Cheap Vacations in Keewaydin Island

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3-night Keewaydin Island vacations

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Fort Myers/at The Forum

Hyatt Place Fort Myers/at The Forum

3 out of 5
Price was $635, price is now $409 per person
$409
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Marco Polo by Avantstay Waterfront 5bdr, Pool, Spa, Fire Pit, Walk to Beach

Marco Polo by Avantstay Waterfront 5bdr, Pool, Spa, Fire Pit, Walk to Beach

3 out of 5
Save 100% on your flight
Price was $4,230, price is now $3,384 per person
$3,384
per person
Feb 4 - Feb 7
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
Price was $866, price is now $497 per person
$497
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Innovation Hotel

Innovation Hotel

4 out of 5
Save 100% on your flight
Price was $1,101, price is now $646 per person
$646
per person
Jan 24 - Jan 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Save 100% on your flight
Price was $1,425, price is now $847 per person
$847
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Save 100% on your flight
Price was $714, price is now $426 per person
$426
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Home2 Suites by Hilton Fort Myers Airport

Home2 Suites by Hilton Fort Myers Airport

3 out of 5
Price was $701, price is now $480 per person
$480
per person
Feb 6 - Feb 9
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
Save 100% on your flight
Price was $2,074, price is now $1,512 per person
$1,512
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Embassy Suites by Hilton Fort Myers Estero

Embassy Suites by Hilton Fort Myers Estero

3.5 out of 5
Price was $734, price is now $535 per person
$535
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Pink Shell Beach Resort and Marina

Pink Shell Beach Resort and Marina

4 out of 5
Save 100% on your flight
Price was $1,336, price is now $976 per person
$976
per person
Feb 6 - Feb 9
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 $1,203, price is now $886 per person
$886
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Hilton Marco Island Beach Resort and Spa

Hilton Marco Island Beach Resort and Spa

4 out of 5
Save 100% on your flight
Price was $956, price is now $711 per person
$711
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

4-night Keewaydin Island vacations

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Fort Myers/at The Forum

Hyatt Place Fort Myers/at The Forum

3 out of 5
Save 100% on your flight
Price was $591, price is now $322 per person
$322
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Save 100% on your flight
Price was $669, price is now $331 per person
$331
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Innovation Hotel

Innovation Hotel

4 out of 5
Save 100% on your flight
Price was $1,490, price is now $836 per person
$836
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Save 100% on your flight
Price was $968, price is now $553 per person
$553
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Home2 Suites by Hilton Fort Myers Airport

Home2 Suites by Hilton Fort Myers Airport

3 out of 5
Save 100% on your flight
Price was $603, price is now $373 per person
$373
per person
Jan 26 - Jan 30
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 $1,272, price is now $803 per person
$803
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Bellasera Resort

Bellasera Resort

4 out of 5
Save 100% on your flight
Price was $2,941, price is now $1,874 per person
$1,874
per person
Feb 6 - Feb 10
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
Save 100% on your flight
Price was $2,917, price is now $1,890 per person
$1,890
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Embassy Suites by Hilton Fort Myers Estero

Embassy Suites by Hilton Fort Myers Estero

3.5 out of 5
Save 100% on your flight
Price was $822, price is now $536 per person
$536
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Inn on Fifth

Inn on Fifth

4 out of 5
Save 100% on your flight
Price was $3,388, price is now $2,300 per person
$2,300
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Staybridge Suites Naples – Marco Island by IHG

Staybridge Suites Naples – Marco Island by IHG

3 out of 5
Save 100% on your flight
Price was $927, price is now $631 per person
$631
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
Price was $948, price is now $653 per person
$653
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

5-night Keewaydin Island vacations

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Fort Myers Cape Coral

Courtyard by Marriott Fort Myers Cape Coral

3 out of 5
Save 100% on your flight
Price was $678, price is now $394 per person
$394
per person
Feb 2 - Feb 7
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Save 100% on your flight
Price was $788, price is now $403 per person
$403
per person
Feb 2 - Feb 7
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Save 100% on your flight
Price was $2,039, price is now $1,118 per person
$1,118
per person
Feb 2 - Feb 7
found 5 hours ago
Roundtrip 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
Save 100% on your flight
Price was $701, price is now $411 per person
$411
per person
Feb 2 - Feb 7
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
Save 100% on your flight
Price was $3,540, price is now $2,271 per person
$2,271
per person
Feb 2 - Feb 7
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Landing Apartments Fort Myers near Olympia Pointe

