Honeymoon Vacations in Southwest Florida 2026

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Flight and Honeymoon hotel deals in Southwest Florida

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

The Westin Sarasota

Central Sarasota

CA $1,177

per person

Oct 20 - Oct 25

found 4 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Tampa (TPA)

9/10 Wonderful! (1,151 reviews)

Loved the location and roof top bar! Great views

Reviewed on Aug 13, 2026

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

CA $1,190

per person

Sep 16 - Sep 21

found 9 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Fort Myers (RSW)

8.6/10 Excellent! (1,012 reviews)

Pink Shell Beach Resort and Marina

CA $1,401

per person

Sep 18 - Sep 20

found 20 hours ago

Roundtrip flight included

Edmonton (YEG) to Fort Myers (RSW)

9.4/10 Exceptional! (1,417 reviews)

Get location and super staff. Very family friendly with much to do!

Reviewed on Aug 13, 2026

Sundial Beach Resort & Spa

Mid Island

CA $2,077

per person

Sep 30 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Kalispell (FCA) to Fort Myers (RSW)

8.6/10 Excellent! (2,680 reviews)

It was clean The rooms were a good size And the beach was well maintained

Reviewed on Aug 8, 2026

Bellasera Resort

Old Naples

CA $1,320

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Fort Myers (RSW)

9.6/10 Exceptional! (2,310 reviews)

Very nice

Reviewed on Aug 12, 2026

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5* Honeymoon holidays in Southwest Florida

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

Sundial Beach Resort & Spa

Mid Island

CA $2,077

per person

Sep 30 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Kalispell (FCA) to Fort Myers (RSW)

8.6/10 Excellent! (2,680 reviews)

It was clean The rooms were a good size And the beach was well maintained

Reviewed on Aug 8, 2026

The Ritz-Carlton, Sarasota

Central Sarasota

CA $2,466

per person

Oct 20 - Oct 25

found 4 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Tampa (TPA)

9.2/10 Wonderful! (1,003 reviews)

Naples Beach Club, A Four Seasons Resort

Coquina Sands

CA $2,617

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTT) to Fort Myers (RSW)

9.6/10 Exceptional! (28 reviews)

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3 Night Honeymoon holidays in Southwest Florida

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

Inn at Pelican Bay

Pelican Bay

CA $989

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Fort Myers (RSW)

9.6/10 Exceptional! (1,008 reviews)

Rooms are very clean and linen too, bed is comfortable, same as pillow beach shutter service very convenient, but the beach is near and there is a multistory parking by if you don't want to take the shutter attentive and helpful staff pool is small but clean, there is a hot tub continental breakfast: coffee, pastries, bagels, bread, fruits, waffles and pancakes very good hotel

Reviewed on Aug 11, 2026

The Westin Sarasota

Central Sarasota

CA $1,424

per person

Nov 5 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

Syracuse (SYR) to Tampa (TPA)

9/10 Wonderful! (1,151 reviews)

Loved the location and roof top bar! Great views

Reviewed on Aug 13, 2026

Bellasera Resort

Old Naples

CA $1,320

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Fort Myers (RSW)

9.6/10 Exceptional! (2,310 reviews)

Very nice

Reviewed on Aug 12, 2026

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See all available trips from Columbus to Southwest Florida

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4 Night Honeymoon holidays in Southwest Florida

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

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

CA $967

per person

Sep 30 - Oct 4

found 6 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Fort Myers (RSW)

8.6/10 Excellent! (1,012 reviews)

South Seas

CA $1,209

per person

Oct 22 - Oct 26

found 7 hours ago

Roundtrip non-stop flight included

Winnipeg (YWG) to Fort Myers (RSW)

8.4/10 Very good! (1,004 reviews)

We had a wonderful stay at South Seas Resort! Everything was perfect from beginning to end. The staff was very friendly, helpful, and attentive, and the entire resort was extremely clean, well maintained and organize. The location is beautiful, and the water park for the kids was absolutely excellent, they all had a great time! Everything was very family-friendly and made our stay relaxing and enjoyable. I would definitely recommend Southseas Resort to families and anyone looking for a clean, comfortable and fun place to stay .

Reviewed on Aug 13, 2026

Casa Ybel Resort

Mid Island

CA $1,211

per person

Oct 16 - Oct 20

just found

Roundtrip non-stop flight included

Montreal (YMQ) to Fort Myers (RSW)

8.8/10 Excellent! (397 reviews)

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Honeymoon Hotels in Southwest Florida

Marriott Sanibel Harbour Resort & Spa

17260 Harbour Pointe Dr Fort Myers FL

2 hours drive from Siesta Key Beach

Book a stay at this spa resort in Fort Myers. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the helpful staff and the property ...

Naples Grande Beach Resort

475 Seagate Drive Naples FL

3 hours drive from Siesta Key Beach

Book a stay at this luxury resort in Naples. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff in ...

9/10 Wonderful! (1,945 reviews)

"Room was in bad condition and staff was not helpful. The property finally admitted that they were about to shut down for a complete remodel. Please be certain a complete remodel has been completed before you would ever consider staying in this property."

Reviewed on Jun 8, 2026

DiamondHead Beach Resort

2000 Estero Blvd Fort Myers Beach FL

2 hours drive from Siesta Key Beach

Book a stay at this beach resort in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in ...

See all 47,330 properties in Southwest Florida

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.