Monterey Holiday Rentals
- Naples
- ·
- Central Naples
- 1.11 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Naples
- ·
- Central Naples
- 2.30 mi to center
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
- Naples
- ·
- Naples Park
- 0.57 mi to center
- Oceanfront
- Pool
- Ocean View
- View
- Naples
- ·
- Naples Park
- 0.40 mi to center
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
- Naples
- ·
- Naples Park
- 0.63 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Naples
- ·
- Naples Park
- 0.44 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Naples
- ·
- Vanderbilt Beach
- 0.95 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Naples
- ·
- Vanderbilt Beach
- 0.92 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
- Naples
- ·
- Naples Park
- 0.31 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
Luxury Holiday Rentals in Monterey
- Naples
- ·
- Naples Park
- 0.43 mi to center
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Naples
- ·
- Pine Ridge
- 1.14 mi to center
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
- Naples
- ·
- Naples Park
- 0.21 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Naples
- ·
- Naples Park
- 0.60 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Naples
- ·
- Pine Ridge
- 0.64 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
- Naples
- ·
- Vanderbilt Beach
- 0.46 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
- Naples
- ·
- Vanderbilt Beach
- 0.31 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
- Naples
- ·
- Naples Park
- 0.43 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
Top-Rated Holiday Rentals with a Pool in Monterey
- Naples
- ·
- Naples Park
- 0.68 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Naples
- ·
- Naples Park
- 0.49 mi to center
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
- Naples
- ·
- Naples Park
- 0.49 mi to center
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
- Naples
- ·
- Naples Park
- 0.34 mi to center
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
- Naples
- ·
- Naples Park
- 0.21 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Naples
- ·
- Naples Park
- 0.48 mi to center
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
- Naples
- ·
- Naples Park
- 0.61 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Naples
- ·
- Naples Park
- 0.43 mi to center
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
- Naples
- ·
- Naples Park
- 0.55 mi to center
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
Pet-Friendly Holiday Rentals in Monterey
- Naples
- ·
- Naples Park
- 0.27 mi to center
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
- Naples
- ·
- Naples Park
- 0.47 mi to center
- Private Beach
- Oceanfront
- Fireplace/Heating
- Pool
- Naples
- ·
- Naples Park
- 0.30 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Naples
- ·
- Palm River Estates
- 0.26 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Naples
- ·
- Naples Park
- 0.47 mi to center
- Hot Tub
- Pool
- Pet Friendly
- Parking
- Naples
- ·
- Naples Park
- 0.52 mi to center
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
- Naples
- ·
- Park Shore
- 0.47 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Naples
- ·
- Naples Park
- 0.36 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Naples
- ·
- Naples Park
- 0.46 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
Large Holiday Rentals and Private Villas in Monterey
- Naples
- ·
- North Naples
- 1.44 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
- Naples
- ·
- Naples Park
- 0.32 mi to center
- Oceanfront
- Hot Tub
- Pool
- Ocean View
- Naples
- ·
- Naples Park
- 0.59 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
- Naples
- ·
- Naples Park
- 0.65 mi to center
- Fireplace/Heating
- Pool
- View
- Parking
- Naples
- ·
- Pelican Bay
- 0.25 mi to center
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
- Naples
- ·
- North Naples
- 3.72 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Naples
- ·
- Central Naples
- 1.75 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
- Naples
- ·
- North Naples
- 1.29 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Naples
- ·
- North Naples
- 2.29 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
Wheelchair Accessible Holiday Homes in Monterey
- Naples
- ·
- Park Shore
- 0.68 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
- Naples
- ·
- Naples Park
- 0.57 mi to center
- Balcony/Terrace
- Pet Friendly
- Parking
- Air Conditioner
- Naples
- ·
- North Naples
- 0.41 mi to center
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
- Naples
- ·
- Park Shore
- 0.68 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
- Naples
- ·
- Naples Park
- 0.17 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
- Naples
- ·
- Park Shore
- 0.75 mi to center
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
- Naples
- ·
- Vanderbilt Beach
- 0.89 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Naples
- ·
- Vanderbilt Beach
- 0.62 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
- Naples
- ·
- Pelican Bay
- 1.28 mi to center
