Cheap Vacations in Little Gasparilla Island

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Little Gasparilla Island vacations

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 $1,183, price is now $840 per person
$840
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Bellasera Resort

Bellasera Resort

4 out of 5
Old Naples
Save 100% on your flight
Price was $1,368, price is now $867 per person
$867
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $3,787,839, price is now $2,406,971 per person
$2,406,971
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront

3 out of 5
Save 100% on your flight
Price was $1,670, price is now $1,077 per person
$1,077
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $2,424, price is now $1,648 per person
$1,648
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Windward Passage Resort

Windward Passage Resort

2 out of 5
Save 100% on your flight
Price was $1,555, price is now $1,058 per person
$1,058
per person
Nov 19 - Nov 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

4 out of 5
Save 100% on your flight
Price was $1,298, price is now $894 per person
$894
per person
Nov 19 - Nov 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Lighthouse Resort and Club

Lighthouse Resort and Club

4 out of 5
East End
Save 100% on your flight
Price was $1,725, price is now $1,237 per person
$1,237
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Punta Rassa
Save 100% on your flight
Price was $1,456, price is now $1,069 per person
$1,069
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
The Suites at Fishermen’s Village

The Suites at Fishermen’s Village

3 out of 5
Punta Gorda Isles
Save 100% on your flight
Price was $1,519, price is now $1,123 per person
$1,123
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

3-night Little Gasparilla Island vacations

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Hotel & Suites Fort Myers East - The Forum by IHG

Holiday Inn Express Hotel & Suites Fort Myers East - The Forum by IHG

2.5 out of 5
Price was $512, price is now $436 per person
$436
per person
Dec 3 - Dec 6
found 1 day 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 $1,183, price is now $840 per person
$840
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Bellasera Resort

Bellasera Resort

4 out of 5
Price was $1,456, price is now $1,041 per person
$1,041
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

4 out of 5
Price was $617, price is now $450 per person
$450
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Lighthouse Resort and Club

Lighthouse Resort and Club

4 out of 5
Save 100% on your flight
Price was $840, price is now $630 per person
$630
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $759, price is now $575 per person
$575
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront

3 out of 5
Price was $880, price is now $696 per person
$696
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
The Lighthouse Resort Inn & Suites

The Lighthouse Resort Inn & Suites

3 out of 5
Price was $1,531, price is now $1,217 per person
$1,217
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Landing Furnished Apartments minutes from Downtown Fort Myers

Landing Furnished Apartments minutes from Downtown Fort Myers

3 out of 5
Price was $721, price is now $593 per person
$593
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Landing Apartments Fort Myers near Eastwood Village

Landing Apartments Fort Myers near Eastwood Village

3 out of 5
Price was $673, price is now $563 per person
$563
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Lanai & Light by Avantstay Naples Park Retreat Private Pool + Lanai Near Vanderbilt Beach

Lanai & Light by Avantstay Naples Park Retreat Private Pool + Lanai Near Vanderbilt Beach

3 out of 5
Price was $924, price is now $781 per person
$781
per person
Dec 3 - Dec 6
found 13 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Landing Fort Myers Near Highland Pines

Landing Fort Myers Near Highland Pines

4 out of 5
Price was $587, price is now $499 per person
$499
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)

4-night Little Gasparilla Island vacations

Price found within the past 48 hours. Click for updated prices.
The Lighthouse Resort Inn & Suites

The Lighthouse Resort Inn & Suites

3 out of 5
Price was $692, price is now $555 per person
$555
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Bellasera Resort

Bellasera Resort

4 out of 5
Save 100% on your flight
Price was $1,368, price is now $867 per person
$867
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront

3 out of 5
Save 100% on your flight
Price was $968, price is now $690 per person
$690
per person
Dec 4 - Dec 8
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was $800, price is now $571 per person
$571
per person
Nov 30 - Dec 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Windward Passage Resort

Windward Passage Resort

2 out of 5
Price was $1,147, price is now $840 per person
$840
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Price was $1,054, price is now $813 per person
$813
per person
Nov 19 - Nov 23
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Price was $1,006, price is now $783 per person
$783
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Lighthouse Resort and Club

Lighthouse Resort and Club

4 out of 5
Price was $1,258, price is now $981 per person
$981
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Fort Myers (RSW)
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
Price was $883, price is now $702 per person
$702
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Price was $1,231, price is now $1,004 per person
$1,004
per person
Nov 19 - Nov 23
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Edison Beach House

Edison Beach House

3.5 out of 5
Price was $1,013, price is now $827 per person
$827
per person
Nov 28 - Dec 2
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
Price was $2,031, price is now $1,671 per person
$1,671
per person
Nov 19 - Nov 23
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Myers (RSW)

5-night Little Gasparilla Island vacations

Price found within the past 48 hours. Click for updated prices.
Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

4 out of 5
Price was $593, price is now $471 per person
$471
per person
Dec 1 - Dec 6
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Lighthouse Resort and Club

Lighthouse Resort and Club

4 out of 5
Save 100% on your flight
Price was $1,344, price is now $1,005 per person
$1,005
per person
Dec 5 - Dec 10
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Latitude 26 Waterfront Resort & Marina

Latitude 26 Waterfront Resort & Marina

3 out of 5
Price was $788, price is now $630 per person
$630
per person
Nov 16 - Nov 21
found 1 day ago
Roundtrip flight included
Milwaukee (MKE) to Fort Myers (RSW)
GullWing Beach Resort

