Florida Weekend Getaways

Best Weekend Getaways in Florida

Anna Maria Island: Old Florida Charm

Escape to the tranquil shores of Anna Maria Island, where time slows down. This picturesque destination features powdery white sands, turquoise waters, and cozy beach cafes. Promising carefree R and R by the beach, Anna Maria Island is perfect for couples and families seeking some serenity away from the theme parks of Central Florida. Beachlovers should head to either the family-friendly Bradenton Beach or the less crowded Holmes Beach, which is perfect for kayaking. Later, explore the quirky shops along Pine Avenue, Coquina Beach Market or on Bridge Street Pier. Fishing enthusiasts will enjoy passing the time at Anna Maria City Pier, whilst foodies will love tucking into the fresh seafood served at the iconic waterfront restautant, Rod & Reel Pier.

Adventurous groups meanwhile will enjoy kayaking through mangroves, cycling along the scenic paths and taking a boat tour out to Egmont Key, for a spot of snorkeling, shelling and to visit the historic lighthouse. Nature fans will relish the dolphin and manatee spotting tours in Anna Maria Island, as well as the tranquil nature trails and boardwalks which meander through the Leffis Key Preserve. As dusk falls on your weekend getaway, soak up the sunset from Bean Point, or with an island boat tour or romantic sunset cruise.

Where to stay in Anna Maria Island

Our Anna Maria Island rentals in beach communities such as Holmes Beach and Bradenton Beach provide a carefree base for scenic Florida weekend getaways - with scenic dining terraces, private pools, sun-drenched backyards and more to soak up.

Orlando: A Weekend of Fun & Adventure

Home to the iconic theme parks of Walt Disney World and Universal Studios, Orlando is home to no less than 18 theme parks, making it the perfect destination for experiencing fun-filled Florida weekend getaways. Orlando offers much more than theme parks though - it’s an iconic, year-round entertainment hub for all manner of thrilling and unique experiences, world-class golf courses, sporting arenas and luxury upscale resorts.

With plenty of things to do in Orlando besides the theme parks for weekenders, this Central Florida destination attracts every type of Florida vacationer. Whatever the weather, you'll find endless indoor activities to do in Orlando when it rains - from indoor go-karting and escape rooms to immersive museums and more. Enjoy visiting Gatorland, the Orlando Science Center, Dreamworks, the epic waterparks and shopping malls or take a trip to the nearby Kennedy Space Center. Weekenders seeking a moment's respite will enjoy exploring Lake Eola Park or the Leu Botanical Gardens. Orlando offers endless dining options too, including upscale dining and immersive theater dinner shows. Culture fans will relish a concert or musical at the the Dr. Philips Center for the Performing Arts and the Kia Center, whilst sports' fans can catch a game at one of the city's top sporting arenas and stadiums. The Orange County Convention Center also hosts a plethora of first-class events - for an unforgettable long weekend.

Where to stay in Orlando

Our exclusive Orlando resorts offer proximity to the parks, luxury home comfort and first-class amenities. Whether it's a luxury golf villa, fun family pool villa with themed rooms, resort condo or lavish mansion, our short-term rentals offer the perfect base for fun Florida weekend getaways.

Miami: Sun, Style, & Nightlife

For cosmopolitan Florida weekend getaways, look no further then the iconic city of Miami. Explore the upscape shops, restaurants and contemporary art in Miami Design District and the waterfront Perez Art Museum Miami (PAMM). Weekenders seeking something unique will love visiting Wynwood Walls and savoring the Cuban-inspired food and ambience of Little Havana. The Frost Science Musuem and the Vizcaya Museum and Gardens also promises to be a first-class, immersive experience. Nature fans meanwhile will relish a day trip to the Fairchild Tropical Botanic Garden and nearby Everglades National Park.

Beach-goers seeking the mild waters of Miami can soak up South Beach, the quieter beaches of Key Biscayne or another one of Miami's top beaches. Once you've recharged, don't forget to rev it up and experience Miami's world-famous nightlife during your long weekend.

Where to stay in Miami

Our award-winning collection of Miami villas with pools and sophisticated enetertainment and relaxation zones are ideally placed for hosting exclusive Florida getaways with family, friends and corporate groups.

Fort Lauderdale: The Venice of America

Just 30 miles north of Miami, Fort Lauderdale is known for its upscale resort vibe and vast canal network. Fort Lauderdale is the perfect setting for scenic Florida weekend getaways, both on the water and off it!

