Win one of 11 two-night summer staycations at some of Florida’s best resorts and boutique hotels.

Beat the heat this summer with a staycation at one of the many resorts and hotels across Orlando, Tampa and beyond. Now offering spectacular summertime rates, these sprawling properties provide the perfect elements of a getaway for two.

We’ve gathered all the details for nearly a dozen different staycation packages but even better… we’re giving all 11 away during our Annual Great Summer Staycation Giveaway. 11 lucky couples in total will enjoy some much needed summertime QT.

Beginning Tuesday, May 28, 2019, we’ll start giving away different staycation packages every week with the final getaway prize awarded on Thursday, June 20, 2019.

Only one entry necessary per email address. One email entry equals entry into all 11 giveaways. We draw a new winner each week from the total list of entries to date through Orlando Date Night Guide.

Enter below and be sure your sweetie enters too… double your chances!

[gravityform id=”34″ title=”false” description=”false”]

Rules & Fine Print

All winners are chosen completely at random using the random number generator at No exchanges, cash alternatives or substitutions for prizes. You get what you get, and you don’t get upset! NO PURCHASE NECESSARY. Void where prohibited. Open only to individuals who are, as of entry date, at least 21 years of age + legal residents of, and physically located within, the U.S. and Puerto Rico and who are not minors. Sweepstakes drawing starts 12:01 AM (ET) on 5/28/19 and ends 12:01 AM (ET) on 6/20/19. Click here for full Official Rules.


TUESDAY, MAY 28: Hilton Orlando 

WINNER: Rachel Halscott (5/28/19 6:50)
Tucked away in the heart of Orlando is where you’ll discover Hilton Orlando, a vibrant, contemporary resort with an exciting personality to complement an exceptional location. Centrally located to all the major theme parks and attractions and just minutes from the eclectic dining scene and entertainment of International Drive, this resort sits on over 26 acres of lush landscaping and tropical inspirations.

Hilton Orlando offers seven distinct dining options from the fine-dining experience at Spencer’s to the more leisurely Tropics Pool Bar & Grill. The heart of the resort is the expansive recreation area featuring a tropical oasis with sweeping waterfalls overflowing into two pools and a lazy river lined with luxurious cabanas. For more activity, take a plunge down the winding waterslide, or splash in the Splash Zone. Inside, take the time for wellness and enjoy eforea, the on-site spa and fitness center.

One winner will receive a two-night stay, which includes daily resort charge and complimentary self-parking. Subject to availability, some blackout dates may apply. Valid through 5/30/2020.

For more information, visit

Hilton Orlando

THURSDAY, MAY 30: Reunion Resort 

WINNER: Diane Rivers (5/23/2019 8:53:05 PM)
Reunion Resort features luxury resort accommodations including private villas and vacation homes surrounded by 2,300 acres of lush landscape as well as a nature preserve. It is the only location in the United States with three signature golf courses designed by the golf greats Jack Nicklaus, Arnold Palmer and Tom Watson.

The resort also features a boutique spa and salon, 10 pools and a 5-acre water park with a 1,000-foot long lazy river. The resort’s modern award-winning steakhouse restaurant, Eleven, features a rooftop pool patio and nightly views of the fireworks from nearby Walt Disney World.

One winner will receive 2-nights in a 1-bedroom villa, with breakfast for two each morning. Package includes resort fee and self-parking. Subject to availability, some blackout dates may apply. Valid through 7/1/2020.

Learn more about Reunion Resort's Free Night Offer: Receive a 3rd night free with mid-week stays or a 4th night free all week long. 

For details, visit

Reunion Resort

TUESDAY, JUNE 4: Hilton Daytona Beach Oceanfront Resort

WINNER: Giavanna Miles (5/24/2019 7:51:04 PM)
Located in the heart of Daytona Beach and steps away from the city’s best oceanside shopping and visitor attractions, the Hilton Daytona Beach Oceanfront Resort is a couples-oriented and pet-friendly property offering world-class amenities on The World’s Most Famous Beach. Recently named one of Florida’s best hotels by US News and World Report, the property has undergone a $25 million renovation and is home to 744 rooms, including 32 suites and 30 beachfront cabana suites, as well as two resort-style pools, a spa, gift shop, fitness center, seasonal events, kid-friendly activities and several premiere restaurant and bar venues for every taste. In addition, Hilton Daytona Beach Oceanfront Resort offers more than 60,000 square feet of indoor and outdoor space for weddings, meetings and other special events.

One winner will receive a 2-night package including deluxe accommodations, free valet parking, breakfast for 2, 1-hour beach bike rental, comp resort fee (providing guest Internet access, $5 food credit, 15% off facial or massage, 15% off gift shop regular priced clothing, 1hr board or bike rental,1 select D-Dawgs arts-crafts, Breakfast free for ages 12 and under off the kid menu with parent, and local-toll free calls), and full use of resort amenities.

