Title: Summerland Key Vacation Packages 2026 from $787 | Expedia.com [Summerland Key Travel Guide](https://expedia.com/Summerland-Key.dx6177802)[Hotels in Summerland Key](https://expedia.com/Summerland-Key-Hotels.d6177802.Travel-Guide-Hotels)[Vacation Rentals in Summerland Key](https://expedia.com/Summerland-Key-Vacation-Rentals.d6177802.Travel-Guide-VacationRentals)[Flights to Summerland Key](https://expedia.com/Cheap-Flights-To-Summerland-Key.d6177802.Travel-Guide-Flights)[Things to do in Summerland Key](https://expedia.com/Things-To-Do-In-Summerland-Key.d6177802.Travel-Guide-Activities)[Car Rentals in Summerland Key](https://expedia.com/Car-Rentals-In-Summerland-Key.d6177802.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6177802/bda449a1-0506-4d80-94a6-fb19766bc7f4.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Summerland Key Vacations from $787 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Your Summerland Key Vacation The hassle-free way to experience this interesting city is with a tailor-made Summerland Key vacation package. Base yourself in the neighborhood of Sugarloaf Shores, which is great for families, fishing and views or go someplace else — our package deals are all about you. [Cook Island](https://www.expedia.com/Cook-Island-Big-Pine-Key.d553248635976197877.Vacation-Attraction), [Big Pine Key Flea Market](https://www.expedia.com/Big-Pine-Key-Flea-Market-Big-Pine-Key.d553248621533115810.Vacation-Attraction) and [Blue Hole](https://www.expedia.com/Blue-Hole-Big-Pine-Key.d553248621532652323.Vacation-Attraction) are just some of the sights you'll want to see during your trip to Summerland Key. Stop daydreaming and start traveling. Browse the wide range of options on Expedia today and put your Summerland Key vacation plans in motion! ## The Latest Summerland Key vacation packages Price found within the past 48 hours. Click for updated prices. ![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/4743fa46_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Creekside Inn $787 per person Apr 7 - Apr 14 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 7.8/10 Good! (1,013 reviews) Great pool. Great staff Reviewed on Mar 6, 2026 ![Casablanca Miami Beach](https://images.trvl-media.com/lodging/32000000/31660000/31652200/31652150/f54c02bb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Casablanca Miami Beach North Beach $2,262 per person May 18 - May 22 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 5.8/10 (320 reviews) Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it. Reviewed on Feb 22, 2026 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/e518a34f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach $7,541 per person May 14 - May 18 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) ![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Siesta Resort & Villas Matecumbe $1,669 per person Apr 7 - Apr 14 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.8/10 Excellent! (1,001 reviews) Grrat view from room and location is awesome. Reviewed on Mar 4, 2026 ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cheeca Lodge & Spa Matecumbe $1,263 per person May 17 - May 23 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9.2/10 Wonderful! (1,298 reviews) Simone and Aisha at the front desk were amazing! The staff were kind, friendly and helpful. A little island gem! Reviewed on Mar 5, 2026 Don't see what you're looking for? See all available trips from Columbus to Summerland Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-07/2026-04-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_6177802) ## Where to stay in Summerland Key Find the best Summerland Key areas and neighborhoods for the activities you enjoy most. [Learn more about Summerland Key](https://expedia.com/Summerland-Key.dx6177802) ![Bird refuge wildlife background panorama banner of nature landscape ocean birds in Key West, Florida. Animals of the USA.](https://images.trvl-media.com/place/553248635976481702/7efc6f73-bf7b-4c19-9424-6ca3071f1ffe.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Cutthroat Harbor Estates While Cutthroat Harbor Estates isn't home to many top sights, Venture Key and Venture Out Keys are some notable places to visit nearby. [Find hotel + flight trips in Cutthroat Harbor Estates](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Cutthroat%20Harbor%20Estates&DestID=553248635976481702&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Sugarloaf Shores featuring a bay or harbor](https://images.trvl-media.com/place/6270983/44cc35b6-7c5a-4d30-8d33-616900dbf0d6.