Upper Matecumbe Key Holiday Rentals
About Casai's Private Villas and Holiday Rentals in Upper Matecumbe Key
Discover more than 1445 vacation rentals available in Upper Matecumbe Key. 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 Upper Matecumbe Key.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Upper Matecumbe Key, 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 Upper Matecumbe Key. On average, places to stay near Upper Matecumbe Key offer 687.24 ft², with nightly prices averaging R12,653.
With Casai, finding and comparing holiday rentals in Upper Matecumbe Key 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 Upper Matecumbe Key
| Type | Count |
|---|---|
| Vacation Homes | 771 |
| Holiday Apartments | 135 |
| Villas | 103 |
| Cottages | 12 |
Use these Quick Filters to Find a Holiday Rental in Upper Matecumbe Key
★ 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 Upper Matecumbe Key.
Weather in Upper Matecumbe Key, FL
View the weather forecast for Upper Matecumbe Key before booking your Upper Matecumbe Key Vacation Rentals to confirm your best time to go.
Top Attractions Around Upper Matecumbe Key, FL
Casai offers a large selection of top attractions around Upper Matecumbe Key . Research things to do on your vacation before you visit Upper Matecumbe Key.
Other Places to Stay in Upper Matecumbe Key, FL
Frequently Asked Questions About Upper Matecumbe Key?
What are the top holiday rentals in Upper Matecumbe Key?
With numerous options available in Upper Matecumbe Key, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Upper Matecumbe Key:
- OCEANSIDE ANGLERS REEF 2/2.5 HOME- Gated community- Pool, Dock, Private Beach
- The Caribbean Resort
- WATERFRONT FISHING COTTAGE/DOCKAGE + Walking distance to world famous Lorelei
- Serenity by the Sea! Anglers Reef with Boat Slip Available!
- 4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL
- Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip
- Islamorada Oceanfront Home with Ocean View, Dock, Comm Pool & Beach, plus Den
- Truly OceanFRONT-BestPanoramicOceanViews-VLgDecks-QuietestLocation-AvailableSlip
- Now booking heavily for 2027! - Oceanfront - Heated Pool - Dock
- Front Row, DIRECT Ocean/Pool Views, Anglers Reef, Islamorada. Boat Dock, Beach
How many holiday rentals have private pools in Upper Matecumbe Key?
Discover a selection of holiday rentals with private pools near Upper Matecumbe Key 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.
- Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,
- Pineapple Beach by Florida Keys Luxury Rentals
- Islamorada retreat "Bungalow Blue" w/heated pool, Bikes, BBQ, amenities galore!
- Port Antigua NEW Luxury one bedroom/2 bath apt with pool
Which holiday homes in Upper Matecumbe Key are best for families?
If you're searching for a family-friendly holiday home in Upper Matecumbe Key, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Upper Matecumbe Key:
- Room #2 in Charming hotel with AC in sunny Islamorada
- Key Lime Cottage in the heart of Islamorada
- Topsider Resort
How many Casai.co.za holiday rentals are available in Upper Matecumbe Key?
As of 2026, Casai boasts over 1445 properties listed in the Upper Matecumbe Key area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Upper Matecumbe Key.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Coral Cove Vacation Rentals in Florida | 643 |
