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Downtown Vacation Packages

Downtown Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Bonita Springs Naples N.

La Quinta Inn & Suites by Wyndham Bonita Springs Naples N.

3 out of 5
Bonita Shores
Price was $560, price is now $419 per person
$419
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Bonita Springs. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Barefoot Beach and Bonita Springs Public Beach are located nearby.
Landing Incredible 1bd, Gym, Clubhouse

Landing Incredible 1bd, Gym, Clubhouse

3 out of 5
Hancock
Price was $1,164, price is now $894 per person
$894
per person
Nov 16 - Nov 23
found 8 hours ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this apartment in North Fort Myers. Enjoy free parking, an outdoor pool, and a fitness center. Popular attractions Pine Island Shopping Center and Fort Myers Shopping Center are located nearby.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,187, price is now $759 per person
$759
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Punta Rassa
Save 100% on your flight
Price was $1,182, price is now $861 per person
$861
per person
Nov 14 - Nov 20
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this spa resort in Fort Myers. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
Shell Island Beach Club

Shell Island Beach Club

4 out of 5
East End
Price was $2,208, price is now $1,703 per person
$1,703
per person
Nov 21 - Nov 28
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach aparthotel in Sanibel. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Key West Express and Sanibel Island Southern Beach are located nearby.
Blue Sunset by Avantstay Pool + Spa + Fire Table Near Beaches + Naples

Blue Sunset by Avantstay Pool + Spa + Fire Table Near Beaches + Naples

3 out of 5
Save 100% on your flight
Price was $2,542, price is now $1,969 per person
$1,969
per person
Nov 14 - Nov 20
found 10 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
Stay at this cottage in Bonita Springs. Enjoy free parking, patios, and in-room washers/dryers. Popular attractions Barefoot Beach and Bonita Springs Public Beach are located nearby.
Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Punta Rassa
Price was $1,370, price is now $1,065 per person
$1,065
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach condo in Fort Myers. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Save 100% on your flight
Price was $1,792, price is now $1,399 per person
$1,399
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this luxury resort in Naples. Enjoy a full-service spa, 2 restaurants, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.

3-4 Night Vacations in Downtown

Price found within the past 48 hours. Click for updated prices.
Stay Inn & Suites

Stay Inn & Suites

2.5 out of 5
Winkler
Price was $254, price is now $198 per person
$198
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $585, price is now $384 per person
$384
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Punta Rassa
Price was $1,370, price is now $1,065 per person
$1,065
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Blue Sunset by Avantstay Pool + Spa + Fire Table Near Beaches + Naples

Blue Sunset by Avantstay Pool + Spa + Fire Table Near Beaches + Naples

3 out of 5
Save 100% on your flight
Price was $1,946, price is now $1,571 per person
$1,571
per person
Dec 2 - Dec 6
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)

5-7 Night Vacations in Downtown

Price found within the past 48 hours. Click for updated prices.
Landing Incredible 1bd, Gym, Clubhouse

Landing Incredible 1bd, Gym, Clubhouse

3 out of 5
Hancock
Price was $1,164, price is now $894 per person
$894
per person
Nov 16 - Nov 23
found 8 hours ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,877, price is now $1,226 per person
$1,226
per person
Nov 25 - Dec 1
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Save 100% on your flight
Price was $4,150, price is now $2,791 per person
$2,791
per person
Nov 25 - Dec 1
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Casa Playa Beach Resort

Casa Playa Beach Resort

2.5 out of 5
Save 100% on your flight
Price was $1,520, price is now $1,024 per person
$1,024
per person
Nov 27 - Dec 4
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

Cheap Hotel Deals in Downtown

Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
17260 Harbour Pointe Dr Fort Myers FL
Book a stay at this spa resort in Fort Myers. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the helpful staff and the property ...
Opens in a new windowMarriott Sanibel Harbour Resort & Spa
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff ...
Opens in a new windowMargaritaville Beach Resort Fort Myers
Fairways Inn of Naples

Fairways Inn of Naples

3 out of 5
103 Palm River Blvd Naples FL
Stay at this hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
Opens in a new windowFairways Inn of Naples
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Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
1400 Estero Blvd Fort Myers Beach FL
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, 3 restaurants, and a beach locale. Popular attractions Key West Express and Estero Boulevard ...
Opens in a new windowLani Kai Beachfront Resort
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
11800 Coconut Cove Drive Bonita Springs FL
Book a stay at this golf hotel in Bonita Springs. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Coconut Point Mall and Bonita Springs ...
Opens in a new windowHyatt Vacation Club at Coconut Cove, Bonita Springs
Compass by Margaritaville Hotel Naples

Compass by Margaritaville Hotel Naples

4 out of 5
4805 Tamiami Trl N Naples FL
Book a stay at this business-friendly hotel in Naples. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
Opens in a new windowCompass by Margaritaville Hotel Naples
The Lighthouse Resort Inn & Suites

The Lighthouse Resort Inn & Suites

3 out of 5
1051 5th St Fort Myers Beach FL
Stay at this hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Opens in a new windowThe Lighthouse Resort Inn & Suites
Sanibel Island Beach Resort

Sanibel Island Beach Resort

3 out of 5
1231 Middle Gulf Dr Sanibel FL
Book a stay at this beach hotel in Sanibel. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the restaurant in our reviews. ...
Opens in a new windowSanibel Island Beach Resort
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

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Tue, Dec 1 - Tue, Dec 8
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$103 Roundtrip, just found
$103
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Dec 1 from Detroit Metropolitan Wayne County to Southwest Florida Intl., returning Tue, Dec 8, priced at $103 just found
Frontier Airlines
Mon, Dec 7 - Sun, Dec 13
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$118 Roundtrip, found 3 hours ago
$118
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Mon, Dec 7 from O'Hare Intl. to Southwest Florida Intl., returning Sun, Dec 13, priced at $118 found 3 hours ago
Frontier Airlines
Sun, Nov 15 - Sat, Dec 5
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$153 Roundtrip, found 3 hours ago
$153
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sun, Nov 15 from Hopkins Intl. to Southwest Florida Intl., returning Sat, Dec 5, priced at $153 found 3 hours ago
Breeze Airways
Sat, Jan 23 - Sat, Feb 6
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$193 Roundtrip, found 3 hours ago
$193
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Sat, Jan 23 from Portsmouth Intl. to Southwest Florida Intl., returning Sat, Feb 6, priced at $193 found 3 hours ago