Top Holiday rentals in Southwest Florida
Find the Top Holiday rentals in Southwest Florida – 40+ Quality Options from Leading Providers
21-40 out of 49 holiday rentals
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Holiday home
6 adults
2 bedrooms
2 beds
From
US$ 5
/night
- Unique tiny houses with custom features
- Proximity to award-winning Siesta Key Beach
- Fun nightlife and dining in Siesta Village
Holiday home
6 adults
2 bedrooms
3 beds
From
US$ 304
/night
- Heated outdoor swimming pool
- On-site spa services available
- Fully equipped kitchen utensils
- Private Pool
- Garden
- Cycling Access
From
US$ 173
/night
- Private pool with garden views
- 3 spacious bedrooms for families
- Outdoor activities like cycling available
Holiday home
- Hot tub
- Outdoor pool
- Children's playground
From
US$ 133
/night
- Private entrance for enhanced privacy
- Outdoor pool and hot tub facilities
- Cycling and fishing activities available
Apartment
- Private Beach
- Outdoor Pool
- Hot Tub
From
US$ 444
/night
- Beachfront accommodation with sea views
- Outdoor swimming pool with loungers
- Private beach area for guests
Apartment
- Private Beach
- Outdoor Pool
- Tennis Court
From
US$ 323
/night
- Private beach access for guests
- Heated outdoor swimming pool
- Tennis court on-site
Apartment
- Private parking
- Flat-screen TV
- Air conditioning
From
US$ 114
/night
- Private entrance with 24-hour security
- Outdoor dining area for relaxation
- Adults-only accommodation for tranquility
Apartment
- Free bikes
- Barbecue garden
- Outdoor dining
From
US$ 103
/night
- Steps from beautiful Lido Beach
- Outdoor dining with barbecue garden
- Free bikes for local exploration
Apartment
- Swimming Pool
- Garden
- Patio
From
US$ 50
/night
- Garden-view terrace and swimming pool
- Fully equipped kitchenette for convenience
- Outdoor dining area with sun loungers
- Air conditioning
- Private entrance
- Garden space
From
US$ 205
/night
- City-view air-conditioned accommodation
- Private entrance for added privacy
- Relaxing garden space available
Holiday home
- Private Pool
- Beach Access
- Barbecue Facilities
From
US$ 1 826
/night
- Private pool with balcony views
- Direct access to Crescent Beach
- Pet-friendly accommodations available
- Rooftop Terrace
- Beach Access
- Air Conditioning
From
US$ 378
/night
- Uninterrupted Gulf views from every room
- Private rooftop terrace with sea views
- Wide range of on-site activities available
- Heated pool
- Hot tub
- Tennis court
From
US$ 635
/night
- Heated private outdoor swimming pool
- Sea view terrace for dining
- On-site hot tub for relaxation
Apartment
- Outdoor pool
- Children's playground
- Private entrance
From
US$ 189
/night
- Private entrance to each unit
- Outdoor swimming pool for relaxation
- Children's playground for family
- Private Pool
- Billiards
- Tennis Court
From
US$ 233
/night
- Heated pool steps from your door
- Private apartment with pool views
- Billiards and fishing on-site
Holiday home
- Barbecue facilities
- Air conditioning
- Flat-screen TV
From
US$ 123
/night
- Outdoor dining area with garden views
- Fully equipped kitchen for self-catering
- Pet-friendly accommodations available
Villa
- Private Pool
- Playground
- Bicycles
From
US$ 198
/night
- Private pool with scenic lake views
- Outdoor playground for children
- Free bikes available for exploring
From
US$ 299
/night
Offering a heated pool, the Siesta Breakers #603, Gulfside In Siesta Key, Fl is placed in the beach area of Siesta Key, 0.6 km from Crescent Arms.
Holiday home
- Full Kitchen
- Garden
- Free Parking
From
US$ 148
/night
- River view holiday homes with patios
- Full kitchen with induction cooktops
- Canoeing and fishing activities available
Holiday home
- Private Entrance
- Hot Tub
- Fully Equipped Kitchen
From
US$ 179
/night
- Private balcony with sea views
- Outdoor swimming pool and hot tub
- Close to cycling and fishing activities
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