GullWing Beach Resort

3.5 out of 5
Price was $1,131, price is now $922 per person
$922
per person
Nov 16 - Nov 21
found 11 hours ago
Roundtrip flight included
Milwaukee (MKE) to Fort Myers (RSW)
Landing Fort Myers Near Highland Pines

Landing Fort Myers Near Highland Pines

4 out of 5
Price was $826, price is now $683 per person
$683
per person
Nov 16 - Nov 21
found 1 day ago
Roundtrip flight included
Milwaukee (MKE) to Fort Myers (RSW)
Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Price was $1,279, price is now $1,059 per person
$1,059
per person
Dec 5 - Dec 10
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Holiday Inn Express Hotel & Suites Fort Myers East - The Forum by IHG

Holiday Inn Express Hotel & Suites Fort Myers East - The Forum by IHG

2.5 out of 5
Price was $750, price is now $627 per person
$627
per person
Nov 16 - Nov 21
found 11 hours ago
Roundtrip flight included
Milwaukee (MKE) to Fort Myers (RSW)
Edison Beach House

Edison Beach House

3.5 out of 5
Price was $1,040, price is now $873 per person
$873
per person
Dec 5 - Dec 10
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Landing Palmetto Apartments

Landing Palmetto Apartments

4.5 out of 5
Price was $920, price is now $785 per person
$785
per person
Nov 19 - Nov 24
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Pointe Estero Beach Resort

Pointe Estero Beach Resort

2 out of 5
Price was $1,050, price is now $913 per person
$913
per person
Dec 5 - Dec 10
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Sanibel Inn

Sanibel Inn

3 out of 5
Price was $1,309, price is now $1,147 per person
$1,147
per person
Dec 5 - Dec 10
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Landing Fort Myers - Eastwood Village

Landing Fort Myers - Eastwood Village

4.5 out of 5
Price was $866, price is now $763 per person
$763
per person
Nov 16 - Nov 21
found 11 hours ago
Roundtrip flight included
Milwaukee (MKE) to Fort Myers (RSW)

6-7 night Little Gasparilla Island vacations

Price found within the past 48 hours. Click for updated prices.
Wiggins Pass Chalet

Wiggins Pass Chalet

4 out of 5
Save 100% on your flight
Price was $1,070, price is now $770 per person
$770
per person
Dec 4 - Dec 10
found 1 day 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 $1,338, price is now $811 per person
$811
per person
Dec 4 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $3,787,839, price is now $2,406,971 per person
$2,406,971
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront

3 out of 5
Save 100% on your flight
Price was $1,670, price is now $1,077 per person
$1,077
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Bellasera Resort

Bellasera Resort

4 out of 5
Save 100% on your flight
Price was $1,822, price is now $1,219 per person
$1,219
per person
Nov 19 - Nov 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $2,424, price is now $1,648 per person
$1,648
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Windward Passage Resort

Windward Passage Resort

2 out of 5
Save 100% on your flight
Price was $1,555, price is now $1,058 per person
$1,058
per person
Nov 19 - Nov 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

4 out of 5
Save 100% on your flight
Price was $1,298, price is now $894 per person
$894
per person
Nov 19 - Nov 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Lighthouse Resort and Club

Lighthouse Resort and Club

4 out of 5
Save 100% on your flight
Price was $1,725, price is now $1,237 per person
$1,237
per person
Nov 28 - Dec 5
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 $2,806, price is now $2,023 per person
$2,023
per person
Dec 4 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Save 100% on your flight
Price was $1,456, price is now $1,069 per person
$1,069
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
The Suites at Fishermen’s Village

The Suites at Fishermen’s Village

3 out of 5
Save 100% on your flight
Price was $1,519, price is now $1,123 per person
$1,123
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

Flight deals to Little Gasparilla Island

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

Fri, Jan 8 - Sat, Jan 9
DTW
Detroit
RSW
Fort Myers
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Jan 8 from Detroit to Fort Myers, returning Sat, Jan 9, priced at $98 found 2 days ago
Mon, Feb 1 - Fri, Feb 5
BOS
Boston
SRQ
Sarasota
$150 Roundtrip, found 1 day ago
$150
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Mon, Feb 1 from Boston to Sarasota, returning Fri, Feb 5, priced at $150 found 1 day ago
Fri, May 14 - Mon, May 17
TTN
Trenton
PGD
Punta Gorda
$170 Roundtrip, found 11 hours ago
$170
Roundtrip
found 11 hours ago
Select Allegiant Air flight, departing Fri, May 14 from Trenton to Punta Gorda, returning Mon, May 17, priced at $170 found 11 hours ago

Top rated hotels for your Little Gasparilla Island vacation

Dream Beach House, steps to the Beach and beautiful Sunsets

Dream Beach House, steps to the Beach and beautiful Sunsets

Placida FL
0.66 mi from city center
Get rates
With a stay at this vacation home in Placida, you'll be a 1-minute walk from Little Gasparilla Island Beach and 8 minutes by foot from Don Pedro Island State Park.
Kitchen
Washer
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
16.35 mi from city center
$146 nightly
The price is $163 total per night
$163 total
Oct 29 - Oct 30
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

The Suites at Fishermen’s Village

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
$175 nightly
The price is $196 total per night
$196 total
Oct 30 - Oct 31
Total with taxes and fees
With a stay at The Suites at Fishermen’s Village in Punta Gorda (Punta Gorda Isles), you'll be steps from Peace River and Military Heritage Museum.
Pool
Kitchen
Don't see what you're looking for?
See all available properties in Little Gasparilla Island
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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.

Top Picks

^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.