Cheap Vacations in Captiva Island

Choose two or more items and save on your trip:

Captiva Island vacations

Price found within the past 48 hours. Click for updated prices.
South Seas Resort

South Seas Resort

3.5 out of 5
Save 100% on your flight
Price was $1,972, price is now $1,544 per person
$1,544
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

3-night Captiva Island vacations

Price found within the past 48 hours. Click for updated prices.
Best Western Naples Inn & Suites

Best Western Naples Inn & Suites

2.5 out of 5
Price was $450, price is now $352 per person
$352
per person
Apr 27 - Apr 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 $779, price is now $539 per person
$539
per person
May 1 - May 4
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 $1,163, price is now $813 per person
$813
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
The Boat House

The Boat House

2 out of 5
Save 100% on your flight
Price was $861, price is now $617 per person
$617
per person
Apr 27 - Apr 30
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 $875, price is now $635 per person
$635
per person
Apr 10 - Apr 13
found 1 day ago
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 $819, price is now $601 per person
$601
per person
Apr 27 - Apr 30
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 $769, price is now $569 per person
$569
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $725, price is now $541 per person
$541
per person
Apr 8 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Hilton Naples

Hilton Naples

4 out of 5
Price was $654, price is now $489 per person
$489
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Marco Beach Ocean Suites

Marco Beach Ocean Suites

2 out of 5
Save 100% on your flight
Price was $1,047, price is now $799 per person
$799
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Landing Furnished Apartments - Naples, FL

Landing Furnished Apartments - Naples, FL

3 out of 5
Price was $688, price is now $529 per person
$529
per person
Apr 27 - Apr 30
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 $1,334, price is now $1,035 per person
$1,035
per person
May 1 - May 4
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.
Lehigh Resort Club

Lehigh Resort Club

3.5 out of 5
Save 100% on your flight
Price was $498, price is now $356 per person
$356
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
DiamondHead Beach Resort

DiamondHead Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,363, price is now $964 per person
$964
per person
Apr 9 - Apr 13
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 $1,714, price is now $1,218 per person
$1,218
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Hilton Naples

Hilton Naples

4 out of 5
Save 100% on your flight
Price was $1,145, price is now $828 per person
$828
per person
Apr 16 - Apr 20
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 $1,136, price is now $823 per person
$823
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $681, price is now $495 per person
$495
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Save 100% on your flight
Price was $1,832, price is now $1,345 per person
$1,345
per person
Apr 9 - Apr 13
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 $1,046, price is now $770 per person
$770
per person
Apr 7 - Apr 11
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
Price was $1,088, price is now $810 per person
$810
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
The Boat House

The Boat House

2 out of 5
Price was $1,284, price is now $957 per person
$957
per person
Apr 16 - Apr 20
found 1 day 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
Price was $733, price is now $548 per person
$548
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Holiday Inn Express Hotel Naples Downtown - 5th Avenue

Holiday Inn Express Hotel Naples Downtown - 5th Avenue

2.5 out of 5
Price was $988, price is now $752 per person
$752
per person
Apr 16 - Apr 20
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.
Landing Apartments near North Fort Myers

Landing Apartments near North Fort Myers

4 out of 5
Price was $732, price is now $545 per person
$545
per person
Apr 22 - Apr 27
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 $1,144, price is now $644 per person
$644
per person
Apr 26 - May 1
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
Price was $1,381, price is now $806 per person
$806
per person
Apr 10 - Apr 15
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
The Boat House

The Boat House

2 out of 5
Save 100% on your flight
Price was $1,367, price is now $961 per person
$961
per person
Apr 26 - May 1
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 $2,074, price is now $1,458 per person
$1,458
per person
Apr 17 - Apr 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
GullWing Beach Resort

GullWing Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,204, price is now $883 per person
$883
per person
Apr 26 - May 1
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
Price was $1,378, price is now $1,018 per person
$1,018
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Hilton Naples

Hilton Naples

4 out of 5
Price was $1,467, price is now $1,091 per person
$1,091
per person
Apr 17 - Apr 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Lovers Key Resort

