FL Vacation Rental Homes Condo Lodging

FL Vacation Rentals

Visit Florida and find some amazing home away home short-term, vacation rental properties. Choose from luxury vacation homes with a private pool and spa and oceanside condo rentals just steps from the beach. Stay in a high-rise gated condo with your own balcony, roof-top pool, and spectacular view. Watch the famous Florida sunsets from your private deck. Stay poolside or golf side at an award-winning Florida golf resort home or condo. Our suggested Florida Vacation Rental Specialists will help you find the ideal Florida Vacation Rental. Share your FL vacation home questions, contact us.

Top 5 Florida Vacation Destinations

Orlando: The Theme Park Capital

Things To Do:

Walt Disney World Resort
Universal Orlando Resort
SeaWorld Orlando
ICON Park
Orlando Science Center

Places to Stay:

Encore Resort at Reunion – 7635 Fairfax Dr, Reunion, FL 34747
Marriott’s Grande Vista – 5925 Avenida Vista, Orlando, FL 32821
VRBO: 6BR Pool Home Near Disney – Listings available in Kissimmee/Clermont
Airbnb: Modern Townhouse near Universal Studios – Orlando area listings

Extended Stay Tip: Book during late January or mid-September for off-peak discounts.

DISNEY ORLANDO FLORIDA VACATION RENTALS

Browse current Disneyworld, Orlando, FL Hotel Specials, VRBO Vacation Rentals, Airbnb Apartment and more below.

Miami: Culture, Nightlife, and Beaches

Things To Do:

South Beach & Ocean Drive
Wynwood Walls
Little Havana
Miami Design District
Biscayne National Park

Places to Stay:

Fontainebleau Miami Beach – 4441 Collins Ave, Miami Beach, FL 33140
EAST Miami Hotel – 788 Brickell Plaza, Miami, FL 33131
Airbnb: South Beach Loft with Ocean View – Miami Beach listings
VRBO: Private Villa with Pool – Coconut Grove area

Extended Stay Tip: Mid-May to early June offers great weather without the peak-season prices.

Tampa Bay Area: Gulf Coast Vacations

Things To Do:

Busch Gardens Tampa Bay
Clearwater Beach
The Florida Aquarium
Ybor City Historic District
Tampa Riverwalk

Places to Stay:

The Don CeSar – 3400 Gulf Blvd, St Pete Beach, FL 33706
Hyatt Place Tampa Downtown – 325 N Florida Ave, Tampa, FL 33602
VRBO: Waterfront Condo on Clearwater Beach – Clearwater listings
Airbnb: Ybor City Bungalow – Tampa listings

Extended Stay Tip: Look for VRBO/Airbnb discounts during late summer or early fall.

Florida Keys: Island Paradise

Things To Do:

Snorkeling in John Pennekamp Coral Reef State Park
Duval Street nightlife in Key West
Ernest Hemingway Home & Museum
Dolphin encounters at Theater of the Sea
Scenic Overseas Highway drive

Places to Stay:

Casa Marina Key West, Curio Collection – 1500 Reynolds St, Key West, FL 33040
Parmer’s Resort – 565 Barry Ave, Little Torch Key, FL 33042
VRBO: Key Largo Oceanfront Cottage – Listings in Key Largo and Islamorada
Airbnb: Tiny House on the Water – Lower Keys listings

Extended Stay Tip: Many resorts offer discounted 7-night stays during shoulder seasons (April-May, Sept-Oct).

Naples & Marco Island: Southwest Florida Luxury

Things To Do:

Naples Botanical Garden
Shopping on Fifth Avenue South
Marco Island Beach & Dolphin Tours
Everglades National Park excursions
Corkscrew Swamp Sanctuary

Places to Stay:

LaPlaya Beach & Golf Resort – 9891 Gulf Shore Dr, Naples, FL 34108
Hilton Marco Island Beach Resort – 560 S Collier Blvd, Marco Island, FL 34145
Airbnb: Modern Beach Condo – Naples listings near Vanderbilt Beach
VRBO: Waterfront Estate with Dock – Marco Island listings

Extended Stay Tip: Snowbirds often book multi-week stays from December to April — reserve early for winter months.

Tips for Booking Florida Vacation Rentals

Book Early for Peak Seasons – Especially for holidays, winter, and spring break.
Use Filters for Pet-Friendly or Kid-Friendly Options – VRBO and Airbnb offer this.
Watch for Resort Fees – Some hotel listings may appear cheaper until fees are added.
Read Reviews Thoroughly – Especially for Airbnb or VRBO rentals.
Ask About Discounts for Longer Stays – Owners may negotiate off-platform.

Florida Travel Seasons & When to Go

High Season: December to April (Dry, sunny, and popular with snowbirds)
Shoulder Seasons: May to early June, September to November (Best for deals)
Low Season: July to August (Hotter, risk of hurricanes, but cheapest)

Extended FL Vacation and Staycation Ideas: Work + Play

With the rise of remote work, Florida is an ideal location for a workcation.

Best Places for Remote Work Rentals:

St. Augustine – Historic charm and fiber internet
Sarasota – Beautiful beaches and quiet neighborhoods
Fort Lauderdale – Urban access, beach views, and strong business centers

Florida Extended Stay Vacations

Florida offers vacation experiences for every kind of traveler — from family-friendly theme parks to romantic island escapes and luxurious beachfront resorts. Choosing the right type of vacation rental — whether it’s a VRBO beach house, an Airbnb condo, or a high-end hotel — will shape your entire travel experience. By booking early, comparing platforms, and knowing the best seasons to travel, you can unlock the best of the Sunshine State.

Featured FL Vacation Rentals & Rental Agents

Matt Brown, William Raveis Real Estate, 720 Fifth Avenue South, Naples, FL 34102 | 239-580-8864
Specializing in luxury homes and condominiums, Matt Brown has 18+ years of experience marketing and selling exceptional properties. He has closed over $500 million and skillfully negotiated over 100 highest and best multiple-bid sales. Unparalleled focus on every detail, his reputation continues to set the bar high in the industry.
Matt Brown, Bonita Springs, Estero, Naples, FL Real Estate Agent

Becky Irwin Realtor� | 954-249-0374
Becky Irwin has been Florida resident for more than 30 years. Her family moved full time to Marco Island in 1980 and then to Fort Lauderdale in 1983. Becky is intimately familiar with both the east-coast (Broward) and west-coast (Collier) communities of Florida. A graduate of both St. Thomas Aquinas High School and Florida State University, she has deep roots and connections across South Florida. Becky is a licensed Florida Broker Associate, a member of the Marco Island Area Association of Realtors, Naples Area Board of Realtors and the Realtor Association of Greater Fort Lauderdale.
Visit Becky Irwin Realtor Listings

Marco Expert - Patrick J. Wilkins Realtor� | 239-260-3550
Certified Luxury Home Marketing Specialist. When you are ready to buy or sell on Marco Island contact the Wilkins Team. Personally sold Over $950 Million. Member RE/MAX Affinity Plus. #1 RE/MAX Agent Worldwide 2004. Browse our website for Marco Island real estate market research, covering all the surrounding areas as well.
Visit Marco Expert - Marco Island, FL