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)
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 $4,230, price is now $3,384 per person
$3,384
per person
Feb 4 - Feb 7
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 7 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
found 2 hours 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 $628, price is now $346 per person
$346
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop 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 $684, price is now $346 per person
$346
per person
Jan 29 - Feb 2
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 $1,250, price is now $695 per person
$695
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop 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 $870 per person
$870
per person
Feb 6 - Feb 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 $1,361, price is now $823 per person
$823
per person
Jan 29 - Feb 2
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 $3,103, price is now $1,909 per person
$1,909
per person
Jan 16 - Jan 20
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 $646, price is now $403 per person
$403
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $955, price is now $628 per person
$628
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop 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 $2,125, price is now $1,421 per person
$1,421
per person
Jan 29 - Feb 2
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 $844, price is now $577 per person
$577
per person
Jan 29 - Feb 2
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 $982, price is now $681 per person
$681
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop 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 $1,387, price is now $966 per person
$966
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop 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 7 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 7 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 7 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 7 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 7 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 7 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 7 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 7 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 7 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 7 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 7 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 23 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
South Seas Resort

South Seas Resort

3.5 out of 5
Save 100% on your flight
Price was $1,950, price is now $1,035 per person
$1,035
per person
Feb 1 - Feb 7
found 2 days ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 23 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)
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
Price was $1,564, price is now $915 per person
$915
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 23 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 $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 7 hours ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
Country Inn & Suites by Radisson, Port Charlotte, FL

Country Inn & Suites by Radisson, Port Charlotte, FL

2.5 out of 5
Save 100% on your flight
Price was $723, price is now $469 per person
$469
per person
Feb 5 - Feb 12
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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)
Hilton Garden Inn Fort Myers Airport/FGCU

Hilton Garden Inn Fort Myers Airport/FGCU

3 out of 5
Save 100% on your flight
Price was $1,008, price is now $670 per person
$670
per person
Jan 31 - Feb 6
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 9 hours ago
$69
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Sat, Jan 17 from Chicago to Fort Myers, returning Tue, Jan 20, priced at $69 found 9 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.
On private beach
Pool
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.
On private beach
Pool
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?
See all available properties in 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.

^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.