Vacation rentals in Summerland Key - HomeToGo base64Hash Vacation rentals in Summerland Key - HomeToGo

Vacation rentals in Summerland Key

Browse 182 available vacation homes and compared across 9 trusted partners
Anytime
Guests
Anytime
Guests

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • House
    • Apartment
    • Private room

  • Distance to center

    • 1 mi
    • 2 mi
    • 3 mi

  • Rating

    • 4.5+
    • 4+

  • Services

    • Pool
    • Air conditioning
    • WiFi
    • Kitchen
    • TV
    • Washing machine
    • Parking
    • Balcony/patio
    • Microwave
    • Dishwasher
    • Yard
    • Hot tub
    • Sauna
    • Fireplace
    • Crib
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Fishing
    • Grill

Top 15 most Recommended Vacation Rentals in Summerland Key

Discover your ideal Summerland Key vacation rental with real-time comparisons of 184 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Summerland Key
House ∙ 8 guests ∙ 3 bedrooms

House with barbeque, garden & patio | Nature view

Summerland Key, Monroe County, Florida, United States
This waterfront house rental in Summerland Key features a private pool, beach access, and a yard, perfect for families and pets.
from $183
per night
Outstanding(68 ratings)
from $183
per night
View deal
House Summerland Key
House ∙ 5 guests ∙ 2 bedrooms

Fully equipped wonderful vacation home with grill & pool

Summerland Key, Monroe County, Florida, United States
This Summerland Key house rental offers a pool, kitchen, and parking for up to 5 guests, perfect for your next getaway.
from $304
per night
Outstanding(2 ratings)
from $304
per night
View deal
House Summerland Key
House ∙ 10 guests ∙ 5 bedrooms

Family-oriented big house with terrace, private pool & garden | Nature view | Good for workation | Pets are welcome

Summerland Key, Monroe County, Florida, United States
This waterfront house rental in Summerland Key offers a private heated pool, yard, and balcony, perfect for family getaways.
from $652
per night
Outstanding(18 ratings)
from $652
per night
View deal
House Summerland Key
House ∙ 6 guests ∙ 2 bedrooms

Fully equipped house with yard & barbeque

Summerland Key, Monroe County, Florida, United States
This waterfront house in Summerland Key features a kitchen, balcony, and yard, perfect for a memorable getaway with friends.
from $239
per night
from $239
per night
View deal
House Summerland Key
House ∙ 20 guests ∙ 8 bedrooms

Family-oriented vacation home with private pool, yard & patio | Nature view | Pets allowed

Summerland Key, Monroe County, Florida, United States
This waterfront house rental in Summerland Key features a private heated pool, yard, and space for 20 guests, perfect for families.
from $1,717
per night
Outstanding(89 ratings)
from $1,717
per night
View deal
House Summerland Key
House ∙ 6 guests ∙ 2 bedrooms

Charming vacation home with terrace

Summerland Key, Monroe County, Florida, United States
from $248
per night
from $248
per night
View deal
House Summerland Key
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with private pool | Sea view

Summerland Key, Monroe County, Florida, United States
This house rental in Summerland Key features a private heated pool, ocean views, and a kitchen, perfect for your getaway with pets.
from $285
per night
from $285
per night
View deal
House Summerland Key
House ∙ 14 guests ∙ 5 bedrooms

Family-oriented vacation home with hot tub, terrace & private pool | Nature view | Good for workation | Dogs allowed

Summerland Key, Monroe County, Florida, United States
This waterfront house rental in Summerland Key features a private heated pool, hot tub, and ample space for family gatherings.
from $884
per night
from $884
per night
View deal
Cabin Summerland Key
Cabin ∙ 4 guests ∙ 1 bedroom

Cottage with patio, barbeque & pool

Summerland Key, Monroe County, Florida, United States
This cabin in Summerland Key features a pool, kitchen, and pet-friendly space, perfect for a family getaway with parking.
from $208
per night
Outstanding(67 ratings)
from $208
per night
View deal
House Summerland Key
House ∙ 14 guests ∙ 6 bedrooms

Children-friendly vacation home with patio, jacuzzi & private pool | Suitable for remote work | Pets allowed

