--- title: "Lower Keys Luxury Vacations 2026 | Expedia" description: "Find incredible offers on Lower Keys Luxury Vacations! Plan your next Luxury trip today with Expedia." canonical: "https://www.expedia.com/lp/theme-vacations/luxury-vacations/553248621593965863/Lower-Keys" language: en-US market: US currency: USD prices_as_of: 2026-11-14T15:42:53Z --- ![A multi-directional signpost with various destination names and distances.](https://images.trvl-media.com/place/630134272121270272/5cd551b7-9ddc-46ed-b43a-d0efd9fb017d.jpg?impolicy=fcrop&w=1200&h=300&q=medium) Photo by Rick Tuers # Lower Keys Luxury Vacations ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $2,000 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 ## Discover the most popular places to visit in Lower Keys ### Bahia Honda State Park ![A beach with clear turquoise water, a sandy shore, palm trees, and a steel bridge over the water.](https://images.trvl-media.com/place/630134272121270272/64f63e69-4dbc-4f88-a3c1-e02794d09e93.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium) Rating: 9.4/10 (50 reviews) You can take time to visit Bahia Honda State Park during your travels to Big Pine Key. While you're in the area, wander around the natural setting. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&star=50®ionId=630134272121270272) ![A beach with clear turquoise water, a sandy shore, and a long pier extending into the water.](https://images.trvl-media.com/place/553248635983993598/074633e6-c13c-4bef-a84a-1bcb606704c9.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium) Photo by Sérgio Veludo ### Calusa Beach Rating: 7.8/10 (9 reviews) Why not spend a lazy afternoon at Calusa Beach during your trip to Big Pine Key? While you're in the area, wander around the natural setting. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&star=50®ionId=553248635983993598) ### Boca Chica Beach ![A beach with a thatched hut, palm trees, and boats in the water.](https://images.trvl-media.com/place/553248635983994029/1843ab8f-593f-4a8b-afe2-7d796cb906fc.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium) Rating: 8.0/10 (1 review) Why not spend a lazy afternoon at Boca Chica Beach during your trip to Key West? Stroll along the area's seaside, or simply savor its lively bars. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&star=50®ionId=553248635983994029) ![A motorcycle parked on a beach with palm trees and a clear sky.](https://images.trvl-media.com/place/553248635983994028/1d746f78-98d9-4591-8682-e70514df330b.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium) Photo by Paul Devall ### Sugarloaf Beach Rating: 8.4/10 (38 reviews) Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key? [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&star=50®ionId=553248635983994028) ### Sandspur Beach ![A clear blue sky, calm sea, and a tree with exposed roots on a sandy beach.](https://images.trvl-media.com/place/553248635983993014/ff36de9c-f1e7-4214-83dd-8ce73bdc6728.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium) Rating: 10.0/10 (1 review) Why not spend a lazy afternoon at Sandspur Beach during your trip to Big Pine Key? While you're in the area, wander around the natural setting. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&star=50®ionId=553248635983993014) ### Shark Key ![A tropical landscape with a calm lake, palm trees, and a white building with a blue roof.](https://images.trvl-media.com/place/553248635976194849/ad7d3af1-00b1-4385-a55a-a8c6038c75da.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium) Commune with nature and explore the great outdoors at Shark Key during your travels in Key West. In the area, take in the lively festivals and beautiful sunsets. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&star=50®ionId=553248635976194849) ### Upper Sugarloaf Key Rating: 8.6/10 (54 reviews) Commune with nature and explore the great outdoors at Upper Sugarloaf Key during your travels in Summerland Key. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&star=50®ionId=553248635975865768) ### Key West Visitors Center Rating: 8.4/10 (85 reviews) After visiting Key West Visitors Center, make a plan to see the other sights and activities in Big Pine Key. Amble around this relaxing area's marina, or seek out the fishing spots. