Naples Luxury Vacations 2026

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Top Luxury vacation packages in Naples

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

Compass by Margaritaville Hotel Naples

Central Naples

$625

per person

Nov 10 - Nov 14

found 16 hours ago

Roundtrip flight included

Chicago (CHI) to Fort Myers (RSW)

9.6/10 Exceptional! (1,842 reviews)

Nos gusto mucho lo recomiendo 👌 es limpio, la habitación bien chula, desayuno delicioso, piscina limpia, un patio increible muy muy hermoso me encanto, y el servicio y las personas q trabajan ahi es muy muy bueno y muy atentos lo recomiendo al 100 de 100 sin dudas volveré.

Reviewed on Oct 11, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$5,125

per person

Nov 11 - Nov 14

found 1 day ago

Roundtrip flight included

Cincinnati (CVG) to Fort Myers (RSW)

9.6/10 Exceptional! (41 reviews)

This resort was amazing!!

Reviewed on Oct 9, 2026

Bellasera Resort

Old Naples

$931

per person

Dec 11 - Dec 14

found 3 hours ago

Roundtrip flight included

White Plains (HPN) to Fort Myers (RSW)

9.6/10 Exceptional! (2,335 reviews)

Nice condo , very clean, a/c works great. Nice restaurant at the Claw Bar. Comfy bed , love the bath products. We were greeted with a bag of cookies in our room

Reviewed on Oct 4, 2026

Hilton Naples

Park Shore

$754

per person

Dec 11 - Dec 13

found 15 hours ago

Roundtrip flight included

Hartford (BDL) to Fort Myers (RSW)

9.2/10 Wonderful! (1,632 reviews)

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

$1,035

per person

Dec 11 - Dec 13

found 15 hours ago

Roundtrip flight included

Hartford (BDL) to Fort Myers (RSW)

9/10 Wonderful! (1,003 reviews)

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5* Luxury vacations in Naples

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

The Ritz-Carlton Naples, Tiburón

$1,258

per person

Dec 13 - Dec 16

found 1 day ago

Roundtrip flight included

Nashville (BNA) to Fort Myers (RSW)

9.2/10 Wonderful! (684 reviews)

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$5,125

per person

Nov 11 - Nov 14

found 1 day ago

Roundtrip flight included

Cincinnati (CVG) to Fort Myers (RSW)

9.6/10 Exceptional! (41 reviews)

This resort was amazing!!

Reviewed on Oct 9, 2026

The Ritz-Carlton, Naples

Pelican Bay

$1,816

per person

Dec 13 - Dec 16

found 1 day ago

Roundtrip flight included

Nashville (BNA) to Fort Myers (RSW)

9.2/10 Wonderful! (520 reviews)

Don't see what you're looking for?

See all available trips from Pretty Prairie to Naples

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3 Night Luxury vacations in Naples

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

Hilton Naples

Park Shore

$736

per person

Dec 11 - Dec 14

found 3 hours ago

Roundtrip flight included

White Plains (HPN) to Fort Myers (RSW)

9.2/10 Wonderful! (1,632 reviews)

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$5,125

per person

Nov 11 - Nov 14

found 1 day ago

Roundtrip flight included

Cincinnati (CVG) to Fort Myers (RSW)

9.6/10 Exceptional! (41 reviews)

This resort was amazing!!

Reviewed on Oct 9, 2026

Inn on Fifth

Old Naples

$995

per person

Nov 11 - Nov 14

found 1 day ago

Roundtrip flight included

Cincinnati (CVG) to Fort Myers (RSW)

9.4/10 Exceptional! (1,010 reviews)

Don't see what you're looking for?

See all available trips from Pretty Prairie to Naples

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4 Night Luxury vacations in Naples

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

Olde Marco Island Inn and Suites

Olde Marco

$832

per person

Dec 11 - Dec 15

found 3 hours ago

Roundtrip flight included

White Plains (HPN) to Fort Myers (RSW)

9/10 Wonderful! (1,005 reviews)

Staff was very kind and attentive

Reviewed on Oct 7, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$1,302

per person

Dec 11 - Dec 15

found 1 day ago

Roundtrip non-stop flight included

Chicago (MDW) to Fort Myers (RSW)

9/10 Wonderful! (1,003 reviews)

Bayfront Inn Fifth Avenue

Redevelopment Area

$885

per person

Dec 11 - Dec 15

found 3 hours ago

Roundtrip flight included

White Plains (HPN) to Fort Myers (RSW)

8.8/10 Excellent! (1,941 reviews)

Didn’t like that I had to pay to park my car

Reviewed on Oct 10, 2026

Don't see what you're looking for?

See all available trips from Pretty Prairie to Naples

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What can I expect from a luxury Naples vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Naples vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

How can I find all-inclusive luxury vacation packages in Naples?

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger. 

Can I book a cheap Naples luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $625. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Naples?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

Can I book a package in Naples with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.   

How can I find the best luxury vacation deals in Naples?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

Can I book a luxury holiday in Naples with free cancellation and/or flexible dates?

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

Why should I book my luxury trip to Naples with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.

Top Luxury Naples Hotels

Signia Hilton Naples Grande Beach Resort

475 Seagate Drive Naples FL

13 min drive from Naples Beach

Signia Hilton Naples Grande Beach Resort is one of the Naples lavish 4.5-star beach properties where you can treat yourself to deep soaking bathtubs and 24-hour ...

The Ritz-Carlton, Naples

280 Vanderbilt Beach Rd Naples FL

20 min drive from Naples Beach

The Ritz-Carlton, Naples is a Naples luxury 5-star beach property where you can treat yourself to 24-hour room service, pillowtop beds, and more. The 2 outdoor ...

Hyatt Regency Coconut Point Resort & Spa

5001 Coconut Rd Bonita Springs FL

45 min drive from Naples Beach

Hyatt Regency Coconut Point Resort & Spa is a classy, 4.5-star beach property where you can pamper yourself with premium channels and more. The 4 outdoor pools, ...

See all 7,177 properties in Naples

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.