Cheap Vacations in Sanibel Captiva Island

Choose two or more items and save on your trip:

Sanibel Captiva Island vacations

Price found within the past 48 hours. Click for updated prices.
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $1,660, price is now $913 per person
$913
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Mid Island
Save 100% on your flight
Price was $1,627, price is now $1,091 per person
$1,091
per person
Oct 2 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Lighthouse Resort and Club

Lighthouse Resort and Club

4 out of 5
East End
Save 100% on your flight
Price was $1,557, price is now $1,210 per person
$1,210
per person
Sep 26 - Oct 3
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)

3-night Sanibel Captiva Island vacations

Price found within the past 48 hours. Click for updated prices.
Windward Passage Resort

Windward Passage Resort

2 out of 5
Price was $702, price is now $576 per person
$576
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Price was $1,164, price is now $862 per person
$862
per person
Sep 25 - Sep 28
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was $948, price is now $703 per person
$703
per person
Oct 9 - Oct 12
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 $3,058, price is now $2,433 per person
$2,433
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Casa Playa Beach Resort

Casa Playa Beach Resort

2.5 out of 5
Price was $844, price is now $675 per person
$675
per person
Oct 16 - Oct 19
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
Price was $1,374, price is now $1,104 per person
$1,104
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Price was $1,132, price is now $917 per person
$917
per person
Oct 16 - Oct 19
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Blue Sunset by Avantstay Pool + Spa + Fire Table Near Beaches + Naples

Blue Sunset by Avantstay Pool + Spa + Fire Table Near Beaches + Naples

3 out of 5
Price was $1,712, price is now $1,419 per person
$1,419
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
The Lighthouse Resort Inn & Suites

The Lighthouse Resort Inn & Suites

3 out of 5
Price was $730, price is now $608 per person
$608
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Price was $873, price is now $742 per person
$742
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Price was $1,081, price is now $919 per person
$919
per person
Oct 15 - Oct 18
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 $680, price is now $588 per person
$588
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)

4-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 $550, price is now $441 per person
$441
per person
Oct 8 - Oct 12
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
Price was $1,135, price is now $795 per person
$795
per person
Oct 8 - Oct 12
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
Price was $1,303, price is now $946 per person
$946
per person
Oct 9 - Oct 13
found 21 hours 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 $1,256, price is now $921 per person
$921
per person
Oct 7 - Oct 11
found 17 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Fort Myers (RSW)
Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $1,336, price is now $980 per person
$980
per person
Oct 7 - Oct 11
found 20 hours ago
Roundtrip non-stop 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
Price was $884, price is now $650 per person
$650
per person
Oct 7 - Oct 11
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Wiggins Pass Chalet

Wiggins Pass Chalet

4 out of 5
Price was $624, price is now $475 per person
$475
per person
Oct 7 - Oct 11
found 17 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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 $1,038, price is now $794 per person
$794
per person
Oct 7 - Oct 11
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 $996, price is now $785 per person
$785
per person
Oct 7 - Oct 11
found 20 hours ago
Roundtrip non-stop 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
Price was $643, price is now $510 per person
$510
per person
Oct 8 - Oct 12
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
Price was $680, price is now $543 per person
$543
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Mariners Boathouse by Coolvacay

Mariners Boathouse by Coolvacay

3 out of 5
Price was $1,037, price is now $834 per person
$834
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)

5-night Sanibel Captiva Island vacations

Price found within the past 48 hours. Click for updated prices.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
Price was $763, price is now $534 per person
$534
per person
Sep 29 - Oct 4
found 20 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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 $1,295, price is now $824 per person
$824
per person
Oct 6 - Oct 11
found 14 hours 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 $1,174, price is now $796 per person
$796
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
The Lighthouse Resort Inn & Suites

The Lighthouse Resort Inn & Suites

3 out of 5
Price was $842, price is now $596 per person
$596
per person
Oct 6 - Oct 11
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 $1,172, price is now $854 per person
$854
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Windward Passage Resort

Windward Passage Resort

2 out of 5
Price was $968, price is now $719 per person
$719
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Price was $1,426, price is now $1,069 per person
$1,069
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Price was $1,087, price is now $820 per person
$820
per person
Oct 6 - Oct 11
found 14 hours 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
Price was $919, price is now $702 per person
$702
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Casa Playa Beach Resort

Casa Playa Beach Resort

2.5 out of 5
Price was $1,072, price is now $821 per person
$821
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Fort Myers (RSW)
Marco Beach Ocean Suites

Marco Beach Ocean Suites

2 out of 5
Save 100% on your flight
Price was $1,547, price is now $1,191 per person
$1,191
per person
Sep 29 - Oct 4
found 20 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Fort Myers (RSW)
The Bay Inn at Lani Kai

The Bay Inn at Lani Kai

3 out of 5
Price was $722, price is now $557 per person
$557
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $493, price is now $338 per person
$338
per person
Sep 26 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,660, price is now $913 per person
$913
per person
Oct 3 - Oct 10
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 $1,342, price is now $844 per person
$844
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Latitude 26 Waterfront Resort & Marina

Latitude 26 Waterfront Resort & Marina

3 out of 5
Save 100% on your flight
Price was $1,020, price is now $644 per person
$644
per person
Sep 26 - Oct 3
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 $1,296, price is now $838 per person
$838
per person
Oct 10 - Oct 16
found 24 hours ago
Roundtrip non-stop 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 $1,627, price is now $1,091 per person
$1,091
per person
Oct 2 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $955, price is now $642 per person
$642
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,430, price is now $1,000 per person
$1,000
per person
Oct 2 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
The Bay Inn at Lani Kai

The Bay Inn at Lani Kai

3 out of 5
Save 100% on your flight
Price was $801, price is now $565 per person
$565
per person
Sep 26 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

4 out of 5
Save 100% on your flight
Price was $1,327, price is now $946 per person
$946
per person
Oct 2 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,041, price is now $760 per person
$760
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip non-stop 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 $2,383, price is now $1,740 per person
$1,740
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.

Mon, Sep 28 - Mon, Oct 5
PHL
Philadelphia
RSW
Fort Myers
$100 Roundtrip, found 3 days ago
$100
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Sep 28 from Philadelphia to Fort Myers, returning Mon, Oct 5, priced at $100 found 3 days ago
Fri, Oct 2 - Fri, Oct 9
CLE
Cleveland
RSW
Fort Myers
$115 Roundtrip, found 2 days ago
$115
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Oct 2 from Cleveland to Fort Myers, returning Fri, Oct 9, priced at $115 found 2 days ago
Sat, Jan 23 - Sat, Jan 30
PSM
Portsmouth
RSW
Fort Myers
$152 Roundtrip, found 14 hours ago
$152
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Sat, Jan 23 from Portsmouth to Fort Myers, returning Sat, Jan 30, priced at $152 found 14 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
$206 nightly
The price is $230 total per night
$230 total
Aug 30 - Aug 31
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 3 minutes by car from J. N. Ding Darling National Wildlife Refuge.
Pool
Pet friendly
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
15951 Captiva Drive Captiva FL
6.65 mi from city center
$311 nightly
The price is $346 total per night
$346 total
Aug 26 - Aug 27
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
$448 nightly
The price is $500 total per night
$500 total
Aug 26 - Aug 27
Total with taxes and fees
With a stay at Sundial Beach Resort & Spa in Sanibel (Mid Island), you'll be a 4-minute drive from J. N. Ding Darling National Wildlife Refuge and 6 minutes from Dunes Golf and Tennis Club.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Sanibel 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.

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.