Summerland Key Holidays
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Where to stay in Summerland Key
Bay Point
While Bay Point may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Lower Sugarloaf Sound and Florida Keys Beaches.
Cutthroat Harbor Estates
Cutthroat Harbour Estates offers a tranquil slice of Florida Keys living with private boat docks and crystal-clear waters. This residential waterfront area provides an authentic escape from tourist crowds. Homes on stilts with weathered wood docks create a classic Keys atmosphere. The neighborhood's canals connect directly to the Gulf, making it perfect for fishing and boating enthusiasts. Gentle waves lap against private docks while tropical birds call at dawn. Nearby Venture Out Keys and Summerland Key provide dining options and additional sights.
Sugarloaf Shores
Sugarloaf Shores offers a tranquil escape on the Florida Keys waterfront. Private homes line peaceful canals where turquoise waters invite fishing, kayaking, and boating adventures. This residential haven sits away from tourist crowds yet provides easy access to stunning ocean views. The neighborhood's charm lies in its authentic Keys lifestyle with homes on stilts and tropical landscaping. Nearby Sugarloaf Beach and Lower Sugarloaf Sound provide perfect spots for swimming and snorkelling. Visitors appreciate the quiet streets for evening strolls and stargazing.
Cudjoe Gardens
Cudjoe Gardens offers a peaceful waterfront retreat in the Florida Keys. This quiet residential haven features canal-front properties with private docks for easy boat access. Travellers can enjoy fishing, wildlife watching, and stargazing from their holiday rentals. The neighborhood's tropical charm comes alive with pastel homes on stilts surrounded by palm trees and native plants. A hire car is essential for exploring nearby Summerland Key attractions and dining options. Water enthusiasts will appreciate direct canal access to open waters and nearby beaches.
Breezeswept Beach Estates
Escape to the peaceful shores of Breezeswept Beach Estates on Summerland Key. This residential haven offers private waterfront properties with boat docks and direct access to crystal-clear Florida waters. The neighborhood's charm lies in its quiet streets lined with pastel homes and tropical landscaping. Outdoor enthusiasts will love exploring nearby Newfound Harbour Keys by kayak or boat. Fish in the shallow waters, spot native birds, or simply relax under swaying palms. With minimal commercialization and abundant natural beauty, this peaceful retreat captures authentic Keys living without the tourist crowds.
Discover the most popular places to visit in Summerland Key
What to do in Summerland Key
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Mangrove Kayak Eco Tour
Summerland Key Hotel Deals
"Very cute place, like at home, the lady on the desk is very sweet and helpful. Good price and close to Kea West."
"The privacy was fantastic, the staff was helpful and we were right down the street from Robbie’s"
Starlight Serenity - Hideaway w Stunning Views
Starlight Serenity - Hideaway w Stunning Views"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
Atlantic View Luxury Villa with Pool
Atlantic View Luxury Villa with Pool"Everything the description states is inaccurate. The Host was not available at any time, it plain as day states to contact host for gate code and I notified 24hrs before, I called at 1pm the next day, no response, I called at 3pm and texted that i would arrive at house by 5pm like check in states with no response, I stopped for lunch and my new arrival was at 6pm, which is the time I arrived at the house, I called several times to host for gate code, and no success again, It was frustrating I...
The Perry Hotel & Marina Key West
The Perry Hotel & Marina Key West"Beautiful property with great food!"
Old Wooden Bridge Resort and Marina
Old Wooden Bridge Resort and Marina"Excellent"
Hilton Key West Resort & Marina
Hilton Key West Resort & Marina"Fire alarm went off at 3 AM on Novembe 5th, but the siren could not be heard at all inside room 2306 due to the front vestibule. I only realized what was happening when I looked out the window and saw a crowd outside. There was absolutely zero communication or direction from hotel staff and no fire department at all on site . After 40 minutes, the alarm finally stopped, and everyone just went back inside without any directions or updates. Major safety concern. Also, when i booked the room for 2...
Frequently Asked Questions
How much does a Summerland Key holiday package cost?
You'll find cheap prices on Expedia for your Summerland Key break. However, factors like the season, length of stay and your choice of hotel will determine how much your holiday to Summerland Key costs.
What are the cheapest months to go to Summerland Key?
If you're hoping to score a cheap Summerland Key holiday package, consider travelling in September, October and November. You'll typically find lower rates on accommodation and flights during these quieter months — ideal for a budget-friendly break.
How many days is enough for Summerland Key?
Generally, a handful of days is enough to tick off the major attractions during your Summerland Key holiday. However, if you'd like to have some time to relax or go on day trips, think about extending your trip.
How to find the best Summerland Key package deals?
Begin your search for a Summerland Key package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Summerland Key package deal right away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Summerland Key escape off to a flying start.
Is it cheaper to book a Summerland Key holiday as a package?
An Expedia holiday package could land you considerable savings when compared to booking stays and flights separately. Better still, you can customise your Summerland Key escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a holiday package to Summerland Key?
If you've got your Summerland Key holiday dates confirmed, book as soon as you can to score some incredible deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Summerland Key?
- Choose when to go: Check your calendar and pack your bags. Your favourite season and the activities available will also help you decide when to holiday in Summerland Key.
- Set a budget: Factor in costs such as transportation, flights and meals when calculating how much to save for your trip to Summerland Key. Then, choose a hotel that suits your budget, whether that's an economical stay or a swankier getaway.
- Decide how long to go away for: Now that you're more familiar with Summerland Key, you can figure out the ideal length of your holiday. Put together a draft plan and allocate enough time to cover everything you want to see.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a customised Summerland Key holiday package.