Summerland Key, Monroe County, Florida, United States
This waterfront house rental in Summerland Key features a private heated pool, hot tub, and a yard, perfect for family gatherings.
from $563
per night
Outstanding(10 ratings)
from $563
per night
View deal
House Summerland Key
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with private pool, terrace & barbeque | Nature view | Perfect for remote work

Summerland Key, Monroe County, Florida, United States
This waterfront house rental in Summerland Key offers a private heated pool, a fireplace, and family-friendly amenities for 8.
from $300
per night
Outstanding(24 ratings)
from $300
per night
View deal
House Summerland Key
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with grill, private pool & patio

Summerland Key, Monroe County, Florida, United States
This house rental in Summerland Key features a private heated pool, a kitchen, and a balcony for up to 8 guests to enjoy.
from $353
per night
Outstanding(10 ratings)
from $353
per night
View deal
House Summerland Key
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with barbecue & private pool | Pet-friendly

Summerland Key, Monroe County, Florida, United States
This house rental in Summerland Key features a private pool, kitchen, and parking, accommodating up to 10 guests and pets.
from $521
per night
Outstanding(4 ratings)
from $521
per night
View deal
House Summerland Key
House ∙ 6 guests ∙ 2 bedrooms

Fully equipped house with barbecue, terrace & pool | Perfect for remote work | Pets are welcome

Summerland Key, Monroe County, Florida, United States
This house rental in Summerland Key features a pool, kitchen, and pet-friendly options, perfect for 6 guests seeking relaxation.
from $232
per night
from $232
per night
View deal
House Summerland Key
House ∙ 12 guests ∙ 4 bedrooms

Family-friendly beautiful house with garden, barbeque & private pool | Nature view | Dogs allowed

Summerland Key, Monroe County, Florida, United States
This house rental in Summerland Key features a private pool, beach access, and spacious yard, perfect for family getaways.
from $771
per night
Very good(82 ratings)
from $771
per night
View deal

Vacation rentals and apartments with air conditioning

House Summerland Key
from $304
per night
House ∙ 6 guests ∙ 2 bedrooms

House with grill, terrace & private pool

5.0
Outstanding(4 ratings)
Summerland Key, Monroe County, Florida, United States
Air conditioning
View deal
House Summerland Key
from $1,131
per night
House ∙ 6 guests ∙ 3 bedrooms

Child-friendly wonderful house with barbecue & garden | Beach nearby | Pets allowed

4.8
Outstanding(16 ratings)
Summerland Key, Monroe County, Florida, United States
Air conditioning
View deal
House Summerland Key
from $505
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented vacation home with patio & barbeque | Pets are welcome

4.8
Outstanding(76 ratings)
Summerland Key, Monroe County, Florida, United States
Air conditioning
View deal
See all offers

Vacation rentals with a balcony

House Summerland Key
from $1,101
per night
House ∙ 14 guests ∙ 4 bedrooms

Vacation home with private pool, barbecue & terrace

5.0
Outstanding(6 ratings)
Summerland Key, Monroe County, Florida, United States
Balcony
View deal
House Summerland Key
from $226
per night
House ∙ 6 guests ∙ 2 bedrooms

Children-friendly nice house with terrace, BBQ & garden | Pet-friendly

4.8
Outstanding(8 ratings)
Summerland Key, Monroe County, Florida, United States
Balcony
View deal
House Summerland Key
from $513
per night
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped wonderful vacation home with private pool, patio & BBQ

4.5
Excellent(14 ratings)
Summerland Key, Monroe County, Florida, United States
Balcony
View deal
See all offers

Vacation Rentals With Fireplaces

Cabin Summerland Key
from $414
per night
Cabin ∙ 8 guests ∙ 2 bedrooms

Cottage with BBQ & pool

4.7
Excellent(50 ratings)
Summerland Key, Monroe County, Florida, United States
Fireplace
View deal
House Summerland Key
from $306
per night
House ∙ 6 guests ∙ 3 bedrooms

