Compare Southwest Florida Cottage Rentals

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Featured Southwest Florida Cottages

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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 Beach Accommodation

    Outrigger Beach Resort

    Outrigger Beach Resort

    6200 Estero Boulevard, Fort Myers Beach, FL
    9/10 Wonderful! (1,000 reviews)
    West Wind Inn

    West Wind Inn

    3345 West Gulf Drive, Sanibel, FL
    8.8/10 Excellent! (1,000 reviews)
    Lani Kai Beachfront Resort

    Lani Kai Beachfront Resort

    1400 Estero Blvd, Fort Myers Beach, FL
    The price is $210 per night from May 22 to May 23
    $210
    includes taxes & fees
    $189 per night
    May 22 - May 23
    8.4/10 Very Good! (1,020 reviews)
    Sandcastle Resort At Lido Beach

    Sandcastle Resort At Lido Beach

    1540 Ben Franklin Drive, Sarasota, FL
    7.2/10 Good! (1,074 reviews)
    Anna Maria Island Dream Inn

    Anna Maria Island Dream Inn

    2502 North Gulf Drive, Bradenton Beach, FL
    8.2/10 Very Good! (1,000 reviews)
    Punta Gorda Waterfront Hotel and Suites

    Punta Gorda Waterfront Hotel and Suites

    300 Retta Esplanade, Punta Gorda, FL
    7/10 Good! (1,000 reviews)
    Sundial Beach Resort & Spa

    Sundial Beach Resort & Spa

    1451 Middle Gulf Drive, Sanibel, FL
    The price is $643 per night from May 6 to May 7
    $643
    includes taxes & fees
    $577 per night
    May 6 - May 7
    8.6/10 Excellent! (2,562 reviews)
    Pink Shell Beach Resort and Marina

    Pink Shell Beach Resort and Marina

    275 Estero Blvd, Fort Myers Beach, FL
    The price is $306 per night from May 6 to May 7
    $306
    includes taxes & fees
    $274 per night
    May 6 - May 7
    9.2/10 Wonderful! (1,002 reviews)
    DiamondHead Beach Resort

    DiamondHead Beach Resort

    2000 Estero Blvd, Fort Myers Beach, FL
    The price is $283 per night from May 18 to May 19
    $283
    includes taxes & fees
    $254 per night
    May 18 - May 19
    9/10 Wonderful! (1,005 reviews)

Hotel Options in Southwest Florida

    Naples Grande Beach Resort

    Naples Grande Beach Resort

    475 Seagate Drive, Naples, FL
    The price is $344 per night from Jun 1 to Jun 2
    $344
    includes taxes & fees
    $310 per night
    Jun 1 - Jun 2
    8.8/10 Excellent! (1,454 reviews)
    Margaritaville Beach Resort Fort Myers

    Margaritaville Beach Resort Fort Myers

    251 Crescent Street, Fort Myers Beach, FL
    The price is $261 per night from May 20 to May 21
    $261
    includes taxes & fees
    $234 per night
    May 20 - May 21
    8.8/10 Excellent! (1,034 reviews)
    Tropical Beach Resorts

    Tropical Beach Resorts

    6717 Sara Sea Circle, Siesta Key, FL
    The price is $214 per night from May 19 to May 20
    $214
    includes taxes & fees
    $189 per night
    May 19 - May 20
    9.2/10 Wonderful! (4,637 reviews)

Cottages

Book a cottage in Southwest Florida
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Southwest Florida. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Southwest Florida better.

Cottage apartments in Southwest Florida range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Southwest Florida
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Southwest Florida and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Southwest Florida cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Southwest Florida. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Southwest Florida Cottages essential information

Accommodation
51 Cottages
Lowest Price
$210
Highest Price
$643
Popular accommodation
The "Grouper", We will be accepting new reservations from January 2025 going forward only., Cozy Getaway with pool and minutes to the beach!!!, Castaway Cottage + Beach + Heated Private Pool & Spa = R & R! Near Bean Point!, Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!, 2 Bedroom Cottage Sanibel Island Near Beach-Great! Newly renovated & refurnished, Charming cottage in quiet area, close to beach & bay. , Shell Cottage - sleeps 2, Classic dog-friendly cottage with kitchen, washer/dryer, & central AC