Family Escape to Kissimmee & Anna Maria Island

Kissimmee and Anna Maria offer the best of both worlds: family-friendly fun near Orlando’s theme parks, shopping, and outdoor adventures, alongside the serene Gulf Coast charm of white-sand beaches, turquoise waters, and relaxing small-town vibes.

                  
7 Nights Legacy Vacation Resort, Kissimmee
  • Prime Orlando location near major attractions
  • Comfortable, well-appointed condo-style accommodations
  • Complimentary Wi-Fi throughout the resort
  • Four outdoor pools, spa tubs, and a splash pad
  • Fitness centre and sauna
  • Volleyball, basketball, and tennis courts
  • 9-hole miniature golf, children’s playground, and arcade game room
  • On-site resort convenience store

7 Nights Compass Hotel, Anna Maria Sound

  • An unspoilt 7-mile long island of paradise
  • Trendy Boutique Hotel at the Gateway to Anna Maria Island
  • Outdoor Pool with Marina Views
  • Complimentary Buffet Breakfast
  • Great location close to sublime beaches, restaurants and championship golf courses nearby

Prices

Year Dates Prices From
2026-2027 Low Season (Prices may vary) £975 per person
Gatwick Departure / 14 Nights Accommodation / Based on 21st September 2026
2026-2027 High Season (Prices may vary) £1215 per person
Gatwick Departure / 14 Nights Accommodation / Based on 2nd August 2026

Wide Range Of Dates Available
Call 020 3542 8888 for more details

Includes:

  • Round Trip UK Flights
  • Regional airports available on request
  • 14 Nights total accommodation
  • Car Hire for the duration
  • ABTA Protected

Excludes:

  • Hotel Resort Fees where applicable
  • Car parking fees where applicable
  • Attraction tickets – Can be added on request

Love this offer and want to book it? Please contact our Travel Planners and quote the deal reference P5

Based on 2 adults & 2 children sharing

Prices subject to availability at the time of booking

About Family Escape to Kissimmee & Anna Maria Island

Description

Escape to Florida with this fantastic Kissimmee and Anna Maria Island twin centre family holiday! The island’s attractions and  breath taking natural beauty combined with the amazing theme parks and other attractions of Kissimmee – two stunning destinations all wrapped up into one fabulous holiday!

Kissimmee

Located in the Kissimmee area of Orlando, Legacy Vacation Resort offers comfortable, stylish condo accommodations with friendly service and resort-style amenities. The resort is just four miles from Walt Disney World® and close to Orlando’s top attractions, shopping, dining, and recreational activities, making it an ideal base for a family holiday.

The resort features home-style comforts including fully equipped kitchens, separate living areas in larger suites, cable TV, complimentary Wi-Fi, and air conditioning. On-site amenities include four swimming pools, a kids’ splash zone, mini golf, arcade, tennis and basketball courts, a fitness centre, sauna, and organised family activities like scavenger hunts and face painting.

Beyond the resort, Kissimmee offers adventures for all ages, from world-class shopping and hot air balloon rides to Gatorland and Fun Spot America. Explore historic Old Town, enjoy dinner entertainment shows, or visit the Kennedy Space Center for a truly unforgettable Florida experience. Legacy Vacation Resort is the perfect base for families seeking fun, relaxation, and easy access to Orlando’s top attractions.

Anna Maria Island

Experience a part of Paradise and visit the breath-taking Anna Maria Island.  A complete “get away from it all” retreat, this unspoiled Island is the perfect choice to relax and enjoy nature at its best.  Just over 7 miles long, Anna Maria is a barrier island full of ‘old’ Florida charm providing a relaxing holiday of swaying palm trees and incredible sunsets.

Amazing Anna Maria Island is just under one hour’s drive south of Tampa International airport and 20 minutes from downtown Bradenton. With a stunning seven-mile strip of beautiful beaches, it’ll dazzle you with its breath-taking scenery and village like lifestyle. There is lots to see and do and the sugar-white sand beaches are perfect for everyone – very young families, large families, three generations and couples alike. The beaches boast fabulous barefoot dining restaurants where guests can sample the Island’s freshly caught seafood and local Florida cuisine whilst watching the sunset. Another great feature is Anna Maria’s accommodation, largely made up of homes and apartments from one bedroom to larger group party sizes and many of these are waterfront properties. Leave the car keys behind and enjoy exploring the island by foot, bike or on the free Island Trolley which takes visitors from North to South every 20 minutes. Always close to the soft, sandy beaches and warm gulf waters, the outdoor life is the main attraction. With unique animals from sea turtles to manatees and Florida bird life to watch in wonder; this is a true paradise for nature lovers.

Coquina Baywalk offers magnificent views with mangrove tunnels and stunning scenery, the natural parks and nature trails provide hours of exploration. Enjoy kayaking, canoeing, parasailing, fishing and golfing, all within easy reach. Unique cafes, restaurants, home-made ice-cream parlours and pubs are a refreshing change from the large chains of the big cities. Visit fine bakeries for donut treats with a host of icings and toppings to choose from.

One of the main activities of locals and visitors alike is strolling along the astonishingly beautiful beaches looking for unique and stunning shells that have washed up on the shore. Pick up a shell identifying chart from one of the local shops and have fun at the end of the day locating the different shells collected.

Call one of our TravelPlanners 020 3542 8888 to book this family twin centre to Kissimmee and Anna Maria today!

Book your Florida Beaches holiday today!

from £975 per person

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Reference #P5
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