Cruise or paddleboard along the Intracoastal Waterway or take an enlightening journey on the Jungle Queen Riverboat Cruise. Once you're ready to return to shore, venture out and experience the thriving arts scene at the NSU Art Museum. Savor fresh seafood at the lively waterfront restaurants of this cosmopolitan, coastal city and later on indulge in cocktails and the buzzing nightlife at The Wharf. Those seeking a more laid-back evening can enjoy a scenic stroll and photo opportunity at Dani Beach Pier, a popular fishing spot.

Nature fans will also enjoy visiting the wildlife sancutary and botanical backdrop of Flamingo Gardens, whilst a ride on an Everglades airboat offers a great way to embark on a tour of the rich and diverse ecosystem of this renowned National Park. Active groups can also enjoy a kayak or bike ride around the tranquil Hugh Taylor Birch State Park.

Where to stay in Fort Lauderdale

Our collection of Fort Lauderdale rentals near Las Olas Boulevard encompasses a fantastic range of rentals available for short weekend breaks. Dive into sun-drenched private pools with fun relaxation areas, direct waterfront access and chic interiors.

Destin: The Emerald Coast Escape

Home to some of Florida's best beaches, the beautiful Destin area in the Florida Panhandle is a perfect choice for couples, groups and families seeking a fun and captivating weekend away.

First and foremost you'll find the coast will be calling, so head to a Destin Beach and sink your toes into the cooling white quartz sand, for a beguiling day by the glistening emerald waters. Those looking to rev up their beach day can continue the water-based fun at Big Kahuna's Water & Adventure Park or at the legendary Crab Island. Rent a pontoon boat, kayak, paddleboard or hop on a tour and visit this iconic, submerged sand bar, for an upbeat atmopshere and lively drinks with pals.

A weekend getaway in Destin also invites you to visit the Gulfarium Marine Adventure Park and Emerald Coast Science Center, enjoy an invigorating deep-sea fishing trip, relish an open-air shopping trip at Destin Commons and savor a meal and drinks along the vibrant boardwalk. You'll also be able to kick back with a sunset cruise, a timeless swim and sunset walk in Henderson Beach State Park or go kayaking and paddleboarding in the calm waters of Choctawhatchee Bay.

Where to stay in Destin

Our Destin vacation rentals invite groups and families to relax and entertain in style, from exclusive ocean-view locations, with private pools, direct beach access and more to dive into.

Inexpensive Weekend Getaways in Florida

Orlando: Affordable Family Fun

With world-class fun on the doorstep and large multigenerational resort rentals to soak up, families and groups can experience an epic year-round weekend away, that won't break the bank.

Families seeking out the enchantment and excitement of the theme parks can plan ahead and make the most of best-rate-guarantee tickets for Disney World and Universal Studios. Aside from the parks, there are endless cheap and free things to do in Orlando for families, ensuring Florida weekend getaways, whatever the season are both memorable and affordable! Enjoy visiting Lake Eola Park, Disney Springs and the scenic setting of Winter Park, or take in the free downtown CityArts gallery, the free seasonal night events at Orlando Science Center and the popular play area at Icon Park.

Where to stay in Orlando

Surprisingly cost-effective, when priced per person per night, our family-friendly resorts promise the comfort and freedom of home with the luxury amenities of a hotel. Some of our most affordable options include the short-term rental communities of Encore Resort at Reunion, ChampionsGate Resort, Vista Cay Resort and Storey Lake Resort.

Cape Coral: Canal-Side Comfort

Cape Coral on the Gulf of Mexico promises a relaxing tonic of waterfront escapism, that won't break the bank. With over 400 miles of canals to explore, this unique city is a haven for kayaking, boating, and fishing. Enjoy the local dining scene and soak up the sunsets and family-friendly appeal of the free Yacht Club Community Park Beach - featuring calm waters, a quaint fishing pier, playground and picnic area. Within a short drive of Cape Coral, families can also reach more free public beaches in Fort Myers and Sanibel Island.

Aside from the amazing beaches, there's a whole host of cheap and free things to do in Cape Coral, making it a top choice for inexpensive Florida weekend getaways.

Where to stay in Cape Coral

For fun and affordable Florida weekend getaways, our family-friendly Cape Coral rentals include pet-friendly options and waterfront retreats with open concept living rooms and pool tables, scenic lanais with private pools, boat docks and scenic tiki bars.

Fort Myers: Gateway to Island Escapes

Fort Myers is a great choice for inexpensive weekend getaways in Florida, with plenty of family-friendly activities to dive into, whatever budget you're traveling on.

