The Estates Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
The Estates Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Ft Myers
Villas
Save 100% on your flight
Price was $642, price is now $361 per person
$361
per person
Nov 4 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Barbara B Mann Hall and Bell Tower Shops are located nearby.
The Perry Hotel Naples
Save 100% on your flight
Price was $1,239, price is now $639 per person
$639
per person
Nov 4 - Nov 9
found 9 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 4.5-star luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.
Lani Kai Beachfront Resort
Save 100% on your flight
Price was $820, price is now $574 per person
$574
per person
Nov 4 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 3.5-star beach hotel in Fort Myers Beach. Enjoy free WiFi, an outdoor pool, and a beach locale. Popular attractions Key West Express and Crescent Beach Family Park are located nearby.
Home2 Suites by Hilton Fort Myers Airport
Save 100% on your flight
Price was $664, price is now $465 per person
$465
per person
Nov 4 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions JetBlue Park at Fenway South and Hertz Arena are located nearby.
Pointe Estero Beach Resort
South Island
Save 100% on your flight
Price was $1,253, price is now $897 per person
$897
per person
Nov 4 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Fort Myers (RSW)
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free parking, a beach locale, and a garden. Popular attractions Key West Express and Bonita Springs Public Beach are located nearby.
Casa Playa Beach Resort
Save 100% on your flight
Price was $1,020, price is now $732 per person
$732
per person
Nov 4 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Fort Myers (RSW)
Book a stay at this beach resort in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Lynn Hall Memorial Park are located nearby.
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Inn on Fifth
699 5th Ave S, Naples, FL
26.96 km from The Estates
Stay at this 4-star spa hotel in Naples. Enjoy a full-service spa, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Hilton Marco Island Beach Resort and Spa
560 S Collier Blvd, Marco Island, FL
2.69 km from The Estates
Stay at this 4-star beach resort in Marco Island. Enjoy a full-service spa, a beach locale, and room service. Our guests praise the pool and the restaurant in ...
La Quinta Inn & Suites by Wyndham Naples Downtown
1555 5th Ave S, Naples, FL
26.2 km from The Estates
Book a stay at this business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hyatt House Naples/5th Avenue
1345 5th Avenue South, Naples, FL
26.58 km from The Estates
Stay at this 3.5-star business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and a marina. Our guests praise the breakfast and the pool in our reviews. ...
Marco Beach Ocean Suites
480 S Collier Blvd, Marco Island, FL
2.86 km from The Estates
Book a stay at this beach resort in Marco Island. Enjoy free WiFi, a beach locale, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
JW Marriott Marco Island Beach Resort
400 S Collier Blvd, Marco Island, FL
3.08 km from The Estates
Stay at this 4-star beach resort in Marco Island. Enjoy 3 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the helpful staff and the property ...
Bayfront Inn Fifth Avenue
1221 5th Ave S, Naples, FL
26.88 km from The Estates
Stay at this 3.5-star business-friendly hotel in Naples. Enjoy free WiFi, free parking, and a marina. Our guests praise the restaurant and the bar in our reviews. ...
AC Hotel by Marriott Naples 5th Avenue
455 12th Street South, Naples, FL
26.92 km from The Estates
Stay at this 4-star business-friendly hotel in Naples. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Our guests praise the helpful staff in ...
Best Western Naples Inn & Suites
30.53 km from The Estates
Book a stay at this business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Staybridge Suites Naples – Marco Island by IHG
9401 Triangle Blvd, Naples, FL
17.05 km from The Estates
Stay at this 3-star golf hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Hampton Inn & Suites Naples South
5146 Tamiami Trail East, Naples, FL
21.53 km from The Estates
Stay at this hotel in Naples. Enjoy free breakfast, free parking, and room service. Popular attractions Fifth Avenue South and Naples Pier are located ...
Naples Bay Resort & Marina
1500 Fifth Ave S, Naples, FL
26.32 km from The Estates
Stay at this 4-star spa hotel in Naples. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
Red Roof Inn PLUS+ & Suites Naples Downtown-5th Ave S
1925 Davis Blvd, Naples, FL
26.07 km from The Estates
Stay at this hotel in Naples. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sun, Oct 19 - Fri, Oct 24
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$120 Roundtrip, found 5 days ago
$120
Roundtrip
found 5 days ago
Mon, Nov 10 - Thu, Nov 13
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$127 Roundtrip, found 1 day ago
$127
Roundtrip
found 1 day ago
Tue, Oct 14 - Tue, Oct 28
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$127 Roundtrip, found 2 days ago
$127
Roundtrip
found 2 days ago
Sat, Oct 11 - Sat, Nov 1
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$135 Roundtrip, found 4 days ago
$135
Roundtrip
found 4 days ago
Mon, Nov 10 - Fri, Nov 14
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago