Cheap Vacations in South Naples

Choose two or more items and save on your trip:

South Naples 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
Save 100% on your flight
Price was $669, price is now $492 per person
$492
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Altaira - top Location Lake View Pool Spa 4 Bed

Altaira - top Location Lake View Pool Spa 4 Bed

2 out of 5
Crown Pointe
Save 100% on your flight
Price was $2,743, price is now $2,142 per person
$2,142
per person
Apr 15 - Apr 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)

3-night South Naples 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
Save 100% on your flight
Price was $449, price is now $349 per person
$349
per person
Apr 13 - Apr 16
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 $1,128, price is now $745 per person
$745
per person
Apr 10 - Apr 13
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 $708, price is now $508 per person
$508
per person
Apr 13 - Apr 16
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
Save 100% on your flight
Price was $710, price is now $520 per person
$520
per person
Apr 10 - Apr 13
found 1 day 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 $669, price is now $492 per person
$492
per person
Apr 10 - 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 $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 23 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Compass by Margaritaville Hotel Naples

Compass by Margaritaville Hotel Naples

4 out of 5
Save 100% on your flight
Price was $601, price is now $455 per person
$455
per person
Apr 10 - Apr 13
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 $1,036, price is now $787 per person
$787
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Best Western Naples Inn & Suites

Best Western Naples Inn & Suites

2.5 out of 5
Price was $479, price is now $367 per person
$367
per person
Apr 10 - Apr 13
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 $1,242, price is now $971 per person
$971
per person
Apr 24 - Apr 27
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 $631, price is now $495 per person
$495
per person
Apr 5 - Apr 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

4-night South Naples 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
Price was $539, price is now $366 per person
$366
per person
Apr 15 - Apr 19
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 $1,018, price is now $695 per person
$695
per person
Apr 15 - Apr 19
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 $753, price is now $539 per person
$539
per person
Apr 15 - Apr 19
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
Price was $630, price is now $456 per person
$456
per person
Apr 15 - Apr 19
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 $1,686, price is now $1,219 per person
$1,219
per person
Apr 17 - Apr 21
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 $1,596, price is now $1,175 per person
$1,175
per person
Apr 16 - Apr 20
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 4 hours 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 $1,095, price is now $814 per person
$814
per person
Apr 16 - Apr 20
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 $1,161, price is now $864 per person
$864
per person
Apr 17 - Apr 21
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 $1,652, price is now $1,264 per person
$1,264
per person
Apr 16 - Apr 20
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
JW Marriott Marco Island Beach Resort

JW Marriott Marco Island Beach Resort

4 out of 5
Save 100% on your flight
Price was $2,013, price is now $1,567 per person
$1,567
per person
Apr 4 - Apr 8
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 $799, price is now $623 per person
$623
per person
Apr 30 - May 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

5-night South Naples 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 $505, price is now $307 per person
$307
per person
Apr 9 - Apr 14
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 $1,458, price is now $951 per person
$951
per person
Apr 17 - Apr 22
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 $625, price is now $412 per person
$412
per person
Apr 9 - Apr 14
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
Save 100% on your flight
Price was $743, price is now $494 per person
$494
per person
Apr 9 - Apr 14
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
Save 100% on your flight
Price was $1,239, price is now $864 per person
$864
per person
Apr 9 - Apr 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Bayfront Inn Fifth Avenue

Bayfront Inn Fifth Avenue

3.5 out of 5
Save 100% on your flight
Price was $1,021, price is now $716 per person
$716
per person
Apr 12 - Apr 17
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 $2,088, price is now $1,465 per person
$1,465
per person
Apr 16 - Apr 21
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
Save 100% on your flight
Price was $998, price is now $702 per person
$702
per person
Apr 12 - Apr 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Lehigh Resort Club

Lehigh Resort Club

3.5 out of 5
Save 100% on your flight
Price was $603, price is now $431 per person
$431
per person
Apr 9 - Apr 14
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
Save 100% on your flight
Price was $588, price is now $422 per person
$422
per person
Apr 12 - Apr 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Landing Fort Myers Near Highland Pines

Landing Fort Myers Near Highland Pines

4 out of 5
Save 100% on your flight
Price was $754, price is now $543 per person
$543
per person
Apr 9 - Apr 14
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 $1,824, price is now $1,318 per person
$1,318
per person
Apr 9 - Apr 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