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Sugarloaf Shores While Sugarloaf Shores isn't home to many top sights, Upper Sugarloaf Sound and Florida Keys Beaches are some notable places to visit nearby. [Find hotel + flight trips in Sugarloaf Shores](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Sugarloaf%20Shores&DestID=6270983&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Cudjoe Gardens When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Upper Sugarloaf Sound, some noteworthy sights in the nearby area. [Find hotel + flight trips in Cudjoe Gardens](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Cudjoe%20Gardens&DestID=553248635976472640&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Bahia Honda State Park - Calusa Beach, Florida Keys - tropical beach - USA.](https://images.trvl-media.com/place/553248635976468855/342969f8-bf72-47fd-9555-c44c22f7719e.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Breezeswept Beach Estates While Breezeswept Beach Estates isn't home to many top sights, Cook Island and Newfound Harbor Keys are some notable places to visit nearby. [Find hotel + flight trips in Breezeswept Beach Estates](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Breezeswept%20Beach%20Estates&DestID=553248635976468855&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ### Discover the most popular places to visit in Summerland Key ![Stopped by the sea on a ride down the Overseas Highway from Miami to Key West. The bike is a KZ750 lent to me by the guy living in the condo next door. #TheKeys #florida #beach #kawasaki ](https://images.trvl-media.com/place/553248635983994028/1d746f78-98d9-4591-8682-e70514df330b.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Sugarloaf Beach Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key? [](https://expedia.com/Sugarloaf-Beach-Summerland-Key.d553248635983994028.Vacation-Attraction) #### Upper Sugarloaf Key 4/5(21 reviews) Commune with nature and explore the great outdoors at Upper Sugarloaf Key during your travels in Summerland Key. [](https://expedia.com/Upper-Sugarloaf-Key-Summerland-Key.d553248635975865768.Vacation-Attraction) #### Upper Sugarloaf Sound Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key. [](https://expedia.com/Upper-Sugarloaf-Sound-Summerland-Key.d553248635976195391.Vacation-Attraction) ### What to do in Summerland Key ![Passengers enjoying the shade on the Conch Tour Train in Key West](https://mediaim.expedia.com/localexpert/191535/9b448a2f-ece5-45c7-be77-f9172888dc8f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Key West Conch Tour Train $45 per adult **88%** of travellers recommend [](https://expedia.com/things-to-do/key-west-conch-tour-train.a191535.activity-details) ![ Round-trip Transportation to Key West from Miami](https://mediaim.expedia.com/localexpert/2088061/2d239d7a-6886-4e7d-bee2-f3bb8bcc5eb3.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Round-trip Transportation to Key West from Miami $75 per adult [](https://expedia.com/things-to-do/round-trip-transportation-to-key-west-from-miami.a2088061.activity-details) ![Dolphin Watching and Snorkeling](https://mediaim.expedia.com/localexpert/44991362/0af7b5ef-8c18-4f45-a635-e6b2b31df2d6.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Key West Dolphin & Snorkeling Tour - Small Group $135 per adult [](https://expedia.com/things-to-do/key-west-dolphin-snorkeling-tour-small-group.a44991362.activity-details) [See all activities in Summerland Key](https://expedia.com/things-to-do/search?rid=6177802) ## Summerland Key Hotel Deals ![Sugarloaf Key Hotel at KOA Resort](https://images.trvl-media.com/lodging/102000000/101140000/101135800/101135765/afeef809_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sugarloaf Key Hotel at KOA Resort 251 Co Rd 939 Summerland Key FL 9.8/10 Exceptional! (501 reviews) Greeted by very friendly staff and the room was very clean and spacious and came with everything you would need for your stay. All staff was very nice and accommodating. Lots to do around the area and only 30 minutes away from Key West. Would definitely stay here again! Reviewed on Mar 5, 2026 [Get rates](https://expedia.com/Hotel-Search?startDate=3%2F21%2F2026&endDate=3%2F22%2F2026&selected=101135765&PinnedHotelID=101135765&HadPinnedHotel=true®ionId=6177802) [](https://expedia.com/Hotel-Search?startDate=3%2F21%2F2026&endDate=3%2F22%2F2026&selected=101135765&PinnedHotelID=101135765&HadPinnedHotel=true®ionId=6177802) ![Parmer's Resort](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/bc839964_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Parmer's Resort 565 Barry Avenue Summerland Key FL $338 nightly $380 total Mar 29 - Mar 30 Total with taxes