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Summerland Key Vacation Rentals

Find 159 available offers from 6 partners
Summerland Key
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+
3.5+

Best Vacation Home Deals in Summerland Key

Save up to 56%

House Summerland Key
Oct 1 - Oct 8
-31%
$202
$140 per night
House ∙ 5 guests ∙ 1 bedroom
House in Summerland Key with Ample Parking
4.9
Outstanding (130 ratings)
Summerland Key, Monroe County, Florida, United States
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House Summerland Key
Oct 14 - Oct 21
-56%
$754
$328 per night
House ∙ 5 guests ∙ 2 bedrooms
Vacation Home in Summerland Key with Pool
Summerland Key, Monroe County, Florida, United States
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House Summerland Key
Dec 7 - Dec 14
-42%
$600
$350 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Summerland Key with Grill + Paradise Views
4.9
Outstanding (58 ratings)
Summerland Key, Monroe County, Florida, United States
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Browse the 159 vacation rentals listed in Summerland Key and find a welcoming place for your vacation. By directly analyzing these vacation rentals, HomeToGo features the best deals and the most popular accommodations in Summerland Key.

Top-Rated Rentals and Accommodations in Summerland Key

Book Vacation Rental Offers with the Highest User Rating

Cottage Summerland Key
Nov 3 - Nov 10
$150 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Cottage in Summerland Key with Outdoor Pool
4.9
Outstanding (44 ratings)
Summerland Key, Monroe County, Florida, United States
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House Summerland Key
Feb 3 - Feb 10
$657 per night
House ∙ 12 guests ∙ 6 bedrooms
Vacation Home in Summerland Key with Beautiful Pool + Ocean Views
4.9
Outstanding (33 ratings)
Summerland Key, Monroe County, Florida, United States
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House Summerland Key
Sep 30 - Oct 7
$634 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Summerland Key with Pool + Great View
5.0
Outstanding (10 ratings)
Summerland Key, Monroe County, Florida, United States
Details
Florida Rental By Owners
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Recommended Vacation Rentals in Summerland Key

Find your perfect vacation rental in Summerland Key: from $148 per night

Cottage Summerland Key
Nov 11 - Nov 18
$349 per night
Cottage ∙ 8 guests ∙ 2 bedrooms
Cottage in Summerland Key with Grill
Summerland Key, Monroe County, Florida, United States
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House Summerland Key
Sep 14 - Sep 21
$650 per night
House ∙ 10 guests ∙ 4 bedrooms
Pleasant House in Summerland Key with Free Parking + Beach Views
5.0
Outstanding (21 ratings)
Summerland Key, Monroe County, Florida, United States
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House Summerland Key
Oct 14 - Oct 21
$886 per night
House ∙ 10 guests ∙ 3 bedrooms
Vacation Home in Summerland Key with In-Ground Pool + Sunrise Views
4.8
Outstanding (27 ratings)
Summerland Key, Monroe County, Florida, United States
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House Summerland Key
Sep 14 - Sep 21
$642 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Summerland Key with Oceanfront Pool + Ocean Views
5.0
Outstanding (46 ratings)
Summerland Key, Monroe County, Florida, United States
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House Summerland Key
Nov 11 - Nov 18
-42%
$600
$350 per night
House ∙ 6 guests ∙ 2 bedrooms
House in Summerland Key with Yard & Grill + Ocean Views
4.8
Outstanding (42 ratings)
Summerland Key, Monroe County, Florida, United States
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House Summerland Key
Oct 6 - Oct 13
-48%
$1,356
$706 per night
House ∙ 8 guests ∙ 2 bedrooms
Charming House in Summerland Key with Pool & Grill
Summerland Key, Monroe County, Florida, United States
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House Summerland Key
Oct 22 - Oct 29
-75%
$1,425
$354 per night
House ∙ 6 guests ∙ 2 bedrooms
Vacation Home in Summerland Key with Pool
4.5
Excellent (29 ratings)
Summerland Key, Monroe County, Florida, United States
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House Summerland Key
Sep 30 - Oct 7
-54%
$3,586
$1,639 per night
House ∙ 8 guests ∙ 4 bedrooms
Charming House in Summerland Key with Private Balcony
4.8
Outstanding (32 ratings)
Summerland Key, Monroe County, Florida, United States
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House Summerland Key
Dec 3 - Dec 10
$375 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Cudjoe Key with Pool & Grill + Sunrise View
4.5
Excellent (86 ratings)
Summerland Key, Monroe County, Florida, United States
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Budget-friendly Vacation Rentals in Summerland Key

Find Fantastic yet Inexpensive Offers

House Summerland Key
Oct 14 - Oct 21
$500 per night
House ∙ 8 guests ∙ 2 bedrooms
House in Big Pine Key + Ocean Views
Summerland Key, Monroe County, Florida, United States
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House Summerland Key
Sep 14 - Sep 21
$401 per night
House ∙ 8 guests ∙ 3 bedrooms
Charming Vacation Home in Summerland Key with Free Parking + Water Views
4.9
Outstanding (21 ratings)
Summerland Key, Monroe County, Florida, United States
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House Summerland Key
Sep 30 - Oct 7
-54%
$3,274
$1,508 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Summerland Key with Private Balcony
5.0
Outstanding
Summerland Key, Monroe County, Florida, United States
Details
Vacasa
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Vacation rentals with Wi-Fi

Stay connected while traveling and book a Summerland Key accommodation with high-speed internet.

