Seaside Holiday Rentals
- Naples
- ·
- Bonita Springs
- 4.17 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
- Pool
- Balcony/Terrace
- Pet Friendly
- Fort Myers
- ·
- Fountain Lakes
- 0.26 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Fort Myers
- ·
- Three Oaks
- 0.60 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Naples
- ·
- Bonita Springs
- 5.43 mi to center
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
- Fort Myers
- ·
- Estero
- 1.16 mi to center
- Pet Friendly
- Kitchen
- Parking
- Air Conditioner
Luxury Holiday Rentals in Seaside
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Naples
- ·
- Estero Bay Shores
- 0.12 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Fort Myers
- ·
- Estero
- 1.58 mi to center
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
- Fort Myers
- ·
- Estero
- 1.19 mi to center
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
- Fort Myers
- ·
- Estero
- 2.33 mi to center
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
- Naples
- ·
- Bonita Springs
- 4.46 mi to center
- Private Pool
- Pool
- Ocean View
- View
- Naples
- ·
- Bonita Springs
- 4.40 mi to center
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
- Naples
- ·
- Bonita Springs
- 5.56 mi to center
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
Top-Rated Holiday Rentals with a Pool in Seaside
- Fort Myers
- ·
- San Carlos Park
- 0.92 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- 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
- ·
- Fountain Lakes
- 0.26 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
- Fort Myers
- ·
- Estero
- 1.34 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Naples
- ·
- Bonita Springs
- 4.27 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
- Fort Myers
- ·
- Estero
- 0.93 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Naples
- ·
- Bonita Springs
- 5.58 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
- Fort Myers
- ·
- Fountain Lakes
- 0.18 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
Pet-Friendly Holiday Rentals in Seaside
- Naples
- ·
- Bonita Springs
- 4.47 mi to center
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
- Fort Myers
- ·
- Estero
- 1.73 mi to center
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
- Fort Myers
- ·
- Estero
- 1.88 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
- Fort Myers
- ·
- Estero
- 1.88 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
- ·
- 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
- ·
- 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
- Pool
- Kitchen
- Parking
- Air Conditioner
- 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
- 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
Wheelchair Accessible Holiday Homes in Seaside
- Fort Myers
- ·
- Estero
- 1.33 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
- 1.07 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
- Fort Myers
- ·
- Estero
- 1.81 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Pet Friendly
- Fort Myers
- ·
- Estero
- 1.20 mi to center
- Pool
- Kitchen
- Parking
- Air Conditioner
- Fort Myers
- ·
- Estero
- 2.33 mi to center
- Spa
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Fort Myers
- ·
- Estero
- 2.33 mi to center
- Spa
- Fireplace/Heating
- Pool
- Balcony/Terrace
- 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
- 4.37 mi to center
- Oceanfront
- Pool
- Ocean View
- View
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
- Fort Myers
- ·
- Estero
- 1.80 mi to center
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
- Naples
- ·
- Bonita Springs
- 4.36 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Naples
- ·
- Bonita Springs
- 5.17 mi to center
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
- Naples
- ·
- Bonita Springs
- 4.52 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
- Fort Myers
- ·
- San Carlos Park
- 1.55 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
- 4.57 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
Instantly Bookable Holiday Homes in Seaside
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
- Fort Myers
- ·
- Three Oaks
- 0.94 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Fort Myers
- ·
- Estero
- 1.53 mi to center
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
- Fort Myers
- ·
- Fountain Lakes
- 0.04 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
- Fort Myers
- ·
- San Carlos Park
- 0.62 mi to center
- Air Conditioner
- Internet
- Child Friendly
- Bedding/Linens
- Naples
- ·
- Bonita Springs
- 3.98 mi to center
- Private Pool
- Spa
- Fireplace/Heating
- Pool
- Naples
- ·
- Bonita Springs
- 5.03 mi to center
- Fireplace/Heating
- Ocean View
- View
- Kitchen
- Fort Myers
- ·
- The Masters
- 0.05 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
- Fort Myers
- ·
- San Carlos Park
- 0.65 mi to center
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
Book a Last Minute Place to Stay in Seaside
About Casai's Private Villas and Holiday Rentals in Seaside
Discover more than 511 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 703.6 ft², with nightly prices averaging US $315.
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 | 208 |
| Holiday Apartments | 57 |
| Villas | 20 |
| 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:
- Modern 3 bedroom, 2 bath getaway with HEATED private pool and jacuzzi
- 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!
- BEACH & SUNSETS CONDO!
- Newly remodeled 3-bedroom condo in a bundled community
- Spotless 2nd Flr., 2 Bdrm Luxury Condo with Spectacular Golf & Lake Views
- Country Creek -Lovely updated 3 bed/2 bath Estero home with hot tub and golf
- Charming 2-bedroom house with WiFi, AC in fabulous Bonita Springs
- 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 .
- Beautiful updated heated pool home in a quiet, gated community.
- Great Location! W of SR41 and within walking distance to the best attractions
- Renovated open floor plan with large heated pool and screened lanai with dining.
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:
- Beautiful 2BR In Pelican Sound - Golf, Tennis, & Beach Shuttle!
- Fort Myers 2BR Condo | Pool + BBQ + Gym
- Fort Myers Coastal Retreat Hot Tub Yard Games
How many Casai.nz holiday rentals are available in Seaside?
As of 2026, Casai boasts over 511 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.








































































