Estero Vacation Packages 2026 from $495

Estero flight + hotel vacation packages

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

Inn on Fifth

Old Naples

Save 100% on your flight

$495

per person

Aug 24 - Aug 27

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) to Fort Myers (RSW)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free 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.

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$702

per person

Sep 4 - Sep 7

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Fort Myers (RSW)

This luxury resort features a private beach, a full-service spa, and 2 restaurants. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the outdoor pool and visit the 2 bars/lounges and beach bar for drinks.

The Perry Hotel Naples

Save 100% on your flight

$631

per person

Sep 3 - Sep 7

found 9 hours ago

Roundtrip flight included

Chicago (CHI) to Fort Myers (RSW)

A marina, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and a beach shuttle. Relax with a drink at one of the 2 bars/lounges and enjoy the a rooftop terrace.

Chadwick Cove Resort & Marina

Save 100% on your flight

$633

per person

Sep 20 - Sep 26

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Fort Myers (RSW)

This smoke-free condo features a marina and 7 restaurants. Dine at the beachfront restaurant and relax with beach umbrellas. Enjoy a meal in one of the 2 coffee shops/cafes and free perks like free self parking and WiFi in public areas.

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Save 100% on your flight

$756

per person

Aug 27 - Aug 31

found 1 day ago

Roundtrip flight included

Hartford (BDL) to Fort Myers (RSW)

Top Estero hotels deals

Embassy Suites by Hilton Fort Myers Estero

10450 Corkscrew Commons Dr Estero FL

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$123 total

Jul 14 - Jul 15

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the gym and free cooked-to-order breakfast each morning.

Pool

Hot Tub

Margaritaville Beach Resort Fort Myers

251 Crescent Street Fort Myers Beach FL

$228 nightly

$254 total

Jul 26 - Jul 27

Total with taxes and fees

A full-service spa, 4 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the 24-hour gym and visit the 4 bars/lounges and beach bar for drinks.

Pool

Spa

Hyatt House Naples/5th Avenue

1345 5th Avenue South Naples FL

$139 nightly

$154 total

Aug 2 - Aug 3

Total with taxes and fees

A marina, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the outdoor pool and free buffet breakfast each morning.

Pool

Hot Tub

Great Wolf Lodge Naples

3900 City Gate Blvd N. Naples FL

$199 nightly

$221 total

Jul 9 - Jul 10

Total with taxes and fees

A water park, 4 restaurants, and 3 outdoor pools are all featured at this smoke-free hotel. There's fun for all ages with a lazy river and a bowling alley, and families will appreciate the onsite laundry facilities. Enjoy the 8 indoor pools and perks like free WiFi.

Pool

Hot Tub

Lani Kai Beachfront Resort

1400 Estero Blvd Fort Myers Beach FL

Free Cancellation

Reserve now, pay when you stay

$159 nightly

$177 total

Jul 9 - Jul 10

Total with taxes and fees

This smoke-free hotel features 3 restaurants, 3 beach bars, and 6 bars/lounges. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Enjoy the outdoor pool and perks like free WiFi.

Pool

Free WiFi

Sanibel Island Beach Resort

1231 Middle Gulf Dr Sanibel FL

Free Cancellation

Reserve now, pay when you stay

$204 nightly

$225 total

Jul 9 - Jul 10

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Relax with a drink at the poolside bar and enjoy perks like free self parking.

Pool

Pet friendly

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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.

Stay near popular Estero attractions

An aerial view of a large industrial building with a curved roof, surrounded by a parking lot and adjacent roads.

Hertz Arena

8.4/10 (283 reviews)

Catch an event at Hertz Arena during your trip to Estero. Stroll along the seaside or discover the area's beautiful sunsets.

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Frequently asked questions

How much are vacation packages to Estero?

Your travel fantasies can come true in Estero for as little as $495. Our vacation packages include flights and hotels, so booking your trip will be nice and easy. All you'll have to focus on is having an incredible time.

How long should my Estero vacation be?

There are no strict rules when it comes to how long you should spend in Estero, but the majority of people decide to stay around 3 nights. Got some wiggle room in your departure date? Extend your trip by a few extra nights. Then you'll have ample time to check out the area's hidden treasures too.

Where can I get the best vacation package deals for Estero?

You'll discover a fantastic range of Estero package deals on Travelocity. With as many as 400 air carriers and 1,000,000 properties across the globe, piecing together the ultimate vacation will be simple.

Why should I purchase my Estero vacation bundle with Travelocity?

Because life is one incredible journey, and we have all you need to help get you on your way. With our first-rate service and Price Match Guarantee, you can book with confidence. What's more, you can rest easy while you're on the road knowing we're always available to chat via our round-the-clock support.

Can I save money on my Estero car rental if I combine it with a hotel or flight?

With an Estero vacation package, you can combine your hotel, car and flight bookings and save loads. When you're ready to see the best of this impressive city, why not start with Salvador Dali Museum? This must-see attraction is 100 mi from Estero. With your own wheels, you'll be there in a jiffy.

Which airport is best for Estero?

One option is Southwest Florida Intl. Airport (RSW). From here, you'll need to travel southwest for about 7 mi to reach the heart of Estero. Another convenient choice is Naples Municipal Airport (APF), which is 20 mi away from central Estero.

What is there to do in Estero?

You'll feel a certain magic as you stroll the streets of Estero. Hertz Arena and Coconut Point Mall are just two landmarks that lure visitors to this fantastic city, so add them to your travel itinerary.

Where should I stay when visiting Estero?

Many travelers opt to stay at the Embassy Suites by Hilton Fort Myers Estero. It's a great base for your Estero escape.