6-7 night South Naples 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 $668, price is now $445 per person
$445
per person
Apr 15 - Apr 22
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 $1,145, price is now $680 per person
$680
per person
Apr 27 - May 4
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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 $1,572, price is now $993 per person
$993
per person
Apr 26 - May 3
found 23 hours ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Bellasera Resort

Bellasera Resort

4 out of 5
Save 100% on your flight
Price was $2,668, price is now $1,819 per person
$1,819
per person
Apr 15 - Apr 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Hilton Naples

Hilton Naples

4 out of 5
Save 100% on your flight
Price was $1,610, price is now $1,104 per person
$1,104
per person
Apr 15 - Apr 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Bayfront Inn Fifth Avenue

Bayfront Inn Fifth Avenue

3.5 out of 5
Save 100% on your flight
Price was $1,365, price is now $960 per person
$960
per person
Apr 15 - Apr 22
found 1 day ago
Roundtrip non-stop 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 $2,817, price is now $2,010 per person
$2,010
per person
Apr 15 - Apr 22
found 1 day ago
Roundtrip non-stop 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
Save 100% on your flight
Price was $1,330, price is now $954 per person
$954
per person
Apr 15 - Apr 22
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 $1,128, price is now $825 per person
$825
per person
Apr 15 - Apr 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Landing Furnished Apartments - Naples, FL

Landing Furnished Apartments - Naples, FL

3 out of 5
Save 100% on your flight
Price was $1,616, price is now $1,188 per person
$1,188
per person
Apr 15 - Apr 22
found 1 day ago
Roundtrip non-stop 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 $2,309, price is now $1,698 per person
$1,698
per person
Apr 19 - Apr 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Hampton Inn Naples Central

Hampton Inn Naples Central

2.5 out of 5
Save 100% on your flight
Price was $1,168, price is now $862 per person
$862
per person
Apr 15 - Apr 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)

Flight deals to South Naples

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

Sat, May 9 - Thu, May 14
ORD
Chicago
RSW
Fort Myers
$66 Roundtrip, found 6 days ago
$66
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, May 9 from Chicago to Fort Myers, returning Thu, May 14, priced at $66 found 6 days ago
Mon, Mar 23 - Fri, Mar 27
PHL
Philadelphia
RSW
Fort Myers
$94 Roundtrip, found 1 day ago
$94
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Mar 23 from Philadelphia to Fort Myers, returning Fri, Mar 27, priced at $94 found 1 day ago
Mon, Apr 6 - Thu, Apr 9
BOS
Boston
RSW
Fort Myers
$102 Roundtrip, found 2 days ago
$102
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Mon, Apr 6 from Boston to Fort Myers, returning Thu, Apr 9, priced at $102 found 2 days ago

Top rated hotels for your South Naples vacation

Staybridge Suites Naples – Marco Island by IHG

Staybridge Suites Naples – Marco Island by IHG

3 out of 5
9401 Triangle Blvd Naples FL
Free Cancellation
2.49 mi from city center
$202 nightly
The price is $224 total per night
$224 total
Apr 1 - Apr 2
Total with taxes and fees
With a stay at Staybridge Suites Naples – Marco Island by IHG, you'll be centrally located in Naples, within a 15-minute drive of Fifth Avenue South and Naples Pier.
Pool
Breakfast included
Conty's Motel

Conty's Motel

2 out of 5
11238 Tamiami Trail East Naples FL
1.99 mi from city center
$86 nightly
The price is $95 total per night
$95 total
Mar 6 - Mar 7
Total with taxes and fees
Located in Naples, Conty's Motel is within a 10-minute drive of Naples Botanical Garden and Tin City.
La Quinta Inn & Suites by Wyndham Naples East (I-75)

La Quinta Inn & Suites by Wyndham Naples East (I-75)

3 out of 5
185 Bedzel Cir Naples FL
Free Cancellation
Reserve now, pay when you stay
3.73 mi from city center
$102 nightly
The price is $113 total per night
$113 total
Apr 5 - Apr 6
Total with taxes and fees
When you stay at La Quinta Inn & Suites by Wyndham Naples East (I-75) in Naples, you'll be near the airport, within a 15-minute drive of Fifth Avenue South and Naples Zoo at Caribbean Gardens.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in South Naples
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.