The Hilton Daytona Beach’s “Florida Resident's Rate” package is perfect for a summer staycation. It's offered at 10% off of the best available rate. As an added bonus, Friday and Saturday nights from your room or the resort’s pool decks, enjoy the Bandshell Summer Concert Series and Fireworks, July through September starting at 7pm at the adjacent Daytona Beach Bandshell. To book call 386-254-8200 or

Hilton Daytona Beach Oceanfront Resort

WEDNESDAY, JUNE 5: Hilton Orlando Bonnet Creek 

WINNER: Jaclyn Taylor (5/23/2019 3:16:01 PM)
Surrounded by Walt Disney World Resort and nestled on a 482-acre nature preserve, Hilton Orlando Bonnet Creek features family-friendly deluxe accommodations. Amenities include an award-winning lazy river pool, cabanas, championship golf course, Waldorf Astoria Spa, fitness center, and world-class dining. Plus, guests enjoy complimentary transportation to the Disney theme parks and Disney Springs.

One winner will receive a two-night stay, including tax and resort fee. Parking is additional. Valid thru 10/31/2019, based on availability.

Ready to have a blast this summer in Orlando?! At Hilton Orlando Bonnet Creek, celebrate the magic of summer with SummerBlast, a season-long, activity-packed, wave of family fun. As a guest, you’ll also enjoy official Walt Disney World® hotel perks, like Disney’s Extra Magic Hours benefit and FastPass+ service (with booking up to 60 days in advance), and daily shuttle transportation to Walt Disney World theme parks and Disney Springs. The most magical summer in Orlando awaits! Visit to learn more.

Hilton Orlando Bonnet Creek

THURSDAY, JUNE 6: Hard Rock Hotel Daytona Beach 

WINNER: Cristina Del Rosso (5/26/2019 10:32:41 PM)
Hard Rock Hotel Daytona Beach brings the global brand’s iconic vibe and energetic beat to a wide stretch of world-famous Atlantic shoreline. The 200-room beachfront property features renowned, brand-exclusive offerings and amenities, including The Sound of Your Stay® music program, offering complimentary use of Fender guitars and Crosley record players for in-room jam sessions, as well as a full-service Rock Spa® and Salon, a Rock Shop® and a Body Rock® Fitness Center. The hotel also includes the signature Sessions restaurant and bar and open-air Wave Terrace. The beachfront pool features an expansive party deck and outdoor pool bar and grill.

One winner will receive a two-night stay, including tax, resort fees, parking and a $100 dining credit. Valid thru 9/30/2019, based on availability.

Hard Rock Hotel Daytona Beach offers 15% off stays with a 14-day advance purchase early booking. For more information or reservations, call 844-745-1502 or visit

Ad for Orlando World Center

Daytona Beach
Hard Rock Hotel Daytona Beach

TUESDAY, JUNE 11: Rosen Shingle Creek 

WINNER: Kassie Hojnacki (5/26/2019 9:49:59 AM)
Rosen Shingle Creek, a stunning 255-acre luxurious escape set at the headwaters of the Everglades, features 1,501 elegant guestrooms and suites set amidst Spanish Revival-style architecture. Four outdoor swimming pools, The Spa at Shingle Creek, a championship golf course designed by Arnold Palmer Design Company, tennis courts, a sand volleyball court, seasonal fishing, a nature trail and more guarantee guests don’t have to leave the grounds to be perfectly content—yet nevertheless are within minutes of Orlando’s celebrated theme parks and attractions.

One winner will receive a two-night stay, including tax, resort fees and self-parking. Valid thru 10/29/2019, based on availability.

For more information about Rosen Shingle Creek's summer specials and leisure packages, visit or call 866-996-6338.

Rosen Shingle Creek

WEDNESDAY, JUNE 12: Hyatt Regency Orlando 

WINNER: Michelle Covino (6/11/2019 9:41:29 AM)
Located in the heart of International Drive, this magnificent property is just a stone’s throw away from the area’s best nightlight offerings including Orlando Improv, Mango’s Tropical Café, and ICON Park Orlando. Hyatt Regency Orlando features a lush outdoor grotto pool with cabanas, as well as a full service salon and spa, and a newly renovated award-winning restaurant, Fiorenzo.

One winner will receive a two-night stay in the hotel's newly renovated Executive King guestroom, including complimentary valet parking and a private cabana at the Grotto Pool. Gift certificate inclusive of tax and resort fee. Valid through 5/31/2020, based on availability.

This summer, save up to 20% on advance purchase bookings at Hyatt hotels across the globe and take the vacation break you’ve been dreaming of. Be sure to book between May 15 – August 27, 2019 for vacation dates anytime between May 24 – September 2, 2019. Details here. 

Hyatt Regency Orlando

THURSDAY, JUNE 13: TradeWinds Island Resorts

WINNER (REDRAW on July 15, 2019): Jim Tischler (5/23/2019 4:04:20 PM)
Located directly on St. Pete Beach, the TradeWinds Island Resorts offer two distinct beach resorts with endless beach activities, sumptuous dining, sand-in-your toes beach bars, exciting kids programs, spacious accommodations and more! TradeWinds Island Resorts… Enjoy life and just let go!

