Top Beach vacation packages in Summerland Key

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

Bahama Beach Club Pompano

Save 100% on your flight

$399

per person

Nov 4 - Nov 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

10/10 Exceptional! (12 reviews)

This place was awesome. When we arrived there was a welcome basket with all kinds of goodies and info about surrounding restaurants and fun things to do. The beach was a short walk and was beautiful. They had everything you needed and someone was there within minutes if something needed to be done. I will be staying here again when I return to Florida.

Reviewed on Jul 10, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$11,016

per person

Oct 29 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Pelican Grand Beach Resort - A Noble House Resort

East Fort Lauderdale

$679

per person

Nov 4 - Nov 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.8/10 Excellent! (1,156 reviews)

My family and I will absolutely be returning and I highly recommend to anyone looking to stay in the Fort Lauderdale area. Hotel was wonderful and so were the staff!

Reviewed on Aug 18, 2025

1 Hotel South Beach

South Beach

Save 100% on your flight

$914

per person

Oct 24 - Oct 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,245 reviews)

Went for a family trip. Lots of healthy food options.

Reviewed on Aug 17, 2025

YotelPad Miami

Downtown Miami

Save 100% on your flight

$626

per person

Nov 9 - Nov 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (375 reviews)

All good , i would booked again

Reviewed on Aug 15, 2025

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5* Beach vacations in Summerland Key

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

EAST Miami Residences

Downtown Miami

Save 100% on your flight

$800

per person

Nov 8 - Nov 11

found 16 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9/10 Wonderful! (70 reviews)

No me gustó el sector ya que hay mucho ruido en la calle motos carros acelerando No deja dormir La habitación me gustó bastante pero no logré Disfrutarla

Reviewed on May 23, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$11,016

per person

Oct 29 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

1 Hotel South Beach

South Beach

Save 100% on your flight

$914

per person

Oct 24 - Oct 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,245 reviews)

Went for a family trip. Lots of healthy food options.

Reviewed on Aug 17, 2025

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See all available trips from Columbus to Summerland Key

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3 Night Beach vacations in Summerland Key

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

Park Central South Beach

South Beach

$350

per person

Oct 24 - Oct 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (911 reviews)

The elevator broke for most of our first day there, so we had to climb 6 flights of stairs each time we went out, plus the room beside ours woke us up at 4:30 am talking very loudly. I had to bang on the wall twice and eventually had to call the front desk, but it continued past 6am.

Reviewed on Aug 18, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$7,607

per person

Nov 7 - Nov 10

found 21 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

1 Hotel South Beach

South Beach

Save 100% on your flight

$914

per person

Oct 24 - Oct 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,245 reviews)

Went for a family trip. Lots of healthy food options.

Reviewed on Aug 17, 2025

Don't see what you're looking for?

See all available trips from Columbus to Summerland Key

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4 Night Beach vacations in Summerland Key

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

Park Central South Beach

South Beach

Save 100% on your flight

$431

per person

Oct 26 - Oct 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (911 reviews)

The elevator broke for most of our first day there, so we had to climb 6 flights of stairs each time we went out, plus the room beside ours woke us up at 4:30 am talking very loudly. I had to bang on the wall twice and eventually had to call the front desk, but it continued past 6am.

Reviewed on Aug 18, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$8,409

per person

Oct 28 - Nov 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Pelican Grand Beach Resort - A Noble House Resort

East Fort Lauderdale

$679

per person

Nov 4 - Nov 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.8/10 Excellent! (1,156 reviews)

My family and I will absolutely be returning and I highly recommend to anyone looking to stay in the Fort Lauderdale area. Hotel was wonderful and so were the staff!

Reviewed on Aug 18, 2025

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See all available trips from Columbus to Summerland Key

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How do I book the best Summerland Key beach vacation packages?

Life’s a beach when you dive into our brilliant Summerland Key beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Summerland Key?

A rental steps from the shore creates an amazingly affordable Summerland Key beach vacation. Seaside sojourns during low season start from $350. Prices and availability are subject to change. Additional terms may apply.

How can I book the best family beach vacations in Summerland Key?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Summerland Key beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Summerland Key vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Summerland Key beach vacation deals?

Sort your search results by deals to delight in amazing Summerland Key beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Summerland Key beach trip with free cancellation and/or flexible dates?

Just like the Summerland Key tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Summerland Key beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Summerland Key. (OK, maybe not that last part.)

Top Beach Summerland Key Hotels

Parmer's Resort

565 Barry Avenue, Summerland Key, FL

27 min drive from Florida Keys Beaches

Make the most of this fantastic location, as you'll be within walking distance of a private beach when booking a getaway at this motel. An outdoor pool, beach ...

8.8/10 Excellent! (1,002 reviews)

Travelers like: on the beach, sun loungers, beach umbrellas, beach towels

Travelers say...

"Highly recommend Parmers to everyone. Amazing staff, beautiful property, nice beach and pool areas. Our cottage was very comfortable and clean. We will return!!"

Reviewed on Aug 15, 2025

Sugarloaf Key Hotel at KOA Resort

251 Co Rd 939, Summerland Key, FL

10 min drive from Florida Keys Beaches

Stroll along the shore in Summerland Key, as you'll be within walking distance of a private beach when booking a getaway at this hotel. Amenities at Sugarloaf ...

9.6/10 Exceptional! (426 reviews)

Travelers like: on the beach, outdoor pool

Travelers say...

"Staff was very nice and friendly. The resort itself if clean and spacious. There’s a lot of good spots to eat at within a 15 minute drive. The beach was nice and clean"

Reviewed on Aug 14, 2025

Looe Key Reef Resort

27340 Overseas Highway, Summerland Key, FL

23 min drive from Florida Keys Beaches

At this hotel, get ready to enjoy the sunsets on the beach in Summerland Key, as you'll be near the beach. An outdoor pool, a restaurant, and a bar are just ...

7.4/10 Good! (1,002 reviews)

Travelers like: close to beach, outdoor pool

Nice place by Bahia Honda and very close to Keys

"Overall the stay was nice. Good space. Clean. Manager was nice. Pool was clean. Very good rock band that plays at night also country. Bar is standard and the food offered was ok but that’s because they were still fixing something’s and the pizza was good. The only issue I had was the front desk who ..."

Reviewed on Jul 17, 2025

See all 608 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.