
Deals on vacations and trips to Southwest Florida
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Southwest Florida flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.

Hotel Colonnade Coral Gables, Autograph Collection
Coral Gables Section
Price was $1,621, price is now $694 per person
$694
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This hotel features 2 restaurants, an outdoor pool, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. Make the most of the a rooftop terrace and hot tub, and relax with drinks at one of the 2 bars/lounges.

Henrosa Hotel
South Beach
Price was $1,745, price is now $832 per person
$832
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop 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.

The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was $26,855, price is now $12,827 per person
$12,827
per person
Dec 3 - Dec 8
just found
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.

The Local House
South Beach
Price was $1,632, price is now $864 per person
$864
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. A poolside bar, a coffee shop, and a terrace are also provided.

Bay Breeze Premium Apartments By Eskape Collection
Save 100% on your flight
Price was $1,903, price is now $1,051 per person
$1,051
per person
Dec 3 - Dec 8
just found
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
This aparthotel features an outdoor pool and a rooftop terrace. WiFi in public areas is free. Self parking, a garden, and luggage storage are also offered.
Top Southwest Florida hotels deals

Kompose Boutique Hotel
965 University Pkwy, Sarasota, FL
Free Cancellation
Reserve now, pay when you stay
$71 nightly
The price is $81 total per night
$81 total
Sep 23 - Sep 24
Total with taxes and fees
This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

Lani Kai Beachfront Resort
1400 Estero Blvd, Fort Myers Beach, FL
Free Cancellation
Reserve now, pay when you stay
$133 nightly
The price is $149 total per night
$149 total
Sep 22 - Sep 23
Total with taxes and fees
This hotel features 2 beach bars, a bar/lounge, and a restaurant. Enjoy the outdoor pool and perks like free WiFi. There's a poolside bar on site, and a 24-hour front desk and laundry facilities are also provided.
Pool
Free WiFi

Margaritaville Beach Resort Fort Myers
251 Crescent Street, Fort Myers Beach, FL
$205 nightly
The price is $229 total per night
$229 total
Oct 1 - Oct 2
Total with taxes and fees
A full-service spa, 4 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Relax with a drink at one of the 4 bars/lounges and get perks like free WiFi. You'll appreciate the 24-hour gym, beach bar, and concierge services.

Inn on Fifth
699 5th Ave S, Naples, FL
Free Cancellation
$296 nightly
The price is $329 total per night
$329 total
Sep 29 - Sep 30
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this eco-certified hotel. Enjoy the outdoor pool and perks like a free beach shuttle. Enjoy the a rooftop terrace and unwind at the bar/lounge and poolside bar.

Naples Grande Beach Resort
475 Seagate Drive, Naples, FL
Free Cancellation
Reserve now, pay when you stay
$217 nightly
The price is $241 total per night
$241 total
Sep 28 - Sep 29
Total with taxes and fees
A full-service spa, 4 restaurants, and 3 outdoor pools are all featured at this luxury resort. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Family-friendly amenities include a waterslide and kid-friendly dining, along with tennis lessons.

La Quinta Inn & Suites by Wyndham Naples Downtown
1555 5th Ave S, Naples, FL
Free Cancellation
Reserve now, pay when you stay
$71 nightly
The price is $79 total per night
$79 total
Sep 30 - Oct 1
Total with taxes and fees
This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
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View all propertiesLowest 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

Siesta Key Beach
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
Nothing says vacation like spending a lazy day at Lido Beach, a popular beach in Sarasota. Wander the picturesque gardens or discover the area's beautiful sunsets.

Venice Beach
If a restful vacation is part of your travel plans, Venice Beach might be the perfect place to seek out during your trip to Venice.
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