Summerland Key Vacations from $464
Book a Hotel + Flight or Car together to unlock savings
Your Summerland Key Vacation
The hassle-free way to experience this interesting city is with a tailor-made Summerland Key vacation package. Base yourself in the neighborhood of Sugarloaf Shores, which is great for families, fishing and views or go someplace else — our package deals are all about you. Cook Island, Big Pine Key Flea Market and Blue Hole are just some of the sights you'll want to see during your trip to Summerland Key. Stop daydreaming and start traveling. Browse the wide range of options on Expedia today and put your Summerland Key vacation plans in motion!
The Latest Summerland Key vacation packages
Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach
South Beach
Price was $1,083, price is now $464 per person
$464
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
16.8/10 Exceptional! (1,001 reviews)
Room was clean. Staff was friendly beach, restaurants and shops nearby. Also a convenient parking garage within walking distance.
Reviewed on Nov 4, 2025
The Shelborne By Proper, a Member of Design Hotels
South Beach
Price was $1,733, price is now $703 per person
$703
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
18.8/10 Exceptional! (56 reviews)
Staff super friendly and welcoming and helpful, room ready
Reviewed on Nov 16, 2025
The Local House
South Beach
Price was $1,882, price is now $845 per person
$845
per person
Feb 3 - Feb 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
18.4/10 Exceptional! (1,001 reviews)
We had another great stay at the Local House. We will be returning soon!
Reviewed on Nov 15, 2025
Don't see what you're looking for?
See all available trips from Columbus to Summerland Key
View all tripsWhere to stay in Summerland Key
Find the best Summerland Key areas and neighborhoods for the activities you enjoy most. Learn more about Summerland Key
Cutthroat Harbor Estates
While Cutthroat Harbor Estates isn't home to many top sights, Venture Out Keys and Venture Key are some notable places to visit nearby.
Discover the most popular places to visit in Summerland Key
Upper Sugarloaf Sound
Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.
Upper Sugarloaf Key
4/5(21 reviews)
Commune with nature and explore the great outdoors at Upper Sugarloaf Key during your travels in Summerland Key.
Sugarloaf Beach
Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?
What to do in Summerland Key
Key West Haunted Tour : Ghosts & Gravestones
$40
per adult
86% of travellers recommend
Summerland Key Hotel Deals
Parmer's Resort
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $162 total per night from Dec 14 to Dec 15
$162 total
Dec 14 - Dec 15
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
Awesome experience
Reviewed on Nov 14, 2025
Sugar Loaf Lodge
17001 Overseas Hwy Summerland Key FL
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $111 total per night from Nov 23 to Nov 24
$111 total
Nov 23 - Nov 24
Total with taxes and fees
8/10 Very Good! (1,000 reviews)
A very well maintained older facility. Especially enjoyed the high vaulted ceiling on this 2nd floor unit
Reviewed on Nov 17, 2025
Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
Fully refundableReserve now, pay when you stay
$195 nightly
The price is $219 total per night from Nov 24 to Nov 25
$219 total
Nov 24 - Nov 25
Total with taxes and fees
7.4/10 Good! (1,000 reviews)
Room was really clean and receptionist very friendly. Travelling with my son so had a nice big bed each. Balcony was nice and its only 35 mins to Key West which was oerfect
Reviewed on Nov 9, 2025
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.
Find the Best Summerland Key Vacation Packages
Summerland Key Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Key West Intl. Airport (EYW) |
Max Temp Winter | 75ºF |
Max Temp Summer | 85ºF |
Top Sights | Bahia Honda State Park, Florida Keys Beaches and Calusa Beach |
More vacations you might like
Frequently asked questions
Explore a world of travel with Expedia
- Ramrod Key Hotels
- RV Parks in Ramrod Key
- Pet-friendly Hotels in Ramrod Key
- Motels in Ramrod Key
- Hotels with Bars in Ramrod Key
- B&B in Ramrod Key
- Historic Hotels in Ramrod Key
- Condo Rentals in Ramrod Key
- 4 Star Hotels in Ramrod Key
- Vacation Homes in Ramrod Key
- Beach Hotels in Ramrod Key
- Apartments in Ramrod Key
- Luxury Hotels in Ramrod Key
- Cottages in Ramrod Key
- Family Hotels in Ramrod Key
- Cheap Hotels in Ramrod Key
- Lower Keys Hotels
- Fishing Resorts & in Lower Keys
- Cheap Hotels in Lower Keys
- Pet-friendly Hotels in Lower Keys
- Beach Hotels in Lower Keys
- Cottages in Lower Keys
- 5 Star Hotels in Lower Keys
- Resorts in Lower Keys
- Motels in Lower Keys
- Extended Stay Hotels in Lower Keys
- 4 Star Hotels in Lower Keys
- RV Parks in Lower Keys
- Apartments in Lower Keys
- Hotels with Hot Tubs in Lower Keys
- Ski Hotels in Lower Keys
- Little Torch Key Hotels
- Cudjoe Key Hotels
- Resorts in Little Torch Key
- RV Parks in Little Torch Key
- Cottages in Little Torch Key
- Cheap Hotels in Little Torch Key
- Houseboats in Little Torch Key
- RV Parks in Cudjoe Key
- Hotels with Restaurants in Little Torch Key
- Hilton Hotels in Little Torch Key
- Vacation Homes in Little Torch Key
- Romantic Hotels in Little Torch Key
- Hotel Wedding Venues Hotels in Little Torch Key
- Hotels with Laundry Facilities in Little Torch Key
- Family Hotels in Little Torch Key
- Cottages in Cudjoe Key
- B&B in Little Torch Key
- Luxury Hotels in Little Torch Key
- Pet-friendly Hotels in Little Torch Key
- Honeymoon Resorts & in Little Torch Key
- Beach Hotels in Little Torch Key
- Resorts & Hotels with Spas in Little Torch Key
- Fishing Resorts & in Little Torch Key
- Hotels & Resorts for Couples in Little Torch Key
- 3 Star Hotels in Little Torch Key
- Oceanfront Hotels in Little Torch Key
- Condo Rentals in Little Torch Key
- Quiet Resorts & in Little Torch Key
- Hotels with Bars in Little Torch Key
- 4 Star Hotels in Little Torch Key
- Golf Hotels in Little Torch Key
- Resorts in Cudjoe Key
- Beach Hotels in Cudjoe Key
- Hotels with Restaurants in Cudjoe Key
- Villas in Cudjoe Key
- Pet-friendly Hotels in Cudjoe Key
- Cheap Hotels in Cudjoe Key
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.