and fees 9/10 Wonderful! (1,008 reviews) Nice quiet room but couldn’t see the ocean. Reviewed on Mar 6, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=5561465&PinnedHotelID=5561465&HadPinnedHotel=true®ionId=6177802) ![Looe Key Reef Resort](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/a7994045_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Looe Key Reef Resort 27340 Overseas Highway Summerland Key FL $219 nightly $246 total Mar 24 - Mar 25 Total with taxes and fees 7.6/10 Good! (1,011 reviews) Taco Tuesday with trivia and live music at the Tiki Bar was a lot of fun. The room could use some updates and coffee in room would have been nice. Otherwise the beds were comfy and staff was friendly. Location was great for proximity to some nice parks and wildlife spotting. Reviewed on Mar 6, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F24%2F2026&endDate=3%2F25%2F2026&selected=4759500&PinnedHotelID=4759500&HadPinnedHotel=true®ionId=6177802) [See all 605 properties in Summerland Key](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F8%2F2026&endDate=3%2F9%2F2026®ionId=6177802) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ## Find the Best Summerland Key Vacation Packages ## Summerland Key Essential Information | Language | English | | --------------- | ----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | Key West Intl. Airport (EYW) | | Max Temp Winter | 75ºF | | Max Temp Summer | 85ºF | | Top Sights | [Bahia Honda State Park](https://www.expedia.com/Bahia-Honda-State-Park-Big-Pine-Key.d630134272121270272.Vacation-Attraction), [Florida Keys Beaches](https://www.expedia.com/Florida-Keys-Beaches-Florida.d553248635976496782.Vacation-Attraction) and [Calusa Beach](https://www.expedia.com/Calusa-Beach-Big-Pine-Key.d553248635983993598.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.com/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.com/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.com/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Summerland Key vacation package cost? ### What are the cheapest months to go to Summerland Key? ### How many days is enough for Summerland Key? ### How to find the best Summerland Key package deals? ### Is it cheaper to book a Summerland Key vacation as a package? ### When to book a vacation package to Summerland Key? ### How to plan a trip to Summerland Key? > 1. Pick your dates: The things you plan to do in Summerland Key and your preferred season can help you decide when to travel. > 2. Calculate your budget: Make sure you have enough money to pay for everything from transportation and meals to activities and airfares. Your hotel will likely be the largest expense during your trip to Summerland Key. > 3. Use Expedia's [trip planning tool](https://www.expedia.com/why/trip-planning) to explore Summerland Key: Research every part of your trip to Summerland Key with this comprehensive planner. Invite your family and friends to collaborate on a group getaway, search for hotels or things to do and make bookings. > 4. Decide how many days away: Start by listing all the sights and activities you want to experience in Summerland Key. Then, estimate how long you'll need for each, along with any travel time. > 5. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a personalized Summerland Key vacation package. > 6. Book activities and experiences in advance: Whether it's a ticket to a big attraction or a day trip in nature, you won't have to worry about missing out on Summerland Key's best offerings. Find all the fun [things to do in Summerland Key](https://www.expedia.com/Things-To-Do-In-Summerland-Key.d6177802.Travel-Guide-Activities) with our dedicated travel guide. ### Does Expedia offer Book Now, Pay Later Summerland Key vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - More ways to book - [Ramrod Key Hotels ](https://www.expedia.com/Ramrod-Key-Hotels.d6156102.Travel-Guide-Hotels) - [Rv Parks in Ramrod Key ](https://www.expedia.com/Ramrod-Key-RV-Parks.d6156102-aaRVParks.Travel-Guide-Accommodation) - [Pet-Friendly Hotels in Ramrod Key ](https://www.expedia.com/Ramrod-Key-Hotels-Pet-Friendly-Hotel.0-0-d6156102-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Motels in Ramrod Key ](https://www.expedia.com/Ramrod-Key-Motels.d6156102-aaMotels.Travel-Guide-Accommodation) - [Hotels with Bars in Ramrod Key ](https://www.expedia.com/Ramrod-Key-Hotels-Bar-Hotel.0-0-d6156102-tBarHotel.Travel-Guide-Filter-Hotels) - [B&B in Ramrod Key ](https://www.expedia.com/Ramrod-Key-Bed-And-Breakfast.d6156102-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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