Cheap Vacations in Captiva Island

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3-night 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 $391, price is now $312 per person
$312
per person
Sep 1 - Sep 4
found 19 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Fort Myers (RSW)
Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $953, price is now $564 per person
$564
per person
Sep 10 - Sep 13
found 2 hours ago
Roundtrip flight included
Columbus (CMH) 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 $932, price is now $570 per person
$570
per person
Sep 10 - Sep 13
found 2 hours ago
Roundtrip flight included
Columbus (CMH) 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 $762, price is now $511 per person
$511
per person
Sep 10 - Sep 13
found 2 hours ago
Roundtrip flight included
Columbus (CMH) to Fort Myers (RSW)
GullWing Beach Resort

GullWing Beach Resort

3.5 out of 5
Price was $819, price is now $599 per person
$599
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was $890, price is now $666 per person
$666
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Fort Myers (RSW)
Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Price was $1,044, price is now $796 per person
$796
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) 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 $570, price is now $440 per person
$440
per person
Sep 10 - Sep 13
found 2 hours ago
Roundtrip flight included
Columbus (CMH) 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 $698, price is now $542 per person
$542
per person
Sep 10 - Sep 13
found 2 hours ago
Roundtrip flight included
Columbus (CMH) to Fort Myers (RSW)
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Price was $700, price is now $547 per person
$547
per person
Sep 10 - Sep 13
found 2 hours ago
Roundtrip flight included
Columbus (CMH) to Fort Myers (RSW)
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Price was $636, price is now $502 per person
$502
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Fort Myers (RSW)
Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina

4 out of 5
Price was $719, price is now $577 per person
$577
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)

4-night Captiva 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
Price was $664, price is now $507 per person
$507
per person
Aug 20 - Aug 24
found 6 hours ago
Roundtrip flight included
Columbus (CMH) to Fort Myers (RSW)
Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $1,099, price is now $609 per person
$609
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 $1,350, price is now $874 per person
$874
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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 $5,157, price is now $3,813 per person
$3,813
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop 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 $897, price is now $670 per person
$670
per person
Aug 31 - Sep 4
found 1 day ago
Roundtrip flight included
New York (LGA) to Fort Myers (RSW)
Marco Beach Ocean Suites

Marco Beach Ocean Suites

2 out of 5
Save 100% on your flight
Price was $1,919, price is now $1,440 per person
$1,440
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Fort Myers (RSW)
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Price was $781, price is now $592 per person
$592
per person
Aug 19 - Aug 23
found 3 hours ago
Roundtrip flight included
New York (LGA) 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 $806, price is now $612 per person
$612
per person
Aug 31 - Sep 4
found 1 day ago
Roundtrip flight included
New York (LGA) to Fort Myers (RSW)
Inn on Fifth

Inn on Fifth

4 out of 5
Price was $1,137, price is now $876 per person
$876
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Fort Myers (RSW)
Bellasera Resort

Bellasera Resort

4 out of 5
Price was $1,153, price is now $897 per person
$897
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Fort Myers (RSW)
The Lighthouse Resort Inn & Suites

The Lighthouse Resort Inn & Suites

3 out of 5
Price was $730, price is now $581 per person
$581
per person
Aug 20 - Aug 24
found 6 hours ago
Roundtrip flight included
Columbus (CMH) to Fort Myers (RSW)
Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Price was $1,295, price is now $1,034 per person
$1,034
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Fort Myers (RSW)

5-night Captiva Island vacations

Price found within the past 48 hours. Click for updated prices.
Bayfront Inn Fifth Avenue

Bayfront Inn Fifth Avenue

3.5 out of 5
Price was $643, price is now $499 per person
$499
per person
Aug 17 - Aug 22
found 4 hours ago
Roundtrip non-stop flight included
Columbus (CMH) to Fort Myers (RSW)
Walk to Beach, Pool+hot Tub, Game Room Captiva 5bdr Coco Mango by Avantstay

Walk to Beach, Pool+hot Tub, Game Room Captiva 5bdr Coco Mango by Avantstay

3 out of 5
Save 100% on your flight
Price was $4,376, price is now $3,314 per person
$3,314
per person
Sep 1 - Sep 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 $1,661, price is now $985 per person
$985
per person
Aug 17 - Aug 22
found 4 hours ago
Roundtrip non-stop flight included
Columbus (CMH) to Fort Myers (RSW)
Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $1,335, price is now $813 per person
$813
per person
Aug 23 - Aug 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Fort Myers (RSW)
Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Save 100% on your flight
Price was $1,166, price is now $772 per person
$772
per person
Sep 6 - Sep 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
A Wave From it All

A Wave From it All

2 out of 5
Save 100% on your flight
Price was $2,432, price is now $1,616 per person
$1,616
per person
Aug 17 - Aug 22
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 $1,273, price is now $882 per person
$882
per person
Aug 17 - Aug 22
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 $749, price is now $531 per person
$531
per person
Aug 17 - Aug 22
found 4 hours ago
Roundtrip non-stop flight included
Columbus (CMH) 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 $1,302, price is now $945 per person
$945
per person
Aug 26 - Aug 31
found 1 hour ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Inn on Fifth

Inn on Fifth

4 out of 5
Save 100% on your flight
Price was $1,232, price is now $903 per person
$903
per person
Aug 17 - Aug 22
found 4 hours ago
Roundtrip non-stop flight included
Columbus (CMH) to Fort Myers (RSW)
Windward Passage Resort

Windward Passage Resort

2 out of 5
Save 100% on your flight
Price was $1,202, price is now $888 per person
$888
per person
Aug 26 - Aug 31
found 1 hour ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Landing Apartments near North Fort Myers

Landing Apartments near North Fort Myers

4 out of 5
Save 100% on your flight
Price was $807, price is now $602 per person
$602
per person
Sep 6 - Sep 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)

6-7 night 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 $519, price is now $332 per person
$332
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip flight included
New York (LGA) to Fort Myers (RSW)
A Wave From it All

A Wave From it All

2 out of 5
Save 100% on your flight
Price was $3,035, price is now $1,904 per person
$1,904
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip flight included
New York (LGA) to Fort Myers (RSW)
Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Save 100% on your flight
Price was $1,714, price is now $1,121 per person
$1,121
per person
Aug 25 - Sep 1
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
Save 100% on your flight
Price was $1,002, price is now $690 per person
$690
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip flight included
New York (LGA) to Fort Myers (RSW)
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Save 100% on your flight
Price was $1,242, price is now $896 per person
$896
per person
Aug 18 - Aug 25
found 24 hours 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 $948, price is now $691 per person
$691
per person
Aug 21 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Fort Myers (RSW)
Harbour House At The Inn

Harbour House At The Inn

3 out of 5
Save 100% on your flight
Price was $1,193, price is now $881 per person
$881
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip flight included
New York (LGA) to Fort Myers (RSW)
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
Save 100% on your flight
Price was $1,201, price is now $889 per person
$889
per person
Aug 18 - Aug 25
found 24 hours 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 $1,422, price is now $1,069 per person
$1,069
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip flight included
New York (LGA) to Fort Myers (RSW)
The Lighthouse Resort Inn & Suites

The Lighthouse Resort Inn & Suites

3 out of 5
Save 100% on your flight
Price was $956, price is now $721 per person
$721
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip flight included
New York (LGA) to Fort Myers (RSW)
Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
Price was $1,095, price is now $832 per person
$832
per person
Aug 21 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Fort Myers (RSW)
Landing Apartments Fort Myers near Eastwood Village

Landing Apartments Fort Myers near Eastwood Village

3 out of 5
Price was $876, price is now $667 per person
$667
per person
Aug 21 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Fort Myers (RSW)

Flight deals to Captiva Island

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

Sun, Sep 6 - Fri, Sep 11
PHL
Philadelphia
RSW
Fort Myers
$108 Roundtrip, found 11 hours ago
$108
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Sun, Sep 6 from Philadelphia to Fort Myers, returning Fri, Sep 11, priced at $108 found 11 hours ago
Wed, Sep 30 - Tue, Oct 6
CLE
Cleveland
RSW
Fort Myers
$148 Roundtrip, found 6 days ago
$148
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Sep 30 from Cleveland to Fort Myers, returning Tue, Oct 6, priced at $148 found 6 days ago
Sat, Dec 5 - Wed, Dec 9
PSM
Portsmouth
RSW
Fort Myers
$152 Roundtrip, found 2 days ago
$152
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Dec 5 from Portsmouth to Fort Myers, returning Wed, Dec 9, priced at $152 found 2 days ago

Top rated hotels for your Captiva Island vacation

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
15951 Captiva Drive Captiva FL
1.33 mi from city center
$311 nightly
The price is $346 total per night
$346 total
Aug 2 - Aug 3
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 Sanibel Island Southern Beach and Bowman's Beach.
South Seas

South Seas

3.5 out of 5
5400 South Seas Plantation Rd Captiva FL
Free Cancellation
Reserve now, pay when you stay
0.19 mi from city center
$365 nightly
The price is $406 total per night
$406 total
Jul 19 - Jul 20
Total with taxes and fees
With a stay at South Seas in Captiva, you'll be within a 15-minute drive of Bowman's Beach and Alison Hagerup Beach Park.
2026 SUMMER REDUCED RATES!! WATERFRONT HOME, IN VILLAGE, POOL, HOT TUB, DOCK!

2026 SUMMER REDUCED RATES!! WATERFRONT HOME, IN VILLAGE, POOL, HOT TUB, DOCK!

Captiva Island FL
0.55 mi from city center
Get rates
With a stay at this vacation home in Captiva, you'll be on the waterfront, within a 15-minute drive of Bowman's Beach and McCarthy's Marina.
Pool
Hot Tub
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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.