Seaside Holiday Rentals
- Naples
- ·
- Bonita Springs
- 5.17 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Fort Myers
- ·
- Fountain Lakes
- 0.20 mi to center
- Hot Tub
- Spa
- Pool
- Balcony/Terrace
- Fort Myers
- ·
- Three Oaks
- 0.94 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Fort Myers
- ·
- Estero
- 1.16 mi to center
- Pet Friendly
- Kitchen
- Parking
- Air Conditioner
- Fort Myers
- ·
- Three Oaks
- 0.60 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Parking
- Fort Myers
- ·
- Fountain Lakes
- 0.26 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
- Naples
- ·
- Bonita Springs
- 4.27 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
- Naples
- ·
- Bonita Springs
- 5.58 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
- Naples
- ·
- Bonita Springs
- 4.37 mi to center
- Oceanfront
- Pool
- Ocean View
- View
Luxury Holiday Rentals in Seaside
- Naples
- ·
- Estero Bay Shores
- 0.12 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Fort Myers
- ·
- Estero
- 2.33 mi to center
- Spa
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Naples
- ·
- Bonita Springs
- 4.46 mi to center
- Private Pool
- Pool
- Ocean View
- View
- Fort Myers
- ·
- Estero
- 2.33 mi to center
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
- Naples
- ·
- Bonita Springs
- 4.40 mi to center
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
- Naples
- ·
- Bonita Springs
- 4.17 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Naples
- ·
- Bonita Springs
- 4.12 mi to center
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
- Fort Myers
- ·
- Estero
- 1.19 mi to center
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
Top-Rated Holiday Rentals with a Pool in Seaside
- Naples
- ·
- Bonita Springs
- 4.08 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
- Naples
- ·
- Bonita Springs
- 5.00 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
- Fort Myers
- ·
- Cascades
- 0.19 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Fort Myers
- ·
- Estero
- 1.34 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Fort Myers
- ·
- Estero
- 0.93 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Fort Myers
- ·
- Fountain Lakes
- 0.18 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Fort Myers
- ·
- Colonial Oaks
- 0.10 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
- Naples
- ·
- Bonita Springs
- 5.53 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
- Naples
- ·
- Bonita Springs
- 4.62 mi to center
- Fireplace/Heating
- Pool
- Kitchen
- Parking
Pet-Friendly Holiday Rentals in Seaside
- Fort Myers
- ·
- Estero
- 1.88 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Fort Myers
- ·
- Estero
- 1.73 mi to center
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
- Fort Myers
- ·
- Three Oaks
- 0.94 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Fort Myers
- ·
- Three Oaks
- 0.94 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Naples
- ·
- Bonita Springs
- 5.13 mi to center
- Fireplace/Heating
- Pool
- View
- Pet Friendly
- Fort Myers
- ·
- Three Oaks
- 0.94 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Fort Myers
- ·
- Estero
- 1.09 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
- Fort Myers
- ·
- Three Oaks
- 0.94 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Fort Myers
- ·
- Estero
- 0.96 mi to center
- Private Pool
- Hot Tub
- Pool
- Pet Friendly
Large Holiday Rentals and Private Villas in Seaside
- Fort Myers
- ·
- Estero
- 0.95 mi to center
- Oceanfront
- Pool
- Ocean View
- View
- Naples
- ·
- Bonita Springs
- 5.32 mi to center
- Oceanfront
- Spa
- Fireplace/Heating
- Ocean View
- Fort Myers
- ·
- Estero
- 1.33 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
- Fort Myers
- ·
- San Carlos Park
- 0.77 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
- Fort Myers
- ·
- Estero
- 1.47 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
- Fort Myers
- ·
- Estero
- 2.23 mi to center
- Hot Tub
- Air Conditioner
- Child Friendly
- Laundry
- Naples
- ·
- Bonita Springs
- 5.56 mi to center
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
- Fort Myers
- ·
- San Carlos Park
- 1.04 mi to center
- Private Pool
- Fireplace/Heating
- Pool
- Kitchen
- Fort Myers
- ·
- Estero
- 0.54 mi to center
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
Wheelchair Accessible Holiday Homes in Seaside
- Fort Myers
- ·
- Estero
- 1.07 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
- Naples
- ·
- Bonita Springs
- 5.02 mi to center
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
- Fort Myers
- ·
- Estero
- 2.16 mi to center
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
- Fort Myers
- ·
- Estero
- 1.20 mi to center
- Pool
- Kitchen
- Parking
- Air Conditioner
- Fort Myers
- ·
- Estero
- 1.81 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Pet Friendly
- Fort Myers
- ·
- Estero
- 2.33 mi to center
- Spa
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Naples