Nestled on the banks of the Caloosahatchee River, relax along its buzzing yet laid-back Gulf coast beach or soak up the nearby shores of Sanibel and Captiva. Stroll through the Six Mile Cypress Slough Preserve, Lakes Regional Park and Manatee Park, for scenic trails and opportunities to spot local wildlife. Other popular wildlife activities for families in Fort Myers includes a trip to the Shell Factory & Nature Park and the Calusa Nature Center and Planetarium. Families with older kids will also be able to visit the Edison and Ford Winter Estates, for a dose of history and gardens. For budget-friendly dining options, try the local fresh seafood shacks and low key cafes. The local farmers' markets are another great spot for affordable bites whilst out and about.

Where to stay in Fort Myers

When looking to soak up an affordable Florida weekend stay in Fort Myers, our collection of waterfront homes are refreshingly affordable when priced per person per night. Offering amazing amenities such as private docks, pools with scenic lanais and more, our rentals provide a welcoming weekend retreat.

Unique Weekend Getaways in Florida

International Drive: First-class Entertainment & Thrills

For a one-of-a-kind weekend, stay on Orlando’s International Drive (I-Drive). This unique entertainment hub offers endless things to do, from world-class attractions and upscale dining to ICON Park, the home of famous and unique attractions including the 400-ft tall Orlando Eye observation wheel.

Couples can indulge in spa treatments or a romantic dinner, while families will love the endless all-weather activities - from iFly indoor skydiving, Dezerland, WonderWorks and Topgolf Orlando to the quirky wonders at Madame Tussauds, Titanic: The Artifact Exhibition, and Ripley’s Believe It or Not! Savor a tempting tour of Chocolate Kingdom, chill at Icebar Orlando, the world’s largest ice bar, or be gripped by an immersive meal at Sleuths Murder Mystery Dinner Show. When it's time to rev things up, head to Andretti Indoor Karting, for high-speed action on the track.

Where to stay on Orlando's I-Drive

Bring back the excitement of I-Drive, with a weekend stay in nearby Villatel Orlando Resort. Offering resort amenities and contemporary retreats with fully-optimized interiors, these unique Orlando retreats are a destination in themselves!

Okaloosa Island: Emerald Coast Beauty

Located between Destin and Fort Walton Beach, Okaloosa Island offers a unique blend of relaxation and adventure on the stunning Emerald Coast.

Known for its sugar-white sands and emerald-green waters, this unique destination is perfect for snorkeling, paddleboarding and exploring the Gulf Islands National Seashore. A short break highlight has to be a catamaran dolphin cruise or a trip to the Gulfarium Adventure Park, where you can swim with dolphins, snorkel with stingrays and learn about the sea turtles. For a lively evening out, head to the boardwalk on Okaloosa Island, which offers a great buzz with restaurants, shops, laid-back eateries and free beach access. Those seeking a peaceful sunset moment should embark on a picturesque kayak or paddleboard, through the Santa Rosa Sound.

Where to stay on Okaloosa Island

Our spacious Okaloosa Island vacation rentals place families and groups within carefree proximity of the beautiful beaches and activities, with first-class resort amenities to soak up - for a unique and memorable weekend away.

Clearwater: Quartz Beach Gem

Clearwater’s award-winning white quartz beaches and lively atmosphere make it a standout destination for enjoying a unique Florida weekend getaway. You'll find countless things to see and do, making it a great choice for families and multigenerational groups.

Dip your toes into the stunning quartz sand of Clearwater Beach, dive into adventure with watersports like jet-skiing and paddleboarding or take a scenic stroll along the iconic Pier 60, for nightly festivals, live entertainment, and stunning sunsets. Families will love the unique Captain Memo's Pirate Cruise experience as well as a trip to the Clearwater Marine Aquarium, which is home to rescued marine life. Nature enthusiasts can also enjoy exploring the serene trails of Caladesi Island State Park and paddleboarding or kayaking in the Intracoastal waters, past mangrove trails and calm waters which are home to manatees, rays and seabirds. Those looking to celebrate a special occasion can enjoy a unique bird's-eye view of Clearwater Beach and the Gulf, with an unforgettable helicopter tour.

Where to stay in Clearwater

Our luxury rentals near Clearwater Beach let you enjoy the best of this Gulf Coast gem. Soak up sun-drenched private pools and sunsets from your private terrace, entertain within your home-away-from-home and experience a unique weekend away.

Book Your Florida Weekend Getaway

Whether you’re seeking a romantic retreat, a family adventure, or an affordable coastal escape, our luxury Florida vacation rentals with optional Concierge are perfect for every type of traveler. From Anna Maria Island to Miami, your dream long weekend is just a click away. Explore our award-winning Florida vacation rentals and start planning your next unforgettable getaway!