Summerland Key Condo Rentals

A coastal road with a beach on one side and a marina with boats on the other.

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Our top choices for Summerland Key condo rentals

A beach with lounge chairs, palm trees, and a water body.

1. Grand Marina Suite - Poolside & Waterfront Condo

Stock Island

Brent H.

HK$4,199 total

includes taxes & fees

28 Sept - 29 Sept

A swimming pool area with multiple pools, palm trees, lounge chairs, and a clear blue sky.

2. Atlantic Parrot | Oceanfront Condo w/ Pool

Beachside

Misty C.

HK$5,533 total

includes taxes & fees

1 Oct - 2 Oct

A covered balcony with wicker chairs, a view of palm trees, and multiple flags.

3. NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!

Old Town Key West

Taffy M.

HK$2,151 total

includes taxes & fees

28 Sept - 29 Sept

A wooden pathway leading to a beach with palm trees and a clear blue sky.

4. Island Time | Luxury Beach Condo w/ Pool & Hot Tub

Key West

Stacey P.

HK$6,610 total

includes taxes & fees

9 Oct - 10 Oct

A swimming pool with lounge chairs, palm trees, and a view of the sunset over the water.

5. Pool View Suite | Beachside Resort

Key West

"It was a holiday weekend. Key West in general all lodging was expensive. The room was very comfortable and clean. More than enough room. I was on the water which was amazing. The pool area was very awesome. Love that they have a bar and restaurant available. All the available excursions. I took advantage of the Sunset Tour. Property manager was available for any questions. Beachside staff was also very helpful. Would definitely visit again. Great Experience!! Thank you."

Christie Y.

HK$2,434 total

includes taxes & fees

2 Oct - 3 Oct

A tropical garden pathway leading to a building with a yellow facade and green shutters.

6. ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

Old Town Key West

"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The studio and surroundings matched photos posted and provided a Key West atmosphere and experience. Walking to Key West activities and sites was feasible. Very happy with and positive addition to our Key West visit."

Ken L.

HK$2,257 total

includes taxes & fees

28 Sept - 29 Sept

A wooden boardwalk leading to a hotel with a green roof, surrounded by lush greenery and palm trees.

7. The Butterfly Nest | Newly Updated w/ Shared Pool

Key West

Sarah P.

HK$3,711 total

includes taxes & fees

2 Oct - 3 Oct

A wooden boardwalk leading to a hotel with a green roof, surrounded by palm trees and a water feature.

8. The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

Key West

Teri K.

HK$3,700 total

includes taxes & fees

28 Sept - 29 Sept

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Top Summerland Key Hotel Reviews

Sugar Loaf Lodge

10/10 Excellent

"Very accommodating! Staff is very friendly! Been coming to Sugarloaf Lodge for many years! Thanks 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."

Ocean Breeze House - Summer fun Sleeps 8 boating, fishing and 🦞 Lobster season.

10/10 Excellent

"Glen was more than helpful with our visit. He was very prompt and knowledgeable with the area. The property is very large and tranquil. The house was very spacious and accommodating. We would recommend this property!!"

Direct Oceanfront Cottage-Sunrise View- #2,

10/10 Excellent

"Delightful cottage. It can get a little warm without central AC but the window units do a pretty good job of cooling it down. The kitchen doesn’t have a unit and had I actually wanted to cook I imagine it might be too hot. But if you’re not planning to cook and just need a nice comfortable space for o relax after a full day on and in the water this is it! We will definitely be looking to come back next year."

A Tropical Luxury Getaway, Your own private resort!!

10/10 Excellent

"This property is fantastic! It’s in perfect condition, both inside and out. The grounds were immaculate. They had everything you could need, from pool games and beach games to beach towels, life jackets, entertainment around the pool, large porches, a dock for a boat, a fish cleaning area at the dock’s end, paddle boards, kayaks, and more. The layout was ideal for a large group with multiple families. The host was super responsive and helpful with all our questions. We can tell they really care about the home and the property. Definitely recommend! We cannot wait to come back"

Find out more about Summerland Key

Summerland Key Condo Rentals information

Number of reviews	333
Accommodation	1 Condo Rentals
Lowest Price	HK$1,657
Highest Price	HK$5,533

Frequently asked questions

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What is there to do in Summerland Key near my condo?

The ultimate travel accessory is a well-planned itinerary. Florida Keys Beaches is a wonderful place to begin your sightseeing in Summerland Key.

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Summerland Key condo rentals

1. Grand Marina Suite - Poolside & Waterfront Condo

2. Atlantic Parrot | Oceanfront Condo w/ Pool

3. NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!

4. Island Time | Luxury Beach Condo w/ Pool & Hot Tub

5. Pool View Suite | Beachside Resort

6. ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

7. The Butterfly Nest | Newly Updated w/ Shared Pool

8. The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

9. SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

10. Waterfront Dock Pool Condo Near Duval St Pet OK

11. Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

12. The Elizabeth Suite | 1 bedroom condo, shared pool

13. Orchid Suite on Center St - 1/2 block from Duval Sleeps 4

14. Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

15. The Tahiti Suite | Updated Key West Condo w/ Pool, Hot Tub, & Balcony!

16. Hidden Key West Cottage - Walk to Duval !!!

17. The Grenada at Sunrise Suites - Shared Pool

18. Turtle Nest Condo + Pool / 2nd Floor

19. Waterfront Dock Pool Key West Near Duval

20. The Tortuga at Sunrise Suites - Balcony & Pool

Find holiday rentals that suit your style

Top Summerland Key Hotel Reviews

Sugar Loaf Lodge

Find out more about Summerland Key

Summerland Key Condo Rentals information

Frequently asked questions

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