- ·
- Bonita Springs
- 4.61 mi to center
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
- Naples
- ·
- Bonita Springs
- 5.56 mi to center
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
- Fort Myers
- ·
- Estero
- 1.15 mi to center
- Pool
- Ocean View
- Balcony/Terrace
- View
Seaside Private Villas and Holiday Homes Under $200
- Naples
- ·
- Bonita Springs
- 4.36 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Fort Myers
- ·
- Three Oaks
- 0.94 mi to center
- Fireplace/Heating
- Pool
- Pet Friendly
- Parking
- Fort Myers
- ·
- Estero
- 1.80 mi to center
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
- Naples
- ·
- Bonita Springs
- 4.52 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
- Fort Myers
- ·
- Three Oaks
- 1.12 mi to center
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
- Fort Myers
- ·
- San Carlos Park
- 1.55 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
- Fort Myers
- ·
- Fountain Lakes
- 0.04 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
- Naples
- ·
- Bonita Springs
- 4.57 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
- Fort Myers
- ·
- Estero
- 1.53 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
Instantly Bookable Holiday Homes in Seaside
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
- Fort Myers
- ·
- Cascades
- 0.05 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Naples
- ·
- Bonita Springs
- 4.57 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
- Fort Myers
- ·
- San Carlos Park
- 1.19 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Naples
- ·
- Bonita Springs
- 3.98 mi to center
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
- Naples
- ·
- Bonita Springs
- 5.03 mi to center
- Fireplace/Heating
- Ocean View
- View
- Kitchen
- Fort Myers
- ·
- San Carlos Park
- 0.65 mi to center
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
- Fort Myers
- ·
- Estero
- 1.29 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
- Fort Myers
- ·
- San Carlos Park
- 1.20 mi to center
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
Book a Last Minute Place to Stay in Seaside
About Casai's Private Villas and Holiday Rentals in Seaside
Discover more than 510 vacation rentals available in Seaside. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Seaside.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Seaside, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Seaside. On average, places to stay near Seaside offer 706.1 ft², with nightly prices averaging US $310.
With Casai, finding and comparing holiday rentals in Seaside is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Top Accommodation Types in Seaside
| Type | Count |
|---|---|
| Vacation Homes | 206 |
| Holiday Apartments | 56 |
| Villas | 21 |
| Cottages | 3 |
Use these Quick Filters to Find a Holiday Rental in Seaside
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Seaside.
Weather in Seaside, FL
View the weather forecast for Seaside before booking your Seaside Vacation Rentals to confirm your best time to go.
Frequently Asked Questions About Seaside?
What are the top holiday rentals in Seaside?
With numerous options available in Seaside, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Seaside:
- Southwest-facing home: sunny, modern, lake-view - Pelican Landing/Palm colony
- River Ranch Oaks
- NEW Coastal Paradise GEM! Spacious 4BR, 3 Full Baths w/Pool! PET FRIENDLY!
- Beautiful updated pool home in a quiet, gated community.
- BEACH & SUNSETS CONDO!
- Newly remodeled 3-bedroom condo in a bundled community
- Spotless 2nd Flr., 2 Bdrm Luxury Condo with Spectacular Golf & Lake Views
- Charming 2-bedroom house with WiFi, AC in fabulous Bonita Springs
- Country Creek -Lovely updated 3 bed/2 bath Estero home with hot tub and golf
- Fabulous home w/new pool & spa. Minutes to golf, shop, dine, and fun-in-sun.
How many holiday rentals have private pools in Seaside?
Discover a selection of holiday rentals with private pools near Seaside with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Lovely 2-bedroom condo in Pelican Sound Golf and Country club , Estero Fl .
- Tropical Oasis: Stunning Pool Home in Bonita Springs
- Renovated open floor plan with large heated pool and screened lanai with dining.
- Beautiful Relaxing Condo in The Enclave at Rapallo.
Which holiday homes in Seaside are best for families?
If you're searching for a family-friendly holiday home in Seaside, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Seaside:
- “Splendor” Condo Spring Run Bundled Golf Comm w Beach Amenity, Bonita Springs
- 10 Mi to Bonita Beach Pet-Friendly Home with Yard!
- Tropical Oasis: Stunning Pool Home in Bonita Springs
How many Casai.com holiday rentals are available in Seaside?
As of 2026, Casai boasts over 510 properties listed in the Seaside area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Seaside.







































