Landing Apartments Fort Myers near Olympia Pointe

4 out of 5
Save 100% on your flight
Price was $1,156, price is now $766 per person
$766
per person
Feb 2 - Feb 7
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Lehigh Resort Club

Lehigh Resort Club

2.5 out of 5
Save 100% on your flight
Price was $599, price is now $405 per person
$405
per person
Feb 2 - Feb 7
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Embassy Suites by Hilton Fort Myers Estero

Embassy Suites by Hilton Fort Myers Estero

3.5 out of 5
Save 100% on your flight
Price was $948, price is now $642 per person
$642
per person
Feb 2 - Feb 7
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Candlewood Suites Fort Myers Sanibel Gateway by IHG

Candlewood Suites Fort Myers Sanibel Gateway by IHG

3 out of 5
Save 100% on your flight
Price was $634, price is now $433 per person
$433
per person
Feb 2 - Feb 7
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Doubletree by Hilton Fort Myers at Bell Tower Shops

Doubletree by Hilton Fort Myers at Bell Tower Shops

4 out of 5
Save 100% on your flight
Price was $842, price is now $579 per person
$579
per person
Feb 2 - Feb 7
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Landing Apartments - Cape Coral

Landing Apartments - Cape Coral

4.5 out of 5
Save 100% on your flight
Price was $1,384, price is now $959 per person
$959
per person
Feb 2 - Feb 7
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Inn on Fifth

Inn on Fifth

4 out of 5
Save 100% on your flight
Price was $2,323, price is now $1,613 per person
$1,613
per person
Jan 16 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)

Flight deals to Keewaydin Island

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

Sat, Jan 17 - Tue, Jan 20
ORD
Chicago
RSW
Fort Myers
$69 Roundtrip, found 7 hours ago
$69
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, Jan 17 from Chicago to Fort Myers, returning Tue, Jan 20, priced at $69 found 7 hours ago
Wed, Feb 25 - Fri, Feb 27
DTW
Detroit
RSW
Fort Myers
$90 Roundtrip, found 4 days ago
$90
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Feb 25 from Detroit to Fort Myers, returning Fri, Feb 27, priced at $90 found 4 days ago
Tue, Feb 10 - Sat, Feb 28
CLE
Cleveland
RSW
Fort Myers
$98 Roundtrip, found 6 days ago
$98
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Feb 10 from Cleveland to Fort Myers, returning Sat, Feb 28, priced at $98 found 6 days ago

Top rated hotels for your Keewaydin Island vacation

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive Naples FL
9.82 mi from city center
$434 nightly
The price is $482 total per night
$482 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Located in Naples (Park Shore), Naples Grande Beach Resort is within a 5-minute drive of Clam Pass Park and Vanderbilt Beach.
Pool
Hot Tub
La Quinta Inn & Suites by Wyndham Naples Downtown

La Quinta Inn & Suites by Wyndham Naples Downtown

2.5 out of 5
1555 5th Ave S Naples FL
Free Cancellation
Reserve now, pay when you stay
4.73 mi from city center
$125 nightly
The price is $139 total per night
$139 total
Dec 21 - Dec 22
Total with taxes and fees
With a stay at La Quinta Inn & Suites by Wyndham Naples Downtown, you'll be centrally located in Naples, steps from Fifth Avenue South and within a 5-minute drive of Naples Beach.
Pool
Breakfast included
Fairways Inn of Naples

Fairways Inn of Naples

3 out of 5
103 Palm River Blvd Naples FL
Free Cancellation
Reserve now, pay when you stay
14.01 mi from city center
$107 nightly
The price is $119 total per night
$119 total
Dec 18 - Dec 19
Total with taxes and fees
With a stay at Fairways Inn of Naples in Naples (Palm River Estates), you'll be a 4-minute drive from North Collier Regional Park and 6 minutes from Mercato.
Pool
Breakfast included
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.