Historical Hotels in Southwest Florida, FL
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Featured Southwest Florida Historic Hotels

Oak Tree Hotel
6 W Oak St Unit #6 Arcadia FL
Free Cancellation
$168 nightly
The price is $185 total per night
$185 total
Jan 21 - Jan 22, 2026
Total with taxes and fees
At Oak Tree Hotel, guests have access to free WiFi in public areas, a 24-hour business center, and a computer station. There's free parking if you drive. The 24-hour front desk has staff standing by to help with luggage storage, and answer any questions about the accommodations. This smoke-free hotel also has a fireplace in the lobby.
Breakfast included
All inclusive

Naples Bay Resort & Marina
1500 Fifth Ave S Naples FL
$572 nightly
The price is $629 total per night
$629 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Naples Bay Resort & Marina features a marina, a full-service spa, and 5 outdoor pools. Parking is available for USD 21.40 per night (USD 21.40 per night for valet parking), and there's also a free beach shuttle. Multilingual staff at the 24-hour front desk can assist with luggage storage, securing valuables, and concierge services. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this spa hotel include a lazy river, a children's pool, and a gym.
Pool
Hot Tub

Olde Marco Island Inn and Suites
100 Palm St Marco Island FL
$574 nightly
The price is $638 total per night
$638 total
Dec 27 - Dec 28
Total with taxes and fees
Guests of Olde Marco Island Inn and Suites enjoy features like an outdoor pool, free WiFi in public areas, and a computer station. If you decide to drive, there's free parking. Front-desk staff can assist with tours/tickets and securing valuables. Additional amenities include a library, free newspapers, and a terrace.
Pool
Parking included

Punta Gorda Waterfront Hotel and Suites
300 Retta Esplanade Punta Gorda FL
Guests of Punta Gorda Waterfront Hotel and Suites have access to an outdoor pool, a 24-hour gym, and free WiFi in public areas. A stay here includes free parking. Front-desk staff are standing by 24/7 to assist with any requests. Other amenities at this beach hotel include a 24-hour business center, coffee/tea in a common area, and a terrace.
Pool
Breakfast included

Wyvern Hotel, an Ascend Collection Hotel
101 E Retta Esplanade Punta Gorda FL
Free Cancellation
$139 nightly
The price is $155 total per night
$155 total
Dec 29 - Dec 30
Total with taxes and fees
Guests of Wyvern Hotel, an Ascend Collection Hotel enjoy a rooftop terrace, free WiFi in public areas, and conference space. If you drive, put free parking to good use. Multilingual staff at the 24-hour front desk can assist with concierge services, luggage storage, and dry cleaning/laundry. Other amenities at this luxury hotel include express check-in, express check-out, and free newspapers.
Parking included
Free WiFi

Holiday Inn Express Hotel Naples Downtown - 5th Avenue
Naples FL
Free Cancellation
$177 nightly
The price is $197 total per night
$197 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests of Holiday Inn Express Hotel Naples Downtown - 5th Avenue have access to an outdoor pool, a gym, and free WiFi in public areas. If you drive, take advantage of free parking. The 24-hour front desk has multilingual staff ready to assist with securing valuables, luggage storage, and concierge services. Other amenities at this golf hotel include a hot tub, meeting rooms, and conference space.
Pool
Hot Tub

Best Western Fort Myers Waterfront
13021 N Cleveland Ave North Fort Myers FL
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $113 total per night
$113 total
Dec 24 - Dec 25
Total with taxes and fees
Guests staying at Best Western Fort Myers Waterfront enjoy an outdoor pool, a 24-hour gym, and free WiFi in public areas. A stay here includes free parking. The 24-hour front desk has multilingual staff ready to help secure valuables, and answer any questions about the area. Additional amenities include a 24-hour business center, coffee/tea in a common area, and express check-out.
Pool
Breakfast included

Hilton Garden Inn Sarasota - Bradenton Airport
8270 N Tamiami Trl Sarasota FL
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $129 total per night
$129 total
Dec 25 - Dec 26
Total with taxes and fees
At Hilton Garden Inn Sarasota - Bradenton Airport, guests enjoy features like an outdoor pool, a 24-hour gym, and free WiFi in public areas. There's free parking, as well as a free airport shuttle (available on request). Multilingual staff at the 24-hour front desk can assist with luggage storage, dry cleaning/laundry, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Additional amenities include a hot tub, conference space, and a 24-hour business center.
Pool
Hot Tub

