Cheap Vacations in Keewaydin Island

Choose two or more items and save on your trip:

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
Save 100% on your flight
Price was $412, price is now $216 per person
$216
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was $674, price is now $316 per person
$316
per person
Jan 18 - Jan 21
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
Price was $486, price is now $231 per person
$231
per person
Jan 18 - Jan 21
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 $1,111, price is now $626 per person
$626
per person
Jan 24 - Jan 27
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 $2,308, price is now $1,341 per person
$1,341
per person
Jan 18 - Jan 21
found 1 day 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 $731, price is now $432 per person
$432
per person
Jan 24 - Jan 27
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
Save 100% on your flight
Price was $569, price is now $357 per person
$357
per person
Jan 18 - Jan 21
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 $636, price is now $423 per person
$423
per person
Jan 24 - Jan 27
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)
Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Save 100% on your flight
Price was $952, price is now $660 per person
$660
per person
Jan 18 - Jan 21
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 $1,329, price is now $947 per person
$947
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip 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 $492, price is now $353 per person
$353
per person
Jan 24 - Jan 27
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 $585, price is now $319 per person
$319
per person
Feb 1 - Feb 5
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 $691, price is now $339 per person
$339
per person
Feb 1 - Feb 5
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 $985, price is now $562 per person
$562
per person
Jan 23 - Jan 27
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 $2,509, price is now $1,435 per person
$1,435
per person
Jan 23 - Jan 27
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 $686, price is now $405 per person
$405
per person
Feb 1 - Feb 5
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 $966, price is now $601 per person
$601
per person
Jan 23 - Jan 27
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
Save 100% on your flight
Price was $822, price is now $524 per person
$524
per person
Feb 1 - Feb 5
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 $1,386, price is now $964 per person
$964
per person
Feb 8 - Feb 12
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 $1,784, price is now $1,241 per person
$1,241
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip 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 $627, price is now $437 per person
$437
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
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 $586, price is now $409 per person
$409
per person
Feb 1 - Feb 5
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.
Staybridge Suites Naples – Marco Island by IHG

Staybridge Suites Naples – Marco Island by IHG

3 out of 5
Price was $919, price is now $689 per person
$689
per person
Jan 16 - Jan 21
found 20 hours 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 $1,943, price is now $1,070 per person
$1,070
per person
Feb 2 - Feb 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Marco Beach Ocean Suites

Marco Beach Ocean Suites

2 out of 5
Save 100% on your flight
Price was $1,600, price is now $1,207 per person
$1,207
per person
Jan 16 - Jan 21
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
GreenLinks Golf Villas at Lely Resort

GreenLinks Golf Villas at Lely Resort

3 out of 5
Save 100% on your flight
Price was $1,157, price is now $877 per person
$877
per person
Jan 16 - Jan 21
found 20 hours 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 $3,763, price is now $2,887 per person
$2,887
per person
Jan 15 - Jan 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
Great Wolf Lodge Naples

Great Wolf Lodge Naples

2.5 out of 5
Save 100% on your flight
Price was $1,154, price is now $894 per person
$894
per person
Jan 16 - Jan 21
found 20 hours ago
Roundtrip non-stop 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 $1,393, price is now $1,079 per person
$1,079
per person
Jan 15 - Jan 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
Compass by Margaritaville Hotel Naples

Compass by Margaritaville Hotel Naples

4 out of 5
Price was $1,048, price is now $814 per person
$814
per person
Jan 16 - Jan 21
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Home2 Suites Naples I-75 Pine Ridge Road, FL

Home2 Suites Naples I-75 Pine Ridge Road, FL

3 out of 5
Price was $961, price is now $751 per person
$751
per person
Jan 16 - Jan 21
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Olde Marco Island Inn and Suites

Olde Marco Island Inn and Suites

3 out of 5
Save 100% on your flight
Price was $1,321, price is now $1,033 per person
$1,033
per person
Jan 16 - Jan 21
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Park Shore Resort

Park Shore Resort

3 out of 5
Save 100% on your flight
Price was $1,422, price is now $1,114 per person
$1,114
per person
Jan 16 - Jan 21
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)

6-7 night Keewaydin Island vacations

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
Price was $922, price is now $421 per person
$421
per person
Jan 18 - Jan 24
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
Price was $929, price is now $452 per person
$452
per person
Jan 18 - Jan 24
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 $1,680, price is now $901 per person
$901
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Innovation Hotel

Innovation Hotel

4 out of 5
Price was $2,156, price is now $1,161 per person
$1,161
per person
Jan 31 - Feb 6
found 20 hours 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 $1,874, price is now $1,050 per person
$1,050
per person
Jan 29 - Feb 4
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 $4,158, price is now $2,358 per person
$2,358
per person
Jan 18 - Jan 24
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 $1,122, price is now $690 per person
$690
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Home2 Suites Naples I-75 Pine Ridge Road, FL

Home2 Suites Naples I-75 Pine Ridge Road, FL

3 out of 5
Save 100% on your flight
Price was $1,048, price is now $648 per person
$648
per person
Jan 25 - Feb 1
found 1 day ago
Roundtrip 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 $1,153, price is now $729 per person
$729
per person
Jan 25 - Feb 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Southseas

Southseas

3 out of 5
Save 100% on your flight
Price was $3,626, price is now $2,295 per person
$2,295
per person
Jan 25 - Feb 1
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 $4,883, price is now $3,133 per person
$3,133
per person
Jan 25 - Feb 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Hilton Garden Inn Fort Myers Airport/FGCU

Hilton Garden Inn Fort Myers Airport/FGCU

3 out of 5
Save 100% on your flight
Price was $996, price is now $649 per person
$649
per person
Jan 18 - Jan 24
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 10 - Tue, Jan 13
ORD
Chicago
RSW
Fort Myers
$70 Roundtrip, found 19 hours ago
$70
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sat, Jan 10 from Chicago to Fort Myers, returning Tue, Jan 13, priced at $70 found 19 hours ago
Wed, Feb 25 - Fri, Feb 27
DTW
Detroit
RSW
Fort Myers
$90 Roundtrip, found 3 days ago
$90
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Feb 25 from Detroit to Fort Myers, returning Fri, Feb 27, priced at $90 found 3 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 4 - Jan 5, 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.
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.
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
Don't see what you're looking for?
See all available properties in Keewaydin Island
View all properties
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.