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
Monterey Private Villas and Holiday Homes Under $200
- Naples
- ·
- Pine Ridge
- 1.23 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
- Naples
- ·
- Naples Park
- 0.53 mi to center
- Fireplace/Heating
- Balcony/Terrace
- View
- Parking
- Naples
- ·
- Park Shore
- 0.68 mi to center
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
- Naples
- ·
- Vanderbilt Beach
- 0.89 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Naples
- ·
- Central Naples
- 1.28 mi to center
- View
- Parking
- Air Conditioner
- Internet
- Naples
- ·
- Central Naples
- 1.03 mi to center
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
- Naples
- ·
- Naples Park
- 0.51 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Naples
- ·
- Naples Park
- 0.53 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Naples
- ·
- Central Naples
- 1.60 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
Instantly Bookable Holiday Homes in Monterey
- Naples
- ·
- Naples Park
- 0.49 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Naples
- ·
- Central Naples
- 0.96 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
- Naples
- ·
- Park Shore
- 0.33 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Naples
- ·
- Naples Park
- 0.45 mi to center
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
- Naples
- ·
- Vanderbilt Beach
- 0.87 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Naples
- ·
- Vanderbilt Beach
- 0.99 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Naples
- ·
- Park Shore
- 0.73 mi to center
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
- Naples
- ·
- Naples Park
- 0.40 mi to center
- Private Pool
- Pool
- Ocean View
- View
- Naples
- ·
- Park Shore
- 0.33 mi to center
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
Book a Last Minute Place to Stay in Monterey
About Casai's Private Villas and Holiday Rentals in Monterey
Discover more than 3559 vacation rentals available in Monterey. 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 Monterey.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Monterey, 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 Monterey. On average, places to stay near Monterey offer 1087.91 ft², with nightly prices averaging R7,438.
With Casai, finding and comparing holiday rentals in Monterey 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 Monterey
| Type | Count |
|---|---|
| Vacation Homes | 2173 |
| Holiday Apartments | 251 |
| Villas | 82 |
| Cottages | 29 |
Use these Quick Filters to Find a Holiday Rental in Monterey
★ 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 Monterey.
Weather in Monterey, FL
View the weather forecast for Monterey before booking your Monterey Vacation Rentals to confirm your best time to go.
Frequently Asked Questions About Monterey?
What are the top holiday rentals in Monterey?
With numerous options available in Monterey, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Monterey:
- Charming Beach Cottage with private Pool&Spa! Walk to stunning Vanderbilt Beach
- Heated pool home just 19 minutes walk to Vanderbilt Beach
- Relax by the sand at nearby Vanderbilt Beach or hang by heated pool
- Exclusive June-October Special Naples Pool Home Walk to Beach & Mercato
- SEASON SPECIALS! Designer House, Heated Pool & Spa, close to beaches, FREE Bikes
- SEASON SPECIALS! Cute Designer Home, Heated Pool Oasis, Near Beach, FREE Bikes
- Special Offer! Limited-Time Deal Walk to Beach Heated Pool & Spa
- Beautiful Naples Home: Private Pool, 4-Minute Drive to Vanderbilt Beach
- “COZY BEACH HOUSE” CLOSE TO BEACH, RESTAURANTS & SHOPPING
- ⭐️WATERFRONT-CANAL⭐️WALK TO BEACH🏖LARGE POOL 🌟BAYVIEW☀️GULF ACCESS☀️
How many holiday rentals have private pools in Monterey?
Discover a selection of holiday rentals with private pools near Monterey 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.
- Beautifully Decorated Beach Cottage with Sparkling Heated Pool
- Beach Life! Close To Vanderbilt Beach! & ON THE WATER, Private Oasis
- Sorrento Luxury Vacation Home: Expansive 5-Bedroom, 4.5-Bath Retreat with Private Pool, Hot Tub, and Pet-Friendly Accommodations – Just a Short Walk from Stunning Vanderbilt Beach
- Private Backyard Oasis w/New Spectacular Pool & Spa
Which holiday homes in Monterey are best for families?
If you're searching for a family-friendly holiday home in Monterey, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Monterey:
- Beautifully Decorated Beach Cottage with Sparkling Heated Pool
- Naples Beachwalk
- Sorrento Luxury Vacation Home: Expansive 5-Bedroom, 4.5-Bath Retreat with Private Pool, Hot Tub, and Pet-Friendly Accommodations – Just a Short Walk from Stunning Vanderbilt Beach
How many Casai.co.za holiday rentals are available in Monterey?
As of 2026, Casai boasts over 3559 properties listed in the Monterey area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Monterey.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Calusa Bay North Vacation Rentals in Naples, Florida | 3527 |









































