One winner will receive a two-night stay! Sip, Savor & Swoon on St. Pete Beach. Turn your ultimate date night into a romantic getaway with a trip to RumFish Beach Resort by TradeWinds. This perfect 2-night Sip, Savor & Swoon package is full of so much to love, including:

  • 2 nights’ accommodations at RumFish Beach Resort for you and your best catch
  • $100 certificate to dine in the soft glow of a 33,500-gallon aquarium at RumFish Grill
  • Champagne and gourmet chocolate-dipped strawberries
  • The nightly resort amenity fee which includes: parking, a cushioned and hooded beach cabana for two, nightly sunset s’mores, sunset strolls along the shore and so much more.

Valid thru December 31, 2019 based on availability.

For more information about TradeWinds Island Resorts' summer specials and leisure packages, visit or call 800-360-4016. 

TradeWinds Island Resorts

TUESDAY, JUNE 18: Gaylord Palms Resort

WINNER: Maria Olaya (6/11/2019 10:08:52 AM)
Discover the one-of-a-kind enchanted surroundings inside Gaylord Palms Resort with a 4.5-acre soaring glass atrium featuring winding waterways, lush gardens and animal habitats. The resort guest-exclusive Cypress Springs Water Park features a tree house play structure, a variety of thrilling water slides and a FlowRider Double surf simulator, along with the South Beach Pool, a chic cabana-lined oasis for adults only. Other extraordinary amenities include fine and casual dining, Relâche Spa and several shopping options – all conveniently located within minutes of the theme parks.

One winner will receive a two-night stay for up to 4, including room, tax, resort fee and self-parking. Valid thru 10/31/2019, based on availability.

Plan a stay to soak up the sun at Gaylord Palms with the SummerFest Package, available through August 11, 2019 (based on availability) with rates starting at $194 per night, plus taxes and fees. This package features one Florida Explorer Scavenger Hunt book and compass, two drink tumblers that include unlimited soda, and a $25 resort credit per night. Guests can upgrade their overnight experience with the SummerFest Premium Package, limited to a select number each day. This package includes accommodations in an Emerald Bay Atrium room with a view of the Illuminate Florida Light Show, a special family-friendly SummerFest welcome amenity delivered to the room, one Florida Explorer Scavenger Hunt book and compass, two drink tumblers that include unlimited soda refills, and a $25 resort credit per night.

Rates for the SummerFest Premium Package begin at $234 plus taxes and fees. For more details,

Gaylord Palms Resort

WEDNESDAY, JUNE 19: JW Marriott Orlando, Grande Lakes

WINNER: Grace Machado (5/26/2019 11:11:19 AM)
Located just 20 minutes from all major Orlando attractions, 500 acres of exquisite beauty and timeless charm are the setting for a truly one-of-a-kind destination. JW Marriott Orlando, Grande Lakes offers a distinctive array of thoughtful leisure pursuits including farm-to-table dining, signature golf, pampering spa treatments, immersive kids programs, and inspired eco adventure experiences. Guests are often tempted to forego exploration for welcome seclusion. Discover what inspires you.

One winner will receive a two-night stay valid through June 2020 based on availability. JW Marriott Orlando, Grande Lakes adjoins to The Ritz-Carlton Orlando, Grande Lakes featuring Grande Lakes Sports including a two-mile mountain bike trail, fishing and more!

This summer, guests can reserve a summer getaway including 15% off the best available rate and $50 resort credit daily. For information visit or call (800) 576-5750.

JW Marriott Orlando, Grande Lakes

THURSDAY, JUNE 20: Walt Disney World Swan & Dolphin Resort 

WINNER: Sara Fee (5/28/2019 7:15:04 AM)
In the heart of the Walt Disney World® Resort, the award-winning Walt Disney World Swan and Dolphin Resort is your gateway to Central Florida’s greatest theme parks and attractions. The resort is located in between Epcot® and Disney’s Hollywood Studios™, and nearby Disney’s Animal Kingdom® Theme Park and Magic Kingdom® Park.

Come discover 17 world-class restaurants and lounges, sophisticated guest rooms with Westin Heavenly Beds® and the luxurious Mandara Spa. Enjoy five pools, two health clubs, tennis, nearby golf, and many special Disney benefits, including complimentary transportation to Walt Disney World Theme Parks and Attractions, the Extra Magic Hours benefit, and 60-day Disney Fastpass+ booking window.

One winner will receive a two-night stay, including tax and resort fees. Valid thru 5/30/2020, based on availability.

Guests can save money by taking advantage of one of many special offers. Throughout the year you’ll find various specials so that you and your family can experience all that Disney World has to offer at a low, budget-friendly price! Are you a Florida Resident, Marriott Bonvoy® member or an AAA member? You can enjoy additional savings as well! Look through the Disney vacation specials to find the package that best fits your family’s needs.

Visit for current specials and offers.

Walt Disney World Swan & Dolphin Resort