House with terrace, heated pool & jacuzzi | Nature view

5.0
Outstanding(9 ratings)
Summerland Key, Monroe County, Florida, United States
Fireplace
View deal
House Summerland Key
from $367
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented pleasant house with terrace, grill & pool | Suitable for remote work

5.0
Outstanding(4 ratings)
Summerland Key, Monroe County, Florida, United States
Fireplace
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Summerland Key offering exceptional value for money

Cabin Summerland Key
from $243
per night
Cabin ∙ 4 guests ∙ 1 bedroom

Cottage with pool, yard & terrace

4.9
Outstanding(75 ratings)
Summerland Key, Monroe County, Florida, United States
View deal
House Summerland Key
from $321
per night
House ∙ 6 guests ∙ 2 bedrooms

Charming house with private pool & terrace

Summerland Key, Monroe County, Florida, United States
View deal
House Summerland Key
from $924
per night
House ∙ 10 guests ∙ 3 bedrooms

Vacation home with patio, BBQ & private pool

5.0
Outstanding(63 ratings)
Summerland Key, Monroe County, Florida, United States
View deal

Top-Rated Vacation rentals in Summerland Key

Book the highest-rated Summerland Key vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Summerland Key
from $524
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with yard, private pool & terrace

4.9
Outstanding(12 ratings)
Summerland Key, Monroe County, Florida, United States
View deal
Cabin Summerland Key
from $352
per night
Cabin ∙ 6 guests ∙ 3 bedrooms

Cottage with yard, patio & BBQ

5.0
Outstanding(6 ratings)
Summerland Key, Monroe County, Florida, United States
View deal
House Summerland Key
from $484
per night
House ∙ 10 guests ∙ 4 bedrooms

Family-friendly nice house with private pool | Dogs allowed

5.0
Outstanding(2 ratings)
Summerland Key, Monroe County, Florida, United States
View deal

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Verified reviews

Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

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Spend your budget exactly as planned by comparing thousands of providers.

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Find your dream stay

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Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Features & Amenities in Summerland Key

  • Pool (126)
  • Pet-friendly (101)
  • Air conditioning (190)
  • WiFi (188)
  • Kitchen (185)
  • TV (184)
  • Fishing (107)
  • Washing machine (151)
  • Parking (6)
  • Grill (144)
  • Balcony/patio (115)
  • Microwave (175)

Finding a property with a pool shouldn't be too difficult in Summerland Key. Many of the vacation rentals include pools. Additionally, properties with pools in Summerland Key cost, on average, $530 a night. Most of the available vacation rentals with pools are hotel room. You can also rent an accommodation providing a pool near the water, which is the case for nearly half of the rentals there.

Price and Availability Index in Summerland Key

Click on any bar to see price and availability information

Vacation Rental Price Information in Summerland Key

The price graph will give you the average nightly price for the upcoming months of the year in Summerland Key. The most expensive dates to travel to Summerland Key are in December (12/26 – 1/2). Prices decrease in a week of August (8/15 – 8/22), where average prices are $582.

Rental availability information in Summerland Key

Have a look at the above graph to see the average availability of vacation rentals in Summerland Key. More people travel to Summerland Key a week in April (4/17 – 4/24). So far, 59% of the rentals are occupied this week. Conversely, it is in October (10/3 – 10/10) that the highest percentage of rentals are available.

Information about vacation rentals in Summerland Key

🏡 Vacation rentals available 184 rentals
🌙 Nightly prices starting at $149
⭐ Popular amenities Pool, Pets allowed and Air conditioning
🐾 Pet friendly homes 102 homes
🏊 Vacation rentals with pools 117 homes

Frequently Asked Questions

What is the typical nightly price for a vacation rental in Summerland Key?

On average, vacation rentals in Summerland Key cost around $149 per night. $578 is the average nightly price for house rentals in Summerland Key. Cottages in Summerland Key cost on average $314 per night.

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

Currently there are 184 rentals in Summerland Key to browse and rent for your next trip.

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

Summerland Key offers 117 Hotel room and Motel available for booking.

Are pets allowed in vacation rentals in Summerland Key?

Absolutely, currently there are 102 rentals in Summerland Key that allow pets and the average price is $526 per night.

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