House Summerland Key
Aug 17 - Aug 24
-16%
$205
$171 per night
House ∙ 6 guests ∙ 2 bedrooms
Vacation Home in Cudjoe Key with Overnight Parking
4.9
Outstanding (216 ratings)
Summerland Key, Monroe County, Florida, United States
Internet
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House Summerland Key
Nov 11 - Nov 18
$300 per night
House ∙ 4 guests ∙ 2 bedrooms
Vacation Home in Cudjoe Key with Grill & Pool + Beautiful Views
4.5
Excellent (168 ratings)
Summerland Key, Monroe County, Florida, United States
Internet
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Cottage Summerland Key
Dec 9 - Dec 16
-33%
$225
$150 per night
Cottage ∙ 2 guests ∙ 1 bedroom
Comfortable Cottage in Cudjoe Key with Botanical Garden
4.3
Very good (148 ratings)
Summerland Key, Monroe County, Florida, United States
Internet
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Apartments With Balconies or Patios

Looking for a home with a balcony? Check out these vacation homes in Summerland Key with their own private patios and balconies.

Cottage Summerland Key
Dec 2 - Dec 9
-46%
$325
$175 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Spacious Cottage in Cudjoe Key with Grill & Pool
4.6
Excellent (76 ratings)
Summerland Key, Monroe County, Florida, United States
Balcony/Patio
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House Summerland Key
Nov 4 - Nov 11
-38%
$355
$222 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Big Pine Key with Yard & Grill + Amazing Views
5.0
Outstanding (10 ratings)
Summerland Key, Monroe County, Florida, United States
Balcony/Patio
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House Summerland Key
Oct 6 - Oct 13
-25%
$400
$299 per night
House ∙ 4 guests ∙ 2 bedrooms
Vacation Home in Cudjoe Key with Pool & Grill + Ocean Views
5.0
Outstanding (3 ratings)
Summerland Key, Monroe County, Florida, United States
Balcony/Patio
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Best vacation rentals with a balcony

Looking for a home with a balcony? Check out these vacation homes in Summerland Key with their own private patios and balconies.

House Summerland Key
Nov 4 - Nov 11
-22%
$643
$500 per night
House ∙ 12 guests ∙ 5 bedrooms
Vacation Home in Cudjoe Key with Private Pool + Spectacular Views
4.8
Outstanding (75 ratings)
Summerland Key, Monroe County, Florida, United States
Balcony
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House Summerland Key
Nov 18 - Nov 25
-24%
$372
$283 per night
House ∙ 6 guests ∙ 2 bedrooms
House in Cudjoe Key with Grill & Pool + Canal View
4.2
Very good (25 ratings)
Summerland Key, Monroe County, Florida, United States
Balcony
Details
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House Summerland Key
Dec 8 - Dec 15
-32%
$435
$295 per night
House ∙ 6 guests ∙ 2 bedrooms
House in Cudjoe Key with Extra Parking + Ocean View
5.0
Outstanding (77 ratings)
Summerland Key, Monroe County, Florida, United States
Balcony
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Popular Rental Amenities in Summerland Key

  • Pool (86)
  • Pet-friendly (62)
  • Air conditioning (163)
  • WiFi (166)
  • Kitchen (164)
  • TV (155)
  • Fishing (77)
  • Washing machine (135)
  • Parking (10)
  • Grill (119)
  • Balcony/patio (24)
  • Microwave (148)

More than half of the vacation rentals offer a pool, which makes Summerland Key a great place for people looking to relax pool-side. Interestingly, HomeToGo's data shows that more cabin have a pool than hotel room. Also, they can host 4 vacationers, on average, while hotel room with pools can welcome an average of 4 people. In Summerland Key, many of the rentals including a pool are close to the water.

7-Day Weather Forecast in Summerland Key

Sat, 23 Sep
82°
80°

15%

7 h

9 mi/h

Sun, 24 Sep
84°
82°

10%

4 h

12 mi/h

Mon, 25 Sep
86°
84°

15%

9 h

8 mi/h

Tue, 26 Sep
84°
84°

15%

7 h

12 mi/h

Wed, 27 Sep
84°
82°

15%

7 h

10 mi/h

Thu, 28 Sep
84°
82°

10%

8 h

12 mi/h

Fri, 29 Sep
84°
82°

15%

8 h

12 mi/h

Information about vacation rentals in Summerland Key

🏡 Vacation rentals available 159 homes
💳 Possible discounts up to 50%
🌙 Nightly prices starting at $148
⭐ Popular amenities Pool, Pets allowed and Air conditioning
🐾 Pet friendly homes 61 homes
🏊 Vacation rentals with pools 82 homes

Frequently Asked Questions

What is the average nightly price for a vacation home in Summerland Key?

The average accommodation in Summerland Key is priced at $148 per night. If you’re interested in a house rental, the average price is $486 per night. A cabin Summerland Key will cost on average $320 per night.

How many vacation homes are available for booking in Summerland Key?

Currently there are 159 vacation homes in Summerland Key to browse and book for your next trip.

How many vacation rentals with a pool are in Summerland Key?

Summerland Key has 82 Cabin and Hotel room available for booking.

Are dogs allowed in vacation homes in Summerland Key?

If you are traveling with a pet in Summerland Key - 38% of vacation rentals are pet-friendly.

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