Summerland Key Vacation Packages 2026 from $583

Summerland Key flight + hotel vacation packages

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

Solé Miami, A Noble House Resort

Ocean Four

$583

per person

Feb 25 - Mar 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls and an off-leash area. Enjoy the 24-hour gym and unwind at the beach bar and poolside bar.

Creekside Inn

$737

per person

Jan 24 - Jan 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This smoke-free motel's marina and 2 outdoor pools are some of the highlights. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area and barbecue grills are also provided.

The Shelborne By Proper, a Member of Design Hotels

South Beach

$1,235

per person

Feb 24 - Feb 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

A private beach, a 24-hour gym, and a restaurant are all featured at this boutique hotel. Relax with free beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.

Cavalier Hotel South Beach

South Beach

$806

per person

Feb 25 - Mar 2

found 1 day ago

Roundtrip 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.

Hawks Cay Resort

$755

per person

Feb 1 - Feb 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This luxury hotel features a private beach, a full-service spa, and a marina. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. There's fun for all ages with a children's club and a children's pool, and families will appreciate the picnic area.

Top Summerland Key hotels deals

Looe Key Reef Resort

27340 Overseas Highway Summerland Key FL

Free Cancellation

Reserve now, pay when you stay

$140 nightly

$158 total

Jan 5 - Jan 6, 2026

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

Parmer's Resort

565 Barry Avenue Summerland Key FL

Free Cancellation

Reserve now, pay when you stay

$243 nightly

$273 total

Jan 5 - Jan 6, 2026

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

$199 nightly

$224 total

Jan 4 - Jan 5, 2026

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

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

Little Torch Cottages

28501 Channel View Drive Summerland Key FL

Get rates

This hotel's 2 outdoor pools and sauna are among the featured amenities. Free self parking and laundry facilities are also offered on site.

Pool

Parking included

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cudjoe Key FL

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An outdoor pool is featured at this cottage, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

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

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 $583, 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.