Search Deals on
South End Vacation Packages

Photo by Lisa Warmouth Strusowski

South End Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $588, price is now $365 per person
$365
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
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 $2,188, price is now $1,191 per person
$1,191
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this 4.5-star 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.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Price was $618, price is now $395 per person
$395
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Edison Beach House

Edison Beach House

3.5 out of 5
Price was $839, price is now $552 per person
$552
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this 3.5-star beach aparthotel in Fort Myers Beach. Enjoy free parking, a beach locale, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Key West Express and Times Square are located nearby.
Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Save 100% on your flight
Price was $1,203, price is now $795 per person
$795
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
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. Popular attractions Fifth Avenue South and Naples Pier are located nearby.
Casa Playa Beach Resort

Casa Playa Beach Resort

2 out of 5
Price was $841, price is now $592 per person
$592
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
GullWing Beach Resort

GullWing Beach Resort

3.5 out of 5
South Island
Save 100% on your flight
Price was $1,230, price is now $869 per person
$869
per person
Sep 30 - Oct 6
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this 3.5-star beach aparthotel in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Bonita Springs Public Beach are located nearby.
Bellasera Resort

Bellasera Resort

4 out of 5
Old Naples
Save 100% on your flight
Price was $1,469, price is now $1,042 per person
$1,042
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this business-friendly condo in Naples. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. Popular attractions Fifth Avenue South and Naples Pier are located nearby.

3-4 Night Vacations in South End

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Save 100% on your flight
Price was $355, price is now $210 per person
$210
per person
Sep 25 - Sep 28
found 1 day 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 $1,337, price is now $724 per person
$724
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $522, price is now $309 per person
$309
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $588, price is now $365 per person
$365
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

5-7 Night Vacations in South End

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Save 100% on your flight
Price was $622, price is now $362 per person
$362
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop 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 $2,188, price is now $1,191 per person
$1,191
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Hyatt Place Fort Myers/at The Forum

Hyatt Place Fort Myers/at The Forum

3 out of 5
The Forum
Save 100% on your flight
Price was $647, price is now $381 per person
$381
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $931, price is now $550 per person
$550
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)

Cheap Hotel Deals in South End

Hilton Marco Island Beach Resort and Spa

Hilton Marco Island Beach Resort and Spa

4 out of 5
560 S Collier Blvd, Marco Island, FL
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 ...
Hilton Marco Island Beach Resort and Spa
JW Marriott Marco Island Beach Resort

JW Marriott Marco Island Beach Resort

4 out of 5
400 S Collier Blvd, Marco Island, FL
Book a stay at this 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 ...
JW Marriott Marco Island Beach Resort
Marco Beach Ocean Suites

Marco Beach Ocean Suites

2 out of 5
480 S Collier Blvd, Marco Island, FL
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 ...
Marco Beach Ocean Suites
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Marco Beach Vacation Suites

Marco Beach Vacation Suites

3.5 out of 5
901 S. Collier Boulevard, Marco Island, FL
Stay at this 3.5-star condo in Marco Island. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions ...
Marco Beach Vacation Suites
Marriott's Crystal Shores

Marriott's Crystal Shores

3.5 out of 5
600 S Collier Blvd, Marco Island, FL
Book a stay at this beach condo in Marco Island. Enjoy free WiFi, 3 outdoor pools, and 2 restaurants. Popular attractions Marco Golf and Garden and Winterberry ...
Marriott's Crystal Shores
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.

Spirit Airlines
Sun, Oct 5 - Thu, Oct 9
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Oct 5 from O'Hare Intl. to Southwest Florida Intl., returning Thu, Oct 9, priced at $100 found 1 day ago
United
Sat, Sep 20 - Sat, Sep 27
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$120 Roundtrip, found 15 hours ago
$120
Roundtrip
found 15 hours ago
Select United flight, departing Sat, Sep 20 from Newark Liberty Intl. Airport to Southwest Florida Intl., returning Sat, Sep 27, priced at $120 found 15 hours ago
Delta
Tue, Nov 4 - Wed, Nov 12
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$127 Roundtrip, found 5 hours ago
$127
Roundtrip
found 5 hours ago
Select Delta flight, departing Tue, Nov 4 from Logan Intl. to Southwest Florida Intl., returning Wed, Nov 12, priced at $127 found 5 hours ago
Frontier Airlines
Mon, Sep 15 - Fri, Sep 26
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$132 Roundtrip, found 1 day ago
$132
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Sep 15 from Hopkins Intl. to Southwest Florida Intl., returning Fri, Sep 26, priced at $132 found 1 day ago