Summerland Key Vacations from $457

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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.
Seacoast Suites on Miami Beach

Seacoast Suites on Miami Beach

Mid Beach
Save 100% on your flight
$457
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
6.2/10 (1,410 reviews)
Property was very unclean. Elevator did not work.

Reviewed on Oct 8, 2026

Cavalier Hotel South Beach

Cavalier Hotel South Beach

South Beach
Save 100% on your flight
$640
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (1,008 reviews)
President Hotel Villa

President Hotel Villa

South Beach
Save 100% on your flight
$864
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,000 reviews)
The Local House

The Local House

South Beach
Save 100% on your flight
$955
per person
Dec 17 - Dec 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (1,001 reviews)
The hotel has a great atmosphere. The check in lady was very nice she explained everything on details . Beach was just a block from the hotel . Love this hotel and definitely recommend it . Restaurant is downstairs too and very convenient

Reviewed on Oct 5, 2026

Private Oasis at Arya

Private Oasis at Arya

Coconut Grove
Save 100% on your flight
$677
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (1,050 reviews)
Todo excelente

Reviewed on Oct 8, 2026

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Where to stay in Summerland Key

Find the best Summerland Key areas and neighborhoods for the activities you enjoy most. Learn more about Summerland Key
A calm lake with several white birds, including herons and pelicans, on the water's edge.

Cutthroat Harbor Estates

While Cutthroat Harbor Estates isn't home to many top sights, Venture Key and Venture Out Keys are some notable places to visit nearby.

A waterfront property with a pool, palm trees, and a building with a white roof.

Sugarloaf Shores

While Sugarloaf Shores isn't home to many top sights, Florida Keys Beaches and Sugarloaf Beach are some notable places to visit nearby.

An aerial view of a bridge over turquoise water.

Cudjoe Gardens

When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Florida Keys Beaches, some noteworthy sights in the nearby area.

An aerial view of a coastal area with a long bridge connecting two landmasses, clear turquoise waters, and a clear blue sky with scattered clouds.

Breezeswept Beach Estates

While Breezeswept Beach Estates isn't home to many top sights, Cook Island and Big Pine Key Flea Market are some notable places to visit nearby.

Stay near popular Summerland Key attractions

Sugarloaf Beach

8.4/10 (38 reviews)
This secluded private beach on Sugarloaf Key offers a tranquil escape from the busier Florida Keys shorelines. Guests enjoy pristine views and peaceful sunbathing in a natural, amenity-light setting.
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Upper Sugarloaf Key

8.6/10 (54 reviews)
Upper Sugarloaf Key serves as a gateway to the Great White Heron National Wildlife Refuge with pristine waters. Kayak through mangroves at dawn to spot diverse bird species in this tranquil Florida Keys ecosystem.
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Upper Sugarloaf Sound

9.2/10 (17 reviews)
Glide through Upper Sugarloaf Sound's tranquil waters surrounded by vibrant mangroves and diverse birdlife. Kayak or paddleboard this peaceful Florida Keys retreat to experience nature at its most serene.
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Crab Key

Crab Key is a private residential island off Summerland Key in the Florida Keys with no public access. This exclusive enclave remains one of the few truly private islands in the Keys.
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Venture Key

This private Florida Keys community offers waterfront vacation rentals with direct access to pristine boating waters. Enjoy the heated pool and tennis courts before setting out from the marina for a day of fishing.
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Pye Key

This unspoiled island near Summerland Key offers pristine waters for snorkeling and marine life observation. Bring supplies and reef-safe sunscreen for your half-day adventure in this natural Florida Keys sanctuary.
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Squirrel Key

Commune with nature and explore the great outdoors at Squirrel Key during your travels in Summerland Key.
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Boondocks Grille & Draft House

Boondocks Grille & Draft House is just one of the places to see in Summerland Key, so why not enjoy the other things to explore during your travels?
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What to do in Summerland Key

Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

$41
per adult
88% of travellers recommend
Key West Conch Tour Train
Key West's Island Eco Tour: Kayaking, Snorkeling & Sandbar Adventure

Key West's Island Eco Tour: Sandbar Adventure with Kayaking Tour

$130
per adult
98% of travellers recommend
Key West's Island Eco Tour: Sandbar Adventure with Kayaking Tour
12-Hours Day Trip in Key West from Miami

Full Day Trip in Key West from Miami

$33
per adult
Full Day Trip in Key West from Miami
See all activities in Summerland Key

Summerland Key Hotel Deals

Parmer's Resort

Parmer's Resort

565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
$198 nightly
$223 total
Nov 1 - Nov 2
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
"Fishing charter guide pick up from dock every morning. G"

Reviewed on Oct 8, 2026

Parmer's Resort
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

251 Co Rd 939 Summerland Key FL
Sugarloaf Key Hotel at KOA Resort
Looe Key Reef Resort

Looe Key Reef Resort

27340 Overseas Highway Summerland Key FL
Fully refundableReserve now, pay when you stay
$101 nightly
$114 total
Oct 14 - Oct 15
Total with taxes and fees
7.8/10 Good! (1,000 reviews)
"This is a great inexpensive place to stay. Room was clean. Resort is showing some wear but is still good. Staff are very helpful with local recommendations. There is a great gas station next door with some items for sale in case you forget something. I would stay again."

Reviewed on Oct 5, 2026

Looe Key Reef Resort
See all 642 properties in Summerland Key
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

