Lower Florida Keys Vacation Rentals from ￥80,808: Search Short-Term Rentals

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Our top choices for Lower Florida Keys vacation rentals

A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

1. Aqua Lodges at Hurricane Hole Marina

Stock Island

Kagni

￥44,902 total

includes taxes & fees

Oct 15 - Oct 16

A cozy room with a brown leather sofa, a white table, and a ceiling fan.

2. Old Wooden Bridge Resort and Marina

Punta Brisa

Daisybel

￥38,200 total

includes taxes & fees

Oct 26 - Oct 27

A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

3. SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Cudjoe Key

Blue Mountain Footwear F.

￥68,231 total

includes taxes & fees

Oct 15 - Oct 16

4. Island View 1BR Residence With Balcony

Key West

Luis

￥50,412 total

includes taxes & fees

Oct 14 - Oct 15

A waterfront property with a covered porch, a boat dock, and a clear sky.

5. SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Cudjoe Key

Mckayla S.

￥68,113 total

includes taxes & fees

Oct 15 - Oct 16

6. Cozy 1-bedroom apartment with WiFi, AC in charming Cudjoe Key large outdoor

Cudjoe Key

￥19,058 total

includes taxes & fees

Oct 14 - Oct 15

A resort pool area with lounge chairs and palm trees, surrounded by resort buildings.

7. 47ft Viking Yacht · 2 Pools · Perry Marina · Key West

Stock Island

Benjamin

￥79,314 total

includes taxes & fees

Oct 14 - Oct 15

A wooden deck with a large tree, outdoor seating, and a marina in the background.

8. Poolside Cottage #412

Key West

shannon b.

￥47,603 total

includes taxes & fees

Oct 18 - Oct 19

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Top Lower Florida Keys Hotel Reviews

Parmer's Resort

10/10 Excellent

"Great place for the family."

Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball

10/10 Excellent

"We had a great stay! Everything was clean, comfortable, and worked out perfectly for our trip. Having access to the boat ramp and convenient parking for both our boat and trailer was extremely helpful. The marina store was a nice added convenience, and having a pressure washer available made cleaning up after a day on the water much easier. Overall, we really enjoyed our stay and would definitely stay here again."

Waterfront 2BR, Dock,Golf Cart, trailer parking,Open Water Views Venture Out 320

10/10 Excellent

"Our three-night stay at this exceptional waterfront retreat was nothing short of extraordinary. Set against sweeping open-water views, the property offers that rare combination of effortless comfort, understated elegance, and a truly idyllic setting.From the moment we arrived, the home felt like a private escape designed for relaxation. The interiors were inviting and beautifully maintained, while the waterfront setting provided a spectacular backdrop throughout our stay. Mornings overlooking the water and quiet evenings by the dock were among the many memorable moments.The private dock and golf cart elevated the experience even further, making it wonderfully easy to explore the community and enjoy everything the resort has to offer. Every detail seemed to encourage slowing down, savoring the surroundings, and simply enjoying being there.Although we stayed only three nights, the experience felt wonderfully restorative—and we found ourselves wishing we had booked a much longer stay. This is the kind of place where the pace immediately changes, the views become part of the experience, and a short getaway feels like a true escape.Beautifully situated, exceptionally comfortable, and surrounded by breathtaking waterfront scenery, this home is a destination in itself. We would return without hesitation and look forward to our next visit. A truly memorable stay in a spectacular setting. Host Mel is wonderful and very attentive."

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Lower Florida Keys Vacation Rentals

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Check prices for these dates

Our top choices for Lower Florida Keys vacation rentals

1. Aqua Lodges at Hurricane Hole Marina

2. Old Wooden Bridge Resort and Marina

3. SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

4. Island View 1BR Residence With Balcony

5. SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

6. Cozy 1-bedroom apartment with WiFi, AC in charming Cudjoe Key large outdoor

7. 47ft Viking Yacht · 2 Pools · Perry Marina · Key West

8. Poolside Cottage #412

9. Living the Dream Key West Style

10. The Grand Cayman | Beautifully Remodeled Key West!

11. Steps from Duval, Pool on Site & Bikes Included!

12. Kelly's Kabin - Adorable Private Summerland Key Cottage

13. Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views

14. Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

15. Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

16. Ocean Front 1BR Suite With Direct Beach Access

17. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

18. Grand Marina Suite - Poolside & Waterfront Condo

19. The Cat Island Suite | Charmingly Renovated w/ Pool

20. Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Find vacation rentals that suit your style

Top Lower Florida Keys Hotel Reviews

Parmer's Resort

Find out more about Lower Florida Keys

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