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&star=50®ionId=553248621561884396) ### What to do in Lower Keys ![Key West Champagne Sunset Sail](https://mediaim.expedia.com/localexpert/191545/9247a074-806a-429b-9fe1-118b8f91a3e6.jpg?impolicy=resizecrop&rw=1005&rh=565) #### [Champagne and Sunsets: A Key West Catamaran Adventure](https://www.expedia.com/things-to-do/a.a191545.activity-details?rid=553248621593965863) $59 per adult 94% of travelers recommend ![Shark and Wildlife Viewing Adventure in Key West](https://mediaim.expedia.com/localexpert/1343769/0be1ef8e-5416-4b8e-8cda-5cf714b8e21d.jpg?impolicy=resizecrop&rw=1005&rh=565) #### [Shark and Wildlife Viewing Adventure in Key West](https://www.expedia.com/things-to-do/a.a1343769.activity-details?rid=553248621593965863) $99 per adult 100% of travelers recommend ![Key West Half-Day Fishing Charter](https://mediaim.expedia.com/localexpert/5299343/671745e1-9724-45ed-9f6d-20286eca548a.jpg?impolicy=resizecrop&rw=1005&rh=565) #### [Key West Half-Day Fishing Charter](https://www.expedia.com/things-to-do/a.a5299343.activity-details?rid=553248621593965863) $102 per adult 92% of travelers recommend [See all activities in Lower Keys](https://www.expedia.com/things-to-do/search?rid=553248621593965863) ## Top Luxury Lower Keys Hotels ### [Parmer's Resort](https://www.expedia.com/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.Hotel-Information) ![A covered deck with chairs and umbrellas overlooking a beach.](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/75ac6ed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 565 Barry Avenue, Summerland Key, FL, 33042, US - Location: 6.7 mi from Lower Keys - Star rating: 2.5/5 - Guest rating: 9/10 (Wonderful, 1001 reviews) - Price: $199 nightly, $224 total, Dec 1 - Dec 2, Total with taxes and fees, for Top Luxury Lower Keys Hotels - Review: The property is right on the water. The site offers free rentals of bikes and kayaks. The pool is heated. The site has a discount with 2 restaurants that are close by. The area is quiet. Office hours are only until 8pm, but they have an on call person. ### [Sugar Loaf Lodge](https://www.expedia.com/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) ![A beachside dining area with thatched umbrellas, white plastic chairs, and tables.](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/95d2903e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 17001 Overseas Hwy, Summerland Key, FL, 33042, US - Location: 5.1 mi from Lower Keys - Star rating: 2.5/5 - Guest rating: 8.2/10 (Very good, 1000 reviews) - Price: $99 nightly, $111 total, Nov 30 - Dec 1, Total with taxes and fees, for Top Luxury Lower Keys Hotels - Review: We stayed for four nights. The hotel was quiet, clean, and comfortable. The staff was very friendly. Our patio had a beautiful view of the water. We had drinks and pie in the restaurant, and they were delicious. We would definitely stay there again. ### [Old Wooden Bridge Resort and Marina](https://www.expedia.com/Big-Pine-Key-Hotels-Old-Wooden-Bridge-Marina.h17102343.Hotel-Information) ![A cozy room with a brown leather sofa, a white table, and a ceiling fan.](https://images.trvl-media.com/lodging/18000000/17110000/17102400/17102343/dee083de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 1791 Bogie Drive, Big Pine Key, FL, 33043, US - Location: 9.3 mi from Lower Keys - Star rating: 2.5/5 - Guest rating: 8.6/10 (Excellent, 385 reviews) - Price: $201 nightly, $226 total, Dec 4 - Dec 5, Total with taxes and fees, for Top Luxury Lower Keys Hotels - Review: The location could be wonderful, but the unit we were checked into had an active mold problem and was not the one originally booked. The staff was unhelpful about correcting the situation. My party had to split up and find alternative lodging. ### [Looe Key Reef Resort](https://www.expedia.com/Ramrod-Key-Hotels-Looe-Key-Reef-Resort.h4759500.Hotel-Information) ![A thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/974f08a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 27340 Overseas Highway, Summerland Key, FL, 33042, US - Location: 5.7 mi from Lower Keys - Star rating: 2.5/5 - Guest rating: 7.8/10 (Good, 1000 reviews) - Price: $173 nightly, $194 total, Nov 16 - Nov 17, Total with taxes and fees, for Top Luxury Lower Keys Hotels ### [Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access](https://www.expedia.com/Summerland-Key-Hotels-Planktons-Palace-Cozy-2BR-Getaway-In-Oceanfront-Resort-Community-With-Patio-Island-Vibes.h116667062.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/35103395.