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

Vacation rentals in Summerland Key

Browse 162 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 162 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Summerland Key
House ∙ 6 guests ∙ 3 bedrooms

House with terrace, private pool & barbecue | Nature view

Summerland Key, Monroe County, Florida, United States
This waterfront house rental in Summerland Key features a private pool, yard, and kitchen, perfect for family getaways.
from $277
per night
Outstanding(6 ratings)
from $277
per night
View deal
House Summerland Key
House ∙ 10 guests ∙ 3 bedrooms

House with private pool, grill & terrace | Pets are welcome

Summerland Key, Monroe County, Florida, United States
This waterfront house rental in Summerland Key features a private pool, kitchen, and accommodates up to 10 guests with pets allowed.
from $218
per night
Very good(2 ratings)
from $218
per night
View deal
House Summerland Key
House ∙ 20 guests ∙ 8 bedrooms

Family-oriented vacation home with private pool, yard & patio | 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 $1,659
per night
Outstanding(91 ratings)
from $1,659
per night
View deal
House Summerland Key
House ∙ 12 guests ∙ 4 bedrooms

Family-friendly beautiful house with garden, barbeque & private pool | Nature view | Good for workation | 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 $770
per night
Very good(86 ratings)
from $770
per night
View deal
House Summerland Key
House ∙ 10 guests ∙ 4 bedrooms

Family-friendly pleasant house with barbecue & terrace | Perfect for remote work | Pet-friendly

Summerland Key, Monroe County, Florida, United States
This spacious waterfront house rental in Summerland Key offers a kitchen, parking, and pet-friendly amenities for up to 10 guests.
from $838
per night
Outstanding(32 ratings)
from $838
per night
View deal
House Summerland Key
House ∙ 16 guests ∙ 7 bedrooms

Vacation home with hot tub

Summerland Key, Monroe County, Florida, United States
This house rental in Summerland Key accommodates 16 guests and welcomes pets, making it perfect for your next group getaway.
from $1,078
per night
from $1,078
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 $529
per night
Outstanding(4 ratings)
from $529
per night
View deal
House Summerland Key
House ∙ 4 guests ∙ 2 bedrooms

House with hot tub, pool & barbecue

Summerland Key, Monroe County, Florida, United States
This waterfront house rental in Summerland Key features a pool, hot tub, and pet-friendly amenities for a perfect getaway.
from $445
per night
from $445
per night
View deal
House Summerland Key
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with private pool, terrace & barbeque | 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 $315
per night
Outstanding(25 ratings)
from $315
per night
View deal
House Summerland Key
House ∙ 8 guests ∙ 3 bedrooms

House with pool & barbecue

Summerland Key, Monroe County, Florida, United States
This Summerland Key house rental features a pool, pet-friendly amenities, and space for eight, perfect for family getaways.
from $560
per night
Outstanding(2 ratings)
from $560
per night
View deal
House Summerland Key
House ∙ 8 guests ∙ 4 bedrooms

House with barbeque & private pool

Summerland Key, Monroe County, Florida, United States
This waterfront house rental in Summerland Key features a private heated pool, kitchen, and parking, perfect for 8 guests and pets.
from $291
per night
Excellent(12 ratings)
from $291
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 $243
per night
Outstanding(63 ratings)
from $243
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 $364
per night
Outstanding(10 ratings)
from $364
per night
View deal
House Summerland Key
House ∙ 14 guests ∙ 6 bedrooms

Children-friendly vacation home with patio, jacuzzi & private pool | Nature view | 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 $565
per night
Outstanding(10 ratings)
from $565
per night
View deal
House Summerland Key
House ∙ 6 guests ∙ 3 bedrooms

House with private pool, terrace & BBQ | Suitable for remote work

Summerland Key, Monroe County, Florida, United States
This waterfront house rental in Summerland Key offers a private heated pool, kitchen, balcony, and space for up to six guests.
from $242
per night
Outstanding(24 ratings)
from $242
per night
View deal

Vacation houses with Balconies or Patios

House Summerland Key
from $360
per night
House ∙ 10 guests ∙ 4 bedrooms

Pleasant vacation home with private pool | Pets allowed

Summerland Key, Monroe County, Florida, United States
Balcony/Patio
View deal
House Summerland Key
from $227
per night
House ∙ 6 guests ∙ 3 bedrooms

House with patio & hot tub

Summerland Key, Monroe County, Florida, United States
Balcony/Patio
View deal
House Summerland Key
from $531
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/Patio
View deal
See all offers

Vacation rentals with a balcony

House Summerland Key
from $729
per night
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped vacation home with barbeque, garden & pool

Summerland Key, Monroe County, Florida, United States
Balcony
View deal
House Summerland Key
from $529
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
Balcony
View deal
House Summerland Key
from $954
per night
House ∙ 10 guests ∙ 3 bedrooms

Vacation home with patio, BBQ & private pool

5.0
Outstanding(73 ratings)
Summerland Key, Monroe County, Florida, United States
Balcony
View deal
See all offers

Vacation rentals and apartments with air conditioning

Cabin Summerland Key
from $418
per night
Cabin ∙ 8 guests ∙ 2 bedrooms

Cottage with BBQ & pool

4.7
Excellent(49 ratings)
Summerland Key, Monroe County, Florida, United States
Air conditioning
View deal
House Summerland Key
from $507
per night
House ∙ 8 guests ∙ 3 bedrooms

Children-friendly spacious vacation home with patio & barbecue | Good for workation | Pets allowed

5.0
Outstanding(33 ratings)
Summerland Key, Monroe County, Florida, United States
Air conditioning
View deal
House Summerland Key
from $410
per night
House ∙ 6 guests ∙ 2 bedrooms

House with patio, garden & barbecue

5.0
Outstanding(67 ratings)
Summerland Key, Monroe County, Florida, United States
Air conditioning
View deal
See all offers

Budget-friendly rental options

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

House Summerland Key
from $322
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
View deal
House Summerland Key
from $485
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with private pool, garden & BBQ | Nature view

5.0
Outstanding(26 ratings)
Summerland Key, Monroe County, Florida, United States
View deal
House Summerland Key
from $245
per night
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped house with yard & barbeque

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 $737
per night
House ∙ 10 guests ∙ 3 bedrooms

House with private pool, terrace & BBQ

5.0
Outstanding(17 ratings)
Summerland Key, Monroe County, Florida, United States
View deal
House Summerland Key
from $305
per night
House ∙ 6 guests ∙ 2 bedrooms

House with BBQ, yard & private pool

5.0
Outstanding(6 ratings)
Summerland Key, Monroe County, Florida, United States
View deal
House Summerland Key
from $451
per night
House ∙ 9 guests ∙ 3 bedrooms

Family-oriented house with yard, pool & patio | Suitable for remote work | Pets are welcome

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

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

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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, $545 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 one-third of the rentals there.

Information about vacation rentals in Summerland Key

🏡 Vacation rentals available 162 rentals
🌙 Nightly prices starting at $194
⭐ Popular amenities Pool, Pets allowed and Air conditioning
🐾 Pet friendly homes 97 homes
🏊 Vacation rentals with pools 108 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 $194 per night. $593 is the average nightly price for house rentals in Summerland Key. Cottages in Summerland Key cost on average $312 per night.

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

Currently there are 162 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 108 Hotel room and Cabin available for booking.

Are pets allowed in vacation rentals in Summerland Key?

Absolutely, currently there are 97 rentals in Summerland Key that allow pets and the average price is $527 per night.

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