Lovers Key Resort

3 out of 5
Save 100% on your flight
Price was $923, price is now $686 per person
$686
per person
Apr 26 - May 1
found 1 day ago
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 $2,321, price is now $1,727 per person
$1,727
per person
Apr 17 - Apr 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
THE Palmview AND Sandpiper Inns

THE Palmview AND Sandpiper Inns

3.5 out of 5
Price was $1,027, price is now $766 per person
$766
per person
Apr 10 - Apr 15
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Mariners Boathouse by Coolvacay

Mariners Boathouse by Coolvacay

3 out of 5
Save 100% on your flight
Price was $1,159, price is now $875 per person
$875
per person
Apr 26 - May 1
found 1 day ago
Roundtrip 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.
Staybridge Suites Naples – Marco Island by IHG

Staybridge Suites Naples – Marco Island by IHG

3 out of 5
Price was $959, price is now $734 per person
$734
per person
Apr 25 - May 2
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 $2,064, price is now $1,358 per person
$1,358
per person
Apr 18 - Apr 25
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 $2,565, price is now $1,778 per person
$1,778
per person
Apr 25 - May 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
The Boat House

The Boat House

2 out of 5
Save 100% on your flight
Price was $1,927, price is now $1,350 per person
$1,350
per person
Apr 25 - May 2
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 $1,932, price is now $1,408 per person
$1,408
per person
Apr 9 - Apr 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Fort Myers (RSW)
Southseas

Southseas

3 out of 5
Save 100% on your flight
Price was $3,417, price is now $2,531 per person
$2,531
per person
Apr 12 - Apr 19
found 18 hours ago
Roundtrip flight included
Chicago (ORD) 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 $2,685, price is now $2,004 per person
$2,004
per person
Apr 18 - Apr 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Save 100% on your flight
Price was $2,948, price is now $2,202 per person
$2,202
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
GullWing Beach Resort

GullWing Beach Resort

3.5 out of 5
Price was $2,440, price is now $1,826 per person
$1,826
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Marco Beach Ocean Suites

Marco Beach Ocean Suites

2 out of 5
Save 100% on your flight
Price was $2,389, price is now $1,799 per person
$1,799
per person
Apr 25 - May 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Holiday Inn Express Hotel Naples Downtown - 5th Avenue

Holiday Inn Express Hotel Naples Downtown - 5th Avenue

2.5 out of 5
Price was $1,029, price is now $779 per person
$779
per person
Apr 25 - May 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Hilton Naples

Hilton Naples

4 out of 5
Price was $2,025, price is now $1,552 per person
$1,552
per person
Apr 18 - Apr 24
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.

Sun, Mar 22 - Wed, Mar 25
PHL
Philadelphia
RSW
Fort Myers
$80 Roundtrip, found 8 hours ago
$80
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sun, Mar 22 from Philadelphia to Fort Myers, returning Wed, Mar 25, priced at $80 found 8 hours ago
Thu, Apr 23 - Mon, Apr 27
ORD
Chicago
RSW
Fort Myers
$90 Roundtrip, found 3 days ago
$90
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Apr 23 from Chicago to Fort Myers, returning Mon, Apr 27, priced at $90 found 3 days ago
Sun, Apr 5 - Thu, Apr 9
BOS
Boston
RSW
Fort Myers
$102 Roundtrip, found 23 hours ago
$102
Roundtrip
found 23 hours ago
Select Spirit Airlines flight, departing Sun, Apr 5 from Boston to Fort Myers, returning Thu, Apr 9, priced at $102 found 23 hours 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
$486 nightly
The price is $542 total per night
$542 total
Apr 5 - Apr 6
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
$780 nightly
The price is $870 total per night
$870 total
Mar 25 - Mar 26
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
Beach Villa 2313, Upscale and Beautiful Beach Front Condo with Gorgeous Gulf

Beach Villa 2313, Upscale and Beautiful Beach Front Condo with Gorgeous Gulf

Captiva FL
0.11 mi from city center
Get rates
Located in Captiva, this vacation home is by the ocean, within a 15-minute walk of Alison Hagerup Beach Park and Jungle Drums.
Pool
Kitchen
Don't see what you're looking for?
See all available properties in Captiva Island
View all properties
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.