What types of vacation packages are available in Summerland Key?
Summerland Key is primarily a beach destination, and vacation packages can be tailored to several travel styles:
  • Budget package: Most hotels here fall into the midrange tier, but options like Sugar Loaf Lodge, rated 7.8 out of 10 by travelers, offer an outdoor pool, restaurant, and free WiFi, with travelers frequently praising its modern rooms and great location.
  • Pet-friendly package: For those traveling with pets, Looe Key Reef Resort offers pet-friendly accommodations alongside family rooms and an outdoor pool, with travelers often highlighting its clean rooms and perfect overall experience.
  • Family package: Parmer's Resort, rated 8.7 out of 10 by travelers, is a strong choice for families, featuring family rooms, a game room, and an outdoor pool, and travelers often praise its beautiful location and super helpful staff.
  • Beach package: Nearly a third of package hotels offer ocean views, making it easy to find a stay with direct access to the area's beaches.
  • Luxury package: For a premium experience, Little Palm Island Resort & Spa - A Noble House Resort is a 5-star property offering a spa, outdoor pool, and fine dining.
How can I save money on a Summerland Key vacation package?
When you bundle, you can save up to 30%*. To save money on a Summerland Key package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
How much does a Summerland Key vacation package cost?
A Summerland Key vacation package typically costs around $1,450 per adult for a week-long trip. Lower-priced options start around $750 per adult, while premium packages can reach up to $2,500.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
How do I find cheap Summerland Key vacation package deals?
The cheapest Summerland Key vacation package deals can be as low as around $530 per adult for weekend trips. Separately, December typically has the lowest average monthly prices, around $1,190 per adult, for a 6-day trip, while March follows closely at around $1,320, for a 4-day trip. Bundling flights and hotel together also typically saves money on a week-long trip — nearly all Summerland Key packages include some savings versus booking separately, typically around $135 per adult. Browse cheap vacation packages in Summerland Key on Expedia for current deals.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
What is the best time to go to Summerland Key?
The best time to go for a Summerland Key vacation package is typically during the peak booking months of December, February, and March. These months are popular with travelers, so booking your trip in advance is recommended to secure your preferred options.
What's included in a Summerland Key vacation package?
A Summerland Key vacation package lets you combine round-trip flights, a hotel stay, and a rental car. Given Summerland Key's focus on beaches, many hotels offer convenient beach access, allowing you to easily enjoy the coastal environment.Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
What's the best vacation package for Summerland Key?
For families, a Summerland Key vacation package with a stay at Parmer's Resort, rated 8.7 out of 10 by travelers, is a strong choice. This resort offers family rooms, a game room, and an outdoor pool, with travelers often praising its beautiful location and super helpful staff.For a luxury escape, consider a package built around Little Palm Island Resort & Spa - A Noble House Resort. This 5-star property features a spa, outdoor pool, and restaurant, providing an upscale experience.Travelers seeking value can find great options like Sugar Loaf Lodge, rated 7.8 out of 10 by travelers. It includes an outdoor pool, restaurant, and free WiFi, and travelers frequently praise its modern rooms and great location.
Is Summerland Key better suited for a beach vacation or a cultural trip?
Summerland Key is primarily a beach destination, making a Summerland Key vacation ideal for travelers seeking sun, sand, and water activities. The area is known for its beautiful coastline, with options like Florida Keys Beaches about 12 miles from central Summerland Key, Sugarloaf Beach about 13 miles away, and Calusa Beach about 18 miles away.
What is the best time to book a Summerland Key vacation package?
Book your Summerland Key vacation package around 6 weeks in advance. This gives you time to secure your preferred flights and hotel while rates are still competitive. Most travelers book between 3 and 13 weeks out.March, December, and February are the most popular months for Summerland Key packages, so booking earlier is advisable if you're traveling during those times.
What are the top things to do in Summerland Key?
A Summerland Key vacation offers a variety of outdoor and nature-focused activities:Browse and book things to do in Summerland Key on Expedia.
How many days do you need for a Summerland Key vacation?
Most Summerland Key vacation packages last around 5 days, which provide ample time to enjoy the beaches and explore local attractions. This length allows you to visit places like Florida Keys Beaches, discover marine life at Looe Key National Marine Sanctuary, and learn about wildlife at the National Key Deer Refuge Visitor Center. While some travelers choose weekend trips, most opt for week-long trips to fully experience the area.
Is Summerland Key a good destination for a weekend vacation?
A Summerland Key vacation package can certainly work for a weekend trip, though most travelers choose week-long trips to fully explore the area. For a shorter stay, you can focus on enjoying the local beaches and nearby attractions like Crab Key, about a 5-minute walk from central Summerland Key, or Venture Out Keys, about 3 miles away. A weekend provides a refreshing escape, but a longer visit allows for more extensive exploration of the Florida Keys.
Do you need to rent a car in Summerland Key, or is public transport enough?
For a Summerland Key vacation package, renting a car offers the most flexibility for exploring the wider Florida Keys area. While many resorts provide on-site dining and activities, a car allows you to easily visit different beaches, attractions, and dining options beyond your immediate accommodation.Transportation from Key West International Airport (EYW) to your resort will need to be arranged, and a rental car can simplify this journey. For Summerland Key beach vacation packages, a car is highly recommended to make the most of your trip and discover all the region has to offer.
Are Summerland Key vacation package hotels conveniently located?
Summerland Key vacation package hotels offer a range of locations, often balancing proximity to the central area with access to the region's beaches.For example, Sugarloaf Key Hotel at KOA Resort, rated 9.4 out of 10, is about 5 miles from central Summerland Key and about 4 miles from Florida Keys Beaches. Parmer's Resort, rated 8.7 out of 10, sits about 4 miles from central Summerland Key, while Sugar Loaf Lodge, rated 7.8 out of 10, is about 8 miles from central Summerland Key and about 2 miles from Florida Keys Beaches. This variety allows you to choose a stay that best suits your preference for central access or beach proximity.
Can I change or cancel my Summerland Key vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Summerland Key vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Summerland Key vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Summerland Key vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Summerland Key?
To find last-minute vacation packages to Summerland Key, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Summerland Key vacation packages?
Free cancellation on a Summerland Key vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Summerland Key vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Summerland Key getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Summerland Key vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.