Check out Saddlebunch Keys—just one of the popular sights to explore around Summerland Key.
Summerland Key, FL
Travel Guide
Kelly's Kabin Private Cottage on Summerland Key
Summerland Key, FL
Situated in Summerland Key, this cottage is within 9 mi (15 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound, and National Key Deer Refuge Visitor Center. Lower ...
4.8/5Exceptional! (31 reviews)
Cute Kottage
"Excellent communication from owner. Always answered any questions right away. Had a couple small issues and they were take. Care of right away."
Reviewed on Jul 8, 2021
Waterfront, Two-story House W/private Outdoor Pool, Poolside Grill, Boat Access
Summerland Key, FL
Situated on the waterfront, this vacation home is within 9 mi (15 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound, and National Key Deer Refuge Visitor Center. ...
4/5Very Good! (1 review)
Met expectations
"Positives: Spacious comfortable house. Perfect for the family. Very clean and nicely appointed with furniture. Pool and spa were a big hit with children and adults alike. Nice boat slip, but you need to rent your own kayaks, paddle boards, etc. Screen door is in bad need of replacement and only one ..."
Reviewed on Jan 15, 2021
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Summerland Breeze - A Resort Style Three House Retreat
Summerland Key, FL
This family-friendly Summerland Key vacation home is located on the waterfront, 2.4 mi (3.9 km) from Upper Sugarloaf Sound, and within 9 mi (15 km) of Upper ...
Get rates
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Kelly's Kabin Private Cottage on Summerland Key
Summerland Key, FL
Situated in Summerland Key, this cottage is within 9 mi (15 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound, and National Key Deer Refuge Visitor Center. Lower ...
4.8/5Exceptional! (31 reviews)
Cute Kottage
"Excellent communication from owner. Always answered any questions right away. Had a couple small issues and they were take. Care of right away."
Reviewed on Jul 8, 2021
Waterfront, Two-story House W/private Outdoor Pool, Poolside Grill, Boat Access
Summerland Key, FL
Situated on the waterfront, this vacation home is within 9 mi (15 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound, and National Key Deer Refuge Visitor Center. ...
4/5Very Good! (1 review)
Met expectations
"Positives: Spacious comfortable house. Perfect for the family. Very clean and nicely appointed with furniture. Pool and spa were a big hit with children and adults alike. Nice boat slip, but you need to rent your own kayaks, paddle boards, etc. Screen door is in bad need of replacement and only one ..."
Reviewed on Jan 15, 2021
Summerland Breeze - A Resort Style Three House Retreat
Summerland Key, FL
This family-friendly Summerland Key vacation home is located on the waterfront, 2.4 mi (3.9 km) from Upper Sugarloaf Sound, and within 9 mi (15 km) of Upper ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Check Summerland Key hotel prices
Popular places to visit in Summerland Key
Bahia Honda State Park and Beach
Explore Bahia Honda State Park and Beach, a favorite green space in Big Pine Key, and also enjoy the area's jogging trails. Amble around this relaxing area's beautiful beaches and enjoy its top-notch restaurants.
Key West Harbour
Explore the waterfront of Key West Harbour and enjoy activities such as boating in Key West. Discover the area's beautiful sunsets and lively bars.
Seven Mile Bridge
Walk, jog, cycle or drive across one of the longest bridges in North America to take in the scenic ocean views it provides.
Key West Golf Club
Play a round of golf in Key West at Key West Golf Club, and enjoy other activities such as boating. Amble around the area's seaside or seek out the biking trails.
Robbie's
Explore the waterfront of Robbie's and enjoy activities such as boating in Key West. Wander the seaside and beautiful beaches in the area.
Calusa Beach
Why not spend a lazy afternoon at Calusa Beach during your trip to Big Pine Key? While you're in the area, wander around the natural setting.
Top things to do in Summerland Key
Kayak / Paddleboard Backcountry Tours
$70
Per adult
100% of travellers recommend
Private Key West Fishing Charter on 34 Ft Contender
$800
Per adult
- Reel Deal Fishing Charters Vacations
- Bahia Honda State Park and Beach Vacations
- Key West Harbour Vacations
- Seven Mile Bridge Vacations
- Key West Golf Club Vacations
- Robbie's Vacations
- Looe Key National Marine Sanctuary Vacations
- Key West Fly Fishing Vacations
- National Key Deer Refuge Visitor Center Vacations
- Key West Visitors Center Vacations
- Blue Hole Vacations
- Big Pine Flea Market Vacations
- Sheriff’s Animal Farm Vacations
- Perky’s Bat Tower Vacations
- Veterans Memorial Park & Beach Vacations