaxing moments during unpredictable weather here.
- Use Local Transportation:** Maximize your visit by utilizing local transit options to easily access key attractions without hassle in this popular destination.
Transportation Options
- Walking Tours: You can explore the area's unique charm on guided walking tours that highlight its history and vibrant local culture.
- Bike Rentals: Rent a bicycle to comfortably navigate through this destination's scenic streets and enjoy the fresh ocean breeze.
- Public Transportation: The regional bus system offers a convenient and affordable way to reach various attractions in the region surrounding the Observation Tower.
- Taxi and Rideshare Services: Taxis and rideshare options like Uber provide quick, reliable transportation for getting around here effortlessly.
Local Customs Options
- Respect for Local Artisans: Visitors often embrace the region’s vibrant art scene by supporting local artists and their handcrafted creations, reflecting the area's rich cultural heritage.
- Celebration of Maritime Heritage: Engaging in the community’s maritime customs, such as participating in boat parades or learning about seafaring history, offers a meaningful connection to the area’s seafaring traditions.
- Tropical Cuisine Appreciation: Sampling and respecting the local culinary traditions, especially seafood and Caribbean-inspired dishes, is a cherished custom here that enriches your experience.
- Preservation of Historic Sites: Appreciating and maintaining the region’s historic architecture and landmarks demonstrates the community’s commitment to safeguarding its unique past for future generations.
Frequently Asked Questions About Observation Tower?
1. What are the top vacation rentals in Observation Tower?
There are a lot of options in Observation Tower. If you plan on staying in the Observation Tower area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Observation Tower:
- Almond Tree Inn Hotel - Adults Only
- Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
- Bright & Modern Condo—7 MinWalk to the Beach! Pool, Bikes & 2 Furnished Porches!
- ~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
- PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest
- Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
- Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex
- Perfect Location, nPrivate Heated Pool,nPristine Luxury Home!
- Hidden away near the Southernmost Point, Louisa's Hideaway is it!
2. How many Rentbyowner vacation rentals are available in Observation Tower?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 3570 in the Observation Tower 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 Observation Tower.
3. What is the cancellation policy for vacation rentals in this area?
4. How do I ensure my booking in Key West's observation tower area is secure?
5. Are there any additional fees associated with booking these vacation rentals?
6. What amenities should I expect in vacation rentals in the observation tower region of Key West?
7. How can I find the best vacation rental options in the observation tower area of Key West?
Best Vacation Homes in Observation Tower
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Balcony/Terrace
- Security/Safety
- Air Conditioner
- Pool
- Private Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- TV
