Summerland Key Vacation Packages 2025/2026 from $372

Summerland Key flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Henrosa Hotel

South Beach

Save 100% on your flight

$372

per person

Nov 20 - Nov 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This hotel features free WiFi in public areas, concierge services, and valet parking. A terrace, a garden, and luggage storage are also on offer.

Cavalier Hotel South Beach

South Beach

$873

per person

Dec 3 - Dec 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking, a terrace, and express check-out are also offered.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$12,827

per person

Dec 3 - Dec 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

This condo resort features 2 restaurants, 3 outdoor pools, and a gym. There's fun for all ages with a children's club and a children's pool, and babysitting is an added bonus. Enjoy the a rooftop terrace and perks like free WiFi.

President Hotel

South Beach

$890

per person

Dec 3 - Dec 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

This hotel features an outdoor pool and a bar/lounge. Enjoy the free full breakfast each morning. Valet parking, a terrace, and a garden are also offered.

Park Central South Beach

South Beach

$704

per person

Oct 20 - Oct 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This historic resort features 2 restaurants, 2 outdoor pools, and a 24-hour gym. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. There's a poolside bar on site, and a 24-hour front desk and concierge services are also provided.

Top Summerland Key hotels deals

Parmer's Resort

565 Barry Avenue, Summerland Key, FL

Free Cancellation

Reserve now, pay when you stay

$148 nightly

$167 total

Sep 21 - Sep 22

Total with taxes and fees

The private beach and marina are among the highlights at this motel. Spend a day at the beach kayaking, or relax with sun loungers and beach umbrellas. Enjoy the outdoor pool and free perks like on-the-go breakfast and free self parking.

On private beach

Pool

Sugar Loaf Lodge

17001 Overseas Hwy, Summerland Key, FL

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$111 total

Sep 21 - Sep 22

Total with taxes and fees

This hotel features a marina, 2 outdoor tennis courts, and a restaurant. Enjoy the outdoor pool and perks like free self parking and free WiFi. A bar/lounge and a garden are also provided.

Pool

Parking included

Looe Key Reef Resort

27340 Overseas Highway, Summerland Key, FL

Free Cancellation

Reserve now, pay when you stay

$115 nightly

$129 total

Sep 27 - Sep 28

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, express check-in, and luggage storage are also on offer.

Pool

Pet friendly

Sugarloaf Key Hotel at KOA Resort

251 Co Rd 939, Summerland Key, FL

Get rates

The private beach and marina are among the highlights at this hotel. Enjoy the outdoor pool and perks like free self parking and free WiFi. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

On private beach

Pool

Old Florida Style, wrap around porch, boat basin for dockage, open water

$629 nightly

$698 total

Sep 28 - Sep 29

Total with taxes and fees

This vacation home includes a garden and laundry facilities.

Kitchen

Washer

Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

$737 nightly

$818 total

Sep 21 - Sep 22

Total with taxes and fees

An outdoor pool is featured at this vacation home, along with laundry facilities and barbecue grills.

Pool

Kitchen

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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.

Popular places to visit

Upper Sugarloaf Sound

Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.

Sugarloaf Beach

Why not spend a lazy afternoon at Sugarloaf Beach during your trip to 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.

Frequently asked questions

How much are vacation packages to Summerland Key?

With deals starting as low as $372, flight and hotel packages are a fantastic way to make your budget stretch further. Summerland Key, here you come!

Where can I get the best vacation package deals for Summerland Key?

With around 400 air carriers and 1,000,000 hotels across the world, it's hard to top Travelocity. Take advantage of our impressive range and create your dream Summerland Key package deal. Don't you love it when vacation planning is that easy?

Why should I purchase my Summerland Key vacation bundle with Travelocity?

You'll not only save lots, but you'll also have access to our 24/7 customer support, high-quality service and a Price Match Guarantee. Wander across the world, uncover lesser-known sights and make lifelong memories — we'll take care of the little details.

Can I save money on my Summerland Key car rental if I book it with a hotel or flight?

With a Summerland Key vacation package, you can combine your car, flight and hotel bookings and save a tidy sum. If you're eager to explore the best of this fantastic location, why not make tracks to PortMiami? This famous attraction is 110 mi from Summerland Key. With your own rental car, you'll be there belong long.

What is the best time of year to go to Summerland Key?

If you'd rather avoid expensive airfares, hordes of tourists and packed hotels, organize your trip outside of January, February and March. The quietest time to visit Summerland Key is August, September and October. You'll find hotel rates are the highest in and the most economical in .

Which airport is best for Summerland Key?

The top airport for Summerland Key is Key West Intl. Airport (EYW). You'll find it 20 mi east of the downtown area.

Where should I stay when visiting Summerland Key?

If you're after someplace comfortable to base yourself, check out the Tropical Island Sanctuary. It's the top choice for many travelers.