Cheap Vacations in Little Gasparilla Island

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3-night Little Gasparilla 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
Save 100% on your flight
Price was $548, price is now $327 per person
$327
per person
Feb 5 - Feb 8
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 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 $1,728, price is now $1,036 per person
$1,036
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
Save 100% on your flight
Price was $1,539, price is now $936 per person
$936
per person
Jan 17 - Jan 20
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $798, price is now $511 per person
$511
per person
Jan 23 - Jan 26
found 1 day 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 $529, price is now $343 per person
$343
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
Save 100% on your flight
Price was $725, price is now $482 per person
$482
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Inn on Fifth

Inn on Fifth

4 out of 5
Save 100% on your flight
Price was $1,434, price is now $984 per person
$984
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $881, price is now $620 per person
$620
per person
Jan 17 - Jan 20
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
Price was $823, price is now $598 per person
$598
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Landing Fort Myers near Heritage Palms

Landing Fort Myers near Heritage Palms

4 out of 5
Price was $752, price is now $546 per person
$546
per person
Feb 2 - Feb 5
found 6 hours ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
Inn at the Beach

Inn at the Beach

3 out of 5
Save 100% on your flight
Price was $822, price is now $597 per person
$597
per person
Jan 29 - Feb 1
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)

4-night Little Gasparilla 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
Save 100% on your flight
Price was $627, price is now $348 per person
$348
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

3 out of 5
Save 100% on your flight
Price was $911, price is now $525 per person
$525
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
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 $609, price is now $354 per person
$354
per person
Jan 22 - Jan 26
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 $920, price is now $544 per person
$544
per person
Jan 22 - Jan 26
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 $2,210, price is now $1,312 per person
$1,312
per person
Jan 22 - Jan 26
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 $910, price is now $590 per person
$590
per person
Jan 17 - Jan 21
found 15 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 $2,074, price is now $1,428 per person
$1,428
per person
Jan 21 - Jan 25
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 $800, price is now $553 per person
$553
per person
Jan 22 - Jan 26
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 $576, price is now $399 per person
$399
per person
Feb 1 - Feb 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront

2 out of 5
Save 100% on your flight
Price was $2,178, price is now $1,528 per person
$1,528
per person
Feb 12 - Feb 16
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Bradenton Apartments by Landing

Bradenton Apartments by Landing

4.5 out of 5
Save 100% on your flight
Price was $1,128, price is now $793 per person
$793
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Landing Amazing Studio, Yoga Studio, Gym

Landing Amazing Studio, Yoga Studio, Gym

3 out of 5
Save 100% on your flight
Price was $765, price is now $539 per person
$539
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

5-night Little Gasparilla 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 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 $788, price is now $403 per person
$403
per person
Feb 2 - Feb 7
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 $1,064, price is now $565 per person
$565
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Fort Myers (RSW)
Innovation Hotel

Innovation Hotel

4 out of 5
Price was $1,781, price is now $965 per person
$965
per person
Feb 4 - Feb 9
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
Price was $2,928, price is now $1,604 per person
$1,604
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
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 1 day 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 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
Save 100% on your flight
Price was $1,133, price is now $677 per person
$677
per person
Jan 18 - Jan 23
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,304, price is now $806 per person
$806
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
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 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,254, price is now $814 per person
$814
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
Save 100% on your flight
Price was $1,203, price is now $793 per person
$793
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)

6-7 night Little Gasparilla 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
Save 100% on your flight
Price was $894, price is now $464 per person
$464
per person
Jan 19 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Delray House With Hot tub & Game Room

Delray House With Hot tub & Game Room

3.5 out of 5
Save 100% on your flight
Price was $1,343, price is now $603 per person
$603
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Innovation Hotel

Innovation Hotel

4 out of 5
Price was $2,138, price is now $1,146 per person
$1,146
per person
Jan 31 - Feb 6
found 16 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
Price was $2,183, price is now $1,182 per person
$1,182
per person
Jan 31 - Feb 6
found 16 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 $961, price is now $525 per person
$525
per person
Jan 19 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,675, price is now $944 per person
$944
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
South Seas Resort

South Seas Resort

3.5 out of 5
Save 100% on your flight
Price was $2,529, price is now $1,472 per person
$1,472
per person
Jan 27 - Feb 3
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 $3,923, price is now $2,308 per person
$2,308
per person
Jan 19 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
Save 100% on your flight
Price was $1,265, price is now $763 per person
$763
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
Save 100% on your flight
Price was $1,758, price is now $1,070 per person
$1,070
per person
Feb 6 - Feb 13
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
Price was $1,349, price is now $823 per person
$823
per person
Jan 19 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Venice Beach Villas

Venice Beach Villas

3 out of 5
Save 100% on your flight
Price was $1,051, price is now $649 per person
$649
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Sarasota (SRQ)

Flight deals to Little Gasparilla 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 1 day ago
$69
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jan 17 from Chicago to Fort Myers, returning Tue, Jan 20, priced at $69 found 1 day ago
Wed, Feb 25 - Fri, Feb 27
DTW
Detroit
RSW
Fort Myers
$90 Roundtrip, found 5 days ago
$90
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Feb 25 from Detroit to Fort Myers, returning Fri, Feb 27, priced at $90 found 5 days ago
Sat, Jan 24 - Sat, Jan 31
PHL
Philadelphia
RSW
Fort Myers
$100 Roundtrip, found 2 hours ago
$100
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Jan 24 from Philadelphia to Fort Myers, returning Sat, Jan 31, priced at $100 found 2 hours ago

Top rated hotels for your Little Gasparilla Island vacation

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
5500 Sunseeker Way Punta Gorda FL
Free Cancellation
Reserve now, pay when you stay
16.36 mi from city center
$182 nightly
The price is $204 total per night
$204 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
When you stay at Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton in Punta Gorda, you'll be next to a golf course, within a 5-minute drive of Fishermen's Village and Military Heritage Museum.
Pool
Hot Tub
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
1200 W Retta Esplanade Punta Gorda FL
Free Cancellation
Reserve now, pay when you stay
15.5 mi from city center
$210 nightly
The price is $235 total per night
$235 total
Dec 21 - Dec 22
Total with taxes and fees
With a stay at The Suites at Fishermen’s Village- 2 Bedroom Suites in Punta Gorda (Punta Gorda Isles), you'll be steps from Peace River and Military Heritage Museum.
Pool
Kitchen
Wyvern Hotel, an Ascend Collection Hotel

Wyvern Hotel, an Ascend Collection Hotel

4 out of 5
101 E Retta Esplanade Punta Gorda FL
Free Cancellation
16.5 mi from city center
$142 nightly
The price is $159 total per night
$159 total
Dec 21 - Dec 22
Total with taxes and fees
With a stay at Wyvern Hotel, an Ascend Collection Hotel, you'll be centrally located in Punta Gorda, just a 3-minute walk from Peace River and 5 minutes by foot from A. C. Freeman House.
Parking included
Free WiFi
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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.