Seasonal Rentals for 2027
34 properties available
Your Accommodations:Our first floor corner townhome is located in the southeast part of Paseo and it is one of the few condos located on Quad #5 which contains its own pool and more which is separate from the main pool at the amenities center towards the center of the community. Our townhome has a screened front lanai that looks out to the quiet r
First Floor Corner Unit Condo On a Coveted Quad in Paseo of Fort Myers
Condominium
$145 - $270 / per night
2
bedrooms
2
baths
4
guests
**Your Winter Escape Begins Here — Horizon House, Naples FL**Welcome to beachfront living at its finest! Horizon House is an iconic 12-story condo located directly on the white sands of the Gulf of Mexico, offering guests the ultimate winter retreat with *DIRECT BEACH ACCESS*. Wake up to the sound of waves and enjoy sunrise walks on the sand—all ju
Gulf Front Walk to Beach Enjoy Sunsets
Condominium
$335 - $408 / per night
2
bedrooms
2
baths
4
guests
Spacious Lakeside Villa in Hacienda Village – Comfort, Convenience & Coastal CharmCasually situated at the end of a lushly landscaped pathway, this two-story villa offers a peaceful retreat with tranquil lake views and resort-style amenities right outside your door. Thoughtfully designed for comfort and functionality, this home is perfect for seas
Spacious Villa Near Beach in Gated Community
Townhouse
$95 - $750 / per night
2
bedrooms
2
baths
4
guests
Our condo is located in the very quiet and lovely community of Bayview and it has an assigned parking space located right behind the unit and off a quiet alley. This condo is located on the second floor and there is a set of stairs to reach the second floor and then it is a short walk down the open corridor to our condo. There is a view to the co
Walk to the Beach and Downtown Naples From Our Totally Upgraded Condo
Condominium
$140 - $260 / per night
1
bedrooms
1
baths
4
guests
Step inside this seasonal rental home and enjoy scenic views of a brackish canal directly on the property. Our home features 2 bedrooms along with 2 full sized bathrooms. Bedroom #1 has a King bed and bedroom #2 has a Queen bed and the family room has a separate bed. The open kitchen is quite large and has a island with 3 bar stools and the dini
Direct Harbor Access A Water Lovers Paradise
House
$117 - $140 / per night
2
bedrooms
2
baths
6
guests
Key Features of this Second Floor Condo:Accommodates Up to 6 Guests:*Main bedroom with king bed, en-suite bath with single vanity and shower, and sliding doors to the lanai.*Guest bedroom with two twin beds; second full bath located just outside the room.*Living room with queen sleeper sofa for 2 additional guests.Comfort & Convenience:*Full laundr
B 2 Waterfront Condo Near Naples Bay Beaches
Condominium
$125 - $500 / per night
2
bedrooms
2
baths
6
guests
*Welcome to Your Relaxing Getaway with Stunning Golf Course Views*Whether you're escaping the winter chill or planning an off-season retreat, this thoughtfully stocked and comfortably furnished condo offers everything you need for a memorable stay. Located in a serene community with peaceful lake and golf course views, the home provides plenty of s
Cypress Woods for Seasonal or Summer Stays
Condominium
$125 - $235 / per night
3
bedrooms
2
baths
6
guests
Your Naples getaway begins in this two-story townhouse designed for comfort and convenience.* Main Floor: A bright, open living and dining area is perfect for gathering after a day in the sun. The fully equipped kitchen makes it easy to prepare everything from quick beach snacks to fresh Gulf seafood dinners. A half bath, laundry, and garage access
Naples Retreat Walk to Pool and More
Townhouse
$95 - $1,500 / per night
2
bedrooms
2
baths
4
guests
Your seasonal rental home has three full bedrooms and a den and they feature a King, Queen and 2 Twin Beds along with two full bathrooms. The main outdoor feature of the home is the pool with a large screened lanai and a nice covered area with an outdoor dining set!The main living areas of the home include a open concept family room with slider ac
Fantastic Reflection Lakes Pool Home with Fabulous Views in Naples Florida
House
$175 - $325 / per night
3
bedrooms
2
baths
6
guests
This single-family heated pool home has a formal dining area for 6 as well as an informal dining set as an eat in kitchen and guests can also pull up a bar stool to the bar height counter for additional space. Guests can enjoy al fresco meals on the lanai while sitting pool side in the covered and screened pool deck area. Guests will have full us
Pool Home in Spanish Wells with Public Golf
House
$185 - $385 / per night
4
bedrooms
3
baths
8
guests
Live the Southwest Florida lifestyle at Copperleaf at The Brooks, a private gated bundled golf community in Estero. This seasonal (monthly+) rental offers a rare opportunity for transferable club amenities and dining privileges, allowing guests to enjoy championship golf, resort-style pool, fitness center, tennis, bocce, and multiple on-site dining
Relax All Season Pool Spa Golf Included
House
$185 - $1,500 / per night
3
bedrooms
2
baths
6
guests
Your seasonal rental carriage home is tucked away at the end of the building and being situated on the corner you get extra windows for additional light. Your rental includes a paver driveway and sidewalk along with a 1 car attached garage. We make it easy to go to the beach as we have 2 beach chairs, a beach cart and umbrella and a boogie board
Beautiful Corner Unit in Woods Edge W Brand New Kitchen Community Pool Close to Beach
Condominium
$117 - $273 / per night
3
bedrooms
2
baths
6
guests
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