Tarpon Tale Inn
367 Periwinkle Way Sanibel FL
$224 nightly
The price is $250 total per night
$250 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
At Tarpon Tale Inn, guests have access to free WiFi in public areas, free use of bicycles, and express check-out. If you decide to drive, there's free parking. Staff members can help with accommodation requests, and provide front-desk service during limited hours. Other amenities at this beach hotel include a garden, a picnic area, and barbecue grills.
Parking included
Free WiFi

Four Points by Sheraton Punta Gorda Harborside
33 Tamiami Trail Punta Gorda FL
Free Cancellation
Reserve now, pay when you stay
$146 nightly
The price is $163 total per night
$163 total
Dec 29 - Dec 30
Total with taxes and fees
Guests of Four Points by Sheraton Punta Gorda Harborside enjoy a marina, an outdoor pool, and a gym. There's free parking, as well as a free airport shuttle at scheduled times. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, concierge services, and dry cleaning/laundry. Other amenities at this hot springs hotel include a hot tub, meeting rooms, and a conference center.
Pool
Hot Tub

Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway
625 Tamiami Trail S Venice FL
Free Cancellation
Reserve now, pay when you stay
$72 nightly
The price is $81 total per night
$81 total
Dec 24 - Dec 25
Total with taxes and fees
Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway features an outdoor pool, free WiFi in public areas, and a business center. There's free parking if you drive. Friendly staff can provide front-desk service during limited hours, and also offer advice about sightseeing. Additional amenities include coffee/tea in a common area, a computer station, and express check-out.
Pool
Parking included

The Banyan Hotel Fort Myers, Tapestry Collection by Hilton
1520 Broadway Fort Myers FL
Free Cancellation
Reserve now, pay when you stay
$155 nightly
The price is $173 total per night
$173 total
Dec 30 - Dec 31
Total with taxes and fees
The Banyan Hotel Fort Myers, Tapestry Collection by Hilton features free WiFi in public areas, a 24-hour business center, and a computer station. The 24-hour front desk has multilingual staff ready to assist with securing valuables, luggage storage, and dry cleaning/laundry. Additional amenities include express check-in, express check-out, and free newspapers.
Free WiFi
Air conditioning

Americas Best Value Inn Historic Clewiston Inn
108 Royal Palm Avenue Clewiston FL
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $94 total per night
$94 total
Dec 29 - Dec 30
Total with taxes and fees
Americas Best Value Inn Historic Clewiston Inn features free WiFi in public areas, meeting rooms, and a conference center. You can take advantage of free parking if you drive. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include a computer station, laundry facilities, and a vending machine.
Parking included
Free WiFi

The Escalante
290 5th Ave S Naples FL
$1,103 nightly
The price is $1,225 total per night
$1,225 total
Dec 28 - Dec 29
Total with taxes and fees
Guests staying at The Escalante enjoy access to a private beach, an outdoor pool, and free WiFi in public areas. You can take advantage of free parking, along with a free beach shuttle. The front desk has multilingual staff that can help with dry cleaning/laundry, concierge services, and securing valuables. Other amenities at this adults-only hotel include a hot tub, conference space, and a business center.
On private beach
Pool

Golden Host Resort - Sarasota
4675 N Tamiami Trl Sarasota FL
Free Cancellation
$76 nightly
The price is $86 total per night
$86 total
Dec 30 - Dec 31
Total with taxes and fees
Golden Host Resort - Sarasota features an outdoor pool, free WiFi in public areas, and coffee in a common area. Free parking is included with your stay. The 24-hour front desk has multilingual staff ready to help secure valuables, and answer any questions about the area. Additional amenities include a library, express check-out, and free newspapers.
Pool
Parking included
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See all available properties in Southwest Florida
View all propertiesLowest 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.
Southwest Florida hotels essential information
Accommodation | 46,315 hotels |
|---|---|
Lowest Price | $81 |
Highest Price | $1,225 |
Popular hotels | Oak Tree Hotel, Naples Bay Resort & Marina, Olde Marco Island Inn and Suites, Punta Gorda Waterfront Hotel and Suites, Wyvern Hotel, an Ascend Collection Hotel, Holiday Inn Express Hotel Naples Downtown - 5th Avenue, Best Western Fort Myers Waterfront, Hilton Garden Inn Sarasota - Bradenton Airport, Tarpon Tale Inn, Four Points by Sheraton Punta Gorda Harborside, Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway, The Banyan Hotel Fort Myers, Tapestry Collection by Hilton, Americas Best Value Inn Historic Clewiston Inn, The Escalante, Golden Host Resort - Sarasota |
Recent Historic Hotels Reviews

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
5/5 Excellent
"Very Nice all around"
A verified traveler stayed at Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Posted 23 hours ago
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