Location

Dates

Guests

Vacation rentals in Florida, United States

Welcome to Pineapple Paradise SGI!

Plenty of room for parking trucks or boats.

Pineapple Paradise SGI

You can easily see the beach, the lighthouse, and Weber's Donuts from the house.

Main floor full kitchen and dining area.

Pineapple Paradise SGI

2 bedrooms·2 baths

Saint George Island • Florida

5(4 reviews)

$735.93 USD total for 3 nights

Oct 30 – Nov 2, 2026

Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

3 bedrooms·3 baths

Holmes Beach • Florida

5(9 reviews)

$14,959.60 USD total for 28 nights

Oct 23 – Nov 20, 2026

Moana kids' room with bunk bed

Comfort and relaxation is the theme for our master bedrooms. It is complete with a king-sized memory foam bed, a Smart Roku TV for your entertainment needs, and its own spacious en-suite bathroom

Nemo kids' room with a custom bunk bed wall mounted TV, and color changing lights.

Pool with lake-view. (pool heat available)

Beautiful pool and lake-view from the living room.

Lakeview Luxury Villa w/ Pool Heat available

5 bedrooms·3 baths

Davenport • Florida

4.94(80 reviews)

$898.64 USD $798.34 USD total for 3 nights

Oct 25 – 28, 2026

Vacation Rental Villa House of Orange at Watersong Resort

Master bedroom Vacation Rental Villa House of Orange at Watersong Resort

Front of Vacation Rental Villa House of Orange at Watersong Resort

Pool at night Vacation Rental Villa House of Orange at Watersong Resort

Entrance Vacation Rental Villa House of Orange at Watersong Resort

House of Orange at Watersong Resort, Davenport FL

4 bedrooms·3½ baths

Davenport • Florida

4.93(14 reviews)

$1,030.00 USD total for 5 nights

Nov 21 – 26, 2026

The Anastasia House St Augustine Vacation Rental

The Anastasia House St Augustine Vacation Rental

The Anastasia House St Augustine Vacation Rental

The Anastasia House St Augustine Vacation Rental

The Anastasia House St Augustine Vacation Rental

The Anastasia House St Augustine Vacation Rental

2 bedrooms·2 baths

St. Augustine • Florida

4.91(218 reviews)

$711.54 USD total for 3 nights

Oct 23 – 26, 2026

Kitchen, island and and dining table

fully furnished kitchen

Stutzman Beach Cottage

Stutzman Beach Cottage

Bedroom 1, Split King Adjustable bed, on-suite bathroom

Stutzman Beach Cottage

3 bedrooms·2 baths

Laguna Beach • Florida

4.95(22 reviews)

$828.80 USD $765.52 USD total for 3 nights

Oct 23 – 26, 2026

On the 4th Floor! Majestic Beach Resort

Located three floors from the beach makes this condo perfect for getting for getting to the beach. There is no need to wait on elevators!

On the 4th Floor! Majestic Beach Resort

On the 4th Floor! Majestic Beach Resort

New appliances January of 2023!

On the 4th Floor! Majestic Beach Resort

1 bedroom·1 bath

Panama City Beach • Florida

5(27 reviews)

$708.81 USD $573.51 USD total for 3 nights

Oct 23 – 26, 2026

Grand Panama Beach Resort: Tower 1-Gulf-front, Tower 2- Beach via walkover tower

Tower 2 rooftop lagoon pool/hot tub with ocean view

Coastal Breeze Retreat!

View of Tower 2 pool deck at night

View of Gulf from garage-top pool (from across the street)

Coastal Breeze Retreat!

3 bedrooms·3 baths

Panama City Beach • Florida

4.81(16 reviews)

$2,492.00 USD total for 4 nights

Oct 23 – 27, 2026

Tropical oasis with private pool

Aerial view of Villa Pine pool area. Gas and charcoal grills

Spacious dining and living area

Beautiful Villa Pine on the right with private pool

Villa Pine is the 2 story home on the right

HOLY MOLY LOCATION !! Pool, Beach, Publix, Shops

4 bedrooms·2½ baths

Lauderdale-by-the-Sea • Florida

4.87(372 reviews)

$1,902.00 USD $1,822.90 USD total for 4 nights

Oct 23 – 27, 2026

Wake up to this amazing view! Beachfront master suite with balcony access and large en-suite master bath.

Beachfront 3BR with Gulf views and beach chairs available in the condo.

Enjoy the balcony!

Beachfront-Amazing View-Beachfront Master-Balcony!

3 bedrooms·2 baths

Panama City Beach • Florida

5(104 reviews)

$923.96 USD $900.12 USD total for 3 nights

Oct 26 – 29, 2026

Living room and the view

Great views of Gulf from 24' balcony

Great views of Gulf from 24' balcony

Pelican Beach Resort

Pelican Beach Resort

Pelican Beach 518 (2BR)

2 bedrooms·2 baths

Destin • Florida

4.86(295 reviews)

$1,074.30 USD $988.73 USD total for 3 nights

Oct 25 – 28, 2026

Living room with ocean view from the balcony

Living room with ocean view from 17th floor

The view, beachfront zero entry pool and hot tub

Gulf and Dolphin Pools

Living room and dining area

Pelican Beach 1710

1 bedroom·2 baths

Destin • Florida

5(308 reviews)

$1,074.30 USD $988.73 USD total for 3 nights

Oct 25 – 28, 2026

5 mi to Fort Myers & Sanibel Beaches. POOL!