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Cudjoe Key, FL, US - Location: 2.5 mi from Lower Keys - Guest rating: 10/10 (Exceptional, 1 review) - Price: $373 nightly, $416 total, Nov 20 - Nov 21, Total with taxes and fees, for Top Luxury Lower Keys Hotels - Review: Excellent location - clean, quiet, well-kept community. Boat launch was key for us. Pool and beach looked very nice, but we didn't use. The unit is as described and has a nice patio out back that we used every day. ### [SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS](https://www.expedia.com/Cudjoe-Key-Hotels-Ocean-Paradise-AT-Venture-OUT-4-Bikes-2-2-Person-Kayaks.h44556643.Hotel-Information) ![A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/6bfc69e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Cudjoe Key, FL, US - Location: 2.4 mi from Lower Keys - Guest rating: 9.6/10 (Exceptional, 99 reviews) - Price: $501 nightly, $557 total, Dec 3 - Dec 4, Total with taxes and fees, for Top Luxury Lower Keys Hotels - Review: None ### [Kelly's Kabin - Adorable Private Summerland Key Cottage](https://www.expedia.com/Summerland-Key-Hotels-Kellys-Kabin-Adorable-Private-Summerland-Key-Cottage.h84046253.Hotel-Information) ![A small, single-story building with a blue exterior, a white door, and a red 'R' sign indicating a restaurant.](https://images.trvl-media.com/lodging/85000000/84050000/84046300/84046253/0a9b0fee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Summerland Key, FL, US - Location: 2.8 mi from Lower Keys - Guest rating: 9.8/10 (Exceptional, 129 reviews) - Price: $429 nightly, $478 total, Nov 15 - Nov 16, Total with taxes and fees, for Top Luxury Lower Keys Hotels - Review: Great location beautiful accommodations. House is great. Had everything we needed and hopefully we return next year. ### [Affordable Dog Friendly Keys Retreat in Venture Out Near Key West](https://www.expedia.com/Summerland-Key-Hotels-Affordable-Dog-Friendly-Keys-Retreat-In-Venture-Out-Near-Key-West.h126814966.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/127000000/126820000/126815000/126814966/e76b1446.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Cudjoe Key, FL, US - Location: 2.2 mi from Lower Keys - Guest rating: 10/10 (Exceptional, 1 review) - Price: $341 nightly, $381 total, Nov 20 - Nov 21, Total with taxes and fees, for Top Luxury Lower Keys Hotels - Review: This property was meticulously clean and perfect for us. The property was decorated well-very home-like feel. The communication with the host was prompt and they answered all questions asked. In addition, we loved that we could bring our fur-babies (dogs) to the property with us. We highly recommend this property! 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. [See all properties in Lower Keys](https://www.expedia.com/Hotel-Search?startDate=2026-11-28&endDate=2026-11-29®ionId=553248621593965863&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## All you need to know about luxury vacations in Lower Keys ### What can I expect from a luxury Lower Keys vacation? Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Lower Keys vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. ### How can I find all-inclusive luxury vacation packages in Lower Keys? By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5\* filter to find truly sensational stays. You barely need to lift a finger. ### Can I book a cheap Lower Keys luxury vacation? Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at . Prices and availability are subject to change. Additional terms may apply. ### How can I book a luxury family vacation in Lower Keys? Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. ### Can I book a package in Lower Keys with a luxury vacation home? A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package. ### How can I find the best luxury vacation deals in Lower Keys? Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months. ### Can I book a luxury holiday in Lower Keys with free cancellation and/or flexible dates? Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. ### Why should I book my luxury trip to Lower Keys with Expedia? A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind. ## Explore a world of travel with Expedia - [Lodging](?equalTargetTab=tab-0) - [Flights](?equalTargetTab=tab-1) - [Packages](?equalTargetTab=tab-2) - [Cars](?equalTargetTab=tab-3) - [Vacation Rentals](?equalTargetTab=tab-4) - [Things to Do](?equalTargetTab=tab-5) - [Key West Historic District Hotels](https://www.expedia.com/Key-West-Historic-District-Key-West-Hotels.0-n6281809-0.Travel-Guide-Filter-Hotels) - [Houseboats in Key West](https://www.expedia.com/Key-West-Houseboats.d1187-aaHouseboats.Travel-Guide-Accommodation) - [Oceanfront Hotels in Marathon](https://www.expedia.com/Marathon-Hotels-Oceanfront-Hotels.0-0-d2437-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Beach Hotels in Key West](https://www.expedia.com/Key-West-Hotels-Beach-Hotel.0-0-d1187-tBeachHotel.Travel-Guide-Filter-Hotels) - [Summerland Key Hotels](https://www.expedia.com/Summerland-Key-Hotels.d6177802.Travel-Guide-Hotels) - 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