Lower Sugarloaf Key Holiday Rentals, Summerland Key: Private House Rentals

A waterfront with a pier, calm water, and houses with palm trees in the background.

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Go beyond your typical stay in Lower Sugarloaf Key

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Our top choices for Lower Sugarloaf Key hotels

1. Sugar Loaf Lodge

Summerland Key

Kevin

3.096.142 ₫

3.483.290 ₫ total

includes taxes & fees

21 Sept - 22 Sept

Outdoor pool, pool umbrellas, pool loungers

Ocean views, serves lunch and happy hour

Room, 1 King Bed, Accessible (Mobility & Hearing) | Premium bedding, pillow-top beds, in-room safe, desk

2. Hampton Inn Key West FL

Key West

Rabia

3.486.412 ₫

3.922.214 ₫ total

includes taxes & fees

21 Sept - 22 Sept

Double Room, 2 Queen Beds | Terrace/patio

3. Looe Key Reef Resort

Summerland Key

Sarah

1.968.717 ₫

2.214.806 ₫ total

includes taxes & fees

23 Sept - 24 Sept

Room, 1 King Bed | Premium bedding, pillow-top beds, in-room safe, desk

4. Fairfield by Marriott Inn & Suites Key West at The Keys Collection

New Town

Anais

3.020.690 ₫

4.129.903 ₫ total

includes taxes & fees

30 Sept - 1 Oct

5. Ibis Bay Beach Resort

Northside Resort

Stephanie

2.638.225 ₫

3.807.345 ₫ total

includes taxes & fees

21 Sept - 22 Sept

2 outdoor pools, open 7:00 AM to 10:00 PM, pool cabanas (surcharge)

42-inch LCD TV with cable channels, TV, table football

6. Blue Flamingo Resort Key West

New Town

Esteban

2.852.874 ₫

4.672.996 ₫ total

includes taxes & fees

21 Sept - 22 Sept

Ocean View 3BR Condo with Rooftop Balcony | Balcony

Ocean Front 3BR Presidential Suite | Private kitchen | Coffee/tea maker

7. Beachside Resort & Residences

Key West

Jerome

2.271.125 ₫

5.042.987 ₫ total

includes taxes & fees

21 Sept - 22 Sept

Private beach, sun-loungers, beach umbrellas, beach towels

Suite, 1 Bedroom, Kitchen, Sea Facing | Living area | TV, books, stereo

8. Parmer's Resort

Summerland Key

Mireya

3.737.486 ₫

5.053.638 ₫ total

includes taxes & fees

4 Oct - 5 Oct

Outdoor pool, open 6:00 AM to 11:00 PM, pool umbrellas, pool loungers

Daily cooked-to-order breakfast for a fee

9. Courtyard by Marriott Key West Waterfront

Northside Resort

Everton

4.657.222 ₫

5.239.374 ₫ total

includes taxes & fees

23 Sept - 24 Sept

Outdoor pool, open 7:00 AM to 9:00 PM, pool cabanas (surcharge)

10. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Fabio

2.685.058 ₫

3.898.798 ₫ total

includes taxes & fees

27 Sept - 28 Sept

Egyptian cotton sheets, premium bedding, down duvets, in-room safe

11. Hilton Key West Resort & Marina

Stock Island

Molly

2.756.087 ₫

4.653.612 ₫ total

includes taxes & fees

28 Sept - 29 Sept

Outdoor pool, open 6:00 AM to 10:00 PM, pool cabanas (surcharge)

12. Hilton Garden Inn Key West / The Keys Collection

New Town

Marian

2.742.557 ₫

3.817.262 ₫ total

includes taxes & fees

4 Oct - 5 Oct

Suite, 1 King Bed with Sofa bed (ADULT ONLY) | Iron/ironing board, individually decorated, individually furnished

13. The Southernmost Inn - Adults Only

Old Town Key West

ANDREW

1.852.482 ₫

3.254.593 ₫ total

includes taxes & fees

21 Sept - 22 Sept

14. Hyatt Vacation Club at Windward Pointe, Key West

Key West

Tina

4.758.172 ₫

6.523.753 ₫ total

includes taxes & fees

4 Oct - 5 Oct

Williams Cottage, Stand Alone | Terrace/patio

15. Authors of Key West Guest House

Key West Historic District

Christopher

1.931.837 ₫

2.173.284 ₫ total

includes taxes & fees

28 Sept - 29 Sept

16. Southwinds Motel

Old Town Key West

Michael

3.240.730 ₫

4.523.929 ₫ total

includes taxes & fees

21 Sept - 22 Sept

Deluxe King Patio | Free WiFi, bed sheets

17. Westwinds Inn

Key West Historic District

Tricia

3.024.592 ₫

3.402.665 ₫ total

includes taxes & fees

22 Sept - 23 Sept

Cigar House King Suite w/ Poolside porch | Balcony view

18. Island City House Hotel

Key West Historic District

Osvaldo

4.000.267 ₫

4.500.300 ₫ total

includes taxes & fees

21 Sept - 22 Sept

19. Havana Cabana at Key West

New Town

Silvia

3.096.142 ₫

5.127.758 ₫ total

includes taxes & fees

21 Sept - 22 Sept

Audubon Room - Adult Exclusive | Terrace/patio

20. The Mermaid & Alligator

Old Town Key West

Brian

4.683.240 ₫

5.268.645 ₫ total

includes taxes & fees

21 Sept - 22 Sept

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Top Lower Sugarloaf Key Hotel Reviews

Ibis Bay Beach Resort

8/10 Good

"My room was clean and comfortable. Friendly check in staff."

Hampton Inn Key West FL

10/10 Excellent

"clean room!"

Beachside Resort & Residences

10/10 Excellent

"El hotel es muy lindo, el único problema que vimos fueron los elevadores pues el del edificio 2 está fuera de servicio y mi madre tuvo que caminar más y ella es impedida y el elevador del edificio 1 había que bajar a subirlo pues no funcionaba eventualmente desde el piso. Por lo demás todo magnífico."

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent

"Amazing spa, beautiful property, friendly staff and gorgeous beaches."

Southernmost Beach Resort and Guesthouses

8/10 Good

"We enjoyed our stay, the property is beginning to age a little. Major bummer the main pool was closed, made the pi apple bar pool very crowded."

Southwinds Motel

8/10 Good

"Place was ok, Bar on premise and they had music, my room had ants(I told em and came and sprayed), pool was clean, the roosters were cool, They want 22.50 a day to park, waived it I'm handicap"

Hilton Garden Inn Key West / The Keys Collection

8/10 Good

"The room was clean and exceptional. The staff was very friendly. The buffet was delicious 😋. Recommend it."

Blue Flamingo Resort Key West

8/10 Good

"The place was clean and staff were very friendly. The room was nicely appointed. The non-Tesla chargers were all broken which was disappointing but I was able to trickle charge. One elevator was also out but another one nearby was available and quick. Overall, very nice and I’d likely stay again but the lack of a charger when it was billed as being available was a disappointment."

More cheap stays in Lower Sugarloaf Key