5 mi to Fort Myers & Sanibel Beaches. POOL!

Spacious living room, comfy seating

5 mi to Fort Myers & Sanibel Beaches. POOL!

5 mi to Fort Myers & Sanibel Beaches. POOL!

5 mi to Fort Myers & Sanibel Beaches. POOL!

2 bedrooms·2 baths

Fort Myers • Florida

5(19 reviews)

$779.39 USD total for 5 nights

Oct 23 – 28, 2026

Pool with Heated Hot tub

Living area with Smart TV

Primary Bedroom

Kitchen with bar top seating area and eat in kitchen area

Second Primary Suite

Mickey's Hideaway Haven with Pool and Jacuzzi

4 bedrooms·3 baths

Kissimmee • Florida

4.6(52 reviews)

$836.20 USD total for 3 nights

Oct 23 – 26, 2026

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54-web-or-mls-12310 Memorial Hwy-51.jpg

Tampa Event Compound, Hot Tub Bar

Tampa Event Compound, Hot Tub Bar

10 bedrooms·10 baths

Tampa • Florida

5(48 reviews)

$21,590.00 USD $18,426.50 USD total for 7 nights

Oct 23 – 30, 2026

Renovated Beach Paradise. Ground Floor unit 64 image 1

Turtle Crawl Inn 64

1 bedroom·1 bath

Longboat Key • Florida

4.88(73 reviews)

$932.25 USD total for 3 nights

Oct 26 – 29, 2026

Spacious living room with all new furniture and 75" Samsung TV

Living room with beautiful ocean view

Master bedroom with a King bed

Master room with a king bed

Master room with beautiful ocean view

Waterscape/View/Free BCH SVC/Lazy River/2Kings

3 bedrooms·2½ baths

Okaloosa Island • Florida

4.93(120 reviews)

$1,185.37 USD total for 4 nights

Oct 23 – 27, 2026

The treehouse in the woods.

The back deck of the treehouse.

Looking at the living area and ladder to the loft, from the treehouse bed.

Queen bed with loft above in the treehouse

Treehouse Camping Escape

1 bedroom·1 bath

Old Town • Florida

4.89(88 reviews)

$497.50 USD total for 3 nights

Oct 25 – 28, 2026

The lanai has a table that seats 8, privacy bushes, 4 lounge chairs & BBQ

The outdoor table under the lanai seats 8 and the pool has a security fence

The Game room has a pool table, air hockey, foosball, & Air Conditioning

Private screened in, heated salt water pool and spa with oversized pool deck

The covered lanai, lounge chairs & basketball hoop, salt water pool & spa

Villa By The Castle

6 bedrooms·4 baths

Kissimmee • Florida

5(385 reviews)

$2,298.38 USD total for 3 nights

Nov 11 – 14, 2026

Downtown Lake Eola Historic House 1 or 2 Bed

Downtown Lake Eola Historic House 1 or 2 Bed

Downtown Lake Eola Historic House 1 or 2 Bed

Downtown Lake Eola Historic House 1 or 2 Bed

Downtown Lake Eola Historic House 1 or 2 Bed

Downtown Lake Eola Historic House 1 or 2 Bed

2 bedrooms·1 bath

Orlando • Florida

4.72(505 reviews)

$329.00 USD total for 3 nights

Oct 26 – 29, 2026

Beautiful beachfront master suite with access to the beachfront balcony and large en-suite master bath.

Spacious beachfront living room with access to the large beachfront balcony.

Spacious beachfront living area with access to the large balcony.

Relax on the spacious beachfront balcony

Spacious Beachfront Condo with Beachfront Master!

2 bedrooms·2 baths

Panama City Beach • Florida

5(88 reviews)

$827.59 USD $807.61 USD total for 3 nights

Oct 24 – 27, 2026

Magic Emerald Island Villa

4 bedrooms·3 baths

Kissimmee • Florida

5(88 reviews)

$984.03 USD total for 4 nights

Nov 14 – 18, 2026

Gigi’s Sunshine Beach Retreat

Gigi’s Sunshine Beach Retreat

Gigi’s Sunshine Beach Retreat

Gigi’s Sunshine Beach Retreat

Gigi’s Sunshine Beach Retreat

Gigi’s Sunshine Beach Retreat

5 bedrooms·4 baths

Destin • Florida

4.88(195 reviews)

$1,743.90 USD total for 3 nights

Oct 31 – Nov 3, 2026

Downtown private Efficiency Lake Eola

Downtown private Efficiency Lake Eola

Downtown private Efficiency Lake Eola

Downtown private Efficiency Lake Eola

Downtown private Efficiency Lake Eola

Downtown private Efficiency Lake Eola

0 bedrooms·1 bath

Orlando • Florida

4.75(502 reviews)

$357.20 USD total for 3 nights

Oct 24 – 27, 2026