Hot Southwest Florida Cottage Rates

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Featured Cottages in Southwest Florida

2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill

2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill

Sarasota
When you stay at this cottage in Sarasota, you'll be on the beach, just steps from Lido Beach and 8 minutes by foot from St. Armands Circle.
2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill
Adorable Guest house with 2 bedrooms-Great Location

Adorable Guest house with 2 bedrooms-Great Location

Fort Myers
A stay at this cottage places you in the heart of Fort Myers, within a 15-minute walk of Lee Health Family Medicine and Fowler Street Shopping Center.
Adorable Guest house with 2 bedrooms-Great Location
Lido/St. Armands, Sarasota-Walk to Beach & St. Armands, Private cottage w/grill!

Lido/St. Armands, Sarasota-Walk to Beach & St. Armands, Private cottage w/grill!

Sarasota
With a stay at this cottage, you'll be centrally located in Sarasota, just a 4-minute walk from Lido Beach and 10 minutes by foot from St. Armands Circle.
Lido/St. Armands, Sarasota-Walk to Beach & St. Armands, Private cottage w/grill!
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Venetian Vacation! Close To Beaches, Restaurants & Shopping!

Venetian Vacation! Close To Beaches, Restaurants & Shopping!

Venice
With a stay at this cottage in Venice (South Venice), you'll be within a 15-minute drive of Venice Beach and Lemon Bay.
Venetian Vacation! Close To Beaches, Restaurants & Shopping!
Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!

Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!

Sarasota
With a stay at this cottage in Sarasota (Southgate), you'll be within a 15-minute drive of Siesta Key Beach and Turtle Beach.
Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!
Chic cottage, Vamo area, close to beaches, pet friendly, INTACT after storm

Chic cottage, Vamo area, close to beaches, pet friendly, INTACT after storm

Sarasota
With a stay at this cottage in Sarasota (Vamo), you'll be within a 15-minute drive of Siesta Key Beach and Turtle Beach.
Chic cottage, Vamo area, close to beaches, pet friendly, INTACT after storm
Charming cottage in quiet area, close to beach & bay.

Charming cottage in quiet area, close to beach & bay.

Anna Maria
When you a stay at this cottage in Anna Maria, you'll be near the beach, within a 5-minute walk of Anna Maria Island Museum and Historical Park and Island ...
Charming cottage in quiet area, close to beach & bay.
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool

Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool

Sarasota
With a stay at this cottage, you'll be centrally located in Sarasota, steps from Lido Beach and 8 minutes by foot from St. Armands Circle.
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida

Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida

Anna Maria
When you a stay at this cottage in Anna Maria, you'll be by the sea, just steps from Bradenton Beach and Island Players.
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
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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.

Southwest Florida Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Southwest Florida will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Southwest Florida definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Southwest Florida, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Southwest Florida Cottages essential information

Accommodation
21 Cottages
Lowest Price
AU$282
Highest Price
AU$850
Popular accommodation
2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill, Adorable Guest house with 2 bedrooms-Great Location, Lido/St. Armands, Sarasota-Walk to Beach & St. Armands, Private cottage w/grill!, Venetian Vacation! Close To Beaches, Restaurants & Shopping!, Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe! , Chic cottage, Vamo area, close to beaches, pet friendly, INTACT after storm, Charming cottage in quiet area, close to beach & bay. , Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool, Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida

Top trending hotels in Southwest Florida

Hyatt Regency Sarasota

Hyatt Regency Sarasota

4 out of 5
1000 Blvd Of The Arts, Sarasota, FL
Fully refundableReserve now, pay when you stay
The price is AU$360 per night from 24 Dec to 25 Dec
AU$360
includes taxes & fees
24 Dec - 25 Dec
With a stay at Hyatt Regency Sarasota, you'll be centrally located in Sarasota, within a 15-minute drive of Lido Beach and Siesta Key Beach.
Hyatt Regency Sarasota
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
The price is AU$282 per night from 2 Jan to 3 Jan
AU$282
includes taxes & fees
2 Jan - 3 Jan 2025
When you stay at Kompose Boutique Hotel in Sarasota, you'll be near the airport, within a 15-minute drive of Lido Beach and St. Armands Circle.
Kompose Boutique Hotel
Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
The price is AU$850 per night from 12 Jan to 13 Jan
AU$850
includes taxes & fees
12 Jan - 13 Jan 2025
Located in Naples (Park Shore), Naples Grande Beach Resort is within a 5-minute drive of Waterside Shops and Clam Pass Park.
Naples Grande Beach Resort
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Hilton Naples

Hilton Naples

4 out of 5
5111 Tamiami Trl N, Naples, FL
Fully refundableReserve now, pay when you stay
The price is AU$447 per night from 5 Jan to 6 Jan
AU$447
includes taxes & fees
5 Jan - 6 Jan 2025
With a stay at Hilton Naples in Naples (Central Naples), you'll be a 3-minute drive from Vanderbilt Beach and 5 minutes from Mercato.
Hilton Naples
Don't see what you're looking for?
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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.

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^Subject to availability and chosen travel dates.