Name: Inn on Fifth
Price range: $268 total
Rating: 9.2

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Your Southwest Florida Vacation

Set off on your next big adventure with a Southwest Florida vacation package, and leave relaxed knowing the finer details are taken care of. Plus with the ability to customize your escape, you know it'll be one to remember. Begin your trip to Southwest Florida with a couple of days in Tampa visiting popular attractions like Busch Gardens Tampa Bay and Raymond James Stadium. Sarasota is another top city that lures crowds from near and far. Bay Island and Siesta Key Beach are two of the leading places to see here. From the moment you book your Southwest Florida vacation to the second you come back home, Expedia has you covered each step of the way.

The Latest Southwest Florida vacation packages

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

Broadmore Miami Beach

North Beach

Save 100% on your flight

$384

per person

Jan 6 - Jan 12

found 22 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

5.6/10 (359 reviews)

Staff was exceptional during our entire stay, there was always someone at the front desk happy to help with any request.

Reviewed on Oct 13, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$13,625

per person

Dec 3 - Dec 9

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Bahama Beach Club Pompano

$640

per person

Jan 1 - Jan 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

10/10 Exceptional! (12 reviews)

Bahama Beach Club Pompano is going to my place to stay whenever I take trips to the Fort Lauderdale side of Florida. The place was clean, close to the beach and provided all the amenities for anyone who loves the beach...beach chairs, towels, umbrella, cooler. The bbq grill was a plus as well and we actually did BBQed one day Although Bahama Beach is walking distance from the beach, we drove and found parking easily. Sandra was awesome and very quick with responses to our queries. The personal welcome note, wine and snacks made us feel right at home. I definitely rwcommend Bahama Beach to anyone traveling to Fort Lauderdale and neesa a nicr clean, quiet and safe place to stay.

Reviewed on Sep 29, 2025

The Local House

South Beach

$799

per person

Jan 6 - Jan 12

found 22 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (1,000 reviews)

Fantastic small hotel. The staff were all attentive and went out of their way to make my stay comfortable The restraunt serves Brunch (8am to 4pm) i had the opportunity to eat there twice and thoroughly enjoyed both meals. Room Service and Service at the rooftop pool is also available..

Reviewed on Oct 12, 2025

Flow Miami Hotel

Downtown Miami

Save 100% on your flight

$584

per person

Nov 19 - Nov 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9/10 Wonderful! (157 reviews)

Loved that the room came with washer/dryer, dishwasher, stove/oven, etc. View from the balcony was pretty cool. Gym was fully equipped.

Reviewed on Oct 13, 2025

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Where to stay in Southwest Florida

Find the best Southwest Florida areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Florida

South End

While visiting South End, you might make a stop by sights like Winterberry Beach and South Marco Beach.

Discover the most popular places to visit in Southwest Florida

Southwest Florida featuring general coastal views and a beach as well as a large group of people

Siesta Key Beach

4.5/5(1,425 reviews)

The soft, white sand on Siesta Key’s award-winning family-friendly beach is perfect for relaxing under a sun umbrella and taking part in a game of volleyball.

Lido Beach

4.5/5(1,225 reviews)

Visit a beach not far from an upscale shopping area. The warm waters are as inviting as the white sand.

Venice Beach

4.5/5(862 reviews)

Beachside bliss awaits at a Florida coastal gem where you can swim, fish and hunt for ancient fossils in the sand and beneath the waves.

What to do in Southwest Florida

2-Hour Snorkel Guided Experience in the Blue Heron Bridge

2 1⁄2 - Hour Guided Snorkel Tour of Phil Foster Park, Free Videos!

$44

per adult

Palm Beach: Sightseeing Catamaran Cruise

$54

per adult

100% of travellers recommend

Luxury Sunset Catamaran Cruise

$59

per adult

See all activities in Southwest Florida

Southwest Florida Hotel Deals

Kompose Boutique Hotel

965 University Pkwy, Sarasota, FL

Fully refundableReserve now, pay when you stay

$71 nightly

$81 total

Oct 16 - Oct 17

Total with taxes and fees

9/10 Wonderful! (4,440 reviews)

"Beautiful hotel especially for the price."

Reviewed on Oct 9, 2025

Lani Kai Beachfront Resort

1400 Estero Blvd, Fort Myers Beach, FL

Fully refundableReserve now, pay when you stay

$191 nightly

$214 total

Oct 21 - Oct 22

Total with taxes and fees

8.8/10 Excellent! (1,033 reviews)

"The thing that i did not like was that the tub was small and we had to pay for parking each day. Everything else was great."

Reviewed on Oct 11, 2025

Inn on Fifth

699 5th Ave S, Naples, FL

Fully refundable

$241 nightly

$268 total

Nov 3 - Nov 4

Total with taxes and fees

9.2/10 Wonderful! (1,005 reviews)

"The only downside was that the balcony was small. Everything else was excellent!"

Reviewed on Oct 12, 2025

See all 45,047 properties in Southwest Florida

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.