Cheap Vacations in Sanibel Captiva Island

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Sanibel Captiva Island vacations

Price found within the past 48 hours. Click for updated prices.
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Punta Rassa
Price was $676, price is now $526 per person
$526
per person
Dec 10 - Dec 13
found 2 days ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Landing Apartments Fort Myers near Eastwood Village

Landing Apartments Fort Myers near Eastwood Village

3 out of 5
Save 100% on your flight
Price was $1,056, price is now $762 per person
$762
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Landing Apartments Fort Myers - River District

Landing Apartments Fort Myers - River District

4 out of 5
Fort Myers River District
Save 100% on your flight
Price was $873, price is now $652 per person
$652
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 $934, price is now $698 per person
$698
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
The Lighthouse Resort Inn & Suites

The Lighthouse Resort Inn & Suites

3 out of 5
Price was $831, price is now $625 per person
$625
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was $1,261, price is now $949 per person
$949
per person
Dec 16 - Dec 20
found 22 hours ago
Roundtrip flight included
Syracuse (SYR) to Fort Myers (RSW)
Casa Playa Beach Resort

Casa Playa Beach Resort

2.5 out of 5
Save 100% on your flight
Price was $1,236, price is now $969 per person
$969
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
GullWing Beach Resort

GullWing Beach Resort

3.5 out of 5
South Island
Save 100% on your flight
Price was $1,328, price is now $1,047 per person
$1,047
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Punta Rassa
Price was $1,238, price is now $977 per person
$977
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Windward Passage Resort

Windward Passage Resort

2 out of 5
Save 100% on your flight
Price was $1,226, price is now $973 per person
$973
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)

3-night Sanibel Captiva Island vacations

Price found within the past 48 hours. Click for updated prices.
Candlewood Suites Fort Myers Sanibel Gateway by IHG

Candlewood Suites Fort Myers Sanibel Gateway by IHG

3 out of 5
Price was $384, price is now $311 per person
$311
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Price was $676, price is now $526 per person
$526
per person
Dec 10 - Dec 13
found 2 days 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 $463, price is now $368 per person
$368
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Landing Apartments Fort Myers near Eastwood Village

Landing Apartments Fort Myers near Eastwood Village

3 out of 5
Price was $605, price is now $497 per person
$497
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Casa Playa Beach Resort

Casa Playa Beach Resort

2.5 out of 5
Price was $658, price is now $545 per person
$545
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Hampton Inn Fort Myers-Airport & I-75

Hampton Inn Fort Myers-Airport & I-75

3.5 out of 5
Price was $486, price is now $403 per person
$403
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Allure Suites

Allure Suites

3 out of 5
Price was $397, price is now $330 per person
$330
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Landing Apartments Fort Myers near Olympia Pointe

Landing Apartments Fort Myers near Olympia Pointe

4 out of 5
Price was $603, price is now $502 per person
$502
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Holiday Inn Express Cape Coral-Fort Myers Area by IHG

Holiday Inn Express Cape Coral-Fort Myers Area by IHG

2.5 out of 5
Price was $450, price is now $375 per person
$375
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Lovers Key Resort

Lovers Key Resort

3 out of 5
Price was $537, price is now $455 per person
$455
per person
Dec 4 - Dec 7
found 1 day 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 $498, price is now $423 per person
$423
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
Price was $699, price is now $597 per person
$597
per person
Dec 17 - Dec 20
found 1 hour ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)

4-night Sanibel Captiva Island vacations

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Fort Myers-Airport & I-75

Hampton Inn Fort Myers-Airport & I-75

3.5 out of 5
Price was $598, price is now $517 per person
$517
per person
Dec 16 - Dec 20
found 22 hours ago
Roundtrip flight included
Syracuse (SYR) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was $1,261, price is now $949 per person
$949
per person
Dec 16 - Dec 20
found 22 hours ago
Roundtrip flight included
Syracuse (SYR) to Fort Myers (RSW)
Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Price was $1,238, price is now $977 per person
$977
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 $846, price is now $687 per person
$687
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 $690, price is now $575 per person
$575
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Bayfront Inn Fifth Avenue

Bayfront Inn Fifth Avenue

3.5 out of 5
Price was $993, price is now $833 per person
$833
per person
Dec 8 - Dec 12
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Price was $1,443, price is now $1,211 per person
$1,211
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
Price was $981, price is now $831 per person
$831
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Pointe Estero Beach Resort

Pointe Estero Beach Resort

2 out of 5
Price was $2,298, price is now $1,962 per person
$1,962
per person
Nov 25 - Nov 29
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
La Quinta Inn & Suites by Wyndham Naples Downtown

La Quinta Inn & Suites by Wyndham Naples Downtown

3 out of 5
Price was $637, price is now $551 per person
$551
per person
Dec 8 - Dec 12
found 15 hours ago
Roundtrip flight included
Chicago (ORD) 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 $879, price is now $773 per person
$773
per person
Dec 8 - Dec 12
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Sanibel Inn

Sanibel Inn

3 out of 5
Price was $2,041, price is now $1,800 per person
$1,800
per person
Nov 25 - Nov 29
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)

5-night Sanibel Captiva Island vacations

Price found within the past 48 hours. Click for updated prices.
Quality Inn Fort Myers Cape Coral

Quality Inn Fort Myers Cape Coral

2 out of 5
Price was $446, price is now $337 per person
$337
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 $934, price is now $761 per person
$761
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 $761, price is now $630 per person
$630
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Baymont by Wyndham Fort Myers Central

Baymont by Wyndham Fort Myers Central

2.5 out of 5
Price was $417, price is now $364 per person
$364
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Quality Inn & Suites Lehigh Acres Fort Myers

Quality Inn & Suites Lehigh Acres Fort Myers

2.5 out of 5
Price was $470, price is now $414 per person
$414
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
Price was $503, price is now $462 per person
$462
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Days Inn & Suites by Wyndham Fort Myers Near JetBlue Park

Days Inn & Suites by Wyndham Fort Myers Near JetBlue Park

2 out of 5
Price was $451, price is now $419 per person
$419
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Tollgate Inn

Tollgate Inn

2.5 out of 5
Price was $421, price is now $392 per person
$392
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Extended Stay America Premier Suites - Fort Myers - Airport

Extended Stay America Premier Suites - Fort Myers - Airport

2.5 out of 5
Price was $459, price is now $427 per person
$427
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Hyatt Place Fort Myers/at The Forum

Hyatt Place Fort Myers/at The Forum

3 out of 5
Price was $494, price is now $461 per person
$461
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was $821, price is now $782 per person
$782
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
The Westin Cape Coral Resort At Marina Village

The Westin Cape Coral Resort At Marina Village

4 out of 5
Price was $885, price is now $870 per person
$870
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)

6-7 night Sanibel Captiva Island vacations

Price found within the past 48 hours. Click for updated prices.
Quality Inn Fort Myers Cape Coral

Quality Inn Fort Myers Cape Coral

2 out of 5
Price was $547, price is now $375 per person
$375
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 $1,321, price is now $934 per person
$934
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Landing Apartments Fort Myers near Eastwood Village

Landing Apartments Fort Myers near Eastwood Village

3 out of 5
Save 100% on your flight
Price was $1,056, price is now $762 per person
$762
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Landing Apartments Fort Myers - River District

Landing Apartments Fort Myers - River District

4 out of 5
Save 100% on your flight
Price was $873, price is now $652 per person
$652
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 $934, price is now $698 per person
$698
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
The Lighthouse Resort Inn & Suites

The Lighthouse Resort Inn & Suites

3 out of 5
Price was $831, price is now $625 per person
$625
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Save 100% on your flight
Price was $1,690, price is now $1,277 per person
$1,277
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Casa Playa Beach Resort

Casa Playa Beach Resort

2.5 out of 5
Save 100% on your flight
Price was $1,236, price is now $969 per person
$969
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
GullWing Beach Resort

GullWing Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,328, price is now $1,047 per person
$1,047
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Windward Passage Resort

Windward Passage Resort

2 out of 5
Save 100% on your flight
Price was $1,226, price is now $973 per person
$973
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
The Bay Inn at Lani Kai

The Bay Inn at Lani Kai

3 out of 5
Price was $767, price is now $610 per person
$610
per person
Dec 10 - Dec 17
found 1 day 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 $877, price is now $700 per person
$700
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)

Flight deals to Sanibel Captiva 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
$110 Roundtrip, found 18 hours ago
$110
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Fri, Jan 8 from Detroit to Fort Myers, returning Sat, Jan 9, priced at $110 found 18 hours ago
Mon, Dec 7 - Mon, Dec 14
ORD
Chicago
RSW
Fort Myers
$118 Roundtrip, found 16 hours ago
$118
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Mon, Dec 7 from Chicago to Fort Myers, returning Mon, Dec 14, priced at $118 found 16 hours ago
Fri, Dec 18 - Fri, Jan 8
PHL
Philadelphia
RSW
Fort Myers
$125 Roundtrip, found 20 hours ago
$125
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Fri, Dec 18 from Philadelphia to Fort Myers, returning Fri, Jan 8, priced at $125 found 20 hours ago

Top rated hotels for your Sanibel Captiva Island vacation

Sanibel Island Beach Resort

Sanibel Island Beach Resort

3 out of 5
1231 Middle Gulf Dr Sanibel FL
Free Cancellation
Reserve now, pay when you stay
4.03 mi from city center
$204 nightly
The price is $227 total per night
$227 total
Oct 26 - Oct 27
Total with taxes and fees
Located in Sanibel (Mid Island), Sanibel Island Beach Resort is within a 5-minute walk of Sanibel Island Southern Beach and within 5 minutes by car from Sanibel Island Northern Beach.
Pool
Pet friendly
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
15951 Captiva Drive Captiva FL
Free Cancellation
Reserve now, pay when you stay
6.65 mi from city center
$372 nightly
The price is $415 total per night
$415 total
Nov 23 - Nov 24
Total with taxes and fees
When you stay at Tween Waters Island Resort & Spa in Captiva, you'll be near the bay, within a 15-minute drive of Bowman's Beach and Sanibel Island Southern Beach.
On private beach
Pool
Sundial Beach Resort & Spa

Sundial Beach Resort & Spa

5 out of 5
1451 Middle Gulf Drive Sanibel FL
3.75 mi from city center
$416 nightly
The price is $464 total per night
$464 total
Oct 26 - Oct 27
Total with taxes and fees
Located in Sanibel (Mid Island), Sundial Beach Resort & Spa is within a 10-minute drive of Dunes Golf and Tennis Club and BIG Arts Center.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Sanibel Captiva 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.