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.
Hyatt Place Fort Myers/at The Forum

Hyatt Place Fort Myers/at The Forum

3 out of 5
Price was $635, price is now $409 per person
$409
per person
Jan 16 - Jan 19
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 $866, price is now $497 per person
$497
per person
Jan 16 - Jan 19
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 5 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
Save 100% on your flight
Price was $1,425, price is now $847 per person
$847
per person
Feb 6 - Feb 9
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 $714, price is now $426 per person
$426
per person
Jan 16 - Jan 19
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)
Embassy Suites by Hilton Fort Myers Estero

Embassy Suites by Hilton Fort Myers Estero

3.5 out of 5
Price was $778, price is now $557 per person
$557
per person
Feb 6 - Feb 9
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 $2,074, price is now $1,512 per person
$1,512
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Pink Shell Beach Resort and Marina

Pink Shell Beach Resort and Marina

4 out of 5
Save 100% on your flight
Price was $1,336, price is now $976 per person
$976
per person
Feb 6 - Feb 9
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 $1,203, price is now $886 per person
$886
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Landing Amazing Studio, Yoga Studio, Gym

Landing Amazing Studio, Yoga Studio, Gym

3 out of 5
Save 100% on your flight
Price was $633, price is now $469 per person
$469
per person
Jan 23 - Jan 26
just found
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Hilton Marco Island Beach Resort and Spa

Hilton Marco Island Beach Resort and Spa

4 out of 5
Save 100% on your flight
Price was $956, price is now $711 per person
$711
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

4-night Captiva 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 $591, price is now $322 per person
$322
per person
Jan 26 - Jan 30
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 $669, price is now $331 per person
$331
per person
Jan 26 - Jan 30
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 $968, price is now $553 per person
$553
per person
Jan 26 - Jan 30
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 $603, price is now $373 per person
$373
per person
Jan 26 - Jan 30
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 $1,272, price is now $803 per person
$803
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Bellasera Resort

Bellasera Resort

4 out of 5
Save 100% on your flight
Price was $2,941, price is now $1,874 per person
$1,874
per person
Feb 6 - Feb 10
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 $2,917, price is now $1,890 per person
$1,890
per person
Feb 6 - Feb 10
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 $822, price is now $536 per person
$536
per person
Jan 26 - Jan 30
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 $3,388, price is now $2,300 per person
$2,300
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip non-stop 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 $927, price is now $631 per person
$631
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip non-stop 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 $948, price is now $653 per person
$653
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

5-night Captiva 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 5 hours 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 5 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
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 5 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 $701, price is now $411 per person
$411
per person
Feb 2 - Feb 7
found 5 hours 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 $3,540, price is now $2,271 per person
$2,271
per person
Feb 2 - Feb 7
found 5 hours ago
Roundtrip flight included
Boston (BOS) 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 $1,156, price is now $766 per person
$766
per person
Feb 2 - Feb 7
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Lehigh Resort Club

Lehigh Resort Club

2.5 out of 5
Save 100% on your flight
Price was $599, price is now $405 per person
$405
per person
Feb 2 - Feb 7
found 5 hours 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 $948, price is now $642 per person
$642
per person
Feb 2 - Feb 7
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Candlewood Suites Fort Myers Sanibel Gateway by IHG

Candlewood Suites Fort Myers Sanibel Gateway by IHG

3 out of 5
Save 100% on your flight
Price was $634, price is now $433 per person
$433
per person
Feb 2 - Feb 7
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Doubletree by Hilton Fort Myers at Bell Tower Shops

Doubletree by Hilton Fort Myers at Bell Tower Shops

4 out of 5
Save 100% on your flight
Price was $842, price is now $579 per person
$579
per person
Feb 2 - Feb 7
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Landing Apartments - Cape Coral

Landing Apartments - Cape Coral

4.5 out of 5
Save 100% on your flight
Price was $1,384, price is now $959 per person
$959
per person
Feb 2 - Feb 7
found 5 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 $2,323, price is now $1,613 per person
$1,613
per person
Jan 16 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)

6-7 night Captiva 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 $893, price is now $438 per person
$438
per person
Jan 21 - Jan 27
found 21 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 $926, price is now $495 per person
$495
per person
Jan 21 - Jan 27
found 21 hours ago
Roundtrip 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 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 $2,201, price is now $1,196 per person
$1,196
per person
Jan 31 - Feb 6
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 $1,874, 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)
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 $842, price is now $510 per person
$510
per person
Jan 21 - Jan 27
found 21 hours 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 $1,126, price is now $708 per person
$708
per person
Jan 28 - 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 $4,156, price is now $2,614 per person
$2,614
per person
Jan 31 - Feb 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Landing Amazing Studio, Yoga Studio, Gym

Landing Amazing Studio, Yoga Studio, Gym

3 out of 5
Save 100% on your flight
Price was $1,211, price is now $765 per person
$765
per person
Feb 2 - Feb 9
found 5 hours ago
Roundtrip flight included
Detroit (DTW) 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 $1,254, price is now $812 per person
$812
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Shell Island Beach Club

Shell Island Beach Club

4 out of 5
Save 100% on your flight
Price was $2,160, price is now $1,426 per person
$1,426
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
Lehigh Resort Club

Lehigh Resort Club

2.5 out of 5
Save 100% on your flight
Price was $695, price is now $462 per person
$462
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.

Sat, Jan 17 - Tue, Jan 20
ORD
Chicago
RSW
Fort Myers
$69 Roundtrip, found 7 hours ago
$69
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, Jan 17 from Chicago to Fort Myers, returning Tue, Jan 20, priced at $69 found 7 hours ago
Wed, Feb 25 - Fri, Feb 27
DTW
Detroit
RSW
Fort Myers
$90 Roundtrip, found 4 days ago
$90
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Feb 25 from Detroit to Fort Myers, returning Fri, Feb 27, priced at $90 found 4 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 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
$350 nightly
The price is $391 total per night
$391 total
Dec 21 - Dec 22
Total with taxes and fees
With a 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 Captiva Beach.
South Seas Resort

South Seas Resort

3.5 out of 5
5400 South Seas Plantation Rd Captiva FL
0.19 mi from city center
$542 nightly
The price is $598 total per night
$598 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
When you stay at South Seas Resort in Captiva, you'll be on the waterfront, within a 10-minute walk of Alison Hagerup Beach Park and Jungle Drums.
South Seas Bayside Villa 5130: Your Perfect Island Retreat

South Seas Bayside Villa 5130: Your Perfect Island Retreat

Captiva FL
0.35 mi from city center
Get rates
Located in Captiva, this vacation home is by the sea, within a 15-minute walk of Alison Hagerup Beach Park and Jungle Drums.
Pool
Hot Tub
